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In the late afternoon, the boats fetched up on the eastern bank of the tidal Hillsboro River, under the shallow rise to Col. Dummett’s house.

It was a relief. For the whites, anyway. They had put distance between themselves and what they assumed was an incoming Seminole war party. At Dummett’s, on the all-but-deserted barrier island that shelters Florida’s east coast, they hoped to safely pass the night.

A slim quarter moon passed overhead as Christmas night deepened. The refugees could look straight back down a mile-long stretch of river to where it curved at New Smyrna’s waterfront. The black skyline was pancake flat except a lone hill whiskered in scrub oak and cabbage palm. This was an ancient shell midden, the work of the long-gone Timucua people. At the base of this hill stood the plantation manager’s house, which John and Jane Sheldon had abandoned just hours earlier.

In the distance a yellow light flickered, then grew. Soon it surpassed the modest limit of a campfire, then outstripped even a bonfire. It was a structure fire. The plantation house was engulfed in flame. Other buildings followed suit, set alight by the Seminoles. The sky over New Smyrna glowed brightly. John Sheldon later claimed he saw 100 Seminoles dancing before the flames.

The whites at Col. Dummett’s reconsidered the safety of their position. The Sheldons, Hunter, and Dummett hastily boarded their small boats and headed north. They left the black people behind with orders to follow in the cargo-laden lighters when the tide was favorable. Evidently, they thought this a reasonable demand.

Making their way up the river, the Sheldons — John, his wife Jane, and her mother — found a schooner anchored in the Mosquito Inlet (now Ponce Inlet) and clambered aboard. They rode out the night in the shadow of the newly constructed lighthouse that towered over the dunes on the south bank of the inlet. But the lighthouse sat dark. It had been waiting some time for its first shipment of sperm whale oil to fuel the lamp whose beams would be reflected out into the world by giant polished mirrors.

Probably just as well for the Sheldons who were not interested in being seen.

As daylight broke, John took his little boat back to Dummett’s to get the trunks which they had left in the care of the slaves. But John came upon an unexpected scene.

The black people were not, in fact, following as the whites had directed. Instead, they were rowing the lighters back toward the smoldering ashes of New Smyrna. They must have felt this was a more enticing option than rejoining their enslavers. But then John Sheldon witnessed something more alarming. The blacks were intercepted by eleven Seminoles arriving on a raft. The Seminoles then forced them back to the shore by Dummett’s house. There, the Indians commenced “breaking open the trunks and destroying the goods.”1

John Sheldon turned his boat and beat it back to the anchored schooner where he onboarded his wife and mother-in-law and fled up the coastal river.

The Sheldons had watched their lives as plantation managers evaporate in the smoky glow over New Smyrna the night before. Now they knew Seminoles raiders were in hot pursuit.

Refuge in the North

The Sheldons — like all sugar planters on Florida’s east coast — knew that the farther south they were from the gates of old St. Augustine the more precarious their position.

The Seminoles knew it, too. Which is surely why John Caesar and Emathla began their operations in New Smyrna. Some 70 miles from St. Augustine, it was the southernmost, and therefore most vulnerable, of the American settlements. Still, the Seminoles must have been surprised that all it took for complete victory were mere rumors of their presence. Their reputations indeed preceded them.

But the Seminoles did not linger in New Smyrna. They moved rapidly north, targeting every plantation along the way. In the week following Christmas 1835 they took, in turn, the Dunlawton plantation (in today’s Port Orange), Williams’s plantation (Daytona Beach), Heriot’s plantation (Daytona Beach), MaCrae’s plantation, a.k.a. Carrickfergus (Ormond Beach), and Dummett’s plantation, a.k.a. Darley’s or Rosetta (Ormond Beach). Seminoles also struck to the west along the St. Johns River, taking Rees’s Spring Garden plantation (DeLeon Springs in Deland), and Forrester’s (also Deland).

Still, as fast as the Seminoles moved, the white evacuees moved faster. They abandoned their homes throughout Mosquito (environs of New Smyrna) and Tomoka (roughly today’s Daytona and Ormond Beach). As Seminoles arrived expectantly in warpaint, they encountered not a shred of white resistance.

But there was a limit to this cakewalk. As we saw in the previous post, Brig. Gen. Joseph Hernandez at St. Augustine had anticipated trouble. A couple of weeks before Christmas he ordered a detachment of Florida militia south to protect the plantations. This detachment, under Maj. Benjamin Putnam (like Hernandez, a St. Augustine lawyer), stopped 30 miles short of New Smyrna.

Bulow’s Plantation Invaded by … Americans

Putnam chose the plantation of John J. Bulow as headquarters for his field operations. Located on a wide tidal creek, Bulowville was by far the largest of the coastal plantations. At its maximum extent, some 300 black people labored on its 2,200 acres of sugarcane, rice, cotton, corn and indigo. Bulow’s great sugar mill with soaring stone chimneys dwarfed any in the Mosquitoes.

Young bachelor Bulow, who had inherited the plantation from his father, was a difficult man. He protested angrily as Putnam commandeered his estate. It would ruin his cordial relations with the Seminoles, Bulow argued (correctly). Putnam persisted and, it is said, put the spluttering slavemaster under guard while troops seized his cotton bales, timber, and other materials and equipment to build an impromptu fortress around the big plantation house by Bulow Creek. In the crowning insult, Putnam and the militia officers dined at Bulow’s table by candlelight; Bulow was expelled to the yard.

In the days following Christmas 1835, Bulowville became not only a military garrison, but a sanctuary for all the whites fleeing north from Mosquito and Tomoka. This included the Sheldons, Hunter and Dummett, who came ashore at Bulow’s, fearful of traveling on to St. Augustine without guards. The plantation became very crowded and provisions were limited. Some officers quartered in the slave cabins that formed a wide semicircle around Bulow’s plantation house which backed up to the creek.

Hundreds Liberated from Slavery

Whether these militia men displaced the inhabitants is not clear. Bulow may have sent some or all of the black people from his plantation north for safekeeping at St. Augustine. Several slaveholders from Mosquito and Tomoka had done so and more would soon. Anastasia Island, within the protection zone of St. Augustine, quickly became a sprawling camp of enslaved black refugees.

But for many other black people, the chaos of Christmastime 1835 had severed their ties to American slaveholders. By the end of December, roughly 330 had either joined the Seminoles or were on their own in the Florida wilderness. This slave liberation (to be discussed in a future post) was of a magnitude far, far greater than any in American history prior to the Civil War.

Meanwhile at Bulowville, the Florida militia and plantation evacuees hunkered down to wait for the almost-certain onslaught of the Seminoles who were sweeping north with numbers augmented by newly recruited black warriors from the burned plantations.

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It was Christmas morning and John Caesar had some livestock to sell.

Or so he said.

The target of John Caesar’s pitch, Mr. Hunter, wasn’t in a buying mood. In fact, he wasn’t in a door-opening mood, either.

John Caesar stood in the yard. He was a seasoned pro. No longer a young man, he had gained a lifetime of approaches. But try as he might, he could not get Mr. Hunter to come out to have a look at the animals.

Mr. Hunter stayed firmly within his house. As if his life depended on it.

Hunter ran a sugarcane plantation along the tidal river in New Smyrna, about a mile north of the big house where Jane and John Sheldon lived. It was at the slave quarters of Hunter’s place where, the night before, the Sheldons’ servant girl had seen the war-painted Indians. Hunter may have heard about their appearance, too. In any case, there was zero chance Hunter was coming out of the safety of his four walls to converse that morning with the Black Seminole, John Caesar.

A man of distinction

John Caesar was counselor, and possibly vassal, to the ranking regional head man, a Seminole, probably Mikasuki, known to the whites as Emathla or King Philip. John Caesar gallops through the records of this period, but his background is lost to us. Still, from his Anglo first name and the Roman one after it (a quirk of enslavers was to fasten epic Greek or Roman names onto people they enslaved: Pompey, Scipio, etc.), it is a fair surmise that he had escaped bondage or was bought out from it. John Caesar occupied a powerful position. His proximity to American slavery gave him two things valuable to the Seminoles: he understood how whites and blacks thought and behaved, and he spoke their language.

John Caesar was therefore Emathla’s man of business when dealing with whites. That is not to say John Caesar wasn’t on his own errand, too, when he tried to coax Mr. Hunter from his house. John Caesar and Emathla were done with the plantations. Emathla wanted the land free of them. John Caesar wanted freedom for the people on them. Both men were ready for a new era in the Mosquitoes.

Mr. Hunter was keenly aware such an era would have no room for him. If he’d been so foolish as to accept John Caesar’s invitation that Christmas morning, he might have been murdered as he stepped off his front porch.

In time, John Caesar gave up, moved on. When Hunter figured the coast was clear, he hustled down to the Sheldons’ place on the river. Time is short, he told them. An attack is imminent. They must load up the boats with all the property they could carry and get out of New Smyrna.

The Slow Burn

The appearance of painted Seminoles and John Caesar’s failed livestock sale were not the first indications of trouble in the Mosquitoes. Months before Christmas 1835, rumors of unrest roiled the eastern plantations. White interactions with Seminoles had been unpleasant.

To the west in central Florida, the fall was punctuated by isolated episodes of violence. It was said that Seminole warriors were sending their women and children into remote camps. Whites near the reservation border began leaving their homes and crowding into fortified zones at Fort Crum and Newnansville (near today’s Gainesville). With the murder of Charley Emathla in late November near Fort King (today’s Ocala), it was felt that war was certain.

At the same time back in the east, Joseph Hernandez, a St. Augustine lawyer and sugar planter, was getting edgy. Hernandez was also brigadier general of the volunteer militia of east Florida. He was responsible not just for defending the city, but every sugar operation all the way down to New Smyrna in the Mosquitoes, some 70 miles away.

Before John Caesar showed up on Hunter’s plantation, he had come to the attention of Gen. Hernandez. According to an acquaintance of Hernandez’s:

“It was known that, just before the war broke out, a very intelligent and influential Indian negro, named Caesar, had visited the plantations generally on the St. John’s River, and it was supposed that he had been commissioned by the chiefs to hold out inducements to the negroes to join them.”

— Thomas Douglas, p. 121

Another contemporary account was more direct about the threat.

“[I]ntelligence reached Gen. Hernandez at St. Augustine, that a large body of Indians belonging to the tribe of Philip, and headed by an Indian negro slave, by the name of John Caesar, had concentrated themselves near the plantation of David Dunham, Esq., at Mosquito — that they evinced a disposition to be hostile, and had been tampering with the negroes, particularly those on the plantations of Messrs. Cruger and Depeyster.”

— M.M. Cohen, pp. 86-87

The militia is mobilized

In mid-December 1835, Hernandez dispatched militia units to protect plantations in the areas of Matanzas, Tomoka, and Mosquito. The idea was move south to New Smyrna and then turn west to the St. John’s, flushing out Seminoles along the way.

But Hernandez’s militia forces were few and east Florida was a rough and sparsely populated place. The expedition got as far south as Darley’s plantation (just north of today’s Ormond Beach) then pulled back and headquartered at the Bulow plantation, more than 30 miles short of New Smyrna.

The slaveholders of the Mosquitoes had put themselves in a precarious position. If John Caesar was indeed poised at the head of a Seminole war party, and if a good number of enslaved people were disposed to join him, the few whites there had no chance.

It was math. Eighty people were enslaved on the Cruger-dePeyster plantation. There were similar but probably smaller numbers on the Hunter and Dunham farms meaning New Smyrna was home to maybe 150-180 black people. But there were no more than a dozen white people around. There were the Sheldons: Jane, her mother, and husband John. Mr. Hunter and Mr. Dunham were two more and perhaps each had a white overseer on his plantation. Old Col. Dummett resided across the river from New Smyrna and his adult son was somewhere in the area.

For the white community of New Smyrna, trouble was coming. But help wasn’t.

To the boats

After John Caesar’s visit, Mr. Hunter and the Sheldons spent Christmas Day preparing their escape. The boats they used were lighters, oar-powered cargo vessels that shuttled goods between the riverside wharf and ships anchored in deeper water. But it wasn’t just household goods they loaded.

Their understanding of ‘property’ was larger than that. It included the people enslaved on the plantations. On the ledgers of the Cruger-dePeyster sugar operation, these were the most valuable assets. The records do not indicate how many black people boarded the lighters — was it 6 or 36? — but some number did.

By sunset, they had shoved off and were crossing the river. Mr. Hunter and the Sheldons hoped to find temporary safety at old Col. Dummett’s house on the far side.1

We will never know, but perhaps John Caesar stood on the west bank of the Hillsboro River2 watching as the lighters grew smaller in the distance. If he did, maybe he felt that it was just as well his livestock sale had fallen through that morning. Without selling a cow, and more importantly, without firing a shot, John Caesar and the Seminoles, and the specter of slave insurrection, had wrung New Smyrna free of white people. There would be no more masters on these sugar plantations.

For John Caesar, that was a good start.

References:

Mark F. Boyd, “The Seminole War: Its Background and Onset,” The Florida Historical Quarterly, Vol. 30, No. 1 (July 1951).

M.M. Cohen, Notices of Florida and the Campaigns, B.B. Hussey, New York, 1836.

Autobiography of Thomas Douglas, Late Judge of the Supreme Court of Florida, Calkins & Stiles, New York, 1856.

Ryan P. Horvatter, The Florida Volunteers: Territorial Militia in the Opening of the Second Seminole War, Master’s Thesis, U.S. Army Command and General Staff College, Fort Leavenworth, Kansas, 2021.

Kenneth Wiggins Porter, “John Caesar: Seminole Negro Partisan,” The Journal of Negro History, Vol. 31, No. 2 (Apr. 1946).

Jane Murray Sheldon, “Seminole Attacks Near New Smyrna, 1835-1856,” The Florida Historical Quarterly, Vol. VIII, No. 4 (Apr. 1930).

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That morning, when Jane Sheldon heard the news from her servant girl, her heart caught in her throat. It was a shock. But not a surprise.

Nine Indians. The girl had been at the dance in the slave quarters over at the Hunter place the night before, Christmas Eve. People were having a good time by the bonfire, looking forward to some of the few days off they’d get till the following Christmas. It wasn’t unusual for Indians to show up from time to time. They were always about, just beyond the woods to the west. But these, the girl said, were painted. Everyone knew what that meant.

Certainly, Jane Sheldon needed no explanation. She ran to find her husband. The Sheldons occupied the finest home in New Smyrna. From a rise on the west bank of the Hillsboro River, they overlooked the water sweeping out toward its point of escape into the wide blue Atlantic at Mosquito Inlet.1 John Sheldon managed the big sugarcane plantation for absentee owners. The center of the operation — the sugar house and slave quarters where about 80 people lived — lay a couple miles inland.

Jane Sheldon lived at the apex of her insular society. She was a white, 22-year-old mother of two. Her little family prospered modestly. On occasion, they socialized with the small handful of white people who lived thereabout.

But her position was tenuous. And Jane would soon find out that when trouble came, help was a very long way away.

The Mosquitoes

New Smyrna was a remote outpost at the southern tip of a narrow, 70-mile-long cul-de-sac. Civilization lay at the far northern end, St. Augustine, a city of 2,000 people. Between the two a string of plantations was bracketed on the west by the sandy King’s Road and on the east by the intracoastal waterway.

New Smyrna’s plantations were situated on drained swamps, an area aptly called Mosquito. Despite being home to just a couple hundred souls, the great majority of them enslaved black people, New Smyrna was the seat of Mosquito County, or, simply the Mosquitoes, a vast, unsurveyed chunk of Florida roughly 120 miles long and 60 wide at points.2

White people knew virtually nothing of the interior of central and south Florida. Maps left it mostly blank with rough guesses about the location of rivers and hammocks and the towns of indigenous and black people who lived there. In the Mosquitoes, whites and their enslaved labor force mainly stuck to the isolated plantations along the coast and a few along the St. Johns River, well inland.

The Cane — Wealth and Misery

In the Americas, long before cotton, sugar was king. The sweet stuff bestowed stupefying wealth on the empires of Britain, France, Portugal and the Netherlands. In 1493, on his second expedition, Columbus first planted the exotic cane in the Caribbean islands. It thrived in the hot, wet climate of the West Indies and coastal mainland of Central and South America down through Brazil.

Sugar could be measured in dollars. But also in misery. After quickly working to death all the indigenous people they could catch, colonial powers turned to Africa for labor.

It was for sugar that Europeans created the trans-Atlantic trade in African slaves, a practice that persisted for centuries. Of the 12.5 million Africans enslaved, more than 90 percent were destined for the Caribbean and South America; just 3.5 percent came to what is now the United States.

Sugar was the difference. Africans who were brought to the U.S., which had no sugar industry to speak of, largely sustained or increased their own numbers by reproduction, which limited the trade. But the sprawling tropical sugar plantations of the Caribbean and South America were death traps, a voracious maw constantly demanding replacements for people worked into early graves.

Florida Takes a Chance

The great thumb of Florida poking down into the Caribbean was sugarcane’s northern limit. Occasional winter cold snaps made the crop dicey here. Early attempts were failures. But such was the lure of sugar wealth that by the 1820s and ‘30s, entrepreneurs with new steam technology and capital backing were willing to take the capital risk. They gambled on the chance to dip Florida’s thumb into the sugar pie.

The Cruger-dePeyster plantation in New Smyrna was Mosquito central. The two men for whom the plantation was named were New York speculators. Plunking down the nest egg of one of their wives and taking on heavy bank loans, they invested in 600 acres of mostly drained swamp, 80 slaves, and expensive, cutting-edge steam machinery for crushing and processing cane. The owners figured the enterprise would stand or fall by the vicissitudes of weather, management of labor and equipment, market prices, and the idiosyncrasies of cane cultivation.

What they hadn’t properly accounted for was the neighbors.

The Neighbors

One hundred and thirty years before these New Yorkers showed up, Florida’s native people were in freefall. By 1705, warfare around Spain’s disastrous century-old mission venture in north Florida and waves of European plagues had depopulated the northern half of the peninsula. (See Ch. 2 of The Florida War.) A dozen years later, Yamassees fleeing war with the Carolina’s English colonists came south. They were joined, beginning around 1750, by Muskogee, Mikasuki, and Yuchee people from what is today Georgia. These people maintained their distinct ethnic identities and languages but, for political as well as defensive purposes, amalgamated into what was increasingly called the Seminole nation.

Beginning in the 1760s, British and then Spanish authorities tried to lure settlers to east Florida with land grants. Not small plots for yeoman farmers, but huge tracts for wealthy agriculturists who would cultivate silk, cotton, and indigo. Few were inspired to try and fewer still succeeded. (New Smyrna’s Turnbull colony, from 1768-1777, was a colossal fiasco, but that’s another story.) As the years ticked by, however, plantations built on enslaved labor crept south from St. Augustine along the coast.

Indian relations with these planters was sometimes peaceful, sometimes violent. In 1802, for instance, a Mikasuki raiding party attacked and trashed two plantations about 20 miles south of St. Augustine, near today’s Palm Coast. From one, they took ten black people. On the other they killed a white boy and hauled off his mother and four siblings. The whites were ransomed back over the next two years; the blacks were not. In the wake of this episode, plantations in the neighborhood lay abandoned for years.3

New energy came to the Mosquitoes after the United States took Florida from Spain in 1821. The Americans figured the solution to their Indian problem was to clear them away from the plantation zone and concentrate them on a reservation in central Florida. By the Treaty of Moultrie Creek in 1823, the eastern Seminoles were to give up their lands near the coast and the St. Johns River valley.

Perhaps some did.

Among the many who did not was Emathla, an aged leader of high stature. Some reckoned him the #2 man in the Seminole nation and he was known to whites as King Philip.4 Two Yuchee head men, known as Billy and Jack, also stayed by the St. Johns with their people. However, the Yuchees, after the Moultrie Creek Treaty, were bullied off their land to make way for the Spring Garden sugar plantation owned by Orlando Rees (see map, above), complete with a great waterwheel to power its sugar mill.5 The Yuchees remained nearby, waiting for a chance to reclaim what was taken.

In the early 1830s, Emathla’s people allowed cordial relations with the new wave of American sugar planters. Commerce was more common than friction. Indians traded wild game for American goods, including sugar and its derivative rum. Individuals of one side were often well known to the other.

The intrepid Black Seminole John Caesar, Emathla’s right-hand man, was one such person. He was said to have had a wife on one of the plantations and was often seen in the Mosquitoes, bartering from St. Augustine south to New Smyrna.

Despite the detente, memories were long. Each side was keenly aware of the violence the other could bring.

Rumors of War

The remote plantations in east Florida were weeks away from the central Florida environs of Fort King and the Indian Agency. News moved at the speed one could speak it to another in person, or hand it in a letter traveling a tropical course by foot, horse, and boat. Still, by December 1835, word had reached St. Augustine that trouble with the Seminoles was looming.

Which didn’t surprise the people of that town. It jibed with the frightening rumors coming north from the Mosquitoes. Seminoles, particularly Black Seminoles, were seen on the plantations. Their presence wasn’t unusual but their message was. They were looking for recruits, selling rebellion. These men, often escaped from slavery themselves before affiliating with the Seminoles, knew all the right words.

Jane’s Last Night

Jane Sheldon owed her position to unspeakable violence perpetrated and forever threatened. It kept the enslaved at their tasks and Jane in a nice frame house.

But enslavers were always aware that violence could be turned on them. Nat Turner’s 1831 rebellion was fresh in the minds of planters throughout the South. Turner’s army of the enslaved murdered 60 whites before the Virginia state militia could suppress it. In grisly response, vigilante and court-ordered executions claimed the lives of four times as many blacks, mainly bystanders.

Just four years later, whites in the Mosquitoes understood the fear of being murdered in their beds by those who would no longer live as slaves.

A similar fear troubled white settlers on disputed Indian land. On the ever-expanding American frontier, whites slept lightly with the specter of a stealthy warrior returning, tomahawk in hand, to wreak vengeance, scalp by scalp.

Unfortunately for Jane Sheldon, she was cursed with both nightmares.

So when she was told that nine war-painted Indians had a nighttime rendezvous with Africans in the slave quarters, Jane knew she’d spent her last night in the big plantation house. She probably wondered if she and her family would see out the day.

Next: White flight from the Mosquitoes.

References:

Patricia C. Griffin, “Life on the Plantations of East Florida, 1763-1848,” The Florida Anthropologist, Vol. 56, No. 3, Sept. 2003.

Pleasant Daniel Gold, History of Volusia County, Florida, Deland, Florida 1927.

Jane Murray Sheldon, “Seminole Attacks Near New Smyrna, 1835-1856,” The Florida Historical Quarterly, Vol. VIII, No. 4, April 1930.

U.S. Congress, House Doc. No. 225, “Negroes &c., captured from Indians in Florida, &c., Letter from the Secretary of War, Feb. 27, 1839,” 25th Cong. 3rd Sess.

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A Day Trip in Ruins

For central Floridians today, the trip east to New Smyrna Beach is a summertime ritual. An hour’s drive, give or take, over the St. Johns River then east at speed on State Road 44 where it’s little more than pine trees, powerlines and maybe a pop-up produce stand. Traffic slows as civilization picks up. Just before the intersection of Chipotle and Publix, a sun-battered road sign reads:

It’s a criminal understatement.

‘Birthplace of Largest Slave Rebellion in U.S. History’ or ‘Crucible of America’s Longest and Deadliest Indian War’ would be better tags. But neither is quite right. Because what happened there on Christmas Day in 1835, and what raged across Florida for the next seven years, was so complicated, such a uniquely Florida story, that it is hard to capture.

So leave it at Sugar Mill Ruins. A knowable fact. Why ruined? Because the people enslaved on the Cruger-DePeyster sugarcane plantation in New Smyrna did indeed burn that mother to the ground. Or a raiding party of Seminoles did. Or an emancipated band of former slaves come to aid their brethren. Probably it was all three.

And it’s a fact that sparks flying from this plantation were just the first. An alliance of Seminoles and Africans went on to burn all of the sugar plantations around New Smyrna and reduced much of the town itself to ashes within a couple of days.

Then they turned the effort north along the Atlantic coast, burning plantations in today’s Port Orange, Daytona, Ormond Beach and beyond. In total, they destroyed almost 20 sugar plantations throughout what are today Volusia and Flagler counties, pushing before them waves of terrified white people racing north for safety behind the gates of St. Augustine.

When the smoke cleared a month later, about 400 people had been liberated from slavery. That number dwarfs any slave revolt over the entire 250-year span of America’s peculiar institution. And in terms of damage inflicted on the slavery apparatus, it was the death knell for Florida’s incipient sugar industry.

This spasm of destruction was an opening salvo for the Second Seminole War. Lasting from 1835 to 1842, it has been called America’s longest, deadliest, and costliest war against native people. But the war cannot be understood without its African dimensions. It was no accident that the first flames of this war engulfed slave plantations.

Today, Volusia County’s Parks, Recreation and Culture Department tends the Sugar Mill Ruins. The little park sits patiently in its rural setting, surrounded by the incessant buzz of cicadas in the thin shade of scrub oaks and tall, spindly cabbage palms. Fire consumed much 190 years ago, but it barely scarred the stout coquina bones of the sugar house and the deep iron cauldrons where the juice of the crushed cane boiled.

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If you are headed to New Smyrna Beach, or are within striking distance, it is worth taking that short spur south off S.R. 44 onto Mission Road to see the Sugar Mill Ruins. The beach will be crowded but this park will be peaceful. Bring a cooler, have a picnic, take a walk on the nature trail. Get acquainted with Florida’s creation story.

Next: The battle for sugarcane country — how it all kicked off.

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So Charley Emathla was the tragic hero and Osceola the treacherous villain. The victors’ history tells us so. Every contemporary report comes from a white man in the service of the U.S. government. Charley-as-martyr served their purposes.

But what was the Seminole side of the story?

They didn’t leave durable records. Still, there is a possible second-hand source.

It comes from the artist George Catlin, famed for painting the portraits of hundreds of Native Americans across the western U.S. in the 1830s, back when it was mostly all Indian country. Journeying from the Mississippi west to the Rockies, from Texas north to Montana, Catlin visited some 50 tribes, capturing portraits and ’slice of life’ scenes of war dances, ball games, and buffalo hunts. For years, he displayed his work in New York, London and Paris. Perhaps more than anyone else, Catlin cemented in the American and European mind’s eye the image of Native Americans.

Catlin left a written record, too, publishing several books about his travels. In these, we find a very different picture of Charley Emathla.

[Spoiler Alert: we’re jumping ahead two years to 1838, discussing the fate of Osceola and the course of the Florida War.]

In January 1838, Catlin had finished his painting tours of the American West and was promoting his work in New York when he got interesting news. The celebrated Seminole war chief Osceola and other top leaders were prisoners of war at Fort Moultrie on Sullivan’s Island in South Carolina. Along with 240 other men, women and children, they awaited deportation to Oklahoma. Catlin, equal parts entrepreneur and artist, collected his tools and hustled south. At the time, the ongoing Seminoles’ war for independence was a staple of national headlines. These prisoners would make fantastic — not to mention lucrative — additions to Catlin’s oeuvre.

At Fort Moultrie, Catlin found the Seminole captives haggard and resigned to fate. For two years, they had been fighting and fleeing American forces through forests and swamps, continually on the run. Although the war still raged back in Florida, it was over for these people. Osceola was in particularly bad shape, probably suffering from malaria, among other things. “[H]e is grieving with a broken spirit,” Catlin wrote, “and ready to die….”1

Catlin was given the run of the place, including officers’ quarters for his stay. The Seminoles, too, moved freely about the grounds (despite being lightly armed). Catlin reports that “on every evening, after painting all day at their portraits, I have had Os-ce-o-la, Mick-e-no-pa, Cloud, Co-a-had-jo, King Phillip, and others in my room, until a late hour at night, where they have taken great pains to give me an account of the war, and the mode in which they were captured, of which they complain bitterly.”2

Catlin gives a wildly unorthodox account of the war’s origin and progress, bearing little relation to other American versions. One might expect it to be a complex tale with lots of characters. But Catlin’s is concise and focuses exclusively on Osceola and the long-dead Charley Emathla. Did Catlin get it from Osceola in one of the late night sessions? Perhaps we hearing from Osceola, after all.

It is worth quoting Catlin at length:

“With the Seminolees in Florida, the process of moving them was a very disastrous one on both sides. The draft of a treaty for the chiefs to sign, by which they were to agree to exchange their lands for a country west of the Mississippi, was laid before the chiefs in council, who all refused to sign it, assigning as their reason that their parents and their children were buried around them, and that the country was their own, given to them by the Great Spirit, and that they would therefore never remove from it.

“The treaty was several times urged upon them without success; but it being announced to the eleven subordinate chiefs one day, that Charley Omatla [sic], the head chief, had agreed to sign the treaty the next day — which they could not believe — they all assembled, and went to the Government agent's office, where it was to be done, with their rifles in their hands, to see if their chief was going to do so treacherous an act. With these chiefs came Osceola, whose name you all have probably heard; he was not a chief, but a desperate warrior, and of great influence in the tribe.

“The treaty was spread upon the table, and Charley Omatla, according to his promise, supposing the other chiefs would follow him, stepped forward, and leaning over the table, made his signature to the treaty, and as he was rising up from the table, the bullet from Osceola's rifle, and then six others from the chiefs, were through his body before it was to the ground, where he fell a corpse.”3

Catlin’s tale not only elevates Charley Emathla to primary chief, it cuts him down right at the treaty table. But there is more.

“The treaty was ratified; and though it was subsequently proved on the floor of the Senate that the chief Charley Omatla had been bribed with 7000 dollars, still the tribe was removed by force under the treaty….”

There is no telling where Catlin got that. Perhaps Osceola claimed Charley was bribed, but it is doubtful the war chief kept up with the doings on the floor of the U.S. Senate. To my knowledge, this claim that Charley was bribed is unique, appearing in no other source (not to mention that $7,000 would have been an eye-watering sum at the time).

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Catlin’s description of the Florida War, with Charley executed, continues with a singular focus on Osceola.

“Osceola fled into the wilderness, the chiefs following him as their leader—for, by the custom of all American Indian tribes, he who kills the chief in his own tribe is, de facto, chief, as long as they allow him to live: if his act is approved, no one can object to his lead; and if it is not approved, he is at once destroyed….

“The gallant Osceola, at the head of his Spartan band of warriors, retiring before some 10,000 disciplined troops, kept them at bay for six years, bravely disputing every foot of ground. He was at last captured, however (or rather kidnapped)….”4

Catlin’s account is an outlier, a wild card. No piece of it aligns with the verifiable facts or with other American sources. Charley was not the principal chief. He did not mark either treaty first. He was not alone in marking them. (In fact, Osceola put his own mark to at least two Removal documents.) No one was assaulted, much less slain at a treaty table. Osceola did not become the “de facto” primary chief. Osceola was in the field of battle less than two years, not six. The single alignment of Catlin’s tale with the facts was that it was Osceola who shot Charley.

So Charley Emathla is the treacherous villain and Osceola the tragic hero. Maybe Catlin was pumping up Osceola’s status to sell more books or to juice the value of the portraits and sketches he had made of the man. Osceola was already a fixation of the American press. Not for his hand in starting the war, but because of the public outrage that had boiled over at the manner of his capture: American troops took him and 80 of his warriors under a white flag of truce. Newspapers had a field day raining shame on the U.S. Army; its officer corps convulsed with embarrassment. Maybe Catlin was trying to leverage that martyr image.

But the focus on Charley Emathla is odd. The war had a three-year build-up involving a colorful cast of players on both sides. The war itself had been raging for over two years when Catlin visited the Seminoles. Hundreds had died and were dying. Yet Catlin’s whole story boiled down to why, long ago, Charley Emathla had so richly deserved assassination.

This smells less like art promotion than self-justification.

As Osceola neared death (he would die within a week of Catlin’s departure), he may have been haunted by Charley Emathla’s ghost. Osceola had executed a revered head man, perhaps even a fellow Red Stick Muskogee, a man who had helped spring him from jail. A man who, given all the misery and death Osceola and the other captives were leaving behind in Florida, might have been right all along.

In Catlin’s spacious quarters, as a dying prisoner in January 1838, the war chief Osceola still had a story to tell. Maybe one that he hoped would justify murder.

References:

George Catlin, Letters and Notes on the Manners, Customs, and Condition of the North American Indians: Written during eight years' travel amongst the wildest tribes of Indians in North America, in 1832, 33, 34, 35, 36, 37, 38 and 39, Vol. II, London 1841.

George Catlin, Life Among the Indians, London 187-?.

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The fall of 1835 was a bad time among the Seminoles. Pressure mounted as the American date for Removal — January 1836 — closed in. A council was convened at a town in the Big Swamp, west of today’s Ocala. There, in early November, it was agreed1 that anyone collaborating with the American Removal effort would suffer death.

Like a bolt of lightning, this decree produced panic. Hundreds of Seminoles fled their towns. These were the people aligned with Removal-compliant head men Fokke Lusti Hadjo (Black Dirt), Holata Emathla and three others. After legging it over 100 miles, terrified they’d be ridden down by anti-Removal vigilantes, they fetched up at the gates of Fort Brooke on Tampa Bay. The 500 refugees asked the U.S. Army for protection from their own people.

The Big Swamp decree had served its purpose. It extruded from the nation the Removal-minded and silenced the fence-sitters. It eradicated the concept of “friendly chiefs” among the Seminoles.

Except one.

He won’t back down

Charley Emathla was literally unmoved by the threat. He remained with his people at Emathla’s Town, about 15 miles northwest of the Indian Agency (Ocala) and continued preparing for Removal in the procedure been laid out by U.S. Removal Agent Wiley Thompson.

The first step would be the cattle. Thompson’s plan — devised over months with Army officers working logistics in New York, Washington, and New Orleans — began with the Seminoles driving their cattle to Fort King to be left in his custody. A professional would appraise the value of the stock and they would be sold at public auction to white traders and incoming settlers.

In the next step, having divested themselves of everything they could not carry by hand, four or five thousand Seminoles would gather at Tampa Bay to board a U.S.-contracted fleet of steamers and schooners and sail across the Gulf to New Orleans. From there it would be flat-bottomed paddle-wheelers up the Mississippi and White Rivers to remote northern Arkansas. Disembarking 1,000 miles away in the middle of winter, the expelled Seminoles were to receive treaty-promised blankets and shawls for the cold, wet weeks-long march west under armed guard to the bottomlands of the Canadian River in what is today central Oklahoma. This would be the final destination, a demarcated reservation to be shared with the removed Muskogees. Here in the west, the Seminoles would get the value of their surrendered Florida cattle so they could buy livestock and seed to start again when their new ground thawed.

That was the grand plan anyway, and it was to begin with Charley Emathla’s cattle.

Charley hadn’t committed lightly to Removal. He understood it would be an ordeal. Having traveled to the Arkansas Territory once, he could see that some of his people wouldn’t survive it. They would be left behind in riverside or roadside graves as convenience allowed. Others would struggle and die in the cold country awaiting the first harvest from that foreign soil.

For at least three years, Charley Emathla had argued against Removal. As a chief diplomat in the two Removal treaties of 1832 and ‘33, he knew them to be the manifestation of American threats, lies, trickery and bribery. But Charley also knew that the United States, fair or foul, was bent on controlling every inch of the Southeast for its slave-labor economy and that his people were in the way.

In the end, Charley Emathla’s interest in justice was overcome by his will to survive. He came to realize that remaining in Florida would require war against the Americans. Removal, he concluded, was the less deadly option.

The Mikasukis and Alachuas of Big Swamp could threaten if they wished, but Charley Emathla — that amiable, broad-chested rancher — would not back down.

In late November, two weeks since the panicked flight of his allies to Tampa Bay, Charley was calmly continuing his Removal preparations. Surely, he was not surprised when he finally got a visit from Big Swamp.

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War whoops and Judas money

Details of the visit are hazy. We have only a handful of contemporary reports, and these are second- or third-hand.

The most dramatic telling comes from Thomas McKenney and James Hall. They tell of a posse of 400 warriors (a wild exaggeration) surrounding Charley’s house. Two men were prominent in this party: one was Osceola and the other was Abraham, the man who had escaped slavery to become the counselor and interpreter for the nation’s primary head man. They called Charley out and demanded he abandon his Removal plans. Charley emerged and told them to go pound sand, that Removal was the only hope for his people.

At this, Osceola leveled his rifle on Charley. But Abraham grabbed his arm, defusing him. Abraham was in no hurry to shed blood. He called on the posse to retreat awhile and think things over. Executing a top Seminole leader would be a Rubicon move; there must be some way to convince Charley. They withdrew.

In the meantime, Charley Emathla went to the Agency at Fort King, perhaps to arrange the disposition of his cattle. He told his friends there they might not see him again because men had been assigned to kill him. He then turned to face his fate.

“He left the agency accompanied by his two daughters, and preceded by a negro on horseback, and had travelled homewards a few miles, when Asseola, with twelve other Indians, rose from an ambush, gave the war whoop, and fired upon him.”

— McKenny and Hall at p. 381

But Charley wasn’t finished in this rendition. He stood in his stirrups, sang out his own war whoop and charged his assassins. Once in amongst them, he “fell like a hero, perforated by eleven bullets. Thus died the chief of the Witamky band, a gallant, high-minded leader, and a man of sterling integrity….”

Another report, from John T. Sprague, differs. In this one, there is no preliminary meeting or discussion. Osceola and his party lay in ambush for Charley who was returning to his village after selling his cattle at Fort King.

Charley fell in the first fusillade, “prostrate upon his face, and covering his face with his hands, received the death blows of his enemies without uttering a word.”

— Sprague at p. 88

But buried in the footnote is the iconic detail that may forever frame the confrontation between Charley Emathla and Osceola:

“[Charley Emathla] had in his handkerchief a sum of gold and silver received from the agent for his cattle. This Oseola said was made of the red man's blood, and forbid any one touching it, but with his own hands threw it in every direction.”

This was the end of Charley Emathla. The dead man was left on the sandy soil, his bullet-ridden body to be picked clean by wolves and vultures. No one dared touch him until long afterward when an Army detail allegedly buried those bones they could find.

The rising in the stirrups, the bloody gold and silver, even the cattle sale may be true or invented. But all accounts agree: Osceola led the death squad against his former compatriot.

Charley’s death draws the line

If the cold death decree from Big Swamp had put everyone on notice, Osceola’s hot lead finally exploded the notion of a non-violent Removal. In a November 30 letter to his superiors, Wiley Thompson put it this way:

“On the 26th inst. Charley Emartly, the most intelligent, active and enterprising chief in this part of the nation, friendly to removal, was murdered by those opposed to the removal: this murder was effected through the agency of a sub-chief; [Osceola] who professed to be and was considered friendly. The consequences resulting from this murder, leaves no doubt that actual force must be resorted to for the purpose of effecting the removal….”

Fort King was briefly paralyzed. The handful of Native people at the fort refused to venture beyond its gates. Word filtered in that Charley Emathla’s Town had been deserted, his people likely joining the anti-Removal party on tenuous terms. There were rumors that the Seminoles, expecting war, had retired to defensible camps in the vast swampy Cove of the Withlacoochee River.

The bushwhacking of Charley Emathla had not been an act of war. It was an internal matter. Still, it had drawn a bright battle line against the United States. For weeks an uneasy hush settled across central Florida as the two sides crouched and honed their war plans.

Wiley Thompson, the tireless Agent of America’s Removal program, saw his well-crafted plans go up in smoke. But Wiley still had a crucial part to play in this story. Osceola would make sure of it.

References:

Thomas McKenney and James Hall, History of the Indian Tribes of North America: with biographical sketches and anecdotes of the principal chiefs, Vol. II, Philadelphia 1872.

John T. Sprague, The Origin, Progress, and Conclusion of the Florida War, D. Appleton & Co. 1848.

Letter from Gen. Wiley Thompson at Seminole Agency to Brig. Gen. George Gibson, November 30, 1835 in Document No. 271, House of Representatives, 24th Cong., 1st Sess., “A supplemental report respecting the causes of the Seminole hostilities, and the measures taken to suppress them,” June 3, 1836, p. 241.

Woodburne Potter, The War in Florida: being an exposition of its causes, and an accurate history of the campaigns of Generals Clinch, Gaines and Scott, Baltimore 1836, pp. 94-5.

When the shriek broke the stillness, Charley Emathla braced for impact. He recognized the voice before he turned to see the eyes of the man at the other end of the rifle barrel.

Charley Emathla expected the encounter. The warnings had been clear. But maybe Charley was surprised that this would be the man to step forward as his executioner. After all, Charley had saved his neck once, had counted him as an ally. But maybe on reflection — and he had precious little time, for only a moment was given between the war whoop and the first bullet — Charley knew that Osceola would not miss the opportunity.

Not six months earlier, Charley Emathla had considered their argument settled. Osceola had swung to Charley’s side in spectacular fashion. All it took was a brief stint in an American jail to convince him. When Osceola emerged, he had summoned all his friends and relatives to witness his humbling before the U.S. Indian Agent, Wiley Thompson. Osceola took up the inked quill and marked his X on a paper submitting to Removal as Charley Emathla looked on.

It was a stunning reversal. Till that moment in June 1835, Osceola had been the most ardent enemy of the American demand for Removal. His quick conversion was so extraordinary that perhaps, in retrospect, it should have been questioned. Maybe Charley Emathla, an experienced and thoughtful man, had harbored doubts. If not about Osceola’s sincerity, then at least about the younger man’s steadiness.

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But this day in late November 1835, on the sandy trail between Emathla’s Town and Fort King, Charley was in no doubt of Osceola’s intent. This time Osceola meant to mark it with blood.

Contemporary American accounts of this showdown put Osceola’s actions down to low treachery, cold ambition or hot blood thirst. There may truth to each, but they miss the larger picture.

As Charley Emathla faced Osceola, both men understood their confrontation in a broader context — the rumbling of a distant earthquake.

Red Stick Refugee

Florida wasn’t Osceola’s home to begin with. He had come, as a boy, from the Muskogee heartland in Alabama. He was born about 1804 in Tallassee town, part of the vast and vibrant Muskogee (Creek) confederacy that encompassed the western half of Georgia and most of Alabama. The Muskogees were not novices at dealing with whites. They had been trading with, fighting, marrying, and generally abiding the French, English and Spanish for some 250 years. But Osceola’s youth coincided with an accelerating threat: land-hungry Americans were carving off chunks of the Muskogee country and pressing through the borders as never before.

In response, a Nativist movement — called the Red Sticks for their painted war clubs — grew among the Muskogees. The Red Sticks had accepted the warning delivered in September 1811 by the renowned and peripatetic Shawnee diplomat/war chief Tecumseh and his brother, the Prophet, Tenskwatawa. A day was coming when whites would overrun the Muskogee country, or worse, when the Muskogees would lose their way and become as whites themselves. The only hope was the formation of a pan-Indian unity — northern nations combining with the southern — and the purification of society by purging all things American.

Tecumseh and his Shawnee delegation delivered their orations at Tuckabatchee during the huge annual meeting of the Upper Towns of the Muskogee confederacy. Thousands attended. Osceola may have been too young, but his uncles and cousins would have been there, their towns being just a few miles distant. The message was amplified throughout the country.

Tecumseh’s mission south to the Muskogees was stamped with divine authority. After he returned home to Indiana, massive earthquakes shook the region. The New Madrid quakes from December 1811 to February 1812 included the greatest ever recorded east of the Rockies. Centered in the Mississippi River valley, they were so violent they reversed the flow of the great river briefly. Tremors were felt from Canada to New Orleans to Charleston and were said to have rung a Boston church bell.

The Muskogee country shuddered. Hadn’t Tecumseh, with his access to supernatural powers, told them he would send a sign by stamping his foot three times? Roiled by Tecumseh or not, the earth was reporting a deep cosmological imbalance which the Red Sticks were called to answer.

But the Red Stick target wasn’t whites per se; it was fellow Muskogees, the “friendly chiefs” who had long accommodated white culture and commerce. In 1813, following the murders of a number of white settlers by some Muskogees in the borderlands, American authorities demanded justice. Friendly Muskogee chiefs supplied it, hunting down the guilty, whipping some and executing others. Red Stick anger boiled over at this. With religious fervor, they demanded justice of their own. Their trickling campaign of assassinating friendly chiefs roared into a waterfall.

The “peace party” fled as the Red Sticks overtook town after town demanding fealty and threatening those who opposed them. The spreading rebellion drew a furious response from powerful chiefs. White settlers within or on the perimeter of the Muskogee country feared for their lives.

What began as a Muskogee civil war quickly became a war of American conquest. Coming in on the side of the friendly chiefs, U.S. Major General Andrew Jackson shattered the Red Sticks at the 1814 Battle of Horseshoe Bend in Alabama. With an estimated 800-900 warriors slain, not counting the women and children encamped at the Bend, it was perhaps the bloodiest day for Native American fighters in the 200-year chronicle of America’s ‘Indian wars.’ (This Two Egg TV video recounts the battle.)1

In the chaotic aftermath, many Red Sticks fled the Muskogee country, including the family of Osceola who was then just a 10-year-old boy. But even the “friendly” Muskogees suffered. Jackson quickly forced his allies into the Treaty of Fort Jackson by which they surrendered 22 million acres of Muskogee land: roughly the southern fifth of Georgia and half of Alabama.

The Red Stick War, also called the Creek War, precipitated the end of the Muskogee confederacy in the ancient Southeastern homeland and its Removal west of the Mississippi.

But the war also shaped the emerging Seminole nation. So many refugees fled south to Spanish Florida that Muskogee became the dominant language, eclipsing the Hitchiti spoken by the Alachuas and the related tongue of the Mikasukis. The so-called First Seminole War soon followed (1817-18) as Gen. Jackson and his “friendly” Creek allies invaded north Florida in pursuit of former Red Sticks and those who harbored them. The result was to push many of these native and black communities into (or back into) the central part of the Florida peninsula where they continued their amalgamation into the Seminole nation.

The Red Stick War: Lessons Learned

Southeastern people all drew lessons from this catastrophe.

Charley Emathla would have been in his late 20s or early 30s during the Red Stick War, prime fighting age. If indeed he was an emigrant from the Muskogee country (see previous post),2 he would certainly have seen action in that war. In any case he would have listened to bitter tales of the Red Stick War beside hundreds of fires over the years. When he came to be the leader of a Seminole town in his 50s, Charley Emathla concluded it would be suicidal to go to war against the Americans. They had smashed the great Muskogee confederacy; what chance did the smaller, disorganized Seminole nation have? Charley felt the only option was to sell his cattle and swap his Florida situation for one in distant Arkansas.

Osceola, whose young life was entirely shaped by the Red Stick War, drew a far different conclusion. It had been the schism among the Muskogees that had crippled that nation, leaving it weak and exposed to Andrew Jackson’s coup de grâce. Had the Red Sticks redeemed their compromised nation by uniting it under their leadership, they would have whipped Jackson’s army or would have been so clearly invincible that the Americans would never have challenged them in the first place. It was the “friendly” Muskogee chiefs — traitors who had sided with the Americans — that had poisoned the national body. As a grown man, Osceola would spare his nation the same fate. Only by exterminating the traitors could his people regain their strength.

So as Charley Emathla and Osceola stood on opposite ends of the rifle barrel in November 1835, both men could feel Tecumseh’s earthquake shifting the Florida ground under their feet.

___________

References:

Joel W. Martin, Sacred Revolt: The Muscogees’ Struggle for a New World, Beacon Press 1991.

George Stiggins, Creek Indian History: A Historical Narrative of the Genealogy, Traditions and Downfall of the Ispocoga or Creek Indian Tribe of Indians by One of the Tribe, George Stiggins (1788-1845), Birmingham Public Library Press 1989.

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It is generally accepted that Charley Emathla was hardly a Seminole at all. Instead, he is reckoned as something of a carpetbagger — a Creek man only recently arrived from Georgia when he stumbled into the Seminole politics of Removal.

It was no less than J. Leitch Wright, Jr. (1929-1986), an eminent historian at Florida State University, who hung this erroneous tag on Charley. Wright’s groundbreaking book, “Creeks and Seminoles: The Destruction and Regeneration of the Muscogulge People” (1986), charts the complex relationships between Native Americans, European colonizers and African Americans in the Southeast over the course of centuries. Wright deftly wove together the international great power conflict that crashed through the region with the gritty detail of preachers, pirates, gentlemen, traders, traitors, filibusterers, maroons, slavers, kings, princesses, prophets and shamans. The tapestry Wright provided us is rich. It is foundational reading for anyone interested in Southeastern history generally or Native American history in particular.

But where Charley Emathla was concerned, it appears Wright was wrong.

To be fair, Wright prefaced his brief sketch of Charley Emathla by admitting, “[i]t is probably impossible to explain accurately his background and motivations.” But that didn’t stop him from trying.

Wright’s contention was that Charley Emathla had been a farmer in a Creek town near today’s Columbus in western Georgia. There Charley stayed until the late 1820s. For background, the 1810s and 1820s were a miserable time to be a Creek. Bloody wars convulsed the Muskogee country — a huge area encompassing the southwestern third of Georgia and the eastern half of Alabama. Andrew Jackson ran roughshod, forcing the broad and multi-ethnic Creek nation to surrender one great swath of their homeland after another. Professor Wright says that after Charley Emathla signed a treaty with the Americans giving up his Georgia land, he traipsed south into Florida with some followers and set up near Fort King at a place called Wetumpka. Wright dismisses Charley Emathla as an immigrant small-scale cattleman/farmer and “merely . . . a warrior of second rank.”

Not so fast.

First, we should know there were plenty of “Charleys” among Creeks and Seminoles at that time. Charley is likely not a Native name but an Anglo tag whites attached to Native men for ease of reference. Other common ones were Billy, Jim, Sam, Tom and John. Native men didn’t call themselves or each other by these names — they had their own — but these were useful when dealing with whites. (To be sure, Seminole and Creek people often adopted Anglo names in later years as the English language and American customs became more common among them.)

Second, we should know there were many more men called “Emathla,” which is a Native word. It is not so much a name as it is a title denoting civil authority. It was variously spelled Emarthlar, Emartla, Amathla, O’Mathla, Emotely, Imotely, Imala, etc. The variations owed less to the dialectical differences among the widespread Muskogee-speaking populations than to American recordkeepers trying to phonetically sound out what they were hearing from Creeks and Seminoles. Muskogee was not then a written language.1

(Other writers claim that “Charley” was an English approximation of the Muskogee word “Chalo” meaning trout. It was not uncommon for Seminole and Creek men to be named for iconic Southeastern animals like bear (nokose), panther (katcha), deer (etcho), or alligator (halpatter or hulbutta). But trout? Unlikely. Sounds more like an attempt to reverse engineer the name.)

So a person could be an emathla like one could be a doctor or engineer, but to distinguish him from other emathlas, whites might give him another name, too, say Charley or Billy. The point is that, statistically, the random conjoining of ‘Charley’ and ‘Emathla’ was bound to arise with some frequency. Nonetheless, Professor Wright found a Charley Emathla in the record and did not pause before confusing him with the man at the heart of this story.

Professor Wright says that Charley Emathla, as a Creek, had signed the infamous Treaty of Indian Agency in Georgia in 1827. That treaty confirmed the cession of the very last acre of Creek land remaining in Georgia. It was the death knell of centuries of Creek tribal life there. Just 50 years earlier, almost all of Georgia had been under Creek control; in the years after the 1827 treaty, none would. This treaty indeed shows a Charles Emartla marking his X as a head man of Oswichu [sic] Town, Georgia.

Wright tells us correctly that in the wake of this 1827 treaty, choices for Georgia Creeks were limited. They could emigrate west across the Chattahoochee River and join their Muskogee kinsmen in Alabama (Creeks still controlled huge portions of that state), they could relocate to far northern Georgia and join the Cherokees, or move southeast to join the Seminoles in Florida. Charley Emathla, says Wright, chose this last option.

But did he? Aside from the similarity of names, Wright gives us no reason to believe that the Charley Emathla who surrendered the last of the Georgia lands is the same person who appears in the Seminole story. And further, it seems this Charley never migrated to Florida in any case.

Five years after the Treaty of Indian Agency, a Charley Emarthlar was still a head man of Oswichee Town on the Chattahoochee River. He was the head of a household that included three males, three females and two enslaved people, according to an exhaustive 1832 census of the Creek towns. (See below). It’s a safe bet this Charley and the one who signed the 1827 treaty were one and the same.

Now if Professor Wright’s Charley Emathla of 1827 was still in western Georgia or eastern Alabama answering the census as a Creek in 1832, how could he have been 350 miles away in central Florida signing a treaty as a first-rank Seminole chief at the same time? There is no doubt the Charley Emathla of our story made his mark on the Treaty of Payne’s Landing in Florida in May 1832. If Wright asks us to believe this is the same Charles Emarthlar of Oswichee, he asks too much.

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Interestingly, I found yet another Seminole/Creek Charley Emathla in the record. He was one of several “second chiefs” of Davy’s Town in west Florida on the Appalachicola River in 1833. This enterprising 25-year-old father of two and husband of two but slaveholder of none wasn’t actually present for the census because he had gone north into Alabama to try and stake a claim to land being parceled out to Creek people displaced by all the land cessions in Georgia. This, too, is not our guy. In May of ’33 our Charley Emathla was just returning to Florida from a disastrous journey to future Oklahoma where he had scouted land for the Seminole nation.

And closer to home, here’s another. A man called Charley Amathla had marked the Treaty of Moultrie Creek in 1823, a critical moment for the Seminoles. But even this wasn’t our Charley, who, 11 years later at Wiley’s October 1834 conference and among men would know, said he had not attended the parley at Moultrie Creek, just south of St. Augustine.

This profusion of Charley Emathlas shows how viscerally connected the people of the Southeast were. The Florida War can’t really be understood except in the context of a half-century of Creek struggles. Leitch Wright succeeds in arguing that the distinction between Creeks and Seminoles on a personal or local level would have been all but meaningless. Many shared language, custom, and kinship ties. Think of a modern family reunion where some are fans of Alabama football and others go UF Gator. Where the distinction mattered was self-governance. Seminoles (with constituent Mikasuki and Uchee communities) bristled at the U.S. demand that upon Removal to Oklahoma they be folded into and ruled by a Creek nation composed of much larger former Georgia and Alabama Muskogee communities.

It could be that Charley had migrated to Florida from Georgia at some point. Many Creek people had, stretching back to the time of Ahaya, the founder of the Alachua dynasty (ca. 1750, see post here), on through the Florida War in the mid-1830s. Even if Charley didn’t hail from Creek country, it is likely his parents or grandparents did, as was the case with most of the people identified as Seminole in 1835. Their actions in Florida were informed not just by their Creek past, but the Creek present and future in Oklahoma which many were destined to share.

We will probably never know much more about him than what can be gleaned from American recollections of his speech and actions from May 1832 to November 1835. He was a serious man, highly regarded in the Seminole nation. Nothing speaks more clearly to this than that he was named to the select delegation of head men sent to scout the Arkansas territory. This delegation, in a very real sense, held the future of the Seminole nation in its hands. Would the nation have entrusted this charge to a second-rate newcomer?

As we’ll see in the next post, Seminole and Florida history may have been very different without Charley Emathla. This Charley Emathla.

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For Wiley Thompson, it was problem solved. Osceola, the most vocal obstacle to Removal in the Seminole nation, had been tamed. A few days in lock-up was all it took to get Osceola to agree to mark his “X” on what was essentially his own deportation order.

It is harder to imagine what Charley Emathla felt as he watched Osceola humble himself at Fort King in June 1835. Charley, too, had recently agreed to submit to the Americans’ Removal program. But Charley got there through years of reflection, not sudden compulsion. Was Charley revulsed at Osceola’s weakness? Maybe he was relieved to have Osceola on his side, by whatever means. Osceola’s smarts and ambition were not in doubt. It was certainly better to keep such a man as a friend than an enemy. But did he trust that Osceola, mercurial and a generation younger than Charley, would stick to this pledge of pacifism?

Osceola had made a great show of sincerity, trooping in dozens of his townspeople to stand witness to his conversion alongside Charley and several other pro-Removal head men. It was almost too much.

Charley Emathla might have wondered, standing there in the punishing sun as Osceola was delivered into his fold, if he had just been handed a rattlesnake.

By all accounts Charley Emathla was a pivotal figure in the run-up to the Florida War. He was one of the most revered leaders of the coalescing Seminole nation. He strides through the historical record for three years, 1832-1835, a major player at every major point. And he was there in the flashing moment when the Florida War became inevitable. It’s fair to say Charley Emathla was the reason the war became inevitable.

So why don’t we know much about him? Today you can’t swing a cat in Florida without hitting a street, a park or a business named for the valiant Osceola. On Saturdays in the fall you’ll find tens of thousands of people sporting the name, image or likeness of Osceola on t-shirts and hats, some in warpaint, tomahawk-chopping their college football team to victory. But good luck finding Charley Emathla’s name on anything.1

It may be because Charley, in the end, was a leaver. He chose exit. Although we Americans are a nation of leavers, we rarely applaud the exiles. In our stories the heroes are the remainers and defenders, the martyrs and dead-enders. It’s harder to find glory in retreat.

It doesn’t help that we know almost nothing of Charley Emathla’s background, where he came from or who his people were. And the little that is printed on this score is wrong. (See bonus episode, coming soon.)

But it is worthwhile considering this remarkable man. It helps us understand the people who were becoming the Seminoles in 1835. And it exposes the sad trajectory of a war of ethnic removal, the kind still so common today.

Note: this post steps back in time before Osceola’s imprisonment in Chapter 6.

Maitland Meets Charley Emathla

First, let’s turn to Lt. William Maitland, U.S. Army. Perhaps William Maitland knew Charley Emathla on a handshake basis, but he certainly would have had a nodding familiarity with him. Before the war, American soldiers, Seminoles and black people mingled freely around Fort King. The federal Indian Agency operated there, handling the affairs of the reservation, and the fort’s sutler was a draw for trading goods from skins and sugar to ammunition and gunpowder.

How did Maitland view Charley? A good indication is found in the diary and letters of Pvt. John Bemrose — the English runaway turned American soldier. (See Chapter 2.) What Bemrose recorded, Maitland and other soldiers experienced.

“Charlie Omathla . . . was a fine-looking and friendly Indian who was supposed to be very rich and enlightened. His dress and manner gave the impression of a substantial grazier [rancher], which I suppose he was, as he owned a large herd of cattle. He was frequently seen in camp [Fort King] and was the chief of a village nine miles from the fort called Omathla’s Town. He seemed a free and easy, very sociable man, who was received by General Clinch in his quarters as an old acquaintance. [In council] Charlie[’s]… speech was more genial than any of the other speakers. Except for the language he spoke, I could imagine that he was one of the settlers, so free and easy and so like a farming man.”

Charley struck another observer similarly. But we get a little more detail.

“[Charley Emathla] spoke a little English and this faculty with his amiable, sociable countenance and manners, made him an object of interest to all the garrison. He was about 50 years of age, and about 5 feet 11 inches high. His frame was large and muscular. In council he discovered more foresight and common sense than any other of the Chiefs.”

Common sense to the Americans meant Removal. When these observations were made in the spring and summer of 1835, Charley Emathla had undergone a change. For years he had opposed the American demand for Removal. But lately he had come to believe that emigration was the only way forward. The change was not made with enthusiasm but with bleak calculation — it was the less bad of two dismal options.

Charley’s reluctant conversion endeared him to the Americans. Like the rest of the officers, Maitland’s whole purpose at this rugged post on the edge of America’s frontier was to see the Seminoles out of the territory. So when a man of Charley Emathla’s stature turned and spoke in favor of Removal, the boys in blue paid close attention. Charley, now a “friendly chief,” was a welcome sight at Fort King.

But to Seminoles most committed to hold onto their land, like Osceola before his imprisonment, it was Charley’s stature that posed the greatest threat. When respected leaders began wavering, it threatened to tear the fabric of the fragile nation. If that happened, the remainers could not hope to beat the American Removal program.

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Charley Emathla Had a Difficult Journey

Back on May 9, 1832, well before any Seminole agreed to Removal, Charley Emathla first walked into history. Along with many other head men that day he marked his “X” on the Treaty of Payne’s Landing. And he was one of seven “confidential chiefs” appointed to carry out the crucial triggering stipulation of that treaty. The delegation would travel to the part of the Arkansas territory that is today’s Oklahoma to examine the land that the U.S. offered to swap for the Seminoles’ Florida land. If the Seminoles were satisfied with it, then the terms of the Removal treaty would become binding. If not, the treaty would be null.

Charley and the six other head men, accompanied by “their faithful interpreter Abraham,” a black Seminole of signal importance, made the arduous scouting journey northwest to the Arkansas territory in the fall of 1832. There, American agents touted its qualities: a bit cold in winter but well watered, fine to farm and decent to hunt. The Seminoles didn’t disagree, but found the occupants violent and prone to horse theft, particularly the Pawnees and Cherokees.

Then the Americans turned the screws. They demanded the delegation mark a paper declaring that they, “on behalf of their nation,” approved the land and agreed to commence the Seminole Removal from Florida. Charley and the others, of course, refused. In the first place, they didn’t agree. But moreover, the idea that just seven men could speak for the entire Seminole nation was ludicrous. Each Seminole town spoke for itself. This Arkansas delegation was just a fact-finding team. They were to examine the country and report back to the people in Florida who would then, with the facts at hand and in grand council, consider whether to enact the Removal treaty of Payne’s Landing.

But with the seven head men isolated in Arkansas, the Americans wouldn’t relent. They reportedly plied the men with liquor, and when that didn’t work, they abused and threatened them. They told the Seminoles they wouldn’t return them to Florida unless they marked the paper. It got ugly. The men remained for months in wintertime Arkansas. Finally, Charley and the others relented and marked what the Americans hyped as the “Treaty of Fort Gibson” in March 1833. After the Americans got what they wanted, they returned the men home.

A Frank Exchange of Views

Then an interesting thing happened — nothing. It was another year and a half before the Americans pressed Removal. In that time, the Seminoles, having heard all about distant Arkansas, determined not to leave Florida. They gave no credence to the bogus Fort Gibson document and so, in their minds, the 1832 Treaty of Payne’s Landing was a dead letter.

The Americans saw it differently. In October 1834, after the year-and-a-half lull, a new U.S. Indian Agent named Wiley Thompson called his first conference with the Seminoles at Fort King. He had just a few simple questions for them: Did they prefer to be deported by land or by sea? Once in Arkansas (Oklahoma), would they “reunite” with their kinsmen the Creeks on the new reservation? Would they take cash for their Florida livestock or have the animals replaced in-kind out west?

The Seminoles found this puzzling. As Charley Emathla politely told Wiley Thompson:

“If we intended to go, then it would be proper the points be proposed to us should be decided upon. But why quarrel about dividing the hind quarter when we are not going to hunt? Why strain the water when you are not thirsty?”

One by one the top head men joined Charley Emathla. In calm tones, they explained to Wiley Thompson they weren’t interested in leaving their homes. They regarded the Payne’s Landing Treaty as moot and instead focused again and again on the Moultrie Creek Treaty which established the central Florida reservation.

Charley Emathla is the standout in the fascinating transcriptions of this three-day conference. (Versions can be found in Cohen, here, pp. 56-63, and Potter, here, pp. 50-66. For powerful clarity, read the description in the excellent Coacoochee’s Bones by Susan A. Miller, a member of the Seminole Nation of Oklahoma.) We can see the heavy responsibility Charley felt for his people. He recounted the difficult 1,000-mile journey to Arkansas by blue-water ship, flat-bottomed riverboat, horse and foot.

“I endured it because my nation might be benefitted by the result of the expedition; but how will not the women and children suffer in such a passage? When the men, the grown men and warriors, sunk, and their legs were as broken reeds. There were but few of us in the [Arkansas] deputation. We were ill used by the Agent [John Phagan]. We were abandoned when sick on the road…. If the few on that expedition were exposed to such hardships and ill-usage on their journey, how much more suffering must there be, when the whole nation is moving in a body? If the heart is not big enough for tens, how can it contain hundreds?”

(Charley’s caution was sadly borne out as hundreds were to die on the Seminole Trail of Tears.)

Charley’s Emathla’s diplomatic instincts are evident. He does not bluster or pose. In this first meeting with Wiley Thompson, he appeals to the Agent’s humanity.

“You have just come among us. You meet us in council now for the first time. Remain here with us, and be as a father to us, and let us be as your children. The relation of parent and child to each other, is peace — it is soft and sweet as arrow-root and honey.”

Wiley Thompson was not moved. True to form, he responded with insults and threats. He called the head men dishonest and singled out Micco-Nuppa as a straight-up liar. He told them they spoke like foolish children and were not deserving of their offices. Wiley noted that, as their greatest friend, he was bound to tell them this. If they would not remove voluntarily, the Americans would compel them to do so.

The Squeeze Begins

Over the course of the next year, the United States cranked up the pressure on the Seminoles. (See earlier posts here and here.) Wiley Thompson cut off trade in arms and powder and threatened to withhold the annuity. He hectored the Seminoles at two more conferences and disrated the tribal hierarchy. The U.S. President Andrew Jackson sent a long bellicose message to the Tribe. The U.S. Army built up its forces and capacity around the reservation at Fort King (Ocala) and Fort Brooke (Tampa).

Perhaps Charley Emathla and his people felt this pressure more keenly than others. Emathla’s town was at the northernmost border of the reservation. There, they would have experienced more conflict with white settlers and slavery’s bounty hunters than those deeper in Seminole country. Moreover, Charley’s town was perched midway between Fort King and its commanding officer’s sugar plantation, also called Fort Drane (see map at top). The neighbors all pressed for Removal.

At some point, it tipped for Charley. Although he foresaw misery and death on the trail of exile, he came to believe that staying and fighting for Florida would be even worse. By the late spring of 1835, Charley publicly endorsed emigration. He was not alone. Several other leaders — Holata Micco, Fokke Lusti Hadjo (Black Dirt), and Holata Emathla — also concluded it was the only hope for their people.

The summer and fall of 1835 saw the Seminoles increasingly torn over the Removal question. Most of the top leaders remained solid in their commitment to keep Florida. But an increasing minority, representing perhaps one-third of the nation, either favored emigration outright or kept pressing the Americans for better Removal terms before they would commit.2

This was the schism that the most ardent remainers feared. As they stockpiled lead and powder to stay and fight the Americans, men like Charley Emathla spoke of leaving. These were not leaders; they were traitors. They weakened the body and spirit of the nation, sapping the energy needed for armed resistance.

If the Seminole nation was to be saved, the traitors would have to be dealt with.

________________________

Next: Showdown at the Fort King Corral

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References:

Randal Agostini, An Englishman in the Seminole War: A Memoir Based Upon the Letters of John Bemrose (Florida Historical Society, 2021).

Grant Foreman, Indian Removal: The Emigration of the Five Civilized Tribes of Indians, Norman, University of Oklahoma Press, 1953, p. 328, quoting correspondence in Newbern Spectator, North Carolina, February 26, 1836, copied in Army and Navy Chronicle II, p. 197.

Susan A. Miller, Coacoochee’s Bones: A Seminole Saga, University Press of Kansas 2003.

Woodburne Potter, The War in Florida: Being an Exposition of its Causes and an Accurate History of the Campaigns of Generals Clinch, Gaines and Scott, Baltimore: Lewis & Coleman 1836.

Before Black History Month concludes, it is apt that this series gets to the crux of the Florida War because, as the U.S. Army General leading the campaign noted in 1836, “[t]his you may be assured, is a negro, not an Indian war….”

General T.S. Jesup was troubled by the effectiveness of black warriors and galled at what he saw as their outsized influence over Native American leaders to keep the war flames stoked.

But we’re not there yet. This series is still exploring the path to war. That requires discussion of its African roots.

We began in 1835 with Lt. William Maitland being ordered to Florida to hasten the removal of all Native Americans from the territory. But why did the U.S. want them removed?

Florida was an absolute backwater. The Spanish could do nothing with it for 235 years. The British tried for 20 more to no greater effect.

The American era began with little better prospect. In 1821, the U.S. acquired Florida from Spain and administered it as a territory. The few American population clusters were limited to the northern reaches where there was reasonably rich soil. But settlers had little interest in the vast bulk of the Florida peninsula. Everything south of present-day Ocala area was an unmapped wilderness of swamp and pine barren they felt was best left to the mosquitos and alligators.

So why was America so keen to expel the Native Americans who lived there?

Answer: the white people wanted to remove the Indian people because of the black people.

Florida: A Sanctuary from Slavery

Black freedom in Florida had been a thorn in Southern slaveholders’ sides stretching back to the British colonial days. In the 1700s, the Spanish, who then held Florida, offered freedom to defectors from Georgia and Carolina plantations if they’d come south across the border to help defend the city of St. Augustine. The Seminoles, too, offered safe harbor to those escaping American slavery.

Certainly both the Spanish and Seminoles maintained slave systems. But Spanish Florida also was home to free blacks and the slaves there enjoyed basic legal protections not afforded by the British and Americans. For its part, the Seminole slave system was more like vassalage: black people maintained personal and communal freedom so long as they made regular tributes of corn or cattle, or rendered services like blacksmithing and soldiering.

This made Florida an attractive option for black people considering relocation.

White Georgians and Carolinians chafed at this into the 1800s. It peeved slaveholders when their valuable “property” escaped south. But what really rattled them was the specter of black men under arms just across the border in Spanish Florida.

In the lead-up to the War of 1812 (rematch: America vs. Britain), the fear became acute. Americans worried that wild Florida, on which Spain had only the flimsiest grasp, would become a launchpad for international shenanigans. Worse, they feared black warriors would be the tip of the spear. Rumors swirled that Britain was drafting companies of Jamaican soldiers to garrison St. Augustine. Or was it black Cuban troops sponsored by Spain? American slaveholders north of the Florida/Georgia line shuddered at the effect this might have on those they held in bondage.

In 1812, the Governor of Georgia wrote breathlessly to U.S. Secretary of State James Monroe:

“[The Spanish in St. Augustine] have armed every able-bodied negro within their power, and they have also received from the Havana a reinforcement of nearly two companies of black troops! . . . . [I]f they are suffered to remain in the province, our southern country will soon be in a state of insurrection. . . . [This] is of vital importance to every [white] man in the southern states . . . .”

Georgia planters feared widespread slave revolt. Florida, the Georgia Governor demanded, must be tamed.

So Americans hatched a clandestine plot to take Florida from Spain. In 1812, Secretary Monroe’s envoy assembled a rabble army of Georgia frontiersmen and filibusterers. Under the protection of U.S. Navy gunboats, these “Patriots” invaded the Spanish port of Fernandina in northeast Florida. There, they declared themselves a “republic” and tried to rally disaffected Spanish subjects to their side. The idea was that the Patriots would call on the U.S. to formally intervene and liberate them from corrupt Spanish domination (hello Texas, Florida did it first!). While the invading Patriots and defecting locals looted swaths of northeast Florida, U.S. troops dug into a months-long siege of the city of St. Augustine to starve out the Spanish.

This off-the-books adventure — the “Patriot War” — bogged down immediately.

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As the siege dragged on, the Spanish governor finally turned to the Alachua Seminoles — particularly Chief Bowlegs (Micco-Nuppa’s uncle) — for help. It was a big ask. The Seminoles and their Creek forebears had long been adept at playing one colonial power against the other (England, Spain, France, and the U.S.) for their own benefit. But now, for Bowlegs, the choice was stark. The Americans were at the gates. He knew that when the dust settled on this Patriot War, either Spain or America would have Florida. Which was better for the Seminoles?

The Seminoles had long experience with Spain as the distant, doddering old grandma who left them alone and occasionally sent gifts. America, by contrast, would be the violent, jealous boyfriend moving in. Bowlegs and the Spanish governor shook hands.

Soon, Seminole war parties began sacking Patriot-friendly plantations across what is now Duval, Nassau, Clay and St. Johns Counties in northeast Florida. This tipped the scales. The Seminoles pushed the Patriots to the very brink, blow by blow in guerrilla actions. Many Patriots fled to the coastal islands or back to Georgia.

Tangle at Twelve-Mile Swamp

Meanwhile, U.S. troops barely clung to their siege on St. Augustine. The massive Castillo de San Marcos — a stone fort with walls thirty feet high and as thick — was impregnable. The five-month standoff had achieved nothing. The city would not surrender. It was the American besiegers who suffered most. They were hungry, sick and dispirited.

When a relief ship finally arrived for them, a detachment of U.S. Marines and Patriots was selected to convoy a portion of the goods to an inland U.S. encampment. The convoy would have to pass through Twelve-Mile Swamp, an area known for recent grisly Seminole raids.

The nervous American detachment left late in the afternoon September 12, 1812, hoping that nightfall would hide them from the Seminoles. As it turned out, the Americans need not have worried about the Native war parties at all.

It was the black militia that caught them.

Juan Bautista (“Prince”) Witten, a black citizen of St. Augustine, had earlier led his company into the swamp to wait in ambush. Witten’s crew included 25 of the city’s free black militia plus 32 Seminole-allied blacks and six Seminole warriors. As the moon rose over Twelve-Mile Swamp, the U.S. convoy rolled into the trap. The first volley was withering. The second more so. The Marine captain fell (he died two weeks later) and another man was scalped in view of his compatriots.

Hours of close and mid-range combat took a toll on both sides. At midnight, Witten’s men burned one of the captured supply wagons and drove the other one off, carrying their own wounded back to the city. The devastated U.S. detachment huddled in the swamp until dawn when a rescue party arrived.

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This fiasco at Twelve-Mile Swamp effectively ended the siege of St. Augustine. Diplomatically, the U.S. was forced to disavow its actions. It was, after all, officially not at war with Spain and hoped to keep her neutral in America’s newly declared war against Britain, the other War of 1812 (h/t to Prof. James Cusick; see references below). U.S. forces retreated back to bases they could hold while negotiating a peace with Spain. The Patriots followed them or straggled home to Georgia.

Witten’s black militia must have asked themselves the same question as Bowlegs’s Seminoles: would they fare better with the Spanish or the Americans? Witten’s people had experienced Spain’s qualified freedom. And looking across the border to Georgia, they could see the American offer of slavery and subjugation.

The answer for both the Seminoles and the black militia resulted in defeat for the American invasion of northeast Florida.

Seeking Revenge on the Alachua Seminoles

There is poetic justice that an expedition sent to crush black military power in Florida actually called it forth, polished it, and was crushed by it.

But there is disaster in the aftermath.

In the wake of Twelve-Mile Swamp, militia Col. Daniel Newnan gathered a crew of Georgians for a punitive expedition. His target: the Alachua Seminole towns some 80 miles west of St. Augustine, a four-day march. Shortly before the troops arrived at their objective, a Seminole war party stumbled into and engaged the Georgians near today’s Newnan’s Lake, east of Gainesville. Newnan’s men were pinned down for a week. They exhausted their provisions. As the Georgians turned to eating their own horses, the Seminoles continually sniped from the edge of rifle range.

At last, Newnan ordered retreat. The starving and the sick bore the stretchers of the wounded. Throughout the ordeal of their week-long flight, they were harried by the Seminoles. Finally, Newnan limped back to safety. Of the 117 who had followed him into battle, 16 were dead or missing and 9 were wounded. Newnan left Florida, never to return.

But there was little joy in it for the Seminoles. Their leader, the superannuated Payne, had fallen in battle. Far worse, Newnan’s defeat became an American cause célèbre. It inflamed white Southerners all the way to Tennessee. In fact, the Volunteer State drafted 250 of her sons to avenge the newly-famed Newnan. Georgia volunteers and federal troops filled out the rest of a new 550-man expedition that marched against Alachua in February 1813.

Bowlegs, who succeeded his fallen brother Payne as leader, was forewarned of this second invasion. As the Americans approached, Bowlegs oversaw the Seminoles’ hasty evacuation. The Americans arrived to find the Alachua towns deserted. So they burned them — Payne’s Town, Bowlegs’s town, and a Black Seminole town. Returning home, the Americans boasted they had burned nearly 400 homes and stolen 2,000 bushels of corn, 300 horses and 400 head of cattle.

After the ashes cooled, Bowlegs crept back to assess the destruction. There was no going home. All was gone. The area’s vulnerability was proved. Bowlegs moved his refugee Alachua people and black allies 40 miles west to the Suwannee valley. So ended the 70-year tenure of the Seminoles on the rich Alachua Prairie, the birthplace of their nation.

In their absence, the land was soon occupied by white settlers. Many brought enslaved black people to work their farms and plantations.

Florida: A Sanctuary for Enslavers?

Just 10 years after the Americans burned and looted the Alachua towns, things had changed dramatically. By treaty with Spain, the U.S. had acquired Florida, and by treaty with the Seminoles, the U.S. had established the wide Indian reservation over central Florida. The Alachua Prairie had become the center of territorial Alachua County.

But the friction over slavery had not diminished. For Americans, the Seminole reservation was manageable so long as only Seminoles lived there. But true to tradition, it remained a magnet for those escaping bondage. Slaveholders and bounty hunters persistently harassed the Seminoles for the return of fugitives or simply kidnapped blacks from their midst. Federal agents administering the reservation were consumed with navigating slavery disputes.

In 1834, the leading white men of Alachua County penned an urgent appeal to President Jackson:

“… Does a negro become tired of the service of his owner, he has only to flee to the Indian country, where he will find ample safety against pursuit…. [The Seminoles] have connived with, and, through the instrumentality of the negroes living among them, aided such slaves to select new and more secure places of refuge. There are, it is believed, more than 500 negroes residing with the Seminole Indians, four-fifths of whom are runaways, or descendants of runaways…. [I]t is evident that the absconding slave, who succeeds in reaching the Indian territory, is in absolute safety, and may laugh to scorn all exertions for his apprehension.”

Removal of the Indians was seen as the solution. This would spread Florida’s territorial jurisdiction over the entire peninsula, erasing the Seminole reservation as a sanctuary for escaped slaves.

That goal underpinned the 1832 Treaty of Payne’s Landing. But as of 1834 when the Alachua County slaveholders appealed to the President, it was clear the Seminoles and their black allies weren’t going anywhere.

Did the United States government take the matter seriously enough to resort to military force? After all, Florida was mostly wasteland, in itself not worth purchasing much less fighting over. So was the promotion of Southern slavery interests sufficient justification for war?

In the spring of 1835 as Lt. Maitland and hundreds of American soldiers were ordered to Florida for the Removal effort, it appeared the answer was yes. Still, the Americans hoped their show of force would awe the Seminoles into a voluntary mass deportation, averting bloodshed.

It was a miscalculation. The Americans would soon discover that the African desire for freedom was a force multiplier for the Seminole drive to keep their Florida land.

____________

References:

House Doc. No. 271, 24^th Cong., 1^st Sess., pp. 30-33.

James G. Cusick, The Other War of 1812: The Patriot War and the American Invasion of Spanish East Florida, Gainesville, University Press of Florida, 2003.

J.H. Alexander, “The Ambush of Captain John Williams, U.S.M.C.: Failure of the East Florida Invasion, 1812-1813.” Florida Historical Quarterly, Vol. 56, No. 3, Jan. 1978.

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Jail undid Osceola. After just a couple of days shackled in a dark room he was a wreck. White soldiers jailed for theft or drunkenness took their punishment in stride. But incarceration had a dire effect on Osceola.

So much so that he submitted completely. The most ardent opponent of Indian Removal suddenly offered to switch sides. In exchange for his release, he agreed to mark the paper acknowledging the Removal treaties. It was a stunning reversal. For months, Osceola had been at the forefront of resistance to the treaties, always goading his superiors to stand firm against them and threatening those Seminoles who considered emigration.

But this reversal wasn’t enough for the Superintendent for Removal of the Florida Indians, Wiley Thompson. Wiley, who had Osceola thrown in the can on one count of rudeness, wanted more.1

“I informed him that, without satisfactory security that he would behave better and prove faithful in the future, he must remain in confinement. He sent for some of the friendly chiefs and begged them to intercede for him; they did so.”

It’s a fair surmise that Wiley told Osceola he’d rot in jail until he declared, in front of his countrymen, that he had switched from the ‘remain’ to the ‘exit’ side, that he would leave Florida.

At this point, Osceola probably would have done anything to get out of jail. We see this not just from the fact of his abject conversion; there’s a clue in Wiley’s correspondence. Less than a month after these events, Wiley advised a Florida militia captain on how to handle Seminoles who had crossed outside of the reservation boundary without permission.

“[A]nd I think it will have a good effect on them,” Wiley wrote to the captain, “to lodge them in jail. The idea of a jail carries terror to the Indian’s mind.”2

Maybe Wiley had jailed Osceola intending to terrorize him, or maybe Wiley just learned of jail’s terrorizing effect by watching Osceola crater. Either way, Wiley had no compunction about holding Osceola to extort concessions from him. If terror gripped the Seminole war chief’s mind, as Wiley’s words imply, Osceola’s jailhouse conversion becomes more understandable.

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Charley Emathla bails out Osceola

Charley Emathla was among the “friendly chiefs” summoned to Fort King’s jail to vouch for Osceola. He was probably as surprised as anyone at Osceola’s compliance. Charley was the head man of an eponymous town about 15 miles northwest of the fort. He was well respected in the nation, an important figure in council.

Wiley called Charley “friendly” not because of his disposition — though Charley may well have been cheerful — but because he was on board with American policy. There were no enthusiastic Native cheerleaders for Removal. Exile was universally dreaded. But American pressure, military threats, and wretched, near-starving conditions in some Seminole towns led some to see emigration as the only hope for survival.

Charley Emathla had been one of the seven Seminole head men who had traveled more than 1,000 miles with the Americans to scout the Arkansas territory in the winter of 1832-33. Although Charley marked the so-called “Treaty of Fort Gibson” in March 1833, approving that distant country as a liveable place, on his return to Florida that spring and through the winter of 1835, Charley had opposed Removal as did all other head men in the central Florida reservation.

But by May of 1835, Charley had been worn down. He, along with two other principal chiefs — Holata Emathla and Fakki-Lusti-Hadjo (a.k.a. Black Dirt) — had agreed to America’s removal demand so long as they could remain in their homes through the fall harvest and leave in early 1836. These men sat on the minority side of a sharp divide among the Seminoles. The majority, including Micco-Nuppa and most all of the top leadership, had determined to remain at whatever cost.

It wasn’t a simple stay-or-go choice. Many saw Charley, Black Dirt and other emigration men as traitors, collaborators. They weakened the fabric of the nation. These “friendly” chiefs suffered abuse and death threats. Up until the day Wiley had thrown him in jail, Osceola was a leader of these militants. As a boy, he had seen his Muskogee nation broken by the split between “friendly” Creeks and the Red Stick faction that opposed assimilation. He had been determined never to see such division again.

But jail turned Osceola, and now he summoned Charley Emathla and other friendly chiefs to come bail him out.

The men came and sat with shackled Osceola. It must have been an extraordinary humiliation. After some time, they asked Wiley Thompson to release him.

Wiley goes big, Osceola goes bigger

Wiley told Osceola he could walk on the promise he’d return in five days to mark the treaty recognition document in public council with the friendly chiefs. It was an odd demand. Perhaps Wiley felt it would appear less extortionate to give him five days. But conditioning freedom on political compliance is blackmail however you slice it.

Now, Osceola could have walked out of Fort King and never looked back. That would have been perfectly reasonable. Morally, he owed Wiley nothing. Or maybe, recognizing a debt to Charley Emathla and others for their efforts, Osceola could have returned alone and grudgingly marked the document.

But in this bizarre tango, Osceola went all in. After five days, Osceola returned to Fort King leading “79 of his people, men, women, and children.” Osceola told Wiley he’d have brought more but they were out hunting. Then, in front of these and the assembled head men, Osceola took up the feathered quill, dipped it into the inkpot and scratched his X on Wiley’s paper.

It was an impressive show — proud Osceola humbling himself, acknowledging his errant ways.

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Wiley might have guessed that a promise pried under duress was no promise at all. And he surely knew Osceola well enough to know the stakes of the game. According to our Pvt. Bemrose, Wiley had been warned by the fort’s commander, Lt. Col. Alexander Fanning (who later named a fort for our Lt. William Maitland), that “he expected Osceola to become his most determined enemy.”

But Wiley Thompson saw only success. He was overjoyed! This was the result he’d so long sought. To think, after all that wasted breath in those dreadful conferences, all he really had to do was throw a young hothead in jail. Osceola’s conversion fit right into Wiley’s worldview — spare the rod, spoil the child.

Boasted Wiley to his superiors, “I have now no doubt of his sincerity, and as little, that the greatest difficulty is surmounted.”

In fact, so moved was the miserly Agent that he presented Osceola with a special gift. As the crowd looked on, Wiley handed the Tallassee tustenuggee a rifle. For Wiley, the stick of imprisonment had worked well, but he wanted all to see that carrots were also on offer for those who submit.

Osceola accepted the weapon, heavy in his hands. It was a beauty. An expensive, custom number, no standard-issue musket nonsense. Osceola smiled as he balanced the well-weighted rifle. He nodded to the Agent, holding his gaze for a moment, and then turned to Charley Emathla, and nodded to him, too.

This moment, this gift, would spell out the fate of all three men.

_______________

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Sources:

Randal J. Agostini, An Englishman in the Seminole War: A Memoir Based Upon the Letters of John Bemrose, Florida Historical Society Press 2021.

Letter from Gen. Wiley Thompson at Seminole Agency to Brig. Gen. George Gibson, June 3, 1835 in Document No. 271, House of Representatives, 24th Cong., 1st Sess., “A supplemental report respecting the causes of the Seminole hostilities, and the measures taken to suppress them,” June 3, 1836, p. 198.

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Tustenuggee in the stir

Osceola sat in the dirt, his legs stretched out before him, back against the wall. He couldn’t cross his legs as he normally would, prevented by the iron cuffs around his ankles and the snake length of chain connecting them. His headcloth and long feather lay in his lap. He rubbed the stubble of his scalp. It was shaved but for a long-haired swath over his forehead and temples and two thin braids trailing over the crown and down the back of his neck. 

He couldn’t draw a full breath. Not because the wooden bucket just out of reach in the corner held two days’ worth of his own waste. Not because the stale warm air, dim as the indirect light, didn’t move except under the wings of mosquitos and the bucket’s flies. It was because the walls of the room were a vice on his rib cage. Time was getting harder, not easier. He couldn’t focus a thought.

Osceola had suffered plenty of indignities in his life. In the last two years, many had come from the Agent Wiley Thompson. Since he arrived in the Seminoles’ country, proclaiming himself their great friend, the Agent had openly called them cowards and fools. Drunks and animals. Liars and old women. He parceled out their annual treaty payments like it was from his own personal pouch rather than just a pittance from what was rightfully theirs. He failed to give gifts showing respect when due.

But what Osceola couldn’t abide was the Agent’s incessant politicking, ever seeking to peel off one man against another. It was a poison Osceola had seen his whole life. It was what broke the Creek people where he was born. It had caused the slaughter of a thousand souls and made refugees of him and a thousand other survivors. If a people can be divided, they can be removed.

So Osceola had seen no great harm, indeed, he felt he owed it to the Agent that day in his office to remind him just where he was because he had evidently forgotten. He and all the bluejacket soldiers were temporary guests in Seminole country, suffered to remain on good behavior. But the more they trampled the rules the shorter would be their stay.

For this reminder, the Agent, not man enough to do it himself, had sent a team of soldiers to tackle and shackle and lock him in this airless hole. It was a grave insult. And the payback, one day, would be proportional.

But now Osceola really couldn’t breathe and he felt panic licking at the edges, icing his veins. What was the end-game? What would get him out of this? If only he could settle his racing mind and think.

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He had it coming

Wiley sat in his office, replaying in his mind the biting disdain on Osceola’s face as he spat out what must have been a threat, or at least an insult. Osceola, peculiar among Seminole men, wore his long black ostrich plume stretching from the back of his turban rather than sprouting from the top. The Tustenuggee had been so rigid the billowy feather was still as an axe. Wiley couldn’t make out the Muskogee words, but he noticed Cudjo’s eyes widen before his gaze dropped to the ground, hoping the Agent wouldn’t ask for a translation.

Wiley didn’t. But he immediately shot to his feet and ordered Osceola from his office. The sneer never left the Tustenuggee’s face as he turned to leave. Even the long black plume mocked Wiley as it danced cockily in Osceola’s wake.

No, in retrospect Wiley was absolutely certain his course had been correct. Jailing Osceola for repeated insolence was the proper remedy. What else could he have done? The man had left him no choice. Now let him sit in irons and reflect on his actions.

Still, what was the end-game? Wiley was given to fits of temper, but he was also a man who needed a plan. And though he had been congratulated two days earlier on his bold order to imprison Osceola, the back-slapping from his compatriots had tapered into uncertainty. A gray pall had fallen over the entire fort. Where did it go from here? He couldn’t leave the Indian in irons forever. Insolence wasn’t a crime; if it were, Wiley would be running a prison camp. Very soon, the chiefs would come asking about their uncouth friend.

But Wiley couldn’t just set him free. If Osceola walked, it would be a show of Wiley’s weakness. No, America’s weakness. A reward for the insolence. It would come back to haunt. He knew, deep down, he had a wolf by the ear.

Wiley was in the right. Of that there could be no doubt. But what now?

Cudjo brings a stunning offer

“Boss, he sent me to tell you he’ll mark the paper.”

“What?” Quill in hand, Wiley Thompson looked up from the well-ordered stacks on his desk. Cudjo stood just inside the door. “Who will mark what paper?”

“You know, that paper, sir. The one says the other papers is good papers. Powell sends me to say he’ll do it.” Powell was the name the whites used for Osceola so Cudjo used it professionally. 

Wiley looked at the interpreter blankly. The left side of Cudjo’s face was slack from a stroke some years back and he held his withered left arm at an odd angle, hanging his hat on it like it was a peg. Army officers called him King Cudjo, but not Wiley. First, he felt it was derisive. But moreover it was too familiar, could give him airs. Cudjo occupied a rare space around Fort King. He was free. The money he earned interpreting between whites and Natives went into his own pocket unlike the fort’s blacksmith whose wages fell mostly into his master’s. Wiley couldn’t bear Cudjo getting above himself.

“Powell will mark the paper?”

Unwilling to say it a third time, Cudjo nodded.

Wiley worked hard to keep the shock from his face. He never dreamed Osceola would sign that paper, the one acknowledging the treaties were valid. Micco-Nuppa and Jumper and other leading head men refused to do it, largely at Osceola’s urging. Yet now Osceola will sign? When no one asked? Unbelievable.

“Course, he goes free,” Cudjo put in, not sure the slack-jawed Agent was processing this.

He’d sign the paper. Which meant he agrees to go! To remove! To self-deport! With collapsing self-control and a smile hammering to get out, Wiley looked sternly back down at his desk. “That is all, Cudjo.”

“Sir . . . What I tell him?”

“That is all!”

With the interpreter gone, Wiley Thompson stood, beamed a toothy smile and clapped his hands together in triumph. The miracle he needed. The one he deserved! That embarrassing business about him trying to depose the five chiefs would be forgotten. Wiley sat back down and straightened his collar, then his mustache.

He began noodling how this would go down. He would need witnesses. Not just white ones. He imagined gathering a few friendly Natives, the two or three head men partial to emigration. Cudjo to interpret. They’d all go to Osceola’s putrid cell and pass him the paper through the door with an inked quill. While the prisoner’s X mark was drying, the blacksmith would strike off the leg irons and he’d be free to go. A handshake and no hard feelings.

This X mark would change everything. Micco-Nuppa would see that his hardest warriors were meek as lambs and then the fat man could climb down off his ridiculous rejectionist pose like everybody knew he wanted to. He wouldn’t have Osceola prodding him into resistance anymore. In a matter of months, the whole Seminole nation would be peacefully escorted onto removal ships anchored in Tampa Bay, ready to sail off to Arkansas.

With what might pass for giddiness in Wiley, he imagined writing his glorious dispatch to the Secretary of War, massaged, of course, to be placed directly into the hands of the President, because it would be. And as he envisioned the look on that august lion Andrew Jackson’s face, reading aloud this report — because he wasn’t very good at reading — from his man in Florida, General Wiley Thompson, Wiley’s heart stopped.

Thought-bubble Andrew Jackson’s face screwed up as he crumpled the Agent’s report in a wiry claw. “Now that dull son-of-a-bitch is jailing Indians to extort their signatures?!”

The bubble popped. Wiley drew a handkerchief from his coat pocket and dabbed the cold sweat from his forehead.

He thought of the smug Seminole war chief sitting in a cell not fifty yards away. He remembered again Osceola’s sneer as he had sauntered out this very door just two days before.

Was Osceola playing him?

___________________

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Sources:

Same as before, but this chapter falls under the heading of creative nonfiction.

Note on the image: ‘Arrest of Osceola.’ This image purports to depict an event in October 1837, but I would argue it is a more apt illustration of the events of this post in May 1835. I take the liberty because I have not found the real provenance of this image so its relation to 1837 could be erroneous. Several aspects are inconsistent with the 1837 date. In the 1837 event, Osceola, as a combatant, was ‘captured,’ not arrested. The 1837 event took place on a trail well south of St. Augustine, far from any buildings; but the image has a palisade palisade in the background, consistent with Fort King. In the 1837 event, Osceola was captured without resistance in the company of some 80 armed warriors and a like number of soldiers, while this image indicates Osceola was taken violently by a couple of soldiers, as was more nearly the case in May 1835.

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The Indian Agent’s Dilemma

The whole ethnic cleansing thing wasn’t going well for the Indian Agent, Wiley Thompson.

His Washington bosses had given him an additional title — Superintendent of Removal — and expected him to have the Seminoles lined up to depart in the summer of 1835. Army logistics had already swung into action. They were arranging transports to ship thousands of Seminoles out of Tampa Bay across the Gulf to New Orleans, then up the Mississippi River to Arkansas. Government contractors were securing blankets, clothes, seed corn and farm tools to ease the exiles into the West.

The problem for Wiley Thompson, in the late spring of 1835, was that the top Seminole leaders had told him flatly, yet again, they weren’t going anywhere. Wiley had been at the Seminole Agency for a year and a half. In that time, he goaded the Seminoles, bullied them, cut off their supplies. He proclaimed demands directly from the U.S. Secretary of War and even U.S. President Andrew Jackson. He threatened military action. But still, the Seminoles weren’t going anywhere.

Which would make Wiley’s mission a failure. And Wiley wasn’t built to fail. He was a rigid, punctilious man known for getting results. But as summer neared, just three notable head men had agreed to emigrate with their people. The majority of the nation, and its top tier of leadership, remained firmly opposed.

So Wiley mailed excuses to his Washington superiors, he played for time. A summer departure was impossible for a dozen reasons, he wrote to the Secretary of War. But come winter, by God, he’d have the whole nation peacefully deported. Florida would be Indian-free by February 1836.

Wiley had no reason to believe this. In fact, there were growing rumblings of armed resistance from the younger warriors. And the Seminole head men who had agreed to emigrate also appealed to Wiley for protection because of death threats. The wheels of Indian Removal may have been spinning in Washington, but at the Seminole Agency where it counted, they were mired in the ditch. Wiley Thompson knew that barring some miracle, he would soon have to confess his humiliating failure to his bosses.

Then, one day in late May 1835, Wiley’s luck turned. A grim-faced Seminole man walked into his office demanding a meeting.

This would be no ordinary meeting. It altered the course of Wiley Thompson’s life. And this Seminole was no ordinary man.

He was Asin Yahola. Or Osceola. The soul of Seminole resistance.

Osceola - A Lifetime of War

At one time, Osceola was famous throughout the United States. He grew to be a darling of the national press in the 1830s and ‘40s. Cities and counties as far as Iowa, Michigan and Wisconsin were named for him.

But today he is little known to us. His name conjures an angry painted warrior, maybe stabbing a football field with a flaming spear, goading college students into a frenzy. We shouldn’t entomb him in that amber. His story is more interesting.

Osceola came to Florida as a war refugee, probably at about age 10 in 1814. Prior to this, he had grown up among his Creek family in Tallassee, near the Tallapoosa River in eastern Alabama. His family was part of a Nativist movement — the Red Sticks — who violently opposed those Creeks who accommodated white culture and trade. In 1813, this schism led to the Creek civil war. Alarmed at the Red Stick program, Major General Andrew Jackson came in on side of the “friendly” Creeks.

At the insanely bloody Battle of Horseshoe Bend in March 1814, an army of Jackson’s federal troops, with allied Creeks and Cherokees, decimated the last Red Stick stronghold. It is said that more Indian combatants died in that battle than any other in American history — some 800 to 1,000 on the Red Stick side alone. Those that weren’t killed in the desperate fight on the ground were shot as they tried to swim the Tallapoosa River. Surely young Osceola lost cousins, aunts and uncles there.

Horseshoe Bend broke the back of the Creek nation. In its wake, Jackson forced a treaty that took 22 million acres from the Creeks — about half of today’s Alabama and much of southern Georgia. Certainly hundreds and perhaps thousands of refugees, including Osceola’s family, were forced south and crossed the border into Spanish Florida.

Some settled among the Mikasuki people in the Tallahassee area. Some went further east to the Suwannee River towns where they joined the Alachuas and blacks, recently driven west from the Alachua plain (more on this in a later post). In both cases, the respite was short-lived. In 1818, Jackson and his Creek allies attacked these north Florida Seminole settlements in the so-called First Seminole War, pushing the survivors south and east into the Florida peninsula.

Osceola and his people finally found refuge in central Florida where he grew to adulthood. One can only imagine the impact these years of warfare and flight had on him — the humiliation, sorrow, fear, and anger.

But Osceola’s story wasn’t unique. It had become the common Seminole experience. What was so special about Osceola? He was not of noble blood or a prominent clan, so heredity didn’t advance him as it had Micco-Nuppa.

Osceola’s rise was a matter of talent and timing, plus, when the time came, a sure hand at cold-blooded killing.

Osceola Catches America’s Eye

Osceola enters the record in 1834 at Fort King when he was about 30 years old. If American observers uniformly dumped on Micco-Nuppa (see previous post), they mostly adored Osceola.

“In stature he is about at mediocrity, with an elastic and graceful movement; in his face he is good looking, with rather an effeminate smile; but of so peculiar a character, that the world may be ransacked over without finding another just like it.”1

Osceola was lighter-skinned than most Seminoles, owing perhaps to white ancestry (his father may have been an English trader named Powell), but his hair and eyes were jet black. There is broad agreement that Osceola was a good hunter and excellent ball player.

In 1834 and ’35, Osceola was a common sight around Fort King. Among the Seminoles, he had climbed in rank to Tustenuggee, a military leader, perhaps a kind of sheriff policing border disputes among his people and whites. In this capacity he often visited the fort on official business.

But Osceola also came just to hang out. Private Bemrose, the English runaway turned Army hospital steward, says Osceola struck up a particular friendship with a Lt. John Graham:

“They were daily seen with one another in the community. Both shared a strong love of field sports, and it was a very common sight to see both of them, returning to camp after a hunting expedition in the woods. Lieutenant Graham was a fine specimen of a man measuring 6 feet 5 inches tall, young, and doubtless very interesting to his Indian friend.”2

Our Lt. William Maitland, posted at Fort King, also would have been familiar with Osceola in those peaceful days. But just a few months later, Maitland would face Osceola in combat. Perhaps Maitland shared one of the starkly different views of two other men who also faced Osceola in war.

“In his character Osceola combines much of the gallantry, cool courage, and sagacity of the white man, with the ferocity, savage daring and subtlety of the Indian,” wrote one, a South Carolina Militia officer. “We recognize the proof of no ordinary intellect, but of a great mind, steady in the pursuit of its purpose, and, grasping, not vainly, but with energy, the proper means to obtain it.”3

But the other observer, an Army officer, wasn’t having it.

“[Osceola’s] talents are not above mediocre; and he was never known … to possess any of the nobler qualities which adorn the Indian character: all his dealings have been characterized by a low, sordid, and contracted spirit…. Perverse and obstinate in his disposition, he would frequently oppose measures to which it was the interest of his people that he should advocate.”4

This officer hoped his published “description of [Osceola] may perhaps serve to disabuse the public mind of the ‘noble character,’ ‘lofty bearing,’ ‘the high soul,’ ‘amazing powers’ and ‘magnanimity’ of the ‘Miccosukee chief.’”5

Love him or hate him, Osceola was charismatic. And worryingly for Wiley Thompson, Osceola was the prime agitator against the Removal project. As young rank-and-file warriors murmured about armed resistance, they found a voice in this rising war chief. And Osceola was increasingly influential with Micco-Nuppa and other head men.

“The sentiments of the nation have been expressed,” Osceola had admonished Wiley Thompson when the Agent threatened the head men with violent deportation. “There remains nothing worth words! If the hail rattles, let the flowers be crushed – the stately oak of the forest will lift its head to the sky and the storm, towering and unscathed.”6

Wiley Thompson’s Tough Love

Osceola’s portraits may vary, but Wiley Thompson’s is static. Fifty-three years old in 1835, Wiley was a stiff-necked Georgian from Elberton. A strict disciplinarian and able administrator, he was mission-driven to infuse the world with his own habits and ethics. He started his career as the commissioner of a boy’s academy, then climbed to the rank of Major General in the Georgia Militia before being elected to Congress. In Washington, he caught the eye of President Jackson who felt that Wiley was just the sort needed to remove of the Seminoles from Florida. Wiley took the job for $1,500 a year, plus expenses.

Wiley was the personification of America’s Indian Removal project. He was arrogant and relentless in his dealings with Seminoles. When Seminole leaders said they’d been manipulated into the bogus emigration treaties, Wiley mocked them as liars, old women or foolish children.

Then he lectured them about their future should they remain in Florida (which, he insisted, they could not). Their land would be sold to whites and white laws would govern them. When abused, they would have no recourse because American law would not hear evidence from non-whites. Without land to farm or hunt, Seminoles would be left to beg scraps from their white neighbors, vagabonds in their own home.

On this point, Wiley was not wrong. That specter had been playing out for Native people since the Pilgrims landed at Plymouth. So Wiley pushed the Removal Act rationale that Indians could be saved only by emigrating west beyond the reach of admittedly avaricious and violent white settlers.

Of course, there was another option, an obvious one the Seminoles advocated and had a right to expect: the U.S. could respect the Seminoles’ right to remain on their treaty-protected Florida reservation and should patrol its borders to keep settlers, whisky traders and slave catchers out. It was as simple as it was just.

Wiley knew that would never happen. America’s goal was to take all Indian land east of the Mississippi. As a Congressman in 1830, Wiley Thompson had voted for the Removal Act. In 1835, as Indian Agent to the Seminoles, he positioned himself as their tough-love friend. Deportation, he told them, was for their own good.

Bad Day at the Office, or, Wiley Finds a Way

If Wiley Thompson’s singular purpose was to engineer the expulsion of the Seminoles, Osceola’s was to unify them against it. It was inevitable the two men would clash. And they had done so several times before Osceola rolled into Wiley’s office in late May 1835.

Maybe he brought an interpreter or maybe Cudjo was on hand to do the work. Osceola, looking at the four walls, chair and desk, must have wondered what compelled white people to spend their days in these little cells. Maybe it explained Wiley’s poor disposition.

Osceola was serious, perhaps angry. The accounts vary on what his business was. He had come to complain about white settlers abusing two Seminole men. Or about ill treatment of his wife. Or to upbraid the Agent for seizing his whiskey. Or to remind the Agent he was on Indian land and that white men’s days on it were numbered.

Wiley’s own account doesn’t tell us. He reports only that before it was over, Osceola “insulted me by some insolent remarks.”7

Osceola left to go on about his day.

Wiley sat in his office, face reddening. He emerged and quickly consulted a couple of Army officers who confirmed his impulse.

“I was fully satisfied the crisis had arrived,” Wiley wrote, “when it became indispensable to make an example of him.”8

Wiley Thompson passed the order to have Osceola arrested, chained, and thrown into confinement.

“Four of the soldiers of the garrison were detailed for that duty, and it was with difficulty they succeeded in overcoming him; they secured him about two hundred yards from the fort, amidst a shower of the bitterest imprecations upon Gen. Thompson, which he continued to utter in a perfect state of phrensy for some hours after he was secured.”9

In the Overreaction Olympics, Wiley Thompson was Usain Bolt, serial medalist. Jailing Osceola for disrespect was top-drawer, especially with American/Seminole relations as brittle as they were. But Wiley wasn’t done. A rare opportunity had fallen into his lap.

Wiley pondered the price he would exact for Osceola’s freedom. Played well, he figured, it could save his Removal mission and, not coincidentally, his reputation.

Osceola, confined in irons, was incandescent. But he soon mastered his anger and began calculating his next move, too. No one could have guessed it.

Next: The price of Osceola’s release.

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_____________________________

Sources:

Randal J. Agostini, An Englishman in the Seminole War: A Memoir Based Upon the Letters of John Bemrose, Florida Historical Society Press 2021.

Biographical Dictionary of the United States Congress: Thompson, Wiley (1781-1835), https://bioguide.congress.gov/search/bio/T000222, accessed Oct. 12, 2024.

William Boyd, “Asi-Yaholo or Osceola,” Florida Historical Quarterly, No. XXXIII, Jan.-Apr. 1955.

George Catlin, Illustrations of the Manners, Customs & Conditions of the North American Indians with Letters and Notes, Vol. 2, London 1876, accessed at Internet Archive.

Charles H. Coe, “The Parentage of Osceola,” Florida Historical Quarterly, No. XXXIII, Jan.-Apr. 1955.

Document No. 271, House of Representatives, 24th Cong., 1st Sess.,“A supplemental report respecting the causes of the Seminole hostilities, and the measures taken to suppress them,” June 3, 1836.

Susan A. Miller, Coacoochee’s Bones: A Seminole Saga, University Press of Kansas 2003.

Woodburne Potter, The War in Florida: Being an Exposition of its Causes and an Accurate History of the Campaigns of Generals Clinch, Gaines and Scott, Baltimore: Lewis & Coleman 1836.

William Wragg Smith, Sketch of the Seminole War by an Officer of the Left Wing, Daniel J. Dowling, Charleston 1836.

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Micco-Nuppa was a no-show.

Which should have surprised no one. In the annals of chief-to-chief diplomacy, no one consistently ghosted his dates like Micco-Nuppa. He was never rude about it; always sent delegates to give excuses. Often claimed illness.

Still, it rankled Wiley Thompson. How can a host ditch his own meeting? The whole point of agreeing to meet at the Seminole camp was to keep the micco from begging off as he’d done at the fort a month ago when the stage collapsed. Yet here they were, on the morning of April 23, 1835, Thompson and Gen. Duncan Clinch and a company of U.S. troops, which again would have included our Lt. Maitland, having marched the half mile from Fort King.

Fifteen hundred Seminoles were there, but not the one Wiley Thompson wanted. Thompson was pissed, and pissy. Where the hell is he?

The micco is off at his own camp several miles distant, Jumper said, waving in a direction that might have been east or just as easily west but in any case vague enough so no one could run off to fetch him. Sick. Belly ache. Real bad.

Thompson wanted Micco-Nuppa (Micanopy) because he embodied the crucial strain of the Seminole nation. The many bands loosely bound together in this nation fell mostly into one of three dominant groups: the Mikasukis (or Miccosukees), the Tallassees, and the Alachuas. But Alachuas held particular sway and Micco-Nuppa was their governor. A micco was the leader of a town or set of towns held together by personal and spiritual bonds. And Micco-Nuppa was the micco of miccos. Thompson knew that if Micco-Nuppa was absent from the talks, their importance was necessarily diminished. So did Micco-Nuppa.

Micco-Nuppa was of royal lineage. In the mid-1700s, Ahaya, a man from the Oconee Valley in Georgia, had begun the Florida dynasty when he carried the embers of his town’s sacred fire south to Payne’s Prairie, near today’s Gainesville. (See earlier post.) Ahaya, or Cowkeeper, called his new town Cuscowilla.

When Ahaya died in 1785, leadership fell to his able nephew Payne (a.k.a. King Payne), under whom the Alachuas prospered and spread. The Alachuas, like all Muskogees and the Apalachees and Timucuas before them, were a matrilineal society. Clan and inheritance came through the mother. Fathers were bystanders. So Ahaya’s office did not descend to his son but rather to his nephew, the son of his eldest sister. This makes some sense. One could never know with certainty the biological father of a child. But the mother was certain as were the mother’s brothers, the uncles. That’s where the family blood flowed. So uncles and nephews, determined in relation to the mother, had particular ties and obligations to each other.

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Payne’s reign ended in 1812 as he was cut down in battle against adventuring Georgians. (More on this in a later post; Patriots!) The white invaders burned Cuscowilla and other Native and black towns on the Alachua plain. Leadership passed laterally to Payne’s brother, Boleck, a.k.a. Bowlegs, who settled his refugee Alachua people 40 miles west on the banks of the Suwannee River.

Again war came for the Alachuas. This time it was Andrew Jackson who rampaged through the Suwannee towns in 1818 driving the Alachuas, along with Mikasukis, Tallassees and allied blacks (collectively, the Seminoles) east and south into the peninsula of central Florida. This six-month spate of violence is called the First Seminole War. 

It’s not clear when Bowlegs left us, but about this time Alachua leadership passed to his nephew, Micco-Nuppa. The micco was one of many Seminole head men to mark the 1823 Treaty of Moultrie Creek with the United States. In it, the Seminoles exchanged their north Florida lands for a huge, though agriculturally poor, reservation encompassing central Florida.

Now, 12 years later in the spring of 1835, the United States had determined it couldn’t tolerate Indians in Florida after all. It was Agent Wiley Thompson’s job to run the Seminoles out. But without Micco-Nuppa to negotiate the terms, he was hamstrung. And angry.

Maybe he can come in a day or two, Jumper said. But he knew of Thompson’s trademark impatience. Tomorrow was no better than next year.

The Haters Club, or Misunderestimating the Man

What galled Thompson all the more was the low esteem in which he held the Seminole leader. It was a view widely shared by whites. Micco-Nuppa was “a man of but little talent or energy of character,” in Gen. Clinch’s eyes. Another officer described the chief as five-foot-six, 250 pounds, “with a dull eye, rather a stupid countenance, a full fat face, and short neck.” Other observers began with his gluttony, moved on to his carbuncles, and were less charitable from there. He was indecisive, they said, his advisors led him by the nose. He was an indifferent oaf who only waddled onto the throne by virtue of high birth.

We can’t just blame racism because these same chroniclers often waxed poetic about the physical and moral majesty of other Native people. But Micco-Nuppa always came out fat, lazy and stupid. To the micco, American history has been unkind.

And I would say unfair. The man assumed his primacy in some of the most trying times of his emerging nation’s already difficult history and held his office through an unprecedented era of bloodshed, terror and dislocation — a tenure of some 30 years. That is not often the record of the dim and lethargic.

But Micco-Nuppa always came out fat, lazy and stupid. To the micco, American history has been unkind.

Perhaps his longevity is a testament to the tensile strength of the Seminoles’ intertwined logic of governance and cosmology. Some stations were assumed by heredity, others by merit. But in none was incompetence tolerated. A micco inherited hiliswa, a divine governing spirit. This is not unlike a British king or queen at the same time in history. Into Micco-Nuppa’s body was vested the soul of the nation. He held persuasive, though not autocratic, authority. For the Seminoles at a time when they might fragment under tremendous pressure, an enduring micco was required. One emerged, or at least the Seminoles worked with what they were given.

In the American records Micco-Nuppa is a cartoon figure. But we know some of his history and can reconstruct other parts from contemporary events. 

Micco-Nuppa was born about 1780 in north Florida and would have been of prime fighting age, about 30, when conflict came to the Seminoles in earnest. Perhaps he was with his uncles Payne and Bowlegs as they fought the Patriots War (1811-12) from St. Augustine to Alachua. In 1813, he was surely with his people as they evacuated the Alachua plain forever ahead of a vengeful American army. It is not unlikely that he fought rearguard actions against Jackson’s army on the Suwannee in 1818. This is to say nothing of the intramural conflicts that surely arose as the Seminoles were corralled into the central Florida reservation under the terms of the 1823 Moultrie Creek Treaty.

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So Micco-Nuppa knew plenty about war, but he also was schooled in diplomacy. In 1826, he had been part of a Seminole delegation to Washington, D.C. via Charleston and New York. It must have been mind-boggling for these travelers from the Florida sticks: cities crowded with high stone and brick buildings, streets teeming with white and black people jumping on and off wheeled carriages and trains, rivers surging with sail and steamship traffic. The might of this burgeoning American nation must have awed Micco-Nuppa and the others.

But it did not overwhelm them.

Micco-Nuppa and other head men sat down face-to-face with the U.S. President, John Quincy Adams, and his Secretary of War, James Barbour. The Seminole agenda was to get the U.S. to expand the central Florida reservation because it was too poor to sustain them. But the American agenda was to stop the Seminoles from harboring escaped slaves. The President also strongly recommended the Natives quit Florida altogether and migrate west to lands across the Mississippi River.

The Seminoles shrugged at the slave extradition request and told the President they weren’t going anywhere. As Micco-Nuppa later explained:

Micco-Nuppa and the Seminoles left Washington with a U.S. commitment, soon honored, to enlarge their reservation. In return, the Seminoles gave up nothing.

Micco-Nuppa was no dunce. Experience had given him the measure of American military power. He had some grip on diplomacy with whites and was a veteran of Native politics — the jostling for power, position, or just survival among the Mikasukis, Tallassees, and Alachuas. Perhaps Micco-Nuppa, who was settling into his mid-50s as America’s removal project came to a boil, was actually an astute politician masquerading behind a veil of indolence. He knew he was no orator so he left that to Jumper; for counsel regarding whites he relied on Abraham who, having once been enslaved by them, had insight. Perhaps Micco-Nuppa had developed the wisdom to know when the presence of the micco of miccos was really required.

Chiefs on a Roll

“Bah!” Wiley Thompson said, chalking the micco’s absence at the April 1835 conference up to a “shuffling disposition to shun responsibility.”

So a cranky Thompson started the conference without Micco-Nuppa (just as Micco-Nuppa wanted). Predictably, things went sideways. Day one was a continuous drone of each side speechifying, neither side being moved.

On the second day, Thompson turned the screws. He demanded the Seminole leadership mark their X’s on a paper attesting to the validity of the stale Payne’s Landing Treaty as well as the bogus follow-up “treaty” of Fort Gibson.1

The core Seminole leadership scoffed at this. By then they fully recognized the poison in the paper. Holata Micco declined. So did Abayaca and Coa Hadjo and Jumper. Further, Jumper said the absent Micco-Nuppa would have no interest, either. 

Thompson spluttered. Outraged, he declared he would strike these five men from his “Chiefs” roll. No longer would the United States recognize them as the head men of the Seminole nation.

This was worse than the stage collapse at Fort King. These men constituted the top tier of the nation’s leaders. The allegedly defrocked head men must have been stunned at the stupidity of the action. For an American bureaucrat to think he had the power, with the stroke of a pen, to rearrange the hierarchy of the Seminole nation was beyond silly. But such was Thompson’s arrogance, or desperation.

When news of Thompson’s tantrum reached his superiors in Washington, D.C., the Agent was quickly reprimanded and told to walk it back. Even President Jackson disapproved. (You’ve gone way too far when Jackson disapproves.) The Seminole nation’s head men were, of course, its head men. That’s how diplomacy works. Each nation selects its own representatives.

At the end of the day, Thompson’s action only succeeded in driving the wedge deeper between the nations while cementing his own reputation for imperiousness. A trait that would come back to haunt him, as we’ll see.

But whose reputation wasn’t diminished by this conference? Who didn’t have to suffer firsthand the indignity of being insulted? Who may well have seen all this coming and so acted to spare his nation the dishonor of having the incumbent of its most sacred office publicly belittled?

Micco-Nuppa.

We really should reassess the man. 

Next: Wiley can’t help himself.

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Sources

Canter Brown, Jr., “The Florida Crisis of 1826-1827,” Florida Historical Quarterly, Vol. LXXIII, No. 4 (April 1995).

George Catlin, The Boy’s Catlin: My Life Among the Indians, Charles Scribner’s Sons New York 1928.

Myer M. Cohen, Notices of Florida and the Campaigns, Charleston and New York 1836. Accessed at Internet Archive.

John K. Mahon, History of the Second Seminole War 1835 - 1842, University of Florida Press 1967.

Susan A. Miller, Coacoochee’s Bones: A Seminole Saga, University Press of Kansas 2003.

Kenneth W. Porter, “The Cowkeeper Dynasty of the Seminole Nation,” Florida Historical Quarterly, Vol. XXX, No. 4 (April 1952).

Woodburne Potter, The War in Florida, Being an Exposition of Its Causes and an Accurate History of the Campaigns of Generals Clinch, Gaines, and Scott, Baltimore 1836.

John T. Sprague, The Origin, Progress, and Conclusion of the Florida War, Forgotten Books 2012, originally published New York 1848.

Patricia R. Wickman, Osceola’s Legacy, University of Alabama Press 1991. Accessed at Internet Archive.

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The First Seminole

With the Removal Act of 1830 in hand, President Andrew Jackson targeted Florida. He aimed to clear it of the people Americans called Seminoles as well as the black people allied with them.

Who were the Seminoles? There are many claims about where the word “Seminole” comes from. Depending on who you talk to it derives from the Spanish, or no, the Muskogee language. It means — pick one — outlaw, runaway, pioneer, or simply one who camps at a distant fire. The common theme is that it signifies a people apart.

Apart from whom? Apart from the Native American groups who controlled most of what is today Georgia and Alabama. But apart is not unrelated.

In the 1740s, a man called Ahaya led his Oconee people from the banks of the Chattahoochee River in west Georgia south onto Florida’s Alachua plain. They left behind the well-populated heartland of the Muskogees (a.k.a Creeks), which encompassed much of what is today Georgia and Alabama. It was not unusual for any of the dozens of Creek towns to move when corn fields were exhausted or conflict required. But the Oconees were among the first to seek a new place in peninsular Florida.

The Alachua plain was vacant, or nearly so, when Ahaya walked in. But it was haunted. North Florida had been the home of the Apalachee and Timucua people, who, as of 1600, were thicker even than the Muskogees to the north, numbering perhaps 50,000. But by 1705, they were all but gone, victims of the Spanish mission system. European diseases claimed large portions. Many were worked to death. Others were killed or carried off by English and Native (often Creek) slave raiders who sold them directly to Carolina planters or via traders to Caribbean plantations. Still others fled the area entirely.1 After two especially brutal assaults by the Carolinians and Native allies in 1704, Spanish officials ordered the abandonment of the mission provinces and withdrawal to the great stone walls of St. Augustine. 

Ahaya would have known that story well. For 100 years, mission refugees had fled not just south to the central Florida hinterlands, but also north to live among the Creeks, or were hauled there as war booty. Over time, mission-phobic Apalachees established their own towns in Creek country and married into the highest levels of Creek society. The long, tragic arc of the Florida missions became part of Creek culture, too.

So Ahaya, a Creek migrant to Florida, knew who had been there before. He established his new town near the place the Timucua had called “Chua,” or  sinkhole, probably for the great limestone sink in today’s Payne’s Prairie. In the mid-1600s, Spanish colonizers, with a captive Native workforce, began grazing cattle there and called it Rancho La Chua. Ahaya’s Oconee people, resident in the area since the 1740s, became the Alachuas or Alachua Seminoles, their land: Alachua or Elotchoway. And Ahaya became “Cowkeeper” to the whites because of his success as a cattle rancher.

A Philadelphia traveler visited Ahaya at Cuscowilla in 1774, some 30 years after the Oconee arrival, and described the founder of the Seminole dynasty:

The chief is a tall well made man, very affable and cheerful, about sixty years of age, his eyes lively and full of fire, his countenance manly and placid, yet ferocious, … his dress extremely simple, but his head trimmed and ornamented in the true Creek mode. He has been a great warrior, having then attending him as slaves, many Yamasee captives, taken by himself when young. They … waited upon him with signs of the most abject fear.2

Ahaya, or Cowkeeper, may have been the first of the 18^th-century Creek migrants to peninsular Florida, but just barely. Others soon established towns in north and central Florida. The migration increased dramatically after 1814 as a result of the Redstick War in the Muskogee country. And just as mission Indians who had migrated north (voluntarily or not) mixed with Creek people, these southward-migrating Creeks mixed with Florida’s remaining Apalachees, Timucuas, Calusas and others who had escaped Spanish missions and dodged the incessant slave raids of the early 1700s. The Seminole nation was taking shape, having left the Creek confederacy like a young person leaving home but always intimately tied to it.

“Seminole” was a term of convenience for white people. It would have meant nothing to those it was first pinned on. They identified themselves by the Creek town they had migrated from (Tallassee or Eufaula, among many others), or that town’s mother town, or by the survivors of the ancient Florida people with whom they intermarried (Apalachee, Timucua, Calusa), or as Mikasukis of Chattahoochee River valley, or Yemassees driven from Carolina, or with the new towns they founded like Cuscowilla or Chocochatti. (One can imagine a Yankee clerk at a treaty negotiation, quill in hand, eyes glazing over five minutes after asking a Native man what ‘tribe’ he’s from. “Right, Seminole it is.”)

Maitland into Tampa Bay

President Andrew Jackson could tell with certainty who was a Seminole: any Native person within the borders of territorial Florida. And he wanted them all gone.

So in 1832, he dispatched his old friend James Gadsden (whose father gave us the ‘Don’t Tread On Me’ flag) to do the deal. Gadsden met a Seminole delegation in early May at Payne’s Landing near the confluence of the Ocklawaha and St. Johns Rivers (now underwater thanks to the U.S. Corps of Engineers and the Rodman Dam). The result was an ambiguous treaty apparently procured by bribery, by raw coercion or both. Seminole leaders later disavowed the treaty and even some American leaders quailed at it. But Gadsden’s job was done and he went home.

Then an odd thing happened. Nothing. The treaty languished, along with a subsequent bogus treaty, for a couple of years with no action on the ground. When the Americans again got serious about it in late 1834, they found Seminole attitudes had hardened against emigration.

Tensions in the territory rose sharply. No shots had yet been fired, but it was clear that the Seminoles wouldn’t go easily. That’s when, as noted in the previous post, the U.S. Secretary of War directed a show of military muscle.

Lieutenant Maitland answered the call. His job, along with the soldiers of ten companies also sailing into the Florida territory in early 1835, was to see the Seminoles off their land, peacefully if they would, violently if not.

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Fresh off the boat in Tampa, Lt. Maitland marched his Third Artillery Regiment company 100 miles northeast through the Seminole reservation to Fort King in what is today Ocala. There, he had a front row seat at one of the dramatic preludes to the great conflict. What Maitland thought of this, we don’t know. If he was a letter writer or diary keeper, nothing has come to light. With no personal record, we see Maitland only in bureaucratic military dispatches recorded by others.

But as luck would have it, there was another soldier present at many of the places we know Maitland was, and this man was a prolific writer. We can use him as a stand-in for Maitland’s eyes and ears, if not his opinions.

Bemrose the Scrivener

This guy was John Bemrose, a teen runaway from England who, after landing in New York then walking to Philadelphia, presented himself to a U.S. Army recruiter. Bemrose was too short by regulation, just 5’7”, but the recruiter turned a blind eye when he learned the kid had been a druggist’s apprentice back home. A useful trade. Within a year, Private Bemrose was sailing for St. Augustine at the far reaches of the American empire. There he attached himself to an Army doctor and became a hospital steward. Bemrose was an entertaining writer and left us some of the best eyewitness accounts of this period. (Highly recommend An Englishman in the Seminole War by Randal Agostini, or join the Seminole Wars Foundation and they’ll send you a copy of Bemrose’s Reminiscences.)

Maitland and Bemrose were both at Fort King (Ocala) in March 1835, arriving from opposite directions. As noted, Maitland had marched 100 miles northeast from Tampa Bay. Bemrose had marched 100 miles southwest from St. Augustine on an arduous slog with wildly drunk and then terribly hungover soldiers. These movements boosted Fort King to somewhat more than 500 U.S. troops, adequate for the Secretary of War’s show of force. Over the next eight months, Fort King was the fulcrum of interaction between Seminoles and Americans. Maitland and Bemrose would have crossed paths often and perhaps were even friendly. If Maitland got sick (and everyone in Florida got sick), Bemrose, the hospital steward, would have cared for him.

Fort King was a military installation but it also housed the official Indian Agency, that is, it was the American administration center for the vast Seminole reservation in central Florida. “The duties of an Agent are to protect the Indian from the craft and encroachment of the Whites,” Bemrose noted. Here, the Agent contracted an armourer to repair the Indians’ rifles. Here, white settlers and bounty hunters came to complain that Indians were harboring blacks who had escaped slavery. Here also the Agent paid out the $5,000 annuity the U.S. owed the Seminoles for having taken north Florida from them. Finally, just outside the fort’s gates was the trading post, the sutler’s store. It was busy with soldiers and officers and settlers, but also Seminole people who came to barter skins and game meat for trade goods. Fort King in 1834-1835 was always alive with white, black, and Native people.

The Indian Agent was Wiley Thompson, a hard-edged former congressman from Georgia. President Jackson had appointed him after the Payne’s Landing treaty was signed, confident that General Thompson (his rank in the Georgia militia) was the right man to oversee the removal of the Seminoles.

In late March 1835, not long after Maitland and Bemrose arrived at Fort King, Agent Thompson convened the head men of the Seminole nation to read them the riot act. It wasn’t the first time. But now that Gen. Duncan Clinch had at his command a new show of blue-jacketed military might, Thompson hoped to make some headway with the Seminoles.

All the World’s a Stage

Within the fort’s barracks an elevated platform had been built, several feet high, to drill the troops away from the blistering sun or the pouring rain. On this stage, Thompson gathered Gen. Clinch and his phalanx of buttoned-down officers on one side. This probably included our Lt. Maitland. On the other side was seated the august Seminole delegation including Jumper, Holata Micco, Coa Hadjo, Charley Emathla and a number of lesser-ranked men. Spread below were 150 other Seminole men and a similar number of U.S. soldiers.

Crucially, this wasn’t just an Indian-white conference. The interface, the membrane through which communication flowed, was African. Cudjo made a living at the Agency interpreting between Seminoles and Americans. He had escaped enslavement by Americans and had lived for some time among the Seminoles. This gave Cudjo, who was African or African-descended, both languages, Muskogee and English, as well as some understanding of both cultures. Cudjo’s story was not unique. Hundreds of black people lived in the Seminole nation. Virtually all had escaped American slavery, or were born of parents who had.

Kicking off his meeting on this overstuffed stage, Agent Thompson rose and insisted on reading aloud a letter from “the Great Father,” President Andrew Jackson, telling the Seminoles why they must behave like obedient children, must honor the treaty, must leave their homes for the west or be forced to do so.

The Seminoles listened patiently to the lecture. As a rule, Seminoles prized diplomacy. Conflict in meetings was beneath them. So although they certainly bristled at Thompson’s directness, they deflected. Holata Micco rose for the nation. He said they would consider Jackson’s words and come back later with a reply.

This wouldn’t have satisfied Thompson, but neither did it satisfy Jumper, who rose next for the nation. Jumper, a.k.a. Huithli (or Ote) Emathla, was “Sense-Bearer” of the nation’s primary leader, the absent Micco-Nuppa (or Micanopy), and his brother-in-law to boot. Jumper was over 50, likely a veteran of the Muskogee Creek wars against U.S. troops under Jackson two decades earlier in Alabama and again in west Florida in 1818. He was tall, imposing, and, Americans said, exceptionally shrewd. Jumper faced the array of American officers and in tones less measured than Holata Micco’s — he had withstood other Thompson conferences and was weary of the harangue — let it be known that he was not disposed to leave his home. He sat back down. Cudjo duly interpreted Jumper’s words to the American side.

Bemrose reported the interaction:

“Tell him, Cudjo,” said [Agent Thompson], “if he breaks his word with us” at the same time pointing to Gen. Clinch, and the soldiers collected at the back, “I shall be obliged to call upon the White warrior to force him.” 

[At this, Jumper sprang back up], spreading wide his arms, and standing in the graceful attitude, so easy to the savage, his eyes flashing fire, and his countenance at intervals taking a scornful look. Now and then he would burst into a derisive laugh!

“What’s he say, Cudjo?” was the agent’s query, excitement depicted upon his countenance.

“He say talk not to him of war! Is he a child that he fear it? No! He say when he buried the hatchet, he placed it deep in the earth with a heavy stone over it, but he say he can soon unearth it for the protection of his people. When he look upon the White man’s warriors, he’s sorry to injure them, but he cannot fear them, he had fought them before, he will do so again if his people say fight.”

Agent Thompson and Gen. Clinch stewed on this as Seminole leaders took turns with less provoking talk, reminding the Americans that threats and conflict were not the way but remaining firm that they had no intention of leaving their homes.

Before Thompson could speak again, the hand of God struck. With an uneasy wheeze then a thundering crack the timbers gave way, the stage collapsed.

Bemrose reported it this way:

The scene that ensued was most ludicrous. I could not help laughing to see fat and lusty Gen. Clinch, agent, officers, and Indians mixed up in a medley of humanity. The officers, and some of the Indians, took their sudden downfall in high glee. But there were other Indians, who did not fully comprehend the situation, and these rushed out from the supposed trap, screaming most awfully. On the reappearance of the agent, he quickly dispelled all fore-bodings . . . .

But the mood was broken and the Seminoles soon departed, telling Wiley Thompson they’d come back in a few weeks with an answer for him about emigration.

I’m willing to bet newly arrived Lt. Maitland was among the officers spilled from that collapsing stage. In any case, he was certainly a witness. For Maitland, after five years on ordnance duty in Pennsylvania, this was surely high drama.

It was only a taste of things to come.

Next: Have a little respect for Micco-Nuppa 

Sources:

Randal Agostini, An Englishman in the Seminole War: A Memoir Based Upon the Letters of John Bemrose (Florida Historical Society, 2021).

William Bartram, Travels Through North & South Carolina, Georgia, East & West Florida, the Cherokee Country, the Extensive Territories of the Muscogulges, or Creek Confederacy, and the Country of the Chactaws; Containing An Account of the Soil and Natural Productions of Those Regions, Together with Observations on the Manners of the Indians (Literary Classics of the United States, Inc. NY, NY 1996). (First published Philadelphia, 1791.)

John Bemrose, Reminiscences of the Second Seminole War (University of Tampa Press, 2001).

James W. Covington, “Migration of the Seminoles into Florida, 1700-1820,” Florida Historical Quarterly, Vol. XLVI, No. 4 (April 1968).

John H. Hann, Apalachee, The Land between the Rivers (LibraryPress@UF, Gainesville, Fla., reissued 2017).

Alfred J. Hanna, Fort Maitland: Its Origin and History (The Fort Maitland Committee, Maitland, Fla. 1936).

J. Anthony Paredes and Kenneth J. Plante, “A Reexamination of Creek Population Trends, 1738-1832,” American Indian Culture and Research Journal (6:3, 1983).

Kenneth W. Porter, “The Founder of the ‘Seminole Nation,’ Secoffee or Cowkeeper,” Florida Historical Quarterly, Vol. XXVII, No. 4 (April 1949).

Clarence Simpson, Florida Place-Names of Indian Derivation. Florida Geological Survey, Special Publication No. 1 (1952, ed. Mark Boyd 1956).

John E. Worth, The Timucuan Chiefdoms of Spanish Florida, Vol. 2: Resistance and Destruction (University Press of Florida, 1998).

In 1492, Columbus threw a lasso that cinched together the peoples of the Atlantic continents: Europeans, Native Americans, and Africans. In Florida, some 340 years later, the action was still unfolding like nowhere else. The year was 1835. America began what it hoped was the final purge of all indigenous people from the Florida territory. The Seminoles made a stand to defend their land. Africans and their descendants who had escaped American slavery fought alongside them to remain free.

The result was America’s longest, deadliest, and costliest war against its indigenous people. It saw the largest slave liberation in American history by an order of magnitude. It’s one of the few ‘Indian wars’ where the Native people can declare a form of victory.

This is a story worth knowing.

And I’ve been absorbing it since I could read. It has much to tell us about not only about where we come from, but where we are now. The story is highly particular to the Atlantic world of Florida in the 19th century, but we see the sadly familiar patterns continue to play out around the world today.

What caught my imagination as a boy was the valiant struggle of a Native people against an unstoppable foe. Your basic cowboys and Indians stuff. But what keeps the older me fascinated is the personalities, the understandings and misunderstandings among white, black, and Native people fated to become combatants. The record is rich with this though it leaves plenty to the imagination.

As a lawyer, I’ve spent most of my career in the practice of federal Indian law. I also serve as the mayor of a city in central Florida. And I’m a history guy with an interest not just in Florida but in Mexico, Central America, and the Caribbean, among other places. I’d like to think long exposure to and the study of law, politics, and culture has given me some perspective.

Once every two weeks in this space I’ll publish a piece on the Florida War, a.k.a. the Second Seminole War (1835-42). If you sign up with Substack you’ll get these automatically in your inbox. I’ll try to give the posts personal scale and impact and keep it engaging.

That said, let’s go.

Who Was Maitland?

As the mayor of Maitland here in the heart of Florida, I ought to know something about this city. Not just how many miles of road we re-pave every year or the cost of a sewer hookup or how many pickleball courts we lack, though those things are important. I mean the foundational stuff.

Like how did Maitland get its name?

The name is meaningful; it’s not an ad slogan like so many Florida towns (sorry, neighbors). It’s a clue to an incredible story. It connects directly to a turbulent upheaval that set the stage for us suburbanites. If you know how Maitland got its name, you’ll know infinitely more about us all, about the world.

I live almost two miles from Fort Maitland Park, which sits on the western edge of the pricey shores of Lake Maitland. (For those not from here, the park is 2.7 miles north of Orlando in central Florida.) The three-acre park serves mainly as a well-appointed public boat ramp. Lake Maitland is large and picturesque and linked to several other lakes through ferny canals traversed by ski boats and paddlers and the occasional alligator. Boathouses and mossy cypress trees ring the shores.

The city was named for Fort Maitland, which once occupied the area where the park now sits. The U.S. Army built the fort 186 years ago. It was a modest rectangle of 15-foot-long split pine logs pointed to the blue Florida sky. Maybe it had wooden blockhouses at two opposite corners for defense and cover from the elements. There’s no trace of the fort today. (Its actual footprint may have been where the condominium bordering the park on the south now stands.) It was abandoned to the humid mercies of the subtropical forest not long after it was built.

Well and good, but who was this Maitland guy they named the fort after way back in 1838?

He was William Seton Maitland, a New Yorker baptized at Trinity Church on Wall Street in 1798. That was six years before Alexander Hamilton was buried there. We know little about William Maitland but the bare facts. At 15, young William enrolled in the U.S. Military Academy at West Point. (A distant relative of mine, Rawlins Lowndes, was his classmate). Maitland was no world-beater, graduating 28th in a class of 30, but maybe he was having fun.

In 1820, Maitland was commissioned second lieutenant in the Third Regiment of Artillery. He served at posts in New York, Connecticut, and Pennsylvania, but also in Wisconsin, Illinois, and Michigan, much of which was then on the American frontier, that is, the cutting edge where white people were chasing out Native people. Over the next eight years, Maitland slowly climbed to first lieutenant, the rank he held when he sailed into Tampa Bay in 1835.

This is where the story really begins.

First, let’s appreciate that Florida back then was a wilderness. When William Maitland disembarked at Tampa Bay, there was hardly a settlement there at all and just a thinly staffed army outpost — Fort Brooke — on a rise where the Hillsborough River pours into the bay. Elsewhere, a handful of American settlements clung to the periphery of the territory: St. Augustine and satellite plantations on its northeast coast, Tallahassee 200 miles west in the Panhandle, Newnansville and Hog Town (now Gainesville) in between, and Key West some 350 miles south of that. All in, whites, free blacks, and enslaved people at these far-flung settlements, plantations, and farms totaled about 35,000.

The interior of the peninsula, the lion’s share of the territory, was governed by Native people and the Africans and African-descended people affiliated with them. These numbered maybe 6-8,000 spread through dozens of towns and villages like Okahumpka, Pilaklikaha, Chocochatti, and Buckra Woman’s Town. The huge Seminole reservation the U.S. had created in 1823 included most of Florida from just north of today’s Ocala south to a line even with the southern end of Tampa Bay (say, today’s Sebring). The reservation’s eastern boundary cut through swamps west of the St. Johns River; the western boundary lay 20 miles or so from the Gulf coast.

Estimating the total population of Florida generously then at 45,000 gives us the tiniest fraction of a fraction of the 23 million people who live here today. It’s an understatement to say that in 1835 people were few, and aside from small towns and plantations, very, very far between.

So why did Lt. Maitland sail into Tampa Bay in March 1835?

Maitland’s errand, bluntly, was ethnic cleansing.

Maitland wouldn’t have called it that. He would have said ‘removal.’ Not only is that more brutally efficient, it was the proper name of our nation’s policy. Lt. Maitland had come to Florida at the direction of his government to ensure that every Native American and affiliated black person was physically removed from the territory. The Indians were to be exiled to Oklahoma and the blacks mostly re-enslaved.

The Removal Act Congress passed in 1830 did not mandate Indian exile. It simply authorized the President to negotiate with Indian tribes throughout the country to “exchange” their ancestral lands for other land to be set aside in what is today eastern Oklahoma. The treaty-making process, 200 years old by that time, created legal fig leafs for whites to move Indians off their land, typically by bribery, trickery, or plain old threat of violence. But for land-hungry Americans in the 1820s, that rickety one-off process wasn’t moving fast enough. The Removal Act was meant to supercharge it. In the hands of Andrew Jackson — a man already responsible for the deaths of thousands of Native Americans in Georgia, Alabama and west Florida and the dislocation of thousands more — the Removal Act became a mass deportation order. Its result throughout the Southeastern U.S. was, colloquially and predictably, the Trail of Tears.

None of this was William Maitland’s fault. He was born into the world he was born into. The career he chose — at the height of the War of 1812 — provided steady work. Still, if he was digesting the news of the day as military men did, he had opinions about the rapid expansion of his young country at the expense of indigenous nations.

In any case, Lt. Maitland was minding his own business in early 1835, going on his fifth year of less-than-scintillating ordnance duty at a Pennsylvania army post, when he got the call.

Trouble was brewing in the wilds of Florida. No real violence had erupted yet, but the removal of Indians was not going as planned. In fact, it was going nowhere. So the U.S. Secretary of War, sitting in his Washington, D.C. office, hoped that a show of military muscle would intimidate the Seminoles, maybe provide the hint needed to avoid bloodshed.

Lieutenant Maitland received his orders. He was going south.

Next: Maitland goes in-country.