CHAPTER 8

Flight to the Seminoles

Within a relatively short time, Black Georgians came to see the Seminoles as their best hope for securing freedom, a phenomenon that goes to the heart of profound changes in the Creek people during the last decades of the eighteenth century. The Seminoles were a relatively recent creation, fashioned out of dissident Creeks who had migrated from the interior of the South into the largely uninhabited spaces of northern Florida.¹ The interior of northern Florida belonged to these migrants who trickled in from different spaces and for differing reasons.² When asked whether the Florida Natives were part of the Creek Nation, Alexander McGillivray, the Upper Creek mestizo, described them as “wanderers,” while other leaders called them “renegades and vagabonds.”³ After multiple visits, one Carolinian observed, “it has been generally understood that this tribe of Indians were formed originally by a casual association of fugitives and outlaws from the Creek nation”; their name was said to signify outlaws.⁴ Indeed, the term “Seminole” was an Anglicization of the Spanish slang for “wild” and used in reference to cattle lost in the woods or runaway slaves.

The number of Seminole Indians was always small, and their dispersed settlement pattern reinforced a basic lack of unity. “They are more unsettled, in their manner of living, than any other district of people in the nation,” Major Swan commented on a tour through Creek country. “The truth is, they have no government among them.”⁵ Despite this lack of governance, they were evolving into a people with a distinct culture and social organization.⁶ The Seminoles were skillfully adapting their Creek culture to fit the environmental and economic conditions of northern Florida, occupying the grasslands of the prairie once used by the Spanish for cattle herding.

Among the first to appear were Ahaya (Cowkeeper) and his brother Long Warrior, who, according to one source, led 130 families—some 450 Creeks— from the Oconee River to a site in the Flint watershed and then, by the 1750s, onto the rich grasslands of the Alachua Prairie near St. Augustine.⁷ It is probable that he had appeared alongside Oglethorpe during the War of Jenkins’ Ear in 1739 and was returning to where he had captured Yamassee Indians and still held many as slaves. His great determination was to maintain his independence, and so he began a cautious realignment with the Spaniards in Florida. In addition to hunting deer and other game, the Indians raised cattle on the grassy plains and sold the beef and hides to the Spanish, creating an economy that marked a sharp separation from Creek life.⁸

Other groups broke off from the Lower and Upper Towns of the Creeks and crossed into the Apalachicola basin farther west, some as far as the Tampa Bay region. Originally, they functioned as satellite towns (talofas) of the communities from which they came, but they gradually built their own square grounds, council houses, and sacred fires, elevating themselves to the status of autonomous talwas.⁹ Together the various settlements represented an ethnic minority within the Creek Nation. All spoke Hitchiti rather than Muskogee and jealously sought to guard their independence from the Creek Confederacy.

From the Revolution onwards, the Seminoles absorbed growing numbers of Black people, most as fugitives from Spanish Florida, Georgia, and, to a lesser extent, South Carolina; others as war captives taken by raiding parties; and a few as slaves purchased in the markets of St. Augustine and Pensacola, usually by a chief exchanging his cattle.¹⁰ Their relationship with the new masters set them apart. The Seminoles retained older forms of captivity that allowed them to embrace people of African descent and create a pluralistic society that made room for diverse groups of newcomers. Blacks lived in separate villages next to Native settlements, cultivated their own fields, paid an annual tribute in the form of provisions, frequently served as interpreters and cultural intermediaries, and, in time, fought alongside Seminole warriors. Other than a share of agricultural produce, the chiefs expected little from their captives, leaving them, in the words of an American observer, “at liberty to employ themselves as they please.”¹¹

Observers in the 1820s and 1830s were astonished at the independence of the Black towns or “Negro villages” as they called them and puzzled over the paradox. Wiley Thompson had been a trader among the Seminoles since the first years of the nineteenth century and was a federal agent when he knowingly wrote, “They live in villages separate, and, in many cases, remote from their owners, and enjoying equal liberty with their owners.” But he went on to note that they annually supplied to their “owners” a small amount of their crops, typically corn. The house or hut in which a Black family lived was theirs, and Thompson noted, “Many of these slaves have stocks of horses, cows, and hogs, with which the Indian owner never assumes the right to intermeddle.”¹² Another knowledgeable observer, W. H. Simmons, pointed out to his American audience, “The Negroes uniformly testify to the kind treatment they receive from their Indian masters, who are indulgent and require little labor from them.”¹³

Scholars have ever since puzzled over how to call them, whether they should be considered as maroons who lived autonomous lives, half-slaves still owned, partners in an unwritten alliance, or, in Christina Snyder’s felicitous phrasing, “junior members” of the several chiefdoms. Together, she argues, Native and Black Seminoles created a new society, one that increasingly isolated them from other Southerners, white and Native.¹⁴ That isolation owed much to the geopolitics of the region.¹⁵ The presence of Black Seminoles in the heart of the southeastern borderland defined this region in a way that had no parallel in American history. The very act of fleeing across the St. Marys or down the Flint or Chattahoochee exposed the stunning vacuum of power that characterized this unique borderland. To their frustration, the Great Powers were unable to control much of anything that transpired in the interior of northern Florida, a failure that extended at various times into the southern portion of Georgia. Black people were the beneficiaries, able to use the setting to join these idiosyncratic Natives and become players in the delicate balance of power in the Southeast.

This unique set of circumstances evolved into a setting in which Black men originally from Georgia found themselves fighting white Georgians, besting them in a critical engagement in the Patriot War of 1812 and provoking unfounded fears of a slave insurrection in the Georgia Lowcountry. The progression was a measured one, from acting as cultural brokers and interpreters to participating in raids as recognized warriors to emerging fully as Black Seminoles who fought alongside “Blood Seminoles” in substantial numbers. By the first decade of the nineteenth century, they had become integral to the calculations of power in the Southeast.

In their twenty years of ruling East Florida (1763–1783), the British had been no more successful than the former Spanish government in projecting power beyond the St. Johns River. This astonishing impotence was on display from the very moment that the British plunged into transforming East Florida into a booming plantation economy built around the rapid infusion of English capital. Governor James Grant and his administration oversaw the addition of as many as fifteen hundred Africans through the Atlantic trade and another one thousand or so from South Carolina and elsewhere in the Americas.¹⁶

Benefiting from the exchange of trading goods for deerskin and cattle, officials were willing to tolerate a certain level of flight as a safety valve of sorts. Lt. Governor John Moultrie admitted to his superiors, “It has been a practice for a good while past for negroes to run away from their Masters and get into the Indian towns, from whence it proved very difficult and troublesome to get them back.”¹⁷ When four Black freedom seekers from a plantation near St. Augustine met up with a Seminole hunting party on the west bank of the St. Johns River, the slaves were made to accompany the hunters as quasi-servants as the latter continued their hunt. Confronted by whites, the Indians gestured that they were merely giving food to hungry men and surrendered their prizes without a struggle.¹⁸ If fugitives reached a Native town or village, an extended negotiation between Natives and British might be successful or not. Given the small numbers of Seminoles and their sparse settlement pattern, the British saw these Indians as more of an annoyance than a threat and rarely applied significant pressure. The exchange of trading goods for cattle and deerskins more than compensated total losses.

The onset of the Revolution produced a radical change in attitude. Desperate for manpower, Governor Patrick Tonyn of East Florida negotiated with Ahaya for warriors to enter the conflict and agreed that, if he sent raiding parties into Georgia, they might keep all the horses, cattle, and slaves they took, although privately he was determined to minimize contact between Native Americans and Africans.¹⁹ Reality dictated otherwise. During the war, Ahaya travelled to St. Augustine from the Alachua Prairie with cattle to trade for slaves and made his purchases unhindered.²⁰ Captives from the raids in Georgia were taken back to his town.

Meanwhile Black people were voting with their feet. Great numbers were escaping a war-torn economy in Georgia where the reins of authority were loosened. When Jupiter, Auba, and Jack landed at St. Augustine from Ossabaw Island in 1781, they chose to head to “Indian country” and join all those who found that the wartime conditions in the capital offered excellent opportunities to flee a white-dominated society and embrace a vastly different cultural world. The numbers departing testified to the weakness of a colony that still functioned as a military outpost with little authority beyond the St. Johns River in the vast interior of Florida.²¹

The return of the Spanish to Florida in 1783 changed the equation once again. As soon as Governor Vicente de Céspedes announced the restoration of the sanctuary policy and the granting of freedom to those fugitives who converted to Catholicism, freedom seekers from Georgia and South Carolina determined to make their way to St. Augustine or, at the very least, to blend into the Florida countryside. “Indian territory” seems to have been less frequently a destination during the 1780s, although no definitive judgment can be made, given the paucity of sources. But the promised sanctuary for freedom seekers was no more than an interlude. The period of grace lasted until the edict of May 17, 1790, when the Spanish king abolished the decree in the Americas and left the door open to a settlement with the United States, which occurred a year later.²²

During the final decade of the eighteenth century, enslaved men and women in Spanish Florida pioneered the way. Jesse Dupont had arrived in East Florida in 1791 with his wife, eight children, and an unspecified number of slaves. Within months, two of them had run away. Dupont wrote to the governor: “[An] Indian negro Stole a wench and Child, and since she has been amongst the Indians she has had a second.” The story ends there, unfortunately, and we are left with the tantalizing possibility that the “Indian negro” had been her husband. Sometime later, a party of warriors burned Dupont’s rice fields and stole three “valuable” horses as well as cattle.²³

Spanish officials had a self-serving explanation for why their enslaved people were so willing to take flight. Governor Enrique White pointed the finger at Black Georgians who had made it to the safety of Seminole towns and “dedicated themselves to instilling in the minds of the pacific Spanish slaves ideas of the advantage of liberty.”²⁴ In fact, Black Seminoles were instrumental in spreading the word on plantations when acting as interpreters and cultural intermediaries on hunting parties that passed through white settlements. In the late spring of 1795, Col. Carlos Howard, commander of the northern district, confronted a small band of Hitchiti-speaking Indians, ten men with women and children, passing through the countryside near the tiny village of San Vicente de Ferrer at the mouth of the St. Johns River. When he saw several of the men stagger off a docked boat after having traded deerskins for rum with sailors, he expelled them from town. A short time later, a “Negro interpreter,” a man who had either fled or been captured on a Georgia plantation, arrived alone at his office. Howard began lecturing him on the illegal trading of skins and telling him to lead the Seminoles away and not return. Howard wrote, “He told me, laughing in my face, that he would come back, that the Indians were coming behind him and they would make me see reason.”²⁵

Colonel Howard had his own reasons to be uneasy. The Seminoles were hunting among the plantations on the east side of the St. Johns River, burning woods and fields to frighten deer into the open, and occasionally entering the houses of the inhabitants. Of as great a concern were the two Black men who accompanied them, stolen or liberated from the Liberty County plantation of Governor John Houstoun of Georgia some years before, fluent in the difficult Hitchiti language, now serving as interpreters and cultural brokers. The lead interpreter, Peter, conveyed the words of the head-man in a way that showed his delight in being able to tweak the nose of the commander. Howard was less concerned about his own dignity than the role of the two men in recruiting Black people: “Here, let me add that the Negroes . . . go around thinking about the slaves of the neighbors, [telling about] the happy life that the people of their color enjoy in the Nation, where they eat the same food as their masters, and work as much as they want alone without fear of punishment.”²⁶ Blaming the loss of Black people on freedom seekers from Georgia was a common practice among Spanish officials.²⁷ Peter and others like him had a story to tell, and tell it they did.

Once fugitives from Georgia had crossed the St. Marys River, they had an important choice to make. An individual could go due south to the settlements on the Alachua Plain (Payne’s Prairie), only a few miles distant from the St. Johns River, or to the southwest along the Mikasuki Path that wrapped around the eastern flank of the Okefenokee Swamp and on to the towns that lay on the banks of the Apalachicola River or near that river. With a strong sense of self-worth, Seminole towns and villages remained considerably more fractious and independent of each other than was true of Creek towns, where the national council gradually if fitfully set about undermining the authority of local chieftains. As Major Swan observed, there was no effective government over the estimated two thousand Indigenous people, not even a process for consultation among the various towns. That choice placed African Americans in towns with widely differing geopolitical outlooks.²⁸

Through the early 1790s, the Alachua towns retained their primacy as the destination for freedom seekers from Georgia. If proximity was a key factor, so too was their prosperity. In 1788, Chief Payne, referred to as King Payne by whites, succeeded his uncle Ahaya as headman of the Alachua Seminoles. It was a daunting challenge. In his long tenure as chieftain, Ahaye had stood up to the Spanish, the English, and the principal leaders of the Creek Confederacy.²⁹

Shortly after assuming the leadership, Payne abandoned Cuscowilla and founded Paynes Town a few miles away, constructing it plantation-style rather than around the time-honored square ground of Creek towns.³⁰ A superb diplomat rather than a warrior, Payne was keenly aware that his network of settlements was too small to be a military power and too close to the forces that surrounded it to be anything other than unaffiliated. His understanding of power was conditioned by the Spanish military garrison at St. Augustine, the frontier militias of Georgia, and the marauding war parties of the Creeks of the Lower Towns. Over time, he led the settlements on the Alachua Prairie to a remarkable level of prosperity and could boast of possessing fifteen hundred head of cattle, four hundred horses, untold numbers of sheep and goats, and twenty enslaved people.³¹

But there was another choice that could be made by a freedom seeker. Small bands of Creeks had entered northern Florida before, during, and after the Revolution, founding towns along the Apalachicola and Suwanee Rivers and farther south in the Tampa Bay area. The town of Mikasuki (by the waters that now form Lake Miccosukee) and the town of Talahasochti on the Suwanee River were larger and more substantial than those on the Alachua Plain and possessed a point of view that differed in many ways from their eastern neighbors.³² The formidable Kinache, chieftain in Mikasuki and dominant figure in the Apalachicola region, had arrived only after the Revolution from the Lower Towns of the Creeks and remained a fierce partisan of the British, nursing a deep resentment of both Spanish and Americans. Best known as Tom Perryman in his early life, the mestizo did not hesitate to assert the independence of his people against the two dominant powers of the region.³³

As chief, he commanded a substantial population that contained 180 to 200 men capable of bearing arms and a sizeable “Negro village” one and a half miles away, the largest such pairing in the whole of the Seminole polity. In a report some years earlier, Major Swan had described this “half-breed chief ” as a man possessing as much property and influence as Jack Kinnard, with three young wives in tow. “For size and strength, [he] has never yet found his equal,” Swan concluded, “He is master of the art of English boxing—and has been the Sampson of these Philistines from his youth up-wards.”³⁴ A prominent leader, Kinache was dismissive of the relatively passive Payne, who remained uncharacteristically silent when in the presence of the forceful military leader.³⁵

The Seminoles at Mikasuki and in the Apalachicola Basin enjoyed greater freedom from outside influence than did those to the east, while nourishing as deep a hatred for the Spanish as for the Americans. Kinache’s warriors resented the presence of the military outpost at Fort St. Marks and its control of trade. They complained vociferously about the high prices, low quality, and limited range of goods available at Panton’s long-time store not far from the fort. As allies with the British during the Revolution, the Natives never lost their preference for things English and hoped fervently for their return. The Mikasukis continued to make periodic raids against Spanish plantations near St. Augustine for slaves and horses and compounded the terror they inflicted by occasionally killing an unfortunate victim, Black or white.³⁶

In a wrenching change to the geopolitics of the region, Kinache stumbled into an unexpected opportunity to realize his dream of expelling the Spanish and extending his influence over neighboring towns, Creek as well as Seminole. In 1799, his son-in-law, the long-missing William Augustus Bowles, made a surprising reappearance in Mikasuki after an absence of six years. Now thirty-five-years old, he had fought for the British at Pensacola as a young loyalist from Maryland. Disciplined for insubordination, he had reinvented himself after fleeing to a Creek settlement on the Chattahoochee River, marrying the daughter of mestizo Chief Perryman, the future Kinache, and establishing trading relationships with British merchants in the Bahamas. He was quick to pick up on the pan-Native currents circulating among Native Americans in the eastern part of North America and put forth a call for an independent “United Nations of the Creeks and Cherokees.” The quixotic effort spoke to his shrewd reading of the revolutionary ideas of the age as well as his own outsized ambitions. After a three-year chase, the Spanish government had captured the improbable adventurer through a clever ruse and exiled him to the Philippines.³⁷

Undaunted, the persuasive Bowles escaped five years later and caught a vessel to London where he won tacit support from a cautious government, deftly spinning a vision of a British protectorate over an independent Indian state that might give Britain a new role in the American Southeast. He announced his readiness to refloat his bold vision of the State of Muscogee but built this time around the Seminoles rather than the Creek people and with room for dissident Creeks, Black runaways, and disaffected whites in the region.³⁸ Always a brash, self-interested adventurer, Bowles was capable of turning himself into a visionary who grasped the basic outlines of a newly emerging world rooted in the revolutionary Atlantic.

With Bowles’s reappearance, Kinache saw in his son-in-law a new chance to secure a reliable source of reasonably priced goods while checkmating his most hated enemy, the Spanish government. Kinache arranged Bowles’s reelection to his old position as director-general of the State of Muscogee while tacitly embracing the idea of creating a sovereign Indian nation carved out of territory claimed by Spain and the United States.³⁹ The newly installed director-general proceeded to churn out documents declaring war on Spain in the name of the newly formed state, made known his intention of rallying marginal peoples in the Southeast, including Black people and dissident whites, and stated his aim of organizing twin military forces, a navy and an army. As the American surveyor Andrew Ellicott dryly noted in his journal, Bowles was “a man of enterprise.”⁴⁰

For almost three years, the nebulous forces behind the State of Musk-ogee raided plantations along the St. Johns River, attacked Spanish shipping through letters of marque issued to Bahamian mariners, attempted to recruit dissident whites on the Georgia side of the St. Marys River, and assaulted Fort San Marcos. Capitalizing on easy victories early on, Bowles built a pseudo-government that tapped into themes running through the revolutionary Atlantic and energized an unprecedented coalition of Seminoles, Creeks, members of other Indigenous societies, African Americans, and whites of various origins.⁴¹

In the summer of 1800, raiding parties set out from the Seminoles to attack plantations along the St. Johns River. James Seagrove, the federal Indian agent in Georgia, warned his friend John McQueen that a party was headed his way composed of “from twenty-five to thirty Indians, Negroes, and infamous whites all of them direct from Bowles headquarters” with orders to “plunder and break up all the settlements in Florida.”⁴² A party of warriors carried off three Africans and fourteen horses from the plantation of François Richard, the refugee planter from Saint-Domingue and Mc-Queen’s neighbor. Another took five enslaved people from George Fleming, a loyalist who had stayed in Florida.⁴³ Mikasukis canoed across the St. Johns and met up with four other Seminoles and two “hostile Negroes.”⁴⁴ According to an associate of McQueen, the “hostile Negroes” went voluntarily with the Indians and acted as guides when they took Captain Fleming’s enslaved workers, an apt description of how war captives transformed themselves into liberated people. Nor were Black slaveholders exempt. A pillar of the free Black community in St. Augustine and a baptized Catholic, Felipe Edimboro was a part-time farmer who raised pigs for his butcher’s shop. A raid carried off his slave Jack as well as eight members of a free Black family whose farm lay next to his.⁴⁵

That fall, Bowles unleashed an extraordinarily ambitious plan to rally white and Black Georgians in the St. Marys region, whose frontier-like conditions gave him room to maneuver and launch yet another coup to topple the Spanish government. The presence of a pool of frustrated filibusterers, horse thieves, and unregulated deerskin traders seemed a promising source of manpower to overthrow the Spanish in St. Augustine. The abortive attempt to organize an invasion of East Florida offers a measure of Camden County as an unsettled borderland where people of multiple cultural voices interacted in a drama involving an imperial power, a republic that functioned much as an imperial power, and a putative state that threatened both.

The focal point for much of the mischief that beset the region was the small port town of St. Marys, established by ambitious land speculators in 1787 at the entrance of the St. Marys River on Cumberland Sound. The end of the Revolutionary War had seen the frontier between Florida and Georgia explode into a bandit-ridden no-man’s-land, raided by Americans coming south and ravaged by quasi-loyalist gangs from the remnants of British East Florida. After its fretful birth a few years later, St. Marys stood at the center of this curious borderland. Eventually fifty to sixty houses along the riverside sheltered a mixed population of Carolinians (trying to escape debt), Spanish citizens, Americans who claimed both Spanish and U.S. citizenship, French refugees from Saint-Domingue, Georgians looking for quick money, and shippers who engaged in a variety of legal and illegal activities, including smuggling Africans into Georgia. According to the 1790 census, there were 221 white people, 70 enslaved people, and 14 free Blacks. Ten years later, the population had increased substantially to 1,681, of whom 735 were enslaved people.⁴⁶

Maintaining order along the banks of the St. Marys River was beyond the capabilities of Americans or Spanish authorities. The smuggling of slaves was a frequent occurrence made inevitable by the vacuum of power. A white Georgian operated a house on Tyger Island in Spanish Florida that served as a holding pen for people of African descent brought to him by residents of Camden. When confronted about a case involving Robert and James Ross, Samuel Mercer confessed his involvement in such a scheme. “He did so,” it was said, “without asking any questions because he was in the habit of receiving negroes from the Ross brothers.”⁴⁷ The pipeline from the town to Tyger Island was a reality. Indian traders lived on both sides of the river in a largely successfully effort to escape local authority. They engaged in a wide range of illegal activities and counted on the influence of chieftains like Jack Kinnard to keep them out of harm’s way.⁴⁸ Purloined goods or livestock often reappeared on the other side of the river through one means or another. Creek and Seminole raiders regularly stole horses in Camden County and sold them to white traders or brokers who turned a good profit in East Florida.⁴⁹ Professional horse thieves like Bob Allen were caught and locked up in the tiny jail in St. Marys. Allen was adept at escaping, and no one seemed overly concerned.⁵⁰

Bowles turned to a born schemer, Richard Lang, leader of the failed 1795 rebellion, who, after initially hesitating, accepted the proposal for a fresh offensive against St. Augustine. He counted on tapping into a pool of young men eager for land and slaves.⁵¹ Lang had originally migrated from South Carolina as a debtor and moved to Spanish Florida to obtain land. He was involved with wholesale cattle smuggling from Georgia while trafficking in goods and people across the border illegally. When he was found plotting with would-be revolutionaries in St. Marys to invade East Florida, he lost his estate and fled across the river. In 1795, he put those plans into action and took the lead in an actual rebellion that cost the lives of three Spanish soldiers before his tiny force was chased back across the St. Marys River by a path-breaking coalition of Spanish soldiers, the free Black militia, and a white militia.⁵²

In October 1800, Bowles, the director-general, marched on the village of Colerain, located on the St. Marys River, to meet with Lang and finalize plans for the coup. Black people were present at each stage. A Spanish official reported that Bowles’s immediate party consisted of eight whites and eight Blacks and that one of the latter served as a captain.⁵³ A Florida planter led a posse in pursuit and neared the spot where it was rumored that the rendezvous was to take place. They encountered a Black man walking toward them, “one of the Negroes of the Bowles party.” The African readily revealed that their leader planned to link up with Lang and expected to be joined by three hundred Georgians who were “to go into Florida and plunder and kill and take possession of Florida in the name of the King of England.” It was not long before the McQueen party picked up the trail and was almost on an encampment of Bowles and his party early one morning. Hearing noise in the underbrush, the director-general and his three Black companions leaped up from the fire where they were cooking breakfast and escaped, leaving behind horses, clothing, arms, and even papers. Stripping off their clothes, they dived into the river and swam to safety.⁵⁴

Lang weighed the odds of Bowles’s project succeeding and quietly withdrew his offer of support—but not before becoming drunk and leaving Bowles’s colorfully worded letter about invading Florida lying on the floor of a shop. That letter was soon in the governor’s office, eliciting a proclamation that forbade anyone cooperating in any way with the director.⁵⁵ David Garvin, a trader with the Creeks, was deputized to go to every store in the town of St. Marys and buy up all the ammunition and powder still available to prevent African Americans and Native Americans from having access. Taking the threat seriously, Governor James Jackson issued a spirited proclamation that no Georgian could cooperate with this “vagabond and scoundrel” and expect support from the state.⁵⁶ It was the last nail in the coffin of Bowles’s Georgia adventure.

Among those arrested in St. Marys in the aftermath of this fiasco was the “notorious horse thief ” Bob Allen, the freebooter who passed back and forth between Florida and Georgia as opportunity arose.⁵⁷ Taken with him were “three vagabond negro men, (stiling themselves free) from their Town in the Lotchaway country,” according to local sources.⁵⁸ Their presence is of special interest since the Alachua chief, Payne, remained neutral in this contest. That three Black Seminoles in the surrounding villages of Alachua were participating with a man known as a horse thief in Georgia speaks to the network of relationships that made the region so unsettled and anxious.

Well aware of these efforts, Black Georgians responded to Bowles’s vision of a multiracial society. “Many negroes have allredy made an attempt to run from the Overseer, but have been taken,” a justice of the peace in St. Marys warned Governor Jackson.⁵⁹ The Spanish governor reported at least one fugitive from the state hiding on the Little St. Marys River only a short distance south of the border and speculated there were probably more.⁶⁰ The state of alarm in Camden County rose dramatically when two Black men sent by Bowles strode into town by themselves and announced that they had letters for the governor. They were summarily thrown into jail, then released when no evidence could be produced that they were anything more than couriers.⁶¹

The drawing power of Bowles’s vision was immense. A Camden planter showed a remarkable naiveté in writing to the director-general for his help in recovering Caesar, “a stout, likely young fellow about 25 years of age,” who had run away from his plantation and was said “to be in the vicinity of [Bowles’s] neighborhood.”⁶² When a Georgia planter asked for compensation for a slave supposedly kidnapped by the Creeks, Indian agent Benjamin Hawkins detailed the reality for a state official. The bondsman had in fact run away to East Florida but was intercepted as he passed through Creek country, perhaps caught by Natives eager for a reward. Slated to be returned to his master, he “confounded” the jailers and made good his escape to Florida. The African was later said to have been killed fighting alongside Bowles against the Spanish.⁶³ If the State of Muskogee showed no overt ideological opposition to slavery, its welcome of freedom seekers and determined opposition to American and Spanish expansion constituted a substantive challenge to that institution, to the very idea of organizing society according to racial hierarchies.⁶⁴

Although the State of Muskogee emerged as a multiracial, polyglot society that reached out to the marginal and disaffected, Kinache was pursuing his own agenda. He remained a traditional war leader rooted in hatred of the Spanish, devoted to older concepts of clan and family, and more than willing to use his son-in-law to achieve those long-standing aims. He provided a refuge to those alienated by changes in the Southeast, including young men from the Upper and Lower Towns—Coweta, Tallahasse, Apalachicola, “Hitcheta,” Uchee, “Ooseooche,” Oconee, “Eufaulau,” and “Oketeyeconne.”⁶⁵ A knowledgeable planter wrote to his wife that the newcomers included “an assorted pack from all the nations—Chiahas, Cowetas, Hitchitis and a number of High Creeks, who are American, as well as those of Alachua.”⁶⁶ Many among the Creek Indians were people convicted of crime or who came out of curiosity or saw an opportunity to fight when no such opportunity existed in their own towns. Whatever their motives, most Natives preferred their own towns and independence, not a fictive state with abstract powers.

After the initial taking of Fort San Marcos and its subsequent loss, Kin-ache planned a series of terrifying raids along the St. Johns that followed the traditional pattern: sudden surprise strikes, limited goals in terms of plunder, and no intention of killing white or Black people but with a focus on taking slaves as prizes. He went one step further. When Governor Enrique White arrested Mithology, Kinache’s cousin and confidant, for multiple misdeeds and locked him in nearby Fort St. Marks, an infuriated chieftain struck back.⁶⁷ Jack Kinnard had advised the governor to release Mithology or expect dire consequences, and in this he was accurate.⁶⁸ In August 1801, Seminole warriors swooped down on New Switzerland, the model plantation of Francis Phillipe Fatio, and carried off eight Black men, eight women, and twenty-two children. On his own authority, he had launched a raid that captured thirty-eight Africans as revenge against the Spanish government for the imprisonment of a valued member of his clan.

The matter was serious enough to prompt an attempt by the Alachuans to mediate matters. Bowlegs, Payne’s nephew, left his town to visit Mikasuki with horses loaded with goods supplied by Fatio in an effort to negotiate the release of the captives. Instead, Mikasuki warriors jeered him and asked why the owners of these people did not come themselves. Bowles stepped forward to disclaim any responsibility for the raid but then, in his grand theatrical style, proclaimed that the capture was legal since the Spanish were the ones who were stealing their “negroes, horses, and provisions.”⁶⁹ On returning, Bowlegs relayed that the “Negroes” were being kept all together and that a girl had died on the march and another was close to death. The captives were complaining of inadequate food, while Mikasuki families were bitter about the provisions they were having to give up to feed them.⁷⁰

In a second round of negotiations, Francis Philip Fatio Jr. accompanied Payne, leader of the Alachua Seminoles, to continue the delicate discussions. Taking full advantage of the occasion, Kinache and Bowles humiliated the young Fatio verbally, allowed his horse to be stolen, and made threatening noises to the point that the slaveholder feared for his life. A seemingly timorous Payne said nothing in the public assembly of warriors. Few of the bondsmen were ever returned. Records from the 1830s at the time of the Seminole removal to Oklahoma indicate that many of Fatio’s captives were still present, listed as slaves belonging to individual warriors.⁷¹

Nor was Kinache sated with the New Switzerland raid. When Governor White remained adamant in his refusal to release Mithology, his warriors struck again in January 1802 to force the governor’s hand. They broke into the modest home of a Majorcan family on the St. Johns River, where all but the father, Bonnelli, was present. The warriors killed the eldest son and took the wife of Bonnelli and their three daughters, one of the few instances where white people were kidnapped. The Indians seized ten enslaved workers on a neighboring plantation. The white family was eventually ransomed; the bondsmen remained.⁷²

Bowles could not sustain his charade of creating an independent state much longer. His base among the Seminoles and Creeks was rapidly contracting in the wake of his blatant failure to obtain English trading goods for Seminole towns as well as the many military setbacks he had experienced. A dramatic encounter in April 1803 revealed not merely his loss of standing but also the continuing influence of Creeks from the Lower Towns with the Mikasuki Seminoles. The influence of Kinache, mico of Mikasuki, and Kinnard, dominant figure among the Hitchiti-speaking Creeks, extended over a wide-ranging set of villages and settlements united by language, customs, and traditions. Kinache was the aggressive warrior, Kinnard the Machiavellian diplomat, constantly playing ends against the middle. Although known for his pro-American sentiments, Kinnard assiduously cultivated the governors of both East and West Florida and was called on to mediate multiple crises. Their overlapping leadership was part of a larger whole. Hunters hunted across the region. Towns were connected in various ways. And Hitchiti-speaking Seminole and Creek warriors sometimes participated in the same raids and shared the plunder as in the case of the attack on Trader’s Hill.⁷³

Kinnard and his two brothers shared a farm on the Wakulla River in Spanish Florida. The house on that farm became the site of an extraordinary meeting that revealed Kinache’s withdrawal of support for his son-in-law. Florida planters had hired a young Indian trader, Wiley Thompson, to go into various towns that held captives and negotiate a ransom. Only twenty-one years old, Thompson had the intelligence to travel first to Kinnard’s settlement on Kinchafoonee Creek among the Lower Towns to secure his blessings. The Scots-Creek was blunt. Not only was the going rate $50 for each captive, he also demanded a special fee for his warriors to travel from village to village in the attempt to free the captives. Present in the farmhouse were Thompson, the three Kinnard brothers, and Jack Kinnard’s son. Facing them were three Mikasuki warriors who sat glumly in a corner, William Augustus Bowles, and, most importantly, Jack Philips, a free Black accompanying the director of the Muskogee Nation. Philips had escaped from the Panton store at San Marcos.⁷⁴

With the Kinnards sitting beside him, Thompson offered to ransom Philips and return him to his enslaver. Clearly, this was a test case for the status of all fugitive slaves in the Florida hinterland. The scene swiftly descended into confrontation. With his accustomed brashness, Bowles announced that no Spanish enslaved person would be returned under any circumstance and warned that Thompson risked “losing his hair” if he should go in and make such foolish requests elsewhere. Jack Kinnard interrupted to insist that all Black captives be restored to their owners as stated in the Treaty of Coleraine as agreed to by the assembled chiefs. It was a pointed statement. No Seminole chieftain had in fact signed that document. He added that Bowles was the one whose hair was at risk. Kinnard’s brother Billy then ordered Jack Philips to be taken as a fugitive slave and clapped in irons. Bowles jumped up to shield Philips. John Kinnard promptly ordered his two brothers to seize Bowles while his son took a thick stick and began physically beating the defenseless man. The three warriors sat stoically in their corner, not budging, a certain sign that Kinache was no longer vested in his son-in-law. The taking of Philips and the chastising of Bowles underscored the erosion of the grand vision of an independent Indian nation and the hope for free Blacks in this community.⁷⁵

After the confrontation, Kinnard charged a brother-in-law and his own “confidential negro Joe” with escorting Thompson through various Seminole villages as the young trader negotiated for the ransom of captives. Out of as many eighty-two people, the trader obtained the release of only three. If Kinache refused to make the slightest bow to Spanish authorities or elite planters, the reality remained that Bowles’s ability to command had vanished. At a meeting of Upper and Lower Creeks in the meeting town of Tuckabatchee the following month, the adventurer was arrested and turned over to the Spanish. He died the next year in a cramped Spanish prison in Cuba.⁷⁶ The odyssey was over.

After Bowles’s removal, the old Spanish-Seminole alliance that had come apart in so short a time snapped back into place as Americans emerged as the preeminent threat to both groups. In Seminole towns, life resumed its normal rhythm if it had ever changed at all. In the long run, the addition of some eighty Black people taken as war captives and the continuing stream of fugitives only strengthened the emerging pattern of life. Black Seminoles farmed their own plots of land, owned their own livestock, and were free to sell cattle and crafts to the Spanish. When two free Black men from St. Augustine went through Seminole towns on a buying expedition on behalf of the Spanish government, they purchased 18 out of 125 from Molly, a fugitive from Georgia who owned the livestock and kept the proceeds for herself.⁷⁷ Women as well as men had these precious rights.

Of the men, William H. Simmons, a traveler through Seminole towns and a keen observer of customs, observed, “They dress and live pretty much like the Indians, each having a gun, and hunting a portion of his time. Like the Indians, they plant in common, and farm an Indian field apart, which they attend together.”⁷⁸ Enjoying relatively light servitude, Black Seminoles served as laborers, interpreters, and, increasingly, military auxiliaries. They retained their own cultural distinctiveness. Most intermarried among themselves. Many began to adopt Native Seminole dress, as Simmons testified, but others secured the plain cloth they had always worn. Significantly, they preserved their African roots through a creole language, speaking Hitchiti or Muscogee with the Seminoles and English with white Americans. Because of this cultural blending, it is difficult to make the argument that the Black Seminoles were in fact another example of maroons in the North American continent. There was sufficient interaction between the communities that usual definitions of marronage do not fit.⁷⁹

Yet their freedoms had limits. Black Seminoles did not live in an egalitarian society. On the most basic level, chieftains were open to returning fugitives if the ransom price was sufficiently enticing. James Cashen sent an Indian trader to Bowlegs Town to recover four of his people. Three of them had run away six years before. The trader was to offer $25 and, if this were not enough, to suggest trading cattle, perhaps as many as forty head per person. Cashen was prepared to ransom the fourth person, Jacob, only for money because he had fled a short time before and was not “corrupted” by years spent in a Seminole town. Twenty-two years old, Jacob had been born in Charleston and was described as “very knowing and talkative.” He was living in a hut with one of the earlier runaways by the name of Harry, suggesting that Jacob had been in communication with the former fugitives or had found a ready-made support system once he reached Seminole territory.⁸⁰ We do not know if Cashen was successful, but other efforts were.

As chiefs had become ranchers with substantial herds of cattle, they had begun to accumulate wealth and used those resources to buy enslaved people. When Spanish officials auctioned off the assets of those planters who participated in the 1795 rebellion, Seminoles were among the buyers. Kin-ache purchased an African American from Bahamian trader Richard Powers for $400 Spanish dollars. Payne, nephew of Ahaya and his successor, boasted that he owned twenty slaves.⁸¹ When the Black Seminoles were expelled from Florida in the late 1830s as a consequence of the actions of Andrew Jackson, the emigration records list only 18 free people out of a total of 390.⁸² Ironically, the title of “slave” indicated a dependent relationship that concealed considerable freedoms.

The red Seminoles and Black Seminoles were creating a relatively inclusive society unlike any other on the North American continent that defies easy categorization. Scholars continue to debate how to interpret the independence that the people of African descent enjoyed. They were certainly not maroons in the classical sense of that term if one considers that their existence did not include the full ability to shape their own lives but was qualified by dependence on a chieftain. Nor did they fall into the category of “half-slaves still owned,” as one contemporary argued. Their freedoms were too great to fit within the description of half-slave. Were they partners in an unwritten alliance with the Seminoles? Again, at the turn of the nineteenth century, they were still subject to being ransomed and returned to their original enslaver. Christina Snyder, historian and ethnologist, comes closer with her description of the Black Seminoles as junior members of the several chiefdoms, whose requirement of some form of tribute may have been a distant echo of the type of relationships that existed in Mississippian societies.⁸³ Of course, that junior membership came attached with many qualifications.

It is more likely that this unique people were at the beginning of a long, slow evolution toward becoming more like the Seminoles.⁸⁴ If one scratched the surface of any village, one would likely have found free people who had adopted certain Native customs, full-fledged slaves, runaways recently arrived like Jacob who held to their old way of life, and a few who had inter-married with Natives—in short, a diversity of conditions. In this setting, there was a degree of cultural blending on the Florida frontier that the Second Seminole War cut short.⁸⁵

The period from 1803 until 1812 marked the high point for the delicate balance that existed between Seminoles, fugitive slaves, and the Spanish government. East Florida reached a state of prosperity that exceeded the level in many parts of Georgia. In the course of the early years of the century, dozens of planters migrated to the colony and brought with them several thousand enslaved people. Large plantations built around the latest management techniques took shape. A slave trader and planter from the Caribbean, Zephaniah Kingsley, created a series of model plantations with cotton, orange groves, and fields of corn, peas, and sweet potatoes. A representative of a notable Georgia family, John Houstoun McIntosh, purchased much of John McQueen’s estate and moved his enslaved labor force across the St. Marys. Lumber, rice, and cotton were the primary commodities.⁸⁶

The newly founded town of Fernandina on Amelia Island, with its six hundred inhabitants, emerged as the major shipping port for commodities produced in Florida. The economic sanctions imposed by Congress on British commerce—the Embargo Act, Non-Intercourse Act of 1809, and Macon’s Bill #2—diverted a significant amount of trade into its harbor. Dozens of British ships were seen floating in the harbor, many visible from the town of St. Marys. While those vessels became a source of much anger on the American side, Floridians were pleased with their newfound prosperity and had little desire to risk their affluence in asking for change.⁸⁷

Inland, the Seminoles benefited from the upheaval of the Bowles era by the influx of warriors, war captives, and fugitive slaves. Payne and Kinache continued as the acknowledged leaders among the loosely connected network of Seminole towns or settlements. The relative prosperity of the towns was indicated by the amount of cattle, deerskins, and other commodities sold to the Spanish through the Panton, Leslie & Company stores in northern Florida or to Cuban fishermen in the Tampa Bay area. Free Blacks from St. Augustine often conducted the trade in cattle, traveling through Indigenous settlements for weeks at a time.⁸⁸

That prosperity came to an abrupt end as southerners awoke to the vacuum of power on the Georgia border and the opportunities that it presented. The idea of a march on St. Augustine had always been popular in Georgia and a seemingly logical outcome to the issue at hand. Georgians never questioned their notion that the Spanish government was a corrupt, inefficient bureaucracy responsible for the lawlessness that prevailed in the St. Marys region. They feared the status of the Catholic Church in a society that violated deeply rooted American beliefs about the separation of powers. Above all, they deemed dangerous a legal system that recognized enslaved people as human beings holding certain legal rights. For proof, southerners had only to look at East Florida as the ultimate sanctuary for runaway slaves and a haven for an armed Black militia. White Georgians had no intention of tolerating the Spanish deployment of Black soldiers, “the vilest species of troops” in the words of Maj. Gen. John Floyd.⁸⁹

The balance of power in the Southeast was now shifting. For Georgians, the Seminoles were the most pressing issue. Bands were slipping into Camden County and stealing livestock without residents being able to cross the Georgia-Florida border in pursuit. Towns were continuing to shelter Black fugitives whose semi-independence presented a frightening example for their slaves. Seminole chieftains were now acting in alliance with the Spanish government as an effective buffer against American expansion. In the opposite direction, the presence of British vessels in Fernandina was a direct affront to America’s defense of the freedom of the seas and an implied threat to control of the land. As war came closer, it seemed possible, even probable, that Great Britain would take possession of Florida from a faltering Spanish state already in the hands of Napoleon. Georgians heartily subscribed to the belief that the region east of the St. Johns River and the fertile lands of the Alachua Seminoles were ready for incorporation into the Empire of Liberty.⁹⁰

In 1810, those hopes took a more tangible form. Settlers in the Baton Rouge district of the Louisiana Purchase rose up against their Spanish rulers and staged a mini-revolt that put President James Madison in position to secure the cession of a portion of West Florida to the United States. The valuable lands stretched from the Perdido River in today’s Alabama to the Mississippi River and included the towns of Mobile and Natchez. Madison’s idea of “conquer without war” seemed a promising template for East Florida and well within their grasp.

The president asked George Matthews, the former governor of Georgia who had engineered this striking success, to hold a similar conversation with the governor of East Florida and suggest to him a peaceful transfer of power. When the Spanish governor stood firm and refused to betray his country, Matthews went to St. Marys on the Georgia-Florida border and whipped up an impromptu rebellion of a handful of settlers with grudges against Spanish authority. A tiny force of Anglo-Americans in Florida and land-hungry adventurers from Camden County occupied Amelia Island on March 12, 1812. Taking over the port from a frightened Spanish garrison, the self-styled patriots created a shadow government clumsily named the Board of Officers for the Constituted Authority of East Florida. Units of the Georgia militia soon followed to back them up. American naval units hovered off shore, and one hundred men from the federal garrison at Point Peter joined in despite the fact that they had no orders to do so. Madison preferred to overlook the matter.⁹¹

From Fernandina, three separate columns of Americans fanned out across northern Florida to complete the occupation in what appeared to be a surprisingly easy task. Several hundred young men, eager for land and slaves, planted themselves in front of St. Augustine, ready to march into the town. One hundred U.S. troops set up camp two miles north of St. Augustine. Units from the Georgia militia positioned themselves on the St. Johns River near the strategic crossing known as Cowford. In total, eight hundred American troops were scattered across East Florida, with little coordination among them. Refusing to be intimidated by this show of force, the newly appointed governor of East Florida, Sebastián Kindelán, retreated with his forces inside the virtually impregnable walls of the fortress at St. Augustine, where he commanded a regiment of Cuban soldiers, four hundred Pardo (mestizo) and five hundred Moreno (Black).⁹²

The declaration of war on Great Britain in June rendered moot any thought of committing U.S. troops to a border war started by Americans. The president ordered the federal troops not to engage in any offensive action but declined to order a withdrawal, leaving the lone unit on its own. Caught in a web of their own making, President Madison and Secretary of State James Monroe could not bring themselves to make a clean break and so pursued a policy rooted in ambiguity, making worse an already tragic situation. The three different commands were left sitting in possession of most of northern East Florida without clear guidance.⁹³

Eager for action, officers judged that the orders not to engage in offensive action did not apply to the Seminoles and that eliminating the threat from Indigenous people was now a reasonable goal. Maj. Gen. John Floyd, an otherwise cautious man, wrote to an approving Senator William H. Crawford, “An Indian uprising would afford desirable pretext for the Georgians to penetrate their country and Break up a Negro Town; an important Evil growing under their patronage.” He judged, “The Number of these Negroes from the lowest calculation Exceeds 500.”⁹⁴ The general’s estimate was probably near the mark.

In an instant, the war aims dramatically shifted. Destroying Seminole towns and eliminating the Black Seminoles were easy goals to justify, at least in the minds of Georgians frustrated by two decades of inaction. The army commander, Lieutenant Colonel Smith, lent his authority to the conspiracy theories floating about: “[The Seminoles] have, I am informed, several hundred fugitive slaves from the Carolinas & Georgia at present in their Towns & unless they are checked soon they will be so strengthened by desertions from Georgia & Florida that it will be found troublesome to reduce them.”⁹⁵ The governor of Georgia, David Mitchell, upped the stakes. The campaign in Florida was a necessity, he told the president, because the “insolence” of its Negro population threatened to induce rebellion among the Black population in Georgia.⁹⁶ “It is also a fact,” he told Monroe a few days later, “that most of our negroes on the Sea Board are restless and make many attempts to get off to St. Augustine, and many have succeeded, which renders it necessary to have constant guards and patrols.”⁹⁷

In many ways, it was a self-fulfilling prophecy. By the end of 1812, in the midst of the Patriot War, Black men originally from Georgia found themselves fighting white Georgians and besting them in critical engagements. They showed themselves an organized and disciplined fighting force capable of standing up to the American military. The first encounter took place at Twelve Mile Swamp in an ambush of supply wagons guarded by marines making their way from outside St. Augustine to a resupply station on the St. Johns. Thirty-two Black Seminoles joined with six Native Seminoles and twenty-five men from the free Black militia to waylay the wagon train and inflict a stinging defeat on the marine unit. Of the twenty-two men with the commander of the marines, Capt. John Williams, eight were wounded and one died, and Williams himself succumbed to his multiple injuries less than two weeks later.⁹⁸ It was a humiliating and unequivocal defeat for federal forces.

In the main encounter, Col. Daniel Newnan, commander of the Georgia militia, led 116 men and an African American boy in a retaliatory raid on Paynes Town. His troops were a collection of state militiamen whose enlistment was about to expire, federal soldiers, and a handful of patriots who volunteered to guide. A few miles from the town, the party encountered a band of Seminoles who were filing down the same path unaware of the approach of the enemy. In the accidental encounter, a fierce gun battle took place that lasted seven days. Newman’s forces retreated into a crude shelter they erected and survived on limited provisions. Several men were killed and many more wounded. A desperate retreat enabled the beaten soldiers to make it back to the remaining American forces. Writing a long report to Governor Mitchell, Newnan offered a remarkably balanced account of how his men fought three engagements and suffered through a week of intermittent sniping. He observed tellingly, “[The] negroes . . . are [the Seminoles’] best soldiers.”⁹⁹

Newnan’s comment is notable. The Black Seminoles gave the Indians a competitive edge and inspired a wholly new kind of fear among white Georgians as word spread. Despite the small numbers involved, the American military had suffered a major blow. Black soldiers and warriors, many of them former fugitive slaves, had shown themselves the equal of U.S. marines and provided a stunning challenge to the racial stereotype that Blacks could not fight. The short war revealed how the role of the Black Seminole had evolved over the preceding twenty years from interpreters and cultural brokers to fighters in the Mikasuki War to the disciplined warriors of the Patriot War capable of holding their own against federal troops and Georgia militiamen. Native and Black warriors, in concert with Spain’s Black militiamen, had undone the half-hearted patriot rebellion and its attempt to take possession of Florida.

Retaliation came quickly. In January 1813, U.S. Army troops and the Georgia militia, together with Tennessee volunteers eager to fight, marched into East Florida with several hundred men to extract a final settlement with a troublesome Native American polity.¹⁰⁰ The surprise was on the Americans. The entire population of the Seminoles on the Alachua Plain had melted away into the swamps and thick understory of the land, leaving their villages deserted. Nor were the escaped slaves who populated the “Negro villages” to be found. However, the army exacted revenge by virtually destroying the Seminole economy. According to the official record, the troops burned 386 houses, took away three hundred horses and four hundred head of cattle, consumed or threw away between fifteen hundred and two thousand bushels of corn, and spoiled or carried back two thousand deerskins, the most important medium of exchange for the purchase of goods through Panton, Leslie & Company. The first steps in the cruel removal of the Seminoles to Oklahoma in the 1830s had been taken.

With the destruction of the Seminole towns and Negro villages, the Patriot War effectively ended, but the ramifications were immense, not only for the Seminoles but also for Spanish East Florida. The government in St. Augustine reestablished its authority slowly and only with difficulty in the face of outlaws who roamed the northern part of the colony with impunity for several months and a plantation economy that stood in ruins. The naked aggression of the United States laid bare the desperate condition of Florida, with its lack of support from Madrid, its dependence on a Black militia in an increasingly racialized South, a nearly bankrupt treasury, and an Anglo population of decidedly mixed loyalty. That lesson fed the spate of rumors running through the Georgia Lowcountry about the heightened dangers of slave insurrection at a moment when coastal rice and cotton plantations were still trying to digest the infusion of enslaved Blacks from Africa, the Chesapeake Bay, and the French Caribbean.¹⁰¹ It was a distinctly unsettled moment as planters along the Georgia coast increased surveillance over the lives of their enslaved people as they introduced more efficient means to increase production in a rapidly changing Atlantic economy based on cotton.