Empires of Crap - Billy Bowles: Teen Prince Of Florida

Imagine if a person tried to live their dreams only to discover that they actually were a charismatic leader, a talented pirate, and a surprisingly good escape artist. That's the story of Willam Augustus Bowles, aspiring King of Florida, who lived one of the coolest lives of the 18th century before his own delusions of grandeur ate him alive ...
Empires of Crap - Billy Bowles: Teen Prince Of Florida

Do you remember that one kid in your class who was always claiming his uncle worked at Nintendo's secret sex robot division? Do you have a friend who uses the phrase "and then I escaped with the warlord's daughter" in every story? Are you now, or have you ever been Steven Seagal? If so, you'll be familiar with the concept of the fantasist, somebody who gets so invested in dreams of their own greatness that they start to believe that they're real.

Now imagine if that person tried to live their dreams only to discover that they actually were a charismatic leader, a talented pirate, and a surprisingly good escape artist. That's the story of Willam Augustus Bowles, aspiring King of Florida, who lived one of the coolest lives of the 18th century before his own delusions of grandeur ate him alive ...

The Great Escape (Of 1798)

Back in 1798, a British naval frigate named the Pearl was cruising off the coast of West Africa, hunting for French or Spanish shipping to prey on. In March, the Pearl seemingly stumbled on a rich prize when she encountered the Spanish cargo ship Concepcion, anchored in a quiet channel between two islands off Guinea. Unfortunately for the Pearl, the Spanish weren't alone. Two French warships, hired at great expense to protect the Concepcion, slipped anchor and approached the Pearl from either side of the channel. With the French bearing down, the Pearl's captain knew he had no time to turn and escape. Instead, he decided to run the gauntlet and sail directly between the French ships in the hope of making it through the channel and escaping into the open ocean. 

Over the next 90 minutes, the Pearl was raked with cannon fire along both flanks. Her rigging was ripped to shreds, her foreyard splintered, and gaping holes were torn in her hull both above and below the water line. But the wind was at her back, and she eventually cleared the channel and fled north, with her crew frantically pumping out water and a French frigate in hot pursuit. Incredibly, she outpaced her enemy until nightfall, when she slipped away under cover of darkness and made for the nearest British port. Her crew doubtless breathed a sigh of relief, happy to have survived a fierce but ultimately insignificant encounter in the wider Atlantic battleground.


"Well, it was a tough battle, but I think we can salvage her."

But as it turned out, the Pearl didn't pull off the most impressive escape that day. Unbeknownst to the British, the Concepcion was actually carrying one of the Spanish empire's most notorious political prisoners -- a man considered so dangerous he had spent the last five years being shuttled between prisons and fortresses as far-flung as Cuba, Spain, and the Philippines. On board the Concepcion to face further charges in Madrid, he had already attempted at least one mutiny and was being kept under close watch. But with the crew distracted by the battle with the Pearl, the prisoner shimmied his emaciated frame through a narrow porthole and dived unnoticed into the waters below.

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The Return Of The "King"

A year later, an American surveyor was charting the border between Spanish Florida and the United States when he was surprised to encounter a British naval vessel shipwrecked on the reefs off Dog Island. On board, he discovered William Augustus Bowles, the same prisoner who had escaped the Concepcion off the coast of West Africa. Using the wrecked ship as his headquarters, Bowles announced that he was declaring war on Spain, proclaiming, "We the Director General of Muskogee ... declare war against his Catholic Majesty and his subjects and order that a general reprisal be made by both land and sea the goods, ships and subjects of his Catholic Majesty."

Francisco de Goya

“As you can see, our agents have already infiltrated the palace and brutally given his majesty this haircut.”

Before long, a series of sudden and unexpected attacks were reported on ships and trading posts in Spanish Florida. The culprits were a multiethnic band of escaped slaves, Native American warriors, and West Indian mercenaries -- the former allies rallied by Bowles to support his cause once more. Bowles himself led an attack on the key fort of San Marcos, capturing it and burning it to the ground. Meanwhile, groups of "Indians, Negroes and vagabond white men" were reported attacking plantations in East Florida, freeing slaves and carrying off weapons and horses.

Panic quickly set in. The Spanish ordered that Bowles should be found and "executed on the spot." The Americans ordered their local agents to take "every justifiable measure" to stop him. British traders surrendered their outposts and fled. And from the swamps of the Everglades to the merchant boardrooms of the Bahamas, the news on everyone's lips was that Billy Bowlegs, self-proclaimed teen prince of Florida, was back to seek revenge on all those who had wronged him. 

William Bowles: Teenage Warlord

William Bowles was born in rural Maryland in 1763 or '64 (accurate record-keeping being somewhat difficult in an era when calendars were also the only widely available source of toilet paper). Like many Americans, Bowles was a fervent British loyalist who was horrified by the outbreak of the American Revolution. Naturally, he decided the best way to show his support for the crown was by running away from home and signing up to fight for the British Army at the age of 13 or 14. He even managed to get an officer's commission because the 18th century saw no problem with entrusting key battlefield decisions to a squeaky-voiced child in the middle of losing his own personal war on acne.

Library of Congress

“Stowm the bawicades!”

As it turned out, Bowles took to military life like a duck to concrete, frequently being censured for unauthorized absences and insubordination (teenagers!). In 1778, his regiment was sent to Florida, a troubled backwater that had only been ceded from Spain to Britain fifteen years earlier. It was here that the final break took place, with Bowles apparently deserting from the fort at Pensacola and storming off into the wilderness, apparently hoping to live out some kind of Dances-With-Gators fantasy amongst the local Native Americans. Three days later, some local Creek men came across a half-naked, starving white kid stumbling around looking for berries. Figuring they had better shut this down before some kind of Mark Twain novel broke out, they invited Bowles back to their town.    

Somewhat inexplicably, Bowles flourished among the Creek, marrying the two beautiful daughters of two separate chiefs. Meanwhile, Spain had joined the Revolutionary War and was making a determined attempt to seize Florida back, since ruling a vast South American empire is pretty much meaningless if you don't have Tampa as well. Bowles persuaded some of his new friends to back the British and appeared, still a teenager, leading a band of Creek warriors at the battles of Mobile and Pensacola late in the war. It was around this time that he began going by the name Estajoca, which he claimed was a distinguished Creek honorific, even though it actually just means "white boy."

Thomas Hardy

The original crazy-ass white boy. 

History experts (or "past perverts" as they prefer to be known) will be aware that the British did not win the Revolutionary War. Florida was ceded back to Spain, and Bowles fled into exile in the Bahamas. And that's when things got weird. Around 1788, he reappeared in Florida, declaring himself "Director-General of the Creek Nation" and claiming to lead an independent Native American "State of Muskogee." Absolutely no Natives had asked him to do this, but Bowles was nothing if not a talker, and he gradually began to pull support together for his schemes. To understand what he was trying to do, you first have to understand the deeply bizarre situation in Florida at the time. 

The Twink Buccaneers Of Old Florida

In the late 1700s and early 1800s, Florida was caught in a game of imperial pass-the-parcel, being repeatedly handed between Spain and Britain while weathering occasional attacks from American freebooters seeking to annex it on behalf of the United States. This unstable atmosphere meant that Florida became a hotbed of intrigue and the destination of choice for schemers and adventurers from all four corners of the globe. Basically, if you were looking to set yourself up as a king at the start of the 19th century, Florida was where you went to die trying it. 

Let's take Amelia Island -- everyone else tried to. In quick succession, this small island in northeast Florida was occupied by forces loyal to former Georgia governor George Matthews, Scottish con artist Gregor MacGregor, and French pirate-king Luis Aury. Each had their own insane plan for the island -- Matthews wanted to found a new state that could be annexed by the US, Aury needed a new base to raid Spanish shipping after being forced out of Galveston by fellow pirate Jean Lafitte, and Gregor was supposedly a revolutionary, but really just wanted to steal the money he had raised to free Florida from Spanish control. Each saw their plans collapse in the general chaos of Florida, although Gregor did at least get away with a pile of cash. He later returned to Britain, where he became notorious for selling land grants in the fictional South American country of Poyais, leading to hundreds of eager Brits dying in the jungles of Panama while searching for their supposed land.

Louis Michel Aury

You know if you cast Timothee Chalamet as a 19th-century pirate king people would say it was unbelievable, and yet here’s Aury.

The general chaos meant that various Native American alliances were left unbothered in control of most of the state. There were also large free Black communities in the north, who were regularly reinforced by escaped slaves from the American South. Both of these groups were regarded with horror by the emerging United States, who were particularly disturbed by the well-trained Black army operating out of the so-called "Negro Fort" in the Florida Panhandle because America operated on a strict "no cool shit allowed" policy until like 1861.

But the real power in Florida was held by two men. Alexander McGillivray and William Panton, who were essentially running a massive scam on the whole region. McGillivray was the son of a wealthy Scottish trader and a politically influential Muskogee Creek woman. Ruling over a massive plantation worked by hundreds of Black slaves, McGillivray was a classic schemer, using his connections to both Native and European society to establish himself as the key negotiator between the two, allowing him to play both sides for his own benefit. When colonial governors opposed him, he threatened unrest among the Creek. At the same time, he was threatening his Native rivals with European reprisals unless they followed his advice. 

John Trumbull

Sadly McGillivray and Aury never met face-to-face and immediately formed the hottest boy band in Spanish Florida.

Meanwhile, Panton was the founder of Panton, Leslie & Company, a Bahamian trading company active in Florida. But what nobody else knew was that McGillivray was secretly a partner in Panton's company. McGillivray used his influence with the Spanish to have Panton given a monopoly on all trade with Florida's Native Americans. And Panton then used his control over key imports to reinforce McGillivray's power over the Creeks. It was the classic two-man hustle. The only losers were Florida's Native Americans, who were forced to buy shoddy goods at high prices while receiving well below market rate for their theoretically lucrative deerskin exports. 

12th-Century Welsh Princes In Florida History

So Florida was a china shop with about nine bulls in it when Billy Bowles suddenly came crashing through the window on a tank. Adopting "imperial" pretensions, Bowles declared himself "Director-General of the Muskogee Nation" and began writing letters to every king and governor he could think of, demanding recognition for his new state. Under normal circumstances, he would have been led into a pleasant room with no sharp objects and encouraged to take up watercolors, but these were crazy times. Upper Creek chiefs saw Bowles as a useful proxy to test the power of the Lower Creek McGillivray and his Spanish friends. And Panton's business rivals in the Bahamas saw the new state as a way to overturn his Spanish trade monopoly. Meanwhile, a number of free Blacks saw a British-aligned Muskogee Nation as a useful barrier to the looming US invasion. And so, against all the odds, Bowles found himself with financial backing and an army.

Wiki Commons

He also got himself a flag with an extremely stoned sun on it.

To be clear, Bowles' letters suggest he was either a pathological liar or actually mildly deranged. But he was like the guy who thinks he's a beaver on the day the town's only ax breaks -- everyone was suddenly very interested in the exact delusion he was selling. And to general surprise, Bowles turned out to be pretty good at generaling, launching a series of raids on Spanish interests and capturing Panton's chief trading post, allowing him to distribute goods and weapons to his followers. But Bowles knew he would need foreign backing for his new country. Which is why in 1790, he slipped past the Spanish fleet and appeared in London, dressed in feathers and buckskins and talking about Medieval Welsh princes

By tradition, every European country has to have one ancient explorer they claim reached America before Columbus. Ireland has St. Brendan, Scotland has the Earl of Orkney, and of course, everyone in England celebrates the voyages of Darren the Liar. But Bowles arrived in Britain during a rival of interest in Welsh history and culture, particularly the story of Madoc, a 12th-century prince who supposedly sailed off to settle a new land to the west. To drum up interest in his new country, Bowles claimed to have encountered a bunch of Welsh-speaking Native American tribes, who surely must be the descendants of Madoc's original expedition. 

Incredibly, this worked (someone even rushed out a hit poem based on Bowles' stories). And the Welsh weren't his only new friends -- Bowles was a big hit in London, parading around in elaborate costumes accompanied by six Florida chiefs. He was feted in high society and met with the Crown Prince, securing promises of free trade for his new state. Unfortunately, Britain had just resolved a crisis with Spain over Nootka Sound, an area of British Columbia that was considered priceless because it didn't have Vancouver on it at the time. The British were unwilling to risk a fresh confrontation over Florida, and Bowles was forced to return without any offer of military assistance. 

Meanwhile, the Spanish had worked out Bowles' weakness -- his insane ego. They invited him to a high-profile meeting with the top governor in the region. Confident that he was finally getting his due respect, Bowles boarded a Spanish ship to New Orleans and was very surprised when he was immediately clapped in irons. He spent the next five years shuttling between prisons as far afield as the Philippines, causing trouble wherever he went, until staging his famous escape during the Pearl's attack. 

Karen Roe

Dramatic moment when the Spanish captain tore down Bowles’ Rita Hayworth poster to reveal this.

Pirates Of The Caribbean

After escaping his prison ship, Bowles swam to an American trader anchored nearby, who helpfully dropped him at the British colony in Sierra Leone. By this time, the situation had changed, and Britain was once again at war with Spain. Bowles seemed useful as a disruptive force, and the British agreed to return him to Florida aboard the HMS Fox, which subsequently ran aground off Dog Island, providing Bowles with an aquatic fortress to launch his war against Spain. His old allies rallied to him from across the state, and Bowles was soon conducting a major campaign against Spain, causing the local US emissary to predict that the "whole property within power will change owners."

Estajoca (as he preferred to be known) was so serious about his new country that he even formally incorporated a navy, equipping the fast cutters Tostonoke and Mackisuky with elaborate letters of marque, commissioning them to attack Spanish shipping throughout the region. The pair quickly proved highly effective, and Bowles incorporated many of the captured ships into his growing fleet, allowing him to carry out amphibious operations across the region.  Fortunately, this was the last time very fast boats would be used to do something illegal off Florida.

Louis Le Breton

Fortunately, this was the last time very fast boats would be used to do something illegal off Florida.

The Decline And Fall Of The Imaginary Empire

With Bowles threatening St. Augustine, the Spanish were in a panic, and McGillivray was practically hysterical. Although McGillivray retained his power base among the Lower Creek, he could sense his influence among the Upper Creek and Seminoles slipping away. In fear, he turned to local supervillain Benjamin Hawkins. As the US Indian Agent in Creek territory, Hawkins was the senior American official in the area. A thorough racist, he had turned his agency into a base for hunting fugitive slaves throughout the Floridas, paying Native bounty hunters $50 a head for every slave captured. Bowles' abolitionist stance was a threat to this operation, and Hawkins swore to bring him down. But Bowles faded into the swamps, evading every attempt at capture. McGillivray and Hawkins were at their wit's end when suddenly the perfect opportunity came along. 

In 1803, a great conference was held in Tukabatchee, one of the chief Creek towns. As well as the Creek council, the meeting was set to be attended by the leaders of the Cherokee, Choctaw, Chickasaw, and Seminoles. Located across the border in the US, Tukabatchee was firmly in McGillivray and Hawkins territory. But Bowles' giant ego once again got the better of him. As Director-General of Muskogee it was inconceivable that he would miss such an important gathering! In fact, he actually wrote to friends that he expected to be appointed king over all the southern tribes there. And so when the chiefs assembled, they were surprised to see William Bowles stroll into town, accompanied by a heavily armed Seminole bodyguard.

Hawkins reacted first, demanding that Bowles be arrested and placed in his custody. To his shock, the council demurred and invited Bowles to make his case. And it was here that Bowles' second giant flaw reared up: his pathological lying. For months, Bowles had been promising his followers that the British would support them with weapons and ships. And they initially had no reason to doubt this -- Bowles had been delivered back to Florida on a British ship, and the Redcoats certainly looked kindly on his anti-Spanish piracy. But as time went on, people had started to realize that a full British expedition wasn't coming.

Thomas Lawrence

These guys? Untrustworthy? Whaaaat?!

So at the conference, the chiefs were skeptical when Bowles repeated his claims of British support. Not being idiots, they asked to see some written documents from the British government before they effectively declared war on Spain and the US. Bowles was forced to admit that he had none, and the mood turned. Not without a certain sense of sadness, the council allowed Hawkins to clap the Director-General in irons. Incredibly, Bowles quickly escaped once more, but he was in hostile territory, and Hawkins' experienced slave trackers eventually ran him down and re-arrested him. Extradited to Cuba, he died in prison two years later, at the age of 41 or 42.

The wild old Florida that Bowles loved ended in 1816 when American troops crossed the border and attacked the free Black stronghold at the "Negro Fort." Shortly afterward, Andrew Jackson led a major invasion, kicking off the bloody Seminole Wars. Florida was officially ceded to the US in 1819, and most of the Creek and Seminoles were forcibly removed to Oklahoma in the 1830s. Those who remained were forced to scrape a living in the same swamps where Bowles had once evaded his Spanish pursuers. 

In the end, Bowles was the wrong man on the right side of history. Although a lifelong fighter against slavery and Native oppression (plus a hell of an escape artist), he was also a fantasist, a serial liar, and suffered from a white savior complex so bad you couldn't get him off the crucifix with a crowbar. But while it was obvious to everyone else that Bowles was never going to be crowned king of Florida, he did manage to get a surprising amount of traction for a while, proving that if you perfectly time your craziness to match wider political forces, you can get people to humor you long enough to make your mark on history. And if that isn't a little bit inspiring, then we don't know what is. 


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