Billy Bowlegs: Truth, Fiction and a Good Story

Captain Jack Sparrow is once again buckling his swash across the world’s cinema screens, this time tangling with a fictional version of the very real Blackbeard. This weekend, locals and tourists in Fort Walton Beach, Florida will don their eye patches and bandanas, and brandish their cutlasses and muskets in mock battle. The season of pirates be upon us.

Fort Walton’s Billy Bowlegs Pirate Festival owes more to the machinations of commerce than to factual history, it turns out. The festival purports to celebrate the misdeeds of William August Bowles, a.k.a., Billy Bowlegs, a pirate of the late 18th century. Most historians point out that not only did Bowles never use the nickname Billy Bowlegs, there’s no indication he ever set foot in what is present-day Fort Walton Beach.

Yet for nearly six decades, the people of Fort Walton have famously associated Bowles with a name, look and reputation that aren’t necessarily his. To get to the bottom of this, let’s have a look at the real William Augustus Bowles, the name Billy Bowlegs and how the two got mashed together into a four-day summer hootenanny at the beach.

General William Augustus Bowles

William Augustus Bowles - insubordinate, comedian, pirate

The real William Bowles was by all accounts a charismatic, egotistical schemer born in Fredericksburg, Maryland in 1764. Like a Real Southern Man, he often found himself embracing a losing cause. First, he fought on behalf of the English during the Revolutionary War, earning – and later losing due to insubordination – a commission in the British Army.

He was given the boot while his regiment was in Pensacola. There he stayed until joining a band of Creek Indians who had visited for their annual gifts from the British.

He lived among the Creeks for some time, eventually marrying the daughter of the chief and becoming heir apparent to his father-in-law’s chiefdom. (He also married a second wife, a Cherokee. There are no doubt untold accounts of more lost battles…within his own house.)

When, in 1781, Pensacola became a battleground between British and Spanish forces, Bowles led a band of Creek warriors there to fight on behalf of the British. Again, Bowles met defeat. His valor and leadership, however, afforded him reinstatement in the British army at his former rank. (Decoration and commendation for valor in loss? Sounds about like a Southern man.)

His time with the Redcoats was again short-lived, and Bowles retired from their service in New York. There he joined an acting troupe and traveled to the Bahamas, where he did split duty as a comedian and portrait painter. Comedians and painters must hold greater sway in the Bahamas than elsewhere, as Bowles was contracted by the Bahamian governor, Lord Dunmore, to establish trade with the Creek. Doing so meant trying to break the stranglehold the Spanish held on Creek trade through the firm Panton, Leslie & Co. That, of course, was a losing cause.

A key partner in Panton was Alexander McGillivray, a Creek leader who later united the fractious Creek and Seminole nations to resist European and American expansion. He was not only a Panton partner, but was also paid by both the Spanish and American governments for his influence over the Creek nations. Colonel McGillivray offered Bowles a choice: keep his trading post or keep his ears. Bowles must have been fond of hats, as he chose the latter.

According to an excerpted article from the Historical Collections of Georgia, he returned to England, declaring himself an ambassador of the Creek and Cherokee nations, and sought aid in repelling what he described as American aggression. Successful in his plea, Bowles returned to America. Rather than setting his sites on alleged American aggressors, Bowles began a campaign of piracy and land raids against Panton, the trading partner of Creek rival McGillivray – a company founded by British loyalists like himself. Further heightening the irony that was the life of William Bowles, his exploits only gained him fame and favor with the Creek, and he became commander-in-chief of Lower Creek armies.

The Spanish, who had authorized Panton’s trade in the region, were furious. A price of $6,000 and 1,500 kegs of rum was placed on Bowles’ head. Bowles was soon a prisoner of Spain and gained an audience with none other than its sovereign, King Charles IV. Charles was unable to sway Bowles toward a change of sides, presumably as a Spanish privateer. Bowles was transferred to the island of Manilla. Not only did he escape, but he commandeered a schooner and crew to resume his pirating ways, targeting primarily Spanish vessels. Top that, Jack Sparrow.

He returned to the Creek, resuming his profession of undermining McGillivray as well as the reconciliation efforts of Colonel Benjamin Hawkins, General Superintendent of Indian Affairs. He did so by founding the short-lived sovereign nation known as the State of Muskogee. Commissioning privateers – British captains, mostly from Nassau, with crews of mixed race and nationality that included frontiersmen, Creek warriors and former slaves – he continued his campaigns against Spanish vessels.

Even the greatest of comedians can become tiresome for an audience that has seen his act one too many times. Such must have happened with Bowles and the Creek. No longer amused by the anti-authoritarian antics of Bowles, they invited him to a tribal council where he declared himself the “Chief of all Indians Present.” The self-appointed chief was summarily arrested by Col. Hawkins and John Forbes, one of the original Panton partners.

En route to Mobile, Bowles pulled one last daring escape by chewing through his bindings and stealing a canoe under cover of night. Failing to cover his tracks, he was quickly caught again the next day. Soon thereafter, he was transported from Mobile to Castillo del Morro in Havana. Refusing to eat, Bowles died in the dungeon there two years later.

The “Real” Billy Bowlegs(es)

No doubt William Bowles lives up to the reputation of a notorious pirate and ne’er-do-well – though perhaps more fanciful than fearsome. But from whence came the name? There are no less than five possible candidates, all of whom had a history in Florida as well.

Holata Micco, a.k.a. Chief Billy Bowlegs

Holata Micco (Seminole for “alligator chief”) was born a few years after the death of William Bowles. Called Billy Bolek in English, his nickname became Billy Bowlegs. Descended from a line of Seminole chiefs, Bowlegs rose to power during the Second and Third Seminole Wars. Following the death of Micanopy (his uncle) and the defeat of Osceola, Bowlegs’ warriors remained the most fearsome force of the Seminole tribes. The U.S. government recognized the symbolic power of Bowlegs and brought him to D.C. following the cessation of hostilities of the Second Seminole War – primarily to awe the other Seminole chiefs present.

After several years of peace, Bowles was provoked by government agents and began raiding the villages of Florida settlers. These sporadic attacks became known as the Third Seminole War. Using guerilla warfare tactics, Bowlegs was largely successful. But with growing pressure from other notable chiefs and the promise of a sizable payday, Bowlegs and his band of 123 Seminole finally agreed to relocate to Indian Territory in Oklahoma in 1858.

Following the death of Chief Bowlegs in 1859, Sonuk Mikko, a Seminole warrior in the Indian Territory, adopted the nickname Billy Bowlegs for himself. He enlisted as a captain in the U.S. Army during the Civil War, leading Company A of the Indian Home Guard in many successful engagements. He died of small pox before war’s end.

Billy Fewell, a.k.a. Billy Bowlegs III

A third Billy Bowlegs arose in the late 19th century. Born Billy Fewell in 1862, this Bowlegs was the son of a black man and Seminole mother. The grandson of Chief Osceola, he learned the ways of his mother’s people. He became an elder in the tribe and a prominent Seminole historian in Florida. Living to a ripe, old age of 103, Fewell would have been a well-known representative of the Seminole people at the time of the founding of the Billy Bowlegs Festival in the 1950s.

Other accounts point to the pirate William Rogers, one of Jean Lafitte’s men, who was known as “Charlie Bowlegs” among his crew members. Some accounts claim that William Rogers was not called Charlie Bowlegs, but Billy Bowlegs. Treasure hunters speak of this Bowlegs in excited, hushed tones, spinning tales of a scuttled ship laden with treasure and secret tunnels filled with gold. At least one account claims Rogers was the original namesake of the Billy Bowlegs Festival, but that the attribution was changed to recognize Bowles following desecration of Rogers’ grave and complaints by his heirs.

That story, however, is muddied by yet another potential Billy Bowlegs namesake, a 19th century cattleman from Mary Esther, Florida named Jesse Rogers. A bit of a recluse, suspicion about the man and the source of his fortune (and perhaps some confusion with the real pirate of the same surname) led many to believe him a pirate. Local historians point out that Jesse Rogers’ remains had to be moved to a private cemetery following repeated desecration by treasure seekers.

One thing is certain. The Billy Bowlegs Pirate Festival was founded by Fort Walton Jaycees for a very simple reason: tourism. Planned to coincide with an annual water ski show, the pirate-themed festival seemed a perfect fit for a West Florida beach town. Far be it from Real Southern Men to let such a trivial thing as historical fact get in the way of a good story…or a good party.

Whether those early planners only did sketchy research, misremembered their local history, changed the name to protect the innocent or simply wanted a more catchy title for their festival, one can’t deny that “William Augustus Bowles Pirate Festival” doesn’t exactly roll off the tongue.

To borrow the sarcastic jibe of Joshamee Gibbs of the Pirates of the Caribbean films, “Oh, yes, that sounds very piratey.”

17 Responses to “Billy Bowlegs: Truth, Fiction and a Good Story”

  1. Is it just me, or does William Augustus Bowles look uncannily like Rick Springfield?

  2. For those who are interested, the memoirs of William Augustus Bowles are high comedy:

  3. If someone were to go for a Master’s degree, the information for this would be a really cool dissertation. Just sayin’

  4. William Augustus Bowles was my ancestor and I have been doing research on him. He was born in Frederick, Maryland. His father was highly educated in England, so the son had the benefit of his father’s education. I think his life had the makings of a great movie!

  5. my ancestor was Alexander McGillivray who only wanted to preserve his people and their way of life !!!!

  6. imho, the 1st picture appears to be an Anglo person. he may have some native american blood, but certainly looks more Anglo than native.

    • You’ll notice in the article that he was a Colonial, born in Virginia prior to the Revolution. He declared himself a leader of the Creek nation after marrying a chief’s daughter.

      • yes, i agree, i was just making a commentary of comparison to the other pictures. some people have claimed that he was n/a, not anglo


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    […] 1799, that dashing ne’er-do-well William Augustus Bowles (you can read more about him here) proclaimed an area of Florida a sovereign nation known as the State of Muskogee. Born a British […]

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