William Augustus Bowles (aka., "Estajoca" and "Billy Bowlegs")

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William Augustus Bowles

Also Known As: "Estajoca", "Billy Bowlegs"
Birthplace: Tidewater, Frederick, Maryland, United States
Death: December 23, 1805 (42)
Havanna, Morro's Castle, Cuba, Spain
Immediate Family:

Son of Captain Thomas Bowles and Eleanor Bowles
Husband of Mary Bowles
Father of William Augustus Bowles, Jr. and John C. Bowles
Brother of Thomas Augustus Bowles, III; John Bowles; Catherine Bowles; Mary Neil Bowles; Samuel Bowles and 11 others
Half brother of Juliet Bowles; Thomas Bowles; ? Bowles and ? Bowles

Occupation: pirate
Managed by: Private User
Last Updated:

About William Augustus Bowles (aka., "Estajoca" and "Billy Bowlegs")


William Augustus Bowles (1763–1805), also known as Estajoca, was a Maryland-born English adventurer and organizer of Muscogee Creek attempts to create a state outside of Euro-American control.

General William Augustus Bowles was born in Frederick County, Maryland, in the year 1764. During the American Revolution, he joined the British army, in which he soon obtained a commission. After the battle of Monmouth, he sailed, with his regiment, to Jamaica, and from thence to Pensacola. At the latter place, in consequence of some neglect, he was deprived of his commission, and dismissed from the army.

A party of Creeks having come to Pensacola for the purpose of receiving their annual presents, being on their return to their nation, Bowles concluded to join them, and accordingly accompanied them to their home. Here he resided for some time, during which he made great proficiency in the Indian language, and married the daughter of one of the chiefs. On the 9th of May, 1781, when Pensacola surrendered to the arms of Spain, Bowles commanded the Creek Indians, whom he had brought there to assist the English. His services upon that occasion were acknowledged by the commander of the British army, and he was reinstated in his former rank. After the surrender of West Florida to Spain, he was allowed to retire with the garrison to New York, where he joined a company of players, and then sailed for the Bahama Islands. Here he remained some months, following the profession of a comedian, as well as that of a portrait painter, thus exhibiting the versatility of his talents.

The Governor of the Bahamas, Lord Dunmore, appointed Bowles as an agent to establish a trading house among the Creeks. He returned to the nation, and established a commercial house upon the Chattahoochee; but it was of short duration, for Colonel McGillivray sent him word to abandon the enterprise, and leave the country in twenty-four hours, on pain of being deprived of his ears. He fled to New Providence, and from thence was sent to England, for the purpose of asking aid to enable him to repel the aggressions of the Americans. His applications were successful, and he returned to America; and having taught his warriors the art of navigating the Gulf of Mexico, he began a system of piracy upon the vessels of Panton, an Indian merchant, against whom he had long entertained the most inveterate hostility. His success in piratical enterprises, and other circumstances, gained him great popularity among the Creeks, and he was elected commander-in-chief of their armies.

For along time Bowles continued to annoy Georgia, doing every thing in his power to prevent the settlement of her difficulties with the Indians. He denounced Colonel McGillivray as a traitor, and exerted his utmost power to prejudice the Indians against him. In 1792 he was taken prisoner by the Spaniards, and sent to Madrid. The Spanish government endeavored to conciliate him, but was unsuccessful, and he was finally sent to the island of Manilla, from whence he made his escape, and, after various fortunes, obtained a schooner, in which he navigated the Gulf and seized many Spanish vessels. After this he proceeded to the Creek Nation, interfered seriously with the policy of Colonel Hawkins, and captured the fort at St. Marks. At a feast given by the Indians, to which he had been invited, he was made a prisoner, according to a preconcerted plan, by Colonel Hawkins and the Spanish authorities, who placed him in a canoe full of armed warriors. They then rapidly rowed down the river. Col. Hawkins and John Forbes, of Pensacola, were in the town, but were concealed, until Sam McNac, a half-breed, had caused Bowles to be made a prisoner. Arriving at a point in the present Dallas County, Alabama, the canoe was tied up, the prisoner conducted upon the bank, and a guard set over him. In the night the guard fell asleep, when Bowles gnawed his ropes apart, crept down the bank, got into the canoe, quietly paddled across the river, entered a thick cane swamp, and fled. At the break of day, the astonished Indians arose in great confusion, but fortunately saw the canoe on the opposite side, which Bowles had foolishly neglected to shove of swimming over to that point, they got upon his track, and by the middle of the day once more made him a prisoner. He was conveyed to Mobile, and from thence to Havana, where, after a few years, he died in the dungeons of Moro Castle



William Augustus Bowles (1763-1805), also known as Estajoca, was a Maryland-born English adventurer and organizer of Native American attempts to create their own state outside of Euro-American control.

Some sources give his date of birth as 1764.[1] Bowles was born in Frederick County, Maryland. He joined the British Army as a foot soldier at 13 and served with the Maryland Loyalists Battalion as an ensign during the American Revolution. After the Battle of Monmouth he went to Jamaica. He was officer in Royal Navy by age 15, but was cashiered for dereliction of duty for returning too late to his ship. This occurred at Pensacola, Florida.

At this point he moved north to live with the Creek Indians. Apparently he met some of the Creek in Pensacola to receive British aid for their alliance with the British in the war. He would marry two wives, one Creek (the chiefs daughter) and the other Cherokee, became heir to Creek chiefdom. Bowles was the leader of the Creek forces who fought at Pensacola on the British side in the battle in which it fell to the Spaniards. This occurred May 9, 1781, when Bowles was either 16 or 17 years old.

In one of the bizarre twists that makes Bowles so interesting, after this battle, he was reinstated in the British Army, then went to New York. After this, he moved to the Bahamas where he worked as a comedian and a portrait painter. However, after a few months in the Bahamas, Lord Dunmore the British governor there, sent Bowles back among the Creeks with a charge to establish a trading house among them.

Bowles established a trading post along the Chattahoochee River. Alexander McGillivray did not take kindly to this activity and ordered Bowles to leave or have his ears cut off. Bowles chose to keep his ears and returned to the Bahamas.

Pursuing his idea of an American Indian state after the end of the war, he was received by George III as 'Chief of the Embassy for Creek and Cherokee Nations' and it was with British backing that he returned to the Bahamas to train Creek Braves as pirates to attack Spanish ships.

A furious Spain offered $6,000 and 1,500 kegs of rum for his capture, and when he finally was captured, he was transported to Madrid where he was unmoved by Charles IV of Spain's attempts to make him change sides. He then escaped, commandeering a ship and returning to the Gulf of Mexico. One of the main victims of his piracy was the trading firm of Panton, Leslie & Company.

In 1795, along with the Seminoles, he formed a short-lived state in northern Florida known as the "State of Muskogee", with himself as its "Director General", and in 1800, declared war on Spain. Bowles operated two schooners and boasted of a force of 400 frontiersmen, former slaves, and warriors.

In 1803, not long after having declared himself 'Chief of all Indians present' at a trial council, he was betrayed and turned over to the Spanish and died in prison in Havana two years later, having refused to eat.

One of the most interesting individuals ever to live in the Two Egg area was William Augustus Bowles, the individual celebrated in Fort Walton Beach today as the pirate "Billy Bowlegs." Born in Maryland, Bowles was a young boy at the time of the American Revolution. It is little remembered today how divided the colonies were at the time or that many families were steadfast in their loyalty to King George and England. Bowles came from such a family and as a young teenager enlisted in a Tory or Loyalist regiment (i.e. one loyal to the King) in Maryland.

Sent to Pensacola, which was then a major English stronghold on the Gulf Coast (Florida was a British colony during the war), he was not popular with his commanding officers and was drummed out of the service. Cast adrift far from home, with no money and no means of support, he set out from Pensacola in what likely was an attempt to return home.

It is most likely that Bowles was trying to follow the old Pensacola-St. Augustine Road, which despite its name was little more than a foot path through the wilderness. The portion through Jackson County ran along the route of today's State Highway 2. Small parts of the original trail can still be seen in the Forks of the Creek area between Campbellton and Malone.

Following the trading path was not easy and Bowles became lost in the vast wilderness that then covered Northwest Florida. Hungry and exhausted, he was wandering aimlessly through the woods when he was discovered by a party of Indians on their way back from a trading visit to Pensacola. Taking pity on the young man, they rescued him and took him back to their village. Bowles' rescuers were from Tellmochesses, the town of William Perryman which stood just 7 miles east of Two Egg near today's Parramore community. The Perryman family was one of the most important among the Lower Creeks. Allied with the British against the Americans, they provided manpower and horses to the English forces in St. Augustine and led their warriors in battle in both Florida and Georgia. They played a significant role in the American Revolution in the South. The Perrymans were descendants of an English trader and his Creek wife, all spoke English and were prosperous, well- educated people. They lived in regular houses similar to those of frontier plantation owners in Georgia and raised crops as well as large herds of horses and cattle. Bowles returned to Pensacola twice in the coming years, once in an apparent attempt to find a way home and then at the head of a party of Perryman warriors who went to the aid of the city when it was attacked by allied forces. Pensacola fell, but Bowles managed to escape with a party of English troops who made their way overland to the Atlantic Coast. He was charged by English officers with the scalping and mutilation of prisoners, but the evidence was insufficient and he once again left the British service.

After briefly visiting his father in Maryland, he returned to the Two Egg area and resumed his life with the Perryman family.

It was at some point during these travels that he devised a scheme of establishing the "State of Muskogee," basically an empire among the Seminoles and Lower Creeks that he would lead. Thus legitimized, he would form a navy on the Apalachicola River which would prey on shipping on the Gulf of Mexico.

Despite capture by the Spanish and a brief imprisonment (from which he escaped), Bowles went forward with his plans. His "State of Muskogee," however, was little more than a front for a flotilla of pirate ships that he sent out onto the Gulf manned by crews of renegade whites, Indians and both free blacks and escaped slaves. These ships preyed on merchant vessels and even engaged Spanish coast guard ships in battle in Apalachicola Bay.

The captured booty from these raids was sent upriver to be safeguarded by his allies, who included the Perryman family.

The smuggled goods and slaves were then traded or sold to Indians and whites from Georgia allowing Bowles and his allies to accumulate a small fortune. Part of this treasure is said to be hidden to this day at the "Money Pond" about 12 miles northeast of Two Egg.

Bowles eventually turned against his father- in-law, however, and ordered his murder.

Perryman escaped, but his son

William swore revenge on Bowles and ultimately assisted the Spanish in bringing him to justice. He died in a Cuban prison.

He is celebrated each year at Fort Walton's "Billy Bowlegs Festival," although it is not believed that he ever actually used the name.

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William Augustus Bowles (aka., "Estajoca" and "Billy Bowlegs")'s Timeline

October 22, 1763
Tidewater, Frederick, Maryland, United States
Florida, United States
Jackson, Florida, United States
December 23, 1805
Age 42
Havanna, Morro's Castle, Cuba, Spain