Miami

The available evidence indicates that Billy Bowlegs was part of a ruling Seminole family and that his emergence as a primary leader of his people during the second Seminole War (1835-1842) was due in large part to his birth. But Bowlegs also earned his rank, and it was thanks to his skill in negotiation and delay tactics that his people were able to withstand for many years, efforts to force their removal from Florida to the Indian Territory (now Oklahoma).

Ultimately the pressure for removal became too great. After leading his people in the Third Seminole War (1855-1858), Bowlegs finally agreed to take them to the Indian Territory. Shortly after the Civil War broke out in 1861, he turned to protecting his new home from Confederate attempts to control it, and spent his last years serving as captain in the Union Army's First Indian Regiment.

Yes This is True but there was another Billy Bowlegs check this out.

The year is 1779. Adventurer, wanderer, scoundrel, pirate extraordinaire, and notorious bad boy, William Augustus Bowles, affectionately known as Billy Bowlegs, bursts on the scene. A charismatic leader of men uses his egotistical ambition and superior strength of will for self gain.

Bowles originally came to Pensacola with British forces to hold Pensacola from the Spanish. When the effort failed, he developed an undying hatred for the Spanish visitors. At this time, three countries were vying with the new Americans for control of the sea lanes and trade with Europe. Pursuing his idea of an American Indian state after the end of the American Revolution, Bowles managed to get himself received by King 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.

Motley crews in the area were a force to be reckoned with and pirating became a very lucrative business on the high seas. As Bowles' popularity rose, his opponents became more distrustful and vowed to stop at nothing to get him under their control. Resistance came form all sides: the English became afraid Bowles was an agent for the Spanish, the Spanish offered him a Maj. General commission to "change sides" (and later offered $6000 and 1500 kegs of rum for his capture when he refused) and the Americans considered murder to be rid of his devilish activities.

He was briefly captured by the Spaniards. He managed to escape, commandeering a ship and returning to the Gulf of Mexico. 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 president, and in 1800 declared war on Spain.

In 1803, not long after having declared himself 'Chief of all Indians' at a trial council, he was betrayed by disenchanted Indians. They led him into a trap and turned him over to the Spanish authorities. He was imprisoned in Havana where he would neither speak to his captors nor eat their food and subsequently starved to death at the age of 42. This obscure episode in American history has given rise to a festival which is now an integral part of the Fort Walton Beach Community, the Billy Bowlegs Pirate Festival.

..........the year is 2009. Very soon local residents will batten down the hatches in preparation for the invasion of the infamous yet ever popular, Captain Billy Bowlegs. Captain Billy Bowlegs, along with his Queen, has been spotted at several local schools trying to persuade local youngsters to join his Motley Krewe. Captain Billy and his Krewe plan to invade Fort Walton Beach at the 54th Annual Billy Bowlegs Pirate Festival in June at Fort Walton Landing. Although Captain Billy's record stands at 53 wins and 0 losses, nothing is a sure thing when it comes to the city militia. The Fort Walton Beach Mayor and his brave Militia are not about to give up control of the city without a fight. Reports also say the militia has a secret weapon in store for those spineless thieves.