In an earlier post we met William Augustus Bowles, a Anglo-American imposter and adventurer who tried and failed to create an independent State of Muscogee in Spanish Florida and ended up starving himself to death in a Cuban jail. His memory lives on in a festival in Fort Walton Beach called the Billy Bowlegs Pirate Festival. Yes, Bowles was a pirate, but there's no evidence he ever set foot in Fort Walton Beach, nor was he called Billy Bowlegs in his lifetime. The only explanation of how he got that name was that somehow his legend got mixed up with one of four men who were the real Billy Bowlegs. Each of them were important Seminole chiefs and worthy of a post in his own right, but we're listing them here to clear up the confusion.
The first was a Seminole leader named Bolek (d. 1819). He came from families of chiefs on both his father's and mother's sides. His father was Ahaya (Cowkeeper) and his brother was known to White men as King Payne. The name Bowlegs didn't come from any physical deformity on Bolek's part, but was a corruption of his name. He began his career as a village chief, where he became known for preventing Georgia slaveholders from entering Seminole territory to pursue escaped slaves. He and his brother, King Payne, began raiding White settlements in Georgia and Florida until Payne was killed and Bolek succeeded as Principal Chief. He led his people through the First Seminole War (1816-1818). When he died, he was succeeded by his maternal grandnephew, Micanopy
The next Billy Bowlegs (1810-1859), whose nickname again came from the surname of Bolek and not from any physical characteristic, also came from the Cowkeeper family. He was a nephew of Micanopy, which meant that he achieved his status through his mother's relationship to Micanopy, though his father may have been the brother or nephew of the previous Bolek. Billy rose to prominence during the Second Seminole War (1835-42), taking up the fight after Osceola was captured and died, and Coacoochee agreed to remove to Oklahoma. Billy and his remaining band of Unconquered Seminoles remained in Florida until 1855, when surveyors once again moved into their territory, cutting down trees and destroying property. Billy proved to be a successful partisan leader, directing his men on lightening strikes against the enemy. Coacoochee returned to Florida and convinced Billy to remove to Oklahoma, where he became a wealthy planter and lived until his death in 1859.
The next Billy Bowlegs likely wasn't related to this important family, but took the name in honor of the preceding Billy. Sonuk Micco (d. 1864), was a veteran of the Second and Third Seminole Wars. When the Civil War broke out, pro-Confederate forces took control of Oklahoma, including a sizable Cherokee contingent under Stand Watie. Some Seminole and Creek leaders objected to this and wished to remain loyal to the Union. Although their tribes were traditional enemies, Sonuk Micco allied his men with Creek leader Opothleyahola to make the journey to Fort Belmont, Kansas to seek Union protection. In a series of battles known as the Trail of Blood on Ice, Opothleyahola and Sonuk Micco led their men in a running retreat against the advancing Confederates, then suffered a terrible winter at Fort Belmont with little in the way of rations or shelter. Many Creek and Seminole died, including Sonuk Micco himself.
The final Billy Bowlegs also took his name in tribute to Number 2 above, though he wasn't a chief or related to a chiefly family. His ancestry was equally impeccable as he was reputed to be a maternal grandson of the Unconquered himself, Osceola. Billy Fewell (1862-1965) also had African descent, lending credence to the idea that at least one of Osceola's wives was black. He had remained in Florida after most of his people were forcibly relocated to Oklahoma and became an important cultural link to younger generations. He was an elder of his tribe, living on the Brighton Reservation in Florida, until his death.
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