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 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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