Bolek Bolek ( died 1819 ) , also spelled as Boleck or Bolechs and known as Bowlegs by European Americans , was a Seminole principal chief , of the Alachua chiefly line . He was the younger brother of King Payne , who succeeded their father Cowkeeper ( known to the Seminole as " Ahaya " ) as leading or principal chief in Florida . Bolek succeeded King Payne in 1812 when he was killed . Early life and education . Bolek was one of several children born to Ahaya ( Cowkeeper ) and his wife . He and his older brother King Payne were groomed by their mother ' s brother ( in the matrilineal kinship system ) to become chiefs and take leading roles among the Seminole . They inherited that role through their mother ' s people , who were descended from the Alachua chiefly line . Bolek was designated as a village or " itwála " chief while a young man ; he was based near the Suwanee River of western Florida . He began to oppose United States influence in Spanish Florida during the early 19th century . He prevented Georgian slaveholders from entering Seminole territory to pursue escaped slaves from the Low Country . Some of the fugitives married into the Seminole people ; most created independent communities nearby as allies and were known as Black Seminoles . They kept much of their Gullah culture and developed the Afro - Seminole Creole in Florida , which they used through the 19th century . In 1812 , Bolek and his brother King Payne began raiding frontier settlements along the Florida - Georgia border . Seminole bands fought several engagements with militia forces ; Payne was killed in 1812 , and Bolek suffered serious wounds during the same skirmish against Georgia militia forces under Daniel Newnan . An expedition by Colonel John Williams the following year destroyed hundreds of Seminole villages and captured numerous horses and cattle . Border warfare between the Seminole and Georgia settlers contributed to US involvement in the Creek War of 1813 - 1814 . Seminole Wars . During the First Seminole War , beginning in 1818 , American forces under General Andrew Jackson advanced into northern Florida capturing Kinache ' s village of Miccosukee and occupying the British settlement of St . Marks before reaching Bolek ' s abandoned village . They captured two Englishman , Robert Ambrister and Peter Cook , who were taken back to St . Mark . Charged with assisting the Seminole , they were executed by American forces . Although this created an international incident , Jackson continued his offensive and recaptured Pensacola . The US purchased Florida from Spain in 1819 , and the Seminole expected they would have more to do to try to keep the Americans from their territory . Bolek died that year and was succeeded as principal chief by his maternal grandnephew , Micanopy . Micanopy was principal chief through the move into central Florida and the Second Seminole War . He also led the Seminole to Indian Territory , realizing that trying to fight the US superior forces was finally futile . In the West , he worked to gain separate territory and independence for the Seminole from Creek oversight until his death in 1849 . He was succeeded by his sister ' s son , John Jumper , who died in 1853 . John ' s younger brother , Jim Jumper , succeeded as principal chief , leading the Seminole in Indian Territory until after the American Civil War , when the United States government began to interfere with tribal succession . Another member of the Cowkeeper dynasty was Billy Bowlegs .