Early Life and Seminole Wars
Bowlegs was born into a family of hereditary chiefs descended from Cowkeeper of the Oconee tribe of the Seminole in the village of Cuscowilla on the Alachua savannah (present-day Micanopy, Florida). His father's name was Secoffee, while it is thought that the chief Micanopy was his uncle. The surname "Bowlegs" may be an alternate spelling of Bolek, a preceding Seminole chief. (A story that he had bowlegs from riding horses is unsubstantiated.)
Although Bowlegs signed the Treaty of Payne's Landing of 1832, he refused to leave Florida. He was not well-noted at the beginning of the Second Seminole Wars (roughly, 1835 to 1842). After the capture (under a flag of truce offered by Gen. Thomas Jessup) and subsequent death of Osceola and the death of Micanopy, amidst the loss of other prominent Seminole chiefs, Bowlegs and his band of 200 warriors became some of the most prominent fighters surviving at the time hostilities ended on 14 August 1842. To impress and awe the Seminole chiefs, the US government brought Bowlegs to Washington, D.C. to underline the power of the United States.
Bowlegs and his band lived in relative peace until 1855. A group of army engineers and surveyors invaded his territory in southwestern Florida, where they cut down banana trees and destroyed other property in the course of building forts. Some historians have viewed these actions as intentional provocation to make Bowlegs react, so the settlers would have a reason to force the Seminole out. If so, the provocation worked: Bowlegs led his warriors in sporadic attacks against settlers for the next few years, in what is known as the Third Seminole War. The Army was unable to subdue his guerrilla warfare.
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