[4] 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 Payne's Prairie, near Micanopy, Florida).

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.

In early 1858, Chief Wild Cat of the Western Seminole tribe was brought back from Indian Territory to convince Bowlegs to relocate voluntarily.

Sonuk Mikko, aka Billy Bowlegs, gained fame as a captain in the Union Army during the American Civil War.