[5] Bowlegs lived on the Brighton Seminole Indian Reservation after it was established,[6] near Lake Okeechobee in present-day Glades County.

In the late 1800s, Bowlegs was one of the few Seminoles in Florida who knew how to write and speak English, and he often traded with White Floridians.

[8] Bowlegs befriended James Mallory and Minnie Moore Willson, who moved to Florida in the early 1880s.

In the mid-1950s, he performed traditional dances at the Florida Folk Festival in Union County, on the Suwannee River.

A historical marker honors Billie Bowlegs III, also known as Chufi Hajo, near Moore Haven.