Caesar Bowlegs was a man of influence and importance in the Seminole Nation. He served the nation in many capacities, but is best known as an interpreter being fluent in Creek and he moved easily between both Creek and Seminole communities. Bowlegs had traveled during the Civil War into Kansas according to historian Kevin Mulroy. After the war, he worked for some time as a mail carrier between Ft. Gibson and Wewoka, and he later operated a toll bridge over Wewoka Creek as well.
Because of his language skills, he served as a personal interpreter for Dr. C. P. Lynn, and later Dr. Virgil Berry. He instructed the doctors about medicinal practices of Seminoles and Freedmen, and he was later the personal assistant to Dr. Berry accompanying him on medical calls. During an epidemic of smallpox, after inoculating themselves, Caesar Bowlegs and Dr. Berry traveled throughout the nation with the goal of vaccinating the entire nation.
As stated by scholar Mulroy, "Bowlegs helped gain widespread acceptance for scientific principles and medical technology among the Seminoles and freedmen. Caesar Bowlegs died in 1912 in Seminole County, Oklahoma."