Winchester Colbert traveled with one of the first removal groups from the Chickasaw Homeland to Indian Territory in 1837. A staunch proponent for Chickasaw sovereignty and separation from the Choctaw Nation, Colbert served as Chickasaw delegate in Washington, D.C., on numerous trips during the late 1840s to the 1850s. In August 1856, he served as a member of the first Chickasaw Nation legislature following the ratification of the 1856 Constitution. Colbert would go on to serve his fellow Chickasaw people as Governor during Civil War era in Indian Territory. Colbert's leadership distinguished him during times of extreme economic and social change as a Chickasaw Nation diplomat leader and statesman.