During the Civil War, the Five Slaveholding Tribes aligned themselves with the Confederate States of America. In their treaties with the Confederacy, slavery was upheld and in the case of the Seminole Nation, the Confederacy promised reparations payments to slaveholders whose
slaves had been freed during the Second Seminole Wars. Many slaves owned by Seminoles were freed by Jesups Proclamation (the precursor to and the blueprint for the Emancipation Proclamation), so the Confederacy promised reparations payments for those freed slaves.
Pictured are Cherokee Confederate veterans in 1903.
Oh, the Five Slaveholding Tribes consisted of the Cherokee, Creek, Seminole, Chickasaw, and Choctaw Nations. Some example text from the Chickasaw and Choctaw Treaty with the Confederate States of America https://twitter.com/choctawfreedmen/status/1339320476750012416