3. Stand Watie
Stand Watie was a successful planter in the Indian Territory, and after the Principal Chief of the Cherokee John Ross fled to Union territory in 1862, replaced him in that role. He was a fervent supporter of the Confederacy and led the Cherokee in support of Colonel Cooper’s attacks on the Creek and Seminole during the Trail of Blood on Ice. He eventually rose to the rank of Brigadier General of the Confederate States Army. Stand Watie led his followers on numerous attacks against both Union troops and Cherokee supportive of the Union. By the end of 1862, the Cherokee were engaged in a de facto civil war of their own, with Cherokee troops serving in the Armies of the Union and the Confederacy, often fighting each other.
Unlike his opponent John Ross, who was of mostly Scottish descent (7/8ths), Stand Watie was a full-blooded Cherokee. Watie owned a significant number of slaves, though slavery in the Indian Territory was different in some ways than in the Confederacy. The children of Cherokee slaves were not born into slavery as they were in the South. Intermarriage between the races was allowed, something is strictly forbidden in the Confederacy. The troops Watie raised and led as mostly irregulars on raids against Union troops and Cherokee villages which supported them included armed slaves, owned by Watie and some of his most loyal supporters. It was the only area of the Confederacy where armed slaves fought with the knowledge, though not the outright approval, of the government in Richmond.