2. John Ross
During the Indian Removal in the 1830s, the Cherokee split into two main political factions. One, which opposed the removal and sent several delegations to Washington took the name of the National Party and supported assimilation into American life. They were opposed by the Treaty Party, which supported relocation and retaining the Cherokee way of life. The National Party eventually came under the leadership of John Ross, a Cherokee political functionary and one of the wealthiest men of the nation. Ross had numerous business interests before and after the relocation, and owned up to one hundred slaves of African descent.
When the Civil War began Ross, who had extensive experience negotiating with the federal government, urged the Cherokee to either remain neutral or align themselves with the Union. Traditionalists and the members of the Treaty Party opposed him, and by late 1861, Ross began to advocate supporting the Confederacy, partly in the belief that the Confederates would not interfere with Cherokee slaveholders. By 1862 he had changed his mind. When growing support for a military alliance with the Confederacy continued to divide the Cherokee, Ross and his supporters and followers fled the Indian Territory for the protection of Union troops at Fort Leavenworth, Kansas.