Living in the Overhill Towns on the Little Tennessee River, he sporadically took part in the campaigns of Dragging Canoe as they were under a flag of truce during an embassy to the State of Franklin in 1788, until the murder of his brother, and another pacifist chief, Abraham of Chilhowee.
Doublehead's first act in his 1788 crusade was to lead a party of warriors in concert with those of Dragging Canoe in an assault on White's Fort in East Tennessee.
Following the death of Dragging Canoe in 1792, he became part of a triumvirate of leaders among the Chickamauga, along with Bloody Fellow and his nephew, John Watts, who was recognized as the chief of them.
In September 1792, Watts orchestrated a large campaign into the Cumberland region of combined Cherokee and Muskogee forces which included a contingent of cavalry.
[2] In 1793, a delegation of Shawnee stopped in Ustanali, the principal city of the Cherokee, on their way to call on the Muskogee and Choctaw to punish the Chickasaw for joining St. Clair's army in the north.
This party, which included Bob McLemore, Tahlonteeskee, Captain Charley of Running Water, and Doublehead, along with the white delegation, was attacked by militia during a stop at the Overhill town of Coyatee.
The Cherokee agreed to await the outcome of the subsequent trial, which was later proven to be a farce because the man who was responsible was a close friend of John Sevier.
Watts responded by invading the Holston area with one of the largest Indian forces ever seen in the region —over one thousand Cherokee, Muskogee, and Shawnee — intending to attack Knoxville itself.
He became one of the foremost advocates of acculturation and became one of the richest men in The Cherokee Nation — the Lower Towns where he was a leader were then the wealthiest section of the entire country.
In August 1807, because of his ongoing machinations with U.S. Indian Affairs Commissioner Return J. Meigs, Jr. regarding under-the-table land deals, as well as personal animosity going back nearly two decades, several of the younger leaders of the Nation, led by James Vann, conspired to assassinate Doublehead.
The badly wounded Doublehead sought safety in the attic of schoolmaster Jonathan Blacke's house, where the assassins finished the job with knives and tomahawks.
In July 1834, because of his advocacy of removal in the years leading up to the Treaty of New Echota, Walker was assassinated on the road home from Red Clay, Tennessee, after a meeting of the Cherokee National Council.