[1][b] Like his father, Chilly signed the Treaty of Indian Springs on January 8, 1821, which sold the land claimed by the Creeks in the state of Georgia.
"[3] The Lower Creeks, who became known as the McIntosh faction, began negotiating with the Federal government for their removal to Indian Territory.
Chilly attended an intertribal council meeting at Talequah in 1843, where Chief Roley McIntosh addressed the group of some three thousand warriors from eighteen tribes.
He signed a treaty at Fort Gibson on November 11, 1838, which adjusted the payments the Federal Government would make to reimburse the monetary losses of the Creeks during their removal.
He and his half-brother, D. N. McIntosh both signed a treaty on August 6, 1856, defining specific lands that had been allotted to the Creeks that would be turned over to the Seminole Nation.
[5] Despite his age and relative lack of prior military experience, Chilly entered the Confederate Army with the rank of lieutenant colonel, commanding the First Battalion of Creek Cavalry.
He and his troops fought in several battles in the Indian Territory, such as Round Mountain, Pea Ridge, Fort Wayne, and Honey Springs.