He had a successful trading post on Hiwassee Island (in present-day Meigs County) in eastern Tennessee.

[3][4] He was a friendly and low-key person who was dedicated to providing the Cherokee people opportunities to thrive, including the use of technology and formal education.

His brother, one of the first 'Old Settlers' of the western Cherokee, moved after the United States' acquisition of the Louisiana Purchase.

The Cherokee lands were located north of the Arkansas River, in the area designated as Lovely's Purchase.

[7] The Cherokee treaty delegates were bribed by Governor Joseph McMinn and John C. Calhoun to ensure a successful removal from Tennessee.

[8][a] In February 1818, Jolly and his followers left Tennessee with sixteen riverboats, provisions for 70 days, and rifles that they received from the government.

[2] When they began to settle on their land, they learned that they were historic hunting grounds of the Quapaw and Osage people, who fought with them.

He wrote to George Izard, the governor of Arkansas to squelch a rumor that Cherokees were interested in selling any of their land.

Jolly established a plantation at the confluence of the Arkansas and Illinois Rivers,[2] near present-day Webbers Falls, Oklahoma.

One writer states that much of Jolly's success "was due to the counsel and support of John Rogers", his brother-in-law and Cherokee headman.

[14] In 1829, Sam Houston sought refuge with Jolly after his brief marriage to Eliza Allen, which sparked many rumors and theories, and led to his resignation as governor of Tennessee.

[15] Jolly met Houston when the steamboat arrived at Fort Gibson with a number of his enslaved men bearing torches.

[16] Jolly was grateful for Houston's return, both because he was happy to be a place of refuge and because the Nation could use his assistance in ensuring that the Cherokee people's voices were heard by the government.

[3] Black Coat, who served with Jolly as second chief, died in the spring of 1835, and was succeeded by Joseph Vann.