Jolly "was a wealthy merchant and planter. Jolly spoke no English, and dressed in buckskin with a hunting shirt, leggings and moccasins," according to the Cherokee Nation website. Black Coat, who served with Jolly as Second Chief, died in the spring of 1835, and was succeeded by Joseph Vann.
When the young Sam Houston came to live with the Cherokee on Hiwassee Island in 1809, Jolly adopted him and acted as his father in the Cherokee Nation.
Jolly gave Houston the Cherokee name of Ka"lanu, meaning "the Raven". Houston later returned to his family in Maryville, Tennessee, but he lived once again with the Cherokee in the west during the late 1820s and early 1830s.
Hiwassee Island, at the mouth of the Hiwassee River where it meets the Tennessee, used to be commonly known as "Jolly"s Island" after the Cherokee leader. Residents in the area sometimes still call it that.