Emigrated west to Arkansas Territory in 1818. As early as 1820, he was made Principal Chief of the Old Settlers, and he held this office until his death in 1838.
He was a wealthy merchant and planter. Jolly spoke no English, and dressed in buckskin with a hunting shirt, leggings and moccasins.
He was a brother of Old Settler Chief Tahlonteeskee, and both were uncles of Cherokee Chief John Rogers. He was also the uncle of Tiana Rogers, Sam Houstonís Cherokee wife and of Chief John Rogers, Jr.
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