John Jolly

John Jolly (Cherokee: Ahuludegi; also known as Oolooteka) was a leader of the Cherokee in Tennessee, the Arkansas district of the Missouri Territory, and Indian Territory (now Oklahoma). After a reorganization of the tribal government around 1818, he was made Principal Chief of the Cherokee Nation–West. Jolly was a wealthy slave-owning planter, cow rancher, and merchant. In many ways, he lived the life of a Southern planter.

Tennessee John Jolly was born around 1769, into a mixed-race family in Tennessee. He had a successful trading post on Hiwassee Island (in present-day Meigs County) in Eastern Tennessee. The island was located at the confluence of the Tennessee and Hiwassee Rivers.

Jolly was also a wealthy planter. He dressed in buckskin hunting shirts, leggings, and moccasins". 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. Jolly did not speak English, but likely understood it as well as other tribal languages and French. He led the plantation group of Cherokee originating in Tennessee after his brother Tahlonteeskee's departure for 'the west' in 1809. His brother, one of the first 'Old Settlers' of the western Cherokee, moved after the United States' acquisition of the Louisiana Purchase.

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

George Catlin painted his portrait in 1834. He described him as "...a dignified chief … a mixture of white and red blood, of which … the first seems decidedly to predominate". Of his visit to the Cherokee, he mentioned that there were six or seven thousand members of the tribe under Jolly who had removed with him from Tennessee.

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

Jolly served until his death near present-day Webbers Falls, Oklahoma in December 1838. He was succeeded by John Looney, who had been his assistant principal chief.

Legacy 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.