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Henry Timberlake arrived in Tomotley on a diplomatic overture from the British in 1761 and met with Ostenaco at Tomotley. Ostenaco was sufficiently impressed with what Timberlake had to say and led him to Chota to address a gathering of Cherokee leaders. As part of the gathering, Ostenaco made a speech and buried a hatchet in the ground as a gesture of renewed goodwill with the British. Ostenaco later guided Timberlake back to Virginia in 1762. He and Timberlake remained friends and Timberlake had a relationship with Ostenaco's daughter, producing a son, Richard Timberlake. In Williamsburg, Ostenaco met Thomas Jefferson, then a student at William and Mary University. Jefferson described him as a great orator and warrior. Whenever Ostenaco was in Williamsburg, he would stay with Jefferson's family. Ostenaco wanted to go to London to meet personally with King George III. Jefferson traveled with him and Timberlake back to Tomotley, where Jefferson witnessed Ostenaco's farewell oration to his people.
Timberlake, accompanied by Thomas Sumter, who later became a noted Indian Fighter, accompanied Ostenaco and three other leaders to London in 1762. They toured the sites of the capitol, were received at the royal court, had their portraits painted by Joshua Reynolds and did the typical diplomatic social round. While Timberlake remained in London, Sumter escorted the Cherokees back to America. By the time of the American Revolution, Ostenaco was war chief over all the Lower Towns of the Cherokee and remained in his allegiance to Great Britain. After American forces destroyed the Cherokee Lower Towns, Ostenaco and his people drifted further west, some settling in North Georgia at the town of Ustanali, or others joining Dragging Canoe's Chickamauga Cherokee. Ostenaco, now an old man, died at the home of his grandson Richard in the Cherokee town of Ultiwa in 1780.
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