
A Cherokee leader known to Whites as Old Hop (Kanagatucko) arrived at the British camp in what is now Sullivan County, Tennessee to sue for peace. He asked that a British officer accompany him back to his country as proof that peace had been granted. Timberlake volunteered. Timberlake was accompanied by Sergeant Thomas Sumter, who later became a Continental officer and partisan commander during the Revolution, and an interpreter. The plan was to visit the Overhill towns, which, as we've seen, were the most resistant to White encroachment on Cherokee land. Along the way, Timberlake, who was an avid writer and also a skilled cartographer, took notes, drew maps and even sketches of who and what he was seeing. After a harrowing journey, the group arrived at the Overhill town of Tomotley, where they were greeted by the village headman, Ostenaco. Ostenaco accompanied them to the town of Chota where a large council of chiefs had gathered. After a speech, he buried a hatchet in the ground as a symbol of peace between the English and Cherokee. Timberlake disliked smoking pipes as part of the ritual, but was otherwise respectful of what he was seeing and hearing. He later visited other towns, where the constant pipe smoking made him so sick he was ill and unable to travel for days.

Once in Virginia, he was placed on half-pay and semi-retired, which threatened his financial security. He petitioned the Virginia legislature for reimbursement for his expenses on his Overhill expedition and for taking the Cherokee to London, but was denied. In 1764, Cherokee leaders contacted Timberlake, asking him to take them to London again to speak to King George personally about violations of the Proclamation of 1763 and encroachment on their land by Settlers. Timberlake found someone to fund the trip and accompanied the Natives to London. There, the Cherokee were rebuffed by royal officials, as this wasn't considered an official visit. Timberlake was accused of profiting off the Cherokee popularity. Government ministers funded the Cherokee to return home in March, 1765, and Timberlake was imprisoned for debt. He wrote his memoirs in an effort to raise money, but died before he could get them published.
Meanwhile, back in Virginia, Timberlake's son Richard by Sakinny, one of Ostenaco's daughters, grew up. Remaining loyal to his mother's family, as so many mixed-race children did, he took his grandfather Ostenaco into his home during the old man's final years. Timberlake's journals contained such detail that they proved helpful to archaeologists excavating Cherokee town sites and to anthropologists and historians studying Cherokee culture. His maps have helped scientists pinpoint the location of many otherwise lost Cherokee sites. His diaries remain one of the most useful 18th century accounts of the Cherokee. Now, for the possible connection to Justin. The singer has indicated in interviews that a distant ancestor was Cherokee. If that is true, there might be a connection, though it hasn't been proven conclusively.
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