The focus of this chapter alternates throughout from Ostenaco and his travels to the centre of London, to Reynolds’s endeavour to paint his portrait, back to Ostenaco, back to Reynolds, and then finally ends with Ostenaco’s voyage home in October 1762. The chapter covers only six months, but this period turned out to be portentous for both Cherokee and British fortunes. The Cherokees looked set to enjoy some assured independence herein and the British teetered on the verge of wiping out all imperial rivalry. Amid the narrative flipping, we follow Ostenaco’s adventures through the seamier regions of London’s lowlife—including taverns, spas, and drunken escapades in pleasure gardens—to his diplomatic meeting with King George III. We witness Reynolds’s meeting with Ostenaco and his attempt to capture the Cherokee’s image on canvas according to his neoclassical philosophy of art. Reynolds afterwards reckoned the work a failure—an intriguingly rare moment of defeat for the painter—but it nonetheless distils much about attitudes to empire in Britain at the time.