In this provocative essay, the authors explore how John Trumbull, famed painter of the American Revolutionary War period, came to make sketches of five Creek Indian leaders in New York in 1790. By chance, Trumbull was painting George Washington’s portrait for the City of New York when a delegation of Creeks arrived to sign the Treaty of New York. Finding himself in the company of the Creeks, the artist seized the opportunity to draw them. While Drawing By Stealth tells the history of these iconic drawings of American Indians, it also provides details about the clothing and ornaments depicted and corrects a popular—but erroneous—theory that one of the images is of the leader of the Creek delegation to New York, Alexander McGillivray.