The colorful and controversial life of American artist James Abbott McNeill Whistler took many twists and turns. One of the most dramatic and least explicable of the turns came in 1866, when he traveled to Valparaiso, Chile. Generations of Whistler biographers have been puzzled by the reasons for this sojourn, but a recently discovered collection of documents provides significant clues for solving the mystery. Whistler, it seems, had become involved in a scheme to provide weapons to the Chilean navy in a war against Spain. The scheme turned into a fiasco, dashing Whistler's hopes of handsome financial profits, but his weeks in South America significantly shaped his development as an artist.