After the American Civil War, many veterans with disabilities became mendicant organ grinders in order to supplement inadequate pensions or eke out a meager living. Although they may have numbered in the thousands by 1870 little has been written about their lives, their street-vending practices, and the ways they intersected with the public, partly because evidence about them is scant and difficult to locate. One mendicant, however, named Bernard Tobey, “The Armless Sailor,” left behind a trail of newspaper, genealogical, and photographic documentation of his successful plying of the trade and popularity with the press. Our research shows that Tobey, who lost his arms in 1856 while firing a cannon during a festival in California, and who posed as a veteran after the war, nonetheless demonstrates what life may have been like for Reconstruction era street-performing veterans with disabilities. The case of Tobey also shows ways in which mendicant veterans may have become imbricated in post-war politics of the street. Traveling with his son, Bernard, Jr., throughout the Northeast and Midwest from 1866 to 1869, Tobey was heartily patronized as a hero of the Second Battle of Fort Fischer (January 1865), and appropriated by politicians, newspaper editors, and patrons to further veterans’ rights, as well as Republican and Radical political agendas. This paper contributes to the growing scholarship on disabled veterans in history as well as to Disability Studies, in its concern with historical, cultural, and social contexts.