Rudy Caprifolio was orphaned shortly after being born on the Lower East Side of New York City, a block from Chinatown and half a block from Mulberry Street. When their parents died, he and his six brothers and sister were placed under the supervision of their aunt on the Upper West Side. He became interested in drum and bugle corps when his nephew became a member of the Moe Wolff Post VFW corps. Because of his fundraising skills, he was asked to serve as assistant director of the group, helping Bill St. John. The group then became independent, known as the Manhattanville Boys Club, which had its own clubroom for the boys and girls who were members to use at their convenience. Manhattanville sponsors in subsequent years included Colonel John R. Slattery American Legion Post, and the Phoebe Apperson Hearst American Legion Post, named after the mother of publishing giant Randolph Hearst. For seven years, the corps played at all the home games of the Brooklyn Dodgers football team, with drill and music revised for every performance. The corps was playing at the Polo Grounds during an exhibition game between the Dodgers and the New York Giants on December 7, 1941: the day Japan attacked Pearl Harbor. Despite the sponsorship, the corps was considered a poor unit and rarely traveled by bus. On trips, corps members rode on the back of open trucks, and meals consisted of baloney and tomato sandwiches. After World War II, when many drum and bugle corps were re-organized and revitalized, he was associated with the formation of the New York Skyliners and remained part of the organization throughout the rest of his life.
