Walt Winkleman began his drum corps career in 1938, playing soprano horn with the Grand Street Boys and later with Phoebe Hearst Post drum and bugle corps in New York. After serving a hitch in the Merchant Marines during World War 11, he joined New York Skyliners in 1950, and played soprano horn through 1958. The following year, after losing his front teeth, he played cymbals. He is best remembered, though, as the dynamic drum major who marched in front of Skyliners from 1960 through the 1972 season. He was the assistant drum major from 1978 through 1984. He served as corps director of the Skyliners in 1963, 1966, 1968, 1970 and 1972.