"Wimpy," as he was known, was born in Cleveland, Ohio, the son of Joseph "Joe Winnie" Winpisinger, a journeyman printer with The Plain Dealer, and Edith (Knodel) Winpisinger.
Discharged from the Naval Reserve on July 15, 1947, Winpisinger returned to Cleveland where he worked as a "gypsy mechanic," repairing automobile transmissions at local service stations.