In 1944, Winslow played for the Hollywood Rangers of the short-lived American Football League, an eight-team organization based on the Pacific Coast. Head coach Bill Sargent moved him from end to quarterback, which the United Press partly credited for the team's success. The Rangers finished in first place with a perfect 11–0 record in the league's only season. His son, Troy Winslow, played as a quarterback at USC in the 1960s.