This one, if you really want to think about it, could go counter to your initial thinking. #5 is retired for Barilko but he only wore the number for one season in his career.
Bill Barilko (1950-51)
Stats: 58GP - 6G - 6A - 12Pts - 96PM
Stanley Cup: 1951
Most famously known for scoring the winning goal of the 1951 cup final then disappearing, as immortalized in the Tragically Hip song ‘Fifty Mission Cap’.
Barilko came to the Maple Leafs in 1946 after two seasons wit the Hollywood Wolves of the Pacific Coast Hockey League.