 Stapleton was briefly the property of the Toronto Maple Leafs in June 1965 as part of a trade with the Bruins, but he was left unprotected in the intra-league draft and was claimed the next day by the Chicago Black Hawks.Wearing number 7, he played some games with the Hawks' Central Hockey league affiliate, the St. Louis Braves, in 1965–66, but they would be the final minor league games of his career.Stapleton remained in the NHL for eight seasons with the Black Hawks, and was named Second Team All-Star three times (1966, 1971, and 1972).