[4] Shack met his wife, Norma Givens, when she worked at the Eaton’s across from the Empress Hotel in Peterborough, Ont., where the team held its training camps.

Canadian sports writer Stephen Cole likened Shack's playing to that of "a big puppy let loose in a wide field".

His popularity was such that a novelty song called "Clear the Track, Here Comes Shack", written in his honour and performed by Douglas Rankine with The Secrets,[9] reached No.

[10][2] Shack was a member of the Maple Leafs' last Stanley Cup-winning team in 1967, although his production fell significantly and he was traded in May 1967 to the Boston Bruins for Murray Oliver and cash.

[11] Playing on the right wing on a line with Derek Sanderson and Ed Westfall, Shack's performance rebounded and he scored 23 goals.

[12] After his retirement, Shack was a popular advertising spokesman in Canada, most notably for The Pop Shoppe soft drinks[14] and Schick razors, shaving off his moustache for one of their promotions.