After a standout stay in the Manitoba Junior Hockey League and the Ontario Hockey League, McDonald joined the Montreal Canadiens in 1958 for two playoffs games. The next season, he scored 13 goals as a rookie while on a line with Ralph Backstrom and Don Marshall. He would win three times the Stanley Cup with Montreal during his stay before the Habs' management, unsatisfied of the fact he didn't play as well as the player he was replacing, Bert Olmstead. The Habs dealt him to the Chicago Blackhawks with Reg Fleming, Bob Courcy and Cec Hoekstra for Terry Gray, Glen Skov, the rights to Danny Lewicki, Lorne Ferguson and Bob Bailey, June 7, 1960.