McCaffrey won a Stanley Cup in 1930 with the Montreal Canadiens. He played in 22 of 44 regular season for Montreal during the 1930–31 NHL season, and thereby qualified to win the Stanley Cup, however his name was never engraved on the trophy because McCaffrey had been sent to the minors to play with the Providence Reds,[citation needed] and did not play for Montreal in the Stanley Cup playoffs.\n', '

Prior to joining the NHL, McCaffrey played eight seasons of senior hockey in the Ontario Hockey Association, including four with the Toronto Granites, winning two Allan Cups in 1922 and 1923. By virtue of playing for the reigning senior amateur champions, McCaffrey and the Granites represented Canada at the 1924 Winter Olympics in Chamonix, France. He scored 20 goals in five games as the Canadians dominated the tournament, winning the gold medal.\n', '

McCaffrey was born in Lockton, Albion Township, Peel County, Ontario in 1893 but is erroneously listed in numerous resources as being from Chesley. and died in Toronto in 1955.\n', '

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