Jack Riley was born December 29, 1910 in Berckenla, Ireland. A former member of the Detroit Red Wings, Montreal Canadiens and Boston Bruins, Riley's route to the NHL began with the Calgary Indians of the Calgary City Junior Hockey Leagues in 1926-27.
While a member of the Indians, Riley took part in the 1927 Memorial Cup before heading to Vancouver and to the King George of the Vancouver City Amateur Hockey League in 1927-28. A return to Calgary awaited Riley in 1928-29, before he joined the Seattle Eskimos of the Pacific Coast Hockey League the following season.
After beginning the 1929-30 season with the Minneapolis Millers of the American Hockey Association, Jack Riley had his rights traded to the AHA's Chicago Shamrocks where he played for a little over one season before having his NHL rights transferred to Detroit. Riley made his NHL debut with the Red Wings during the 1932-33 season while splitting his time with Detroit and Cleveland of the International Hockey League after being traded by Detroit to Cleveland midway through the season.
In the summer of 1933, Jack Riley was dealt to the Montreal Canadiens where he spent the next two seasons compiling 10 goals and 22 assists for 32 points in 95 games, before being dealt once again, this time to the Boston Bruins.
The Bruins would be Riley's last NHL team he suited up for before returning to play with numerous other minor professional teams across North America. Riley played in eight games with Boston before joining the Boston Cubs of the Canadian-American Hockey League.
From 1936-37 to 1938-39 Jack Riley was a member of the AHA's Tulsa Oilers, before joining the Wichita Hawks (AHA) for the 1940-41 season. The next five years Jack Riley played on seven different teams in three different leagues.