Hillman started his career by playing one season for the Windsor Spitfires of the OHL in 1953. He split the next season between the Buffalo Bisons of the AHL and the Detroit Red Wings of the NHL. He won his first Stanley Cup Championship with Detroit in 1955. He became the youngest player to be engraved on the Stanley Cup. 18 years, 2 months, 9 days. (This is a record that can\'t be broken under the current rules as a player must be eighteen years old by September 15 to be eligible to play in the NHL that season.) Hillman left the Red Wings after 1957 and went to the Boston Bruins. He played two full seasons in Boston before being sent to their minor league team, the Providence Reds, for most of the 1960 season.\n', '

In 1961, Hillman went to the Toronto Maple Leafs where he continued to bounce from the minor leagues to the NHL and back. He played on four Stanley Cup winning teams in Toronto in 1962, 1963, 1964 and 1967. In between those cup wins he played parts of six season with the Rochester Americans and the Springfield Indians.\n', '

After the 1968 season, he signed with the expansion Minnesota North Stars who later traded Hillman to the Montreal Canadiens where he won his sixth and final Stanley Cup Championship. He is one of only 11 players in Stanley Cup history to win the Cup with three or more different teams.\n', '

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