Regan moved to Ottawa as a youth. As a 16-year-old, he joined the Ottawa Jr. Senators organization in 1945-46. Regan then played for the Ottawa Senators in the Quebec Senior Hockey League. He moved to Toronto to play two seasons with the Toronto Marlboros organization, first as a junior, then at the senior level. He returned to the Senators in 1950, playing two seasons before joining the Shawinigan Cataracts. Regan then moved on to the Pembroke Lumber Kings of the Northern Ontario Hockey Association and the Quebec Aces of the Quebec Hockey League.\n', '

In 1956-57, Larry finally got his chance in the National Hockey League with the Boston Bruins as a 27-year-old. He scored 14 goals that season, which would be his career high, and he won the Calder Memorial Trophy, the oldest player to win it at that time (Sergei Makarov won it when he was 31 years old in 1988-89 with the Calgary Flames). He played two and a half seasons with the Bruins before being claimed on waivers, for $15,000 on January 7, 1959, by the Toronto Maple Leafs. He played two further seasons with the Leafs before being demoted to the Pittsburgh Hornets in the American Hockey League. In 1962, he moved to Innsbruck, Austria, coaching the Innsbrucker EV for two seasons before returning to the AHL with the Baltimore Clippers in 1965-66 for one final season.\n', '

While still playing, Regan became a playing-coach in 1961–62 with the Pittsburgh Hornets for part of the season. He was named to coach the Etobicoke Indians of the Ontario Hockey Association in 1966, but left the position to join Jack Kent Cooke, owner of the expansion Los Angeles Kings, as head scout, and later Regan was promoted to general manager. Regan was also the head coach for the 1970-71 and part of the 1971-72 seasons and he remained in the job until 1973.\n', '

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