You could definitely say Larry Regan had a varied career in hockey.
He moved to Quebec in the early 1950s, skating for the Quebec Aces. Though he played well in Quebec, he remained buried in the pecking order of the Toronto Maple Leafs organization, the team that owned his NHL rights.
That all changed in 1956 when he joined the Boston Bruins. At the age of 27 he became one of the oldest NHL rookies of the year. He won the Calder trophy thanks to a strong 14 goal, 33 point campaign.
Described as a brash, cocky and confident individual who was not afraid to succeed, Regan played another season and a half. He enjoyed his time in Boston, and was said to be a good friend of baseball great Ted Williams.
Regan was sent back to the Leafs, playing for another couple of seasons before retiring in 1961. He met Jack Kent Cooke while in Toronto, and that would serve him well later in life.
He initially took a player-coach position with the Leafs farm team in Pittsburgh, but left after one season to head to Europe. The Austrian government hired him to develop their national hockey team in preparation for the 1964 Olympics.
When the NHL expanded in 1967 Regan returned to NHL, landing with Jack Kent Cooke's Los Angeles Kings. He was originally hired as director of player personnel. Soon enough he would become the team's general manager and coach.
"Larry was a fierce competitor both as a player and a general manager. His focus was always making the Kings competitive and successful," remembered long time Kings broadcaster Bob Miller.
Regan was the GM who landed such key pieces as Rogie Vachon, Juha Widing and Terry Harper, but he is probably best remembered for punching a referee!
Regan left LA in 1974. He moved to Montreal initially, coaching a junior hockey team before a series of back operations and a serious blood disorder sidelined him for three years.
By the 1980s he became the managing director of the Canadian Old-Timers' Hockey Association.
Larry Regan died in Ottawa on March 9th, 2009. He had a number of health problems, including Parkinson's disease.