Gregory was the general manager of the Toronto Maple Leafs from 1969 to 1979, where he led the Leafs to eight playoff appearances. After 1979, he became the Director of Central Scouting for the NHL. In 1986, he became the Executive Director of Hockey Operations. Gregory was elected to the Hockey Hall of Fame in 2007. He is also the current chairman of the Hockey Hall of Fame selection committee. On February 27, 2009, Gregory suffered a heart attack at the NHL office in Toronto.
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