St. Patrick led the Montreal Canadiens to an unexpected Stanley Cup title as a rookie in 1986. For his efforts, Roy won his first Conn Smythe Trophy as the playoffs MVP. Then in 1993 he had one of the greatest post-seasons in NHL history when he won 10 overtime games to give Montreal the edge over Wayne Gretzky's Los Angeles Kings. Roy won another Smythe trophy.
Roy moved to Colorado and won two more Stanley Cups, in 1996 and 2001. In 2001 he won his third Smythe award, an impressive 15 years after his first. It also marks the most playoff MVP nods of any player in NHL history.
NHL greatness is cemented with playoff success. Though he owns practically every NHL regular season record for a goalie, he is considered to be the greatest goaltender of all time not for most career wins but for his 4 Stanley Cups and 3 Conn Smythes.
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