Montreal Canadiens

Roy was a legend in Montreal, winning a Stanley Cup in his rookie season at goalie and doing it against seven years later, all while taking home three Vezina Trophies as the best goaltender in the game. But things began crumbling and after Roy was pulled from a 1995 game in which he gave up nine goals before the end of the second period, he glared at his coach and told the team’s president’s, “that’s my last game in Montreal.” He wanted to play in Colorado, which put together a five-player deal to make it happen. Roy won two more Cups with the Avalanche and was a first-ballot Hall of Famer.

Roy was a legend in Montreal, winning a Stanley Cup in his rookie season at goalie and doing it against seven years later, all while taking home three Vezina Trophies as the best goaltender in the game. But things began crumbling and after Roy was pulled from a 1995 game in which he gave up nine goals before the end of the second period, he glared at his coach and told the team’s president’s, “that’s my last game in Montreal.” He wanted to play in Colorado, which put together a five-player deal to make it happen. Roy won two more Cups with the Avalanche and was a first-ballot Hall of Famer.