20. Canadiens Trade Patrick Roy
Dumbass Move By: Ronald Corey and the Montreal Canadiens
When it was said and done, Patrick Roy ended up becoming one of the best goalies to ever play the game. But could you imagine that the Canadiens traded him because of one bad game? In a match against the Red Wings on December 2, 1995, Roy didn't have his best stuff on the ice and gave up five goals in the first period. After getting denied a request to get pulled from the game, St. Patrick gave up another four goals and was finally pulled in the second period. Upon leaving the rink, Roy told the owner that "It's my last game in Montreal." Ronald Corey obliged and Montreal hasn't won another chip since then. The Curse of Roy is alive and well.