3. Patrick Roy to the Colorado Avalanche (1995)
Of all the trades on this list, this one had a very public meltdown. Patrick Roy was the undisputed King for the Montreal Canadiens. His wacky but dominant goaltending had won the Habs cups in 1986 and 1993. However, a coaching change would signify the beginning of the end. Mario Tremblay was a former teammate of Roy’s and the two had not gotten along. Tremblay was known to mock Roy’s English speaking and the two very nearly came to blows on one occasion.
Immediately the tension between the two proved an issue. This culminated in a very unhappy final game for Roy which would prompt one of the most uneven trades in history. On December 2nd, 1995 Roy was having a shocker in net. In a franchise-worst 11-1 defeat, he allowed nine goals on 26 shots. Tremblay didn’t pull him until the middle of the second period. Humiliated and at his wits end, Roy walked up to Habs president Ronald Corey and advised him “This is my last game in Montreal!”
Faced with a seemingly difficult situation, Canadiens GM Rejean Houle dealt Roy to the Colorado Avalanche along with captain Mike Keane for Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko. Immediately the trade was criticized and Habs fans upset about the poor return for their star. Roy would go on to add another Stanley Cup with his new side the same year. Saint Patrick would also win a final cup in 2001 before retiring in 2003. What could have been achieved if Houle had made an effort to diffuse the tension between player and coach?