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NHL Trade Deadline: Ranking every team’s worst ever trade

By David Rouben

SACRAMENTO, CA - APRIL 3: Wayne Gretzky of the Los Angeles Kings in action against the Edmonton Oilers at the Arco Arena on April 3, 1994 in Sacramento, California. The Kings defeated the Oilers 6-1. (Photo by Rocky Widner/Getty Images)
SACRAMENTO, CA - APRIL 3: Wayne Gretzky of the Los Angeles Kings in action against the Edmonton Oilers at the Arco Arena on April 3, 1994 in Sacramento, California. The Kings defeated the Oilers 6-1. (Photo by Rocky Widner/Getty Images) /
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Colorado goaltender Patrick Roy
Colorado goaltender Patrick Roy /

6: Montreal Canadiens

Patrick Roy is one of the greatest goalies in Canadiens franchise history – of that there is no doubt. Did he and the team endure a rough breakup? Sure, but dealing him was for the best. However, just because he was unsettled, that doesn’t decrease his value. The Canadiens should’ve gotten a lot more out of Roy, but what they were left with was extremely disappointing.

After all, we’re talking about a two-time Stanley Cup and three-time Vezina winner, as well as the goalie who brought the butterfly into the mainstream. The last time the Habs won the Stanley Cup was with him, and it can be argued that they haven’t won a Cup ever since because of this deal. However, many knew the end was near when his relationship with new coach Mario Tremblay was documented. He let in seven goals against the Red Wings at home, and mocked the crowd when they gave him a sarcastic cheer:

Roy was later pulled, and the Habs knew they had to move on. The goalie that came in to replace Roy was Jocelyn Thibault, who didn’t last more than two seasons before being traded to the Blackhawks while Kovalenko was traded at the start of the 1996-97 season. Rucinsky stayed with the club for a while, and put up serviceable tallies, but he didn’t make Habs fans forget about Roy.

That’s because Roy picked up right where he left off with the Avalanche. As soon as he landed in Colorado, he won a Cup with them, then another in 2001. He continued to put up consistently high save percentages, and won over the fans by providing memorable chirps and fighting a Red Wings goalie twice. He also had his forgettable moments in the playoffs, where the Red Wings got the better of him once again:

It’s good to see that the Habs have forgiven him by retiring his number, while his time in Colorado served enough fond memories for him to come back and serve as their coach. But if there’s one lesson to be learned from this, it’s never upset your star player – or the Red Wings.

Next: 5: Boston Bruins

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