Looking back at the 5 worst trades in NHL history

1. Patrick Roy For Virtually Nothing

The Montreal Canadiens have won the most Stanley Cups of any NHL franchise. They’ve also arguably made more terrible trades than any franchise over the past 20 years. P.K. Subban for Shea Weber. Ryan McDonagh (and more!) for Scott Gomez. Chris Chelios for Denis Savard.

But no trade in NHL history was as bad as the Canadiens sending Patrick Roy to the Colorado Avalanche for Andrei Kovalenko, Martin Rucinsky, and Jocelyn Thibault. Rucinsky was decent (297 points in 432 games over seven seasons in Montreal), but Kovalenko only spent 51 games with the Habs before moving on to the Edmonton Oilers.

This trade happened because of a reported feud between head coach Mario Tremblay and Roy. They didn’t get along from the moment the former was hired. On December 2, 1995, the Canadiens suffered their worst home loss ever, losing 11-1. Roy was on the ice for nine of those goals.

After he got pulled, the goalie stormed past Tremblay, went straight to team president Ronald Corey, and demanded a trade. Four days later, Roy got traded to the Avalanche.

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The Canadiens have never won a Stanley Cup since that incident. Meanwhile, Roy led the Avalanche to two Stanley Cups, picking up an additional Conn Smythe Trophy in 2001. It took a long time for the Canadiens and Roy to reconcile, but they eventually did. However, the sting of that trade still hurts Montreal fans to this day.