The Most Regretted Trades By The Montreal Canadiens

Since their founding in 1909, the Montreal Canadiens have been involved in several trades with teams across the NHL over multiple decades. There have been some high-profile players moved in and out of the team, with the Canadiens by far the most successful team in league history.

But not all trades can be successful, and many of them could even be considered regrettable for various reasons. Whether that’s because the results that followed a trade disappointed, or a fan favourite was moved under difficult circumstances, or someone with a bright future was lost due to the team’s desire to win now, there have been many regrettable trades in franchise history.

Here are some of the most regrettable trades for the Montreal Canadiens.

Patrick Roy

Naturally, the best trade to begin with is arguably the most infamous in franchise history. Patrick Roy is still viewed as one of the top three goaltenders in the history of the NHL. He is regularly discussed alongside Dominik Hasek and Martin Brodeur in debates over who deserves the title outright.

Entering the 1995-96 season, Roy had already lifted the Stanley Cup twice alongside a plethora of individual awards, including two Conn Smythes, three Jennings Trophies, and two Vezina Trophies. The problem was that the Montreal Canadiens were disappointing in 1994-95. They had just 18 wins in the lockout-shortened season, finishing sixth in the Adams Division and missing the post-season.

After starting 0-4-0 the following season, Jacques Demers was replaced by first-time head coach Mario Tremblay. General manager Serge Savard was also ousted in favour of Réjean Houle. Tremblay had a long playing career with the Canadiens, winning five Cups and even being a roommate with Roy during the earlier stage of the goaltender’s own career.

After retiring, though, Tremblay and Roy’s relationship strained, with the former regularly commenting on him as part of his radio career, which nearly led to a physical confrontation between the pair. Despite this animosity with their star, Canadiens ownership felt that Tremblay was the man to get things back on track.

Results did improve under Tremblay, with the Canadiens going 12-3-1 before facing the Detroit Red Wings in what would become one of the most infamous games in history. On December 2nd 1995, at the Montreal Forum, the Canadiens suffered a devastating 11-1 loss. By the end of the first period, Roy had allowed five goals on just 17 shots. However, Tremblay did not pull him from the game and kept him in for another four goals. His team was down 9-1 before Roy was eventually pulled from the game.

This was the final straw for the goalie. He immediately went to team president Ronald Corey and told him he would never play for the team again. Roy was suspended by the team. Four days later, he was sent to the Colorado Avalanche in a package deal alongside team captain Mike Keane for Jocelyn Thibault, Martin Ručinský and Andrei Kovalenko.

Roy continued to have great success with the Avalanche. They won the Cup the year he was traded and winning another in 2001. He picked up his third Conn Smythe trophy. He added another Jennings in 2002 before retiring in 2003. For the Canadiens, Tremblay lasted just one more season, and the deal is still viewed today as one of the most lopsided trades in NHL history.

Losing a future Hall of Famer, and seeing him succeed so much after leaving the team, for a coach who would never be a head coach in the NHL again, and arrived at the team already on negative terms with the star goalie, is surely one of the most regrettable decisions, let alone trades, in Montreal Canadiens history.