Montreal Canadiens trades: Ranking the worst 3 moves in Habs history

By Sukanya Banerjee

Modified Aug 29, 2023 22:00 GMT

The Montreal Canadiens stand as one of the most renowned teams in the NHL. Its existence has left a significant mark in the hockey realm with impressive trades and amazing players’ performances. Although the Montreal Canadiens have a rich history of players successfully earning spots in the Hall-of-Fame list and several Stanley Cup wins, the team has also made several wrong trades, which have left them regretting for a lifetime.

Having said that, let’s take a look at the worst three trades in the Habs' NHL history:

#3 Pierre Turgeon's trade to the St. Louis Blues (1996)

One of the worst trades of the Montreal Canadiens was that of the then-team captain, Pierre Turgeon, by then-GM Rejean Houle to the St. Louis Blues in 1996. In exchange for former winger Shayne Corson, defenseman Murray Baron, and a fifth-round pick from the St. Louis Blues, the team traded away Turgeon, promising young center Craig Conroy, and minor league center Cory Fitzpatrick.

Turgeon continued to have successful seasons with the Blues. He showcased his scoring prowess in his fourth season with St. Louis Blues with career-high totals of 30 goals and 82 points. Craig Conroy prospered in the meanwhile with impressive scoring abilities.

#2 Patrick Roy's trade to the Avalanche (1995)

The controversial Patrick Roy trade is undoubtedly one of the worst trades on the list of the worst decisions made by the Montreal Canadiens. Patrick was one of the best goaltenders of his time on the ice who brought home two Stanley Cups for the Canadiens. However, he was traded to the Colorado Avalanche due to a heated altercation with the former coach, Mario Tremblay, during a game against the Detroit Red Wings.

The Canadiens exchanged Roy and Mike Keane for Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko from the Colorado Avalanche on December 6, 1995. The team lost a talent of a generation while also failing to get a just return for him. Thibault, Rucinsky, and Kovalenko failed to leave a lasting impression. The trade haunted the Canadiens for years as Roy went on to win two more Stanley Cups with the Avalanche.

#1 Chris Chelios' trade to the Blackhawks (1990)

The Montreal Canadiens’ luck of doom started with the worst trade of Chris Chelios on June 29, 1990, for the first time in NHL history. The Canadiens traded the future Hall of Famer Chelios to the Chicago Blackhawks in an unimaginable move. The star defenseman was a significant member of the Canadiens' blue line whom the team could rely on.

Denis Savard was given to the Montreal Canadiens in exchange for Chelios. Though Savard had a good name in the hockey community for being a forward with amazing skill sets and on-ice prowess, he joined the team only before his retirement. Hence, the deal didn't make sense in light of the Canadiens' requirements.

Montreal Canadiens made a big hole in their defense by trading a top-tier defenseman for an aging forward. Savard's tenure in Montreal was rather brief, although Chelios went on to have an extremely successful career and win three Norris Trophies.