With 24 championships and over 60 members inducted into the Hockey Hall of Fame, the Montreal Canadiens have had no shortage of great players. However, even the most esteemed organizations have their fair share of regrets.
We delved into some of the worst trades in Canadiens’ history, examining deals that left fans scratching their heads and longing for what might have been.
Chris Chelios to the Chicago Blackhawks (1990)
In a regrettable move, the Canadiens sent future Hall of Famer Chris Chelios (and a second-round pick) to the Chicago Blackhawks in exchange for center Denis Savard.
Chelios would go on to become one of the greatest defencemen of his era, winning three Norris Trophies and playing a pivotal role in the Blackhawks’ success.
Savard, on the other hand, would only play with the Canadiens for three seasons.
Patrick Roy to the Colorado Avalanche (1995)
The infamous trade that still haunts Canadiens fans to this day.
In a shocking move, Montreal dealt away their superstar goaltender, Patrick Roy, after he had a heated argument with then-coach Mario Tremblay.
Roy was traded in a package deal with forward Mike Keane to the Colorado Avalanche, in exchange for Andrei Kovalenko, Martin Rucinsky, and goaltender Jocelyn Thibault.
The goalie went on to win two more Stanley Cups with the Colorado Avalanche in the years that followed, while the Habs struggled to fill the void between the pipes for years.
Pierre Turgeon to the St. Louis Blues (1996)
Less than a year after trading Roy, then-GM Rejean Houle made another shocking move nine games into the 1996-97 season.
He dealt team captain Pierre Turgeon, young centre Craig Conroy, and minor league centre Cory Fitzpatrick to the St. Louis Blues for former Montreal winger Shayne Corson, defenceman Murray Baron, and a fifth-round pick (Gennady Razin).
Turgeon went on to have multiple productive seasons with the Blues, netting a career-high 30 goals and 82 points in his fourth season with the team. Meanwhile, Conroy blossomed into a solid NHLer, retiring with over 500 points and 1,000 games under his belt.
It also quickly became clear that Montreal had lost the trade.
Corson was beloved in his first stint with the Canadiens, but the enforcer did not enjoy the same success the second time around, evolving into a depth player in the lineup.
Baron would only suit up for one season with the Habs, while Razin would never make it past the AHL level.
Ryan McDonagh to the New York Rangers (2009)
In another trade that still makes Canadiens fans cringe, the team sent defenceman Ryan McDonagh, along with Chris Higgins, Pavel Valentenko, and Doug Janik, to the New York Rangers in exchange for forwards Scott Gomez, Tom Pyatt, and defenceman Michael Busto.
McDonagh, a former first-round draft pick, quickly emerged as a star for the Rangers, eventually becoming their captain.
To make matters worse, Gomez had signed a seven-year contract with the Rangers in 2007 worth $51.5 million for an annual cap hit of $7.35 million. The overpaid forward would contribute just 21 goals in the three years he spent with Montreal before he was shipped off.
Mikhail Sergachev to the Tampa Bay Lightning (2017)
The Habs had a promising defensive prospect in Mikhail Sergachev.
But before he could fully establish himself among Montreal’s top pairings, he was surprisingly traded to the Tampa Bay Lightning for struggling forward Jonathan Drouin.
While Drouin was highly regarded for his offensive skills at the time, it didn’t take long for fans to realize Montreal had lost the trade.
As Sergachev evolved into one of Tampa Bay’s top blueliners, winning two Stanley Cups in the process, Drouin’s offensive production slowly dwindled.
After six underwhelming seasons, Montreal lost the Quebec-born forward to free agency.
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