The Montreal Canadiens have a rich and celebrated history, filled with championship banners and unforgettable players. But as with any storied franchise, they’ve also made their fair share of regrettable decisions over the years. Some of the worst moves in Habs history come from trades that, in hindsight, have proven costly, whether they moved away future stars, undervalued key players, or failed to capitalize on potential. These trades not only set back the team in the short term but also impacted their long-term success. Despite the franchise’s incredible legacy, certain deals still leave fans scratching their head and wondering, “What could have been?” Let’s take a look at the five worst trades the Canadiens have made over the last 25 years.
5: A French Goalie to Washington
In Feb. 2008, then-general manager (GM) Bob Gainey decided to send French netminder Cristobal Huet to the Washington Capitals for a second-round pick in 2009. The Canadiens had two very promising goalies in their pipeline at that time: 20-year-old Carey Price and 22-year-old Jaroslav Halak. Huet’s days in Montreal were numbered with the two young goalies coming, but in a position to make the playoffs at that time, the Habs still decided to move on from their number-one goalie. While a second-round pick looked decent for the veteran goalie, Montreal could have waited until the summer to trade Huet and move on with the young promising tandem. Montreal ended up trading the second-round pick they received, along with a third-round pick to the Atlanta Thrashers, in return for 39-year-old defenseman Mathieu Schneider.
4: Sergachev Swap That Didn’t Pay Off
On June 15, 2017, GM Marc Bergevin decided to shake things off and bring forward Jonathan Drouin home by parting with young promising defensive prospect Mikhail Sergachev. This trade did not make a lot of sense at the time and still does not. Drouin was drafted third overall by the Tampa Bay Lightning in 2013 and had issues with the team. When sent to the American Hockey League in 2016, the Quebec native decided to hold out, creating friction between the player and the Lightning organization.
After a promising 53-point season in 2016-17, Montreal jumped on the occasion and traded for the young forward. In return, the Habs sent their ninth-overall pick in 2016, Sergachev. In seven seasons in Tampa Bay, Sergachev lifted…
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