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 the Stanley Cup twice while proving to be an excellent top-four defenseman. On the other hand, Drouin never met the expectations in Montreal, recording 186 points in 321 games played. This trade also left a huge hole on Montreal’s blue line.
3 – A Failed Replacement for Kotkaniemi
In August 2021, the Canadiens were taken by surprise when the Carolina Hurricanes decided to offer sheet young forward Jesperi Kotkaniemi to a one-year, $6.1 million deal. Montreal ultimately decided to not match the offer sheet and let the Finnish centre go. To compensate for this loss and the departure of Phillip Danault, the Habs traded for center Christian Dvorak a few days later. In return, the Arizona Coyotes received a conditional first-round pick and a 2024 second-round pick. In 206 games in Montreal, Dvorak only recorded 87 points. In the last year of a six-year deal, the 29-year-old center is probably on his way out this summer. In short, while the Dvorak trade wasn’t necessarily disastrous in isolation, it’s disappointing when you look at what Montreal gave up versus what they received in return.
2 – A Niinimaa Deal That Didn’t Live Up to its Promise
In 2006, the Dallas Stars acquired Montreal native Mike Ribeiro and a sixth-round pick for Janne Niinimaa and a fifth-round pick. If it was not for Ribeiro’s off-the-ice issues, this could have been the worst trade made by the Canadiens in the last 25 years. Ribeiro went on to record 407 points in 461 games. On the other hand, Niinimaa only played 41 games in Montreal before finishing his career in Europe. The Ribeiro trade was a lopsided one that has often been cited as a missed opportunity for Montreal. The Canadiens gave up a talented offensive player for a defenseman who didn’t live up to expectations.
1 – Letting Go of Future Star McDonagh
The Scott Gomez trade is often regarded as one of the worst trades in Montreal’s history. On June 30, 2009, the Canadiens acquired forwards Scott Gomez and Tom Pyatt, and defenseman Michael Busto. In return, the New York Rangers obtained Doug Janik, Chris Higgins, Pavel Valentenko, and most importantly, their future captain, Ryan McDonagh. While Gomez recorded 59 points in his first season in Montreal, he never put up this total after. The big issue with the forward was his contract. Gomez signed a seven-year deal with the Rangers in 2007 that averaging $7.35 million per year. This contract was taking about 13% of Montreal’s cap space at that time. GM Gainey still decided to trade the team’s best prospect and at the same time impact the organization’s future for years. McDonagh went on to be a solid defenseman in the NHL, became the Rangers captain in 2014, and won two Stanley Cups with the Lightning in 2020 and 2021.
In conclusion, while the Canadiens have undoubtedly enjoyed periods of success, their history is also marked by several ill-fated trades that have haunted the franchise for years. Whether it’s letting go of future stars like McDonagh, misjudging the value of players like Ribeiro and Dvorak, or making moves based on short-term needs that ultimately didn’t pay off, these deals have significantly impacted the team’s ability to build a competitive roster over the long haul.
As the Canadiens continue their rebuilding process, these trades serve as painful reminders of missed opportunities and the importance of strategic decision-making. With the hope of learning from past mistakes, the Canadiens will aim to avoid similar blunders in the future, striving to create a team that honours the legacy of one of the NHL’s most storied franchises.
