
The Montreal Canadiens head into the 2025 Trade Deadline as sellers and will look to add some future assets to the organization in the coming days.
Fans hope that general manager (GM) Kent Hughes can execute a major deadline deal that will help make this team a Stanley Cup contender within the next couple of years. In the meantime, we can look back at some of the worst Canadiens deadline trades of this century.
Montreal was cruising through the 2007-08 season near the top of the Eastern Conference, ultimately finishing first overall in the conference. This was due to Alex Kovalev’s resurgence, who recorded more than one point per game (he is the last Canadiens player to do so.) Also, near career-best offensive performances from Tomas Plekanec, Mark Streit, and Andrei Kostitsyn turned Montreal into a deep, high-scoring team with one of the best power-play units at that time. However, instead of looking to add to a team that could have made a deep playoff run, the Canadiens became sellers at the deadline in 2008 as they traded away starting goaltender Cristobal Huet . In return, the Canadiens received a second-round draft pick from the Washington Capitals.
It has since been confirmed that Montreal nearly added Vincent Lecavalier to the roster, but the deal fell through. Yet, they did not acquire a single player for their NHL roster during the season via trade. Instead, then-GM Bob Gainey just moved Huet, who had won 21 games with a .916 save percentage for the club. The Capitals were the beneficiary of his excellent play that season. This trade provided no benefit to the club at the deadline and only removed a veteran goaltender. It did, however, open the door to the next generation of goaltenders for Montreal, giving the opportunity for Carey Price and Jaroslav Halak to take the reins.
Not only was the trade of Michael Cammalleri below market value, but it was done with disrespect to the player as well. During a game against the Boston Bruins, Cammalleri was traded to the Calgary Flames. The main piece in the return for the Canadiens’ sniper was power forward Rene Bourque. The Canadiens also received prospect Patrick Holland and a second-round pick in the 2013 NHL Entry Draft. The Flames picked up goaltender Karri Ramo and a fifth-round pick in the 2012 Draft as part of the deal. The trade came after Cammalleri criticized his teammates’ attitude following practice the previous day.
Cammalleri was a critical member of the Canadiens team that went on a Cinderella run to the Eastern Conference Final in 2010. But in 2012, both Cammalleri and the Canadiens fell on tough times. And in January 2012, during a post-game press availability, Cammalleri was quoted saying “I can’t accept that we will display a losing attitude as we’re doing this year. We prepare for our games like losers. We play like losers. So, it’s no wonder why we lose.” Since that time, it has been disputed that he never used the term “losers,” but nonetheless, his fate was sealed, and then-GM Pierre Gauthier made it his mission to ship him out of Montreal.
While the return on the trade was not to the level expected of a goal scorer, it wasn’t terrible. The real reason this falls into the category of one of the worst deadline deals is the reason it was made. Gauthier’s handling of the Cammalleri trade sent a message to players, prospects, coaches and any other employee of the franchise: that the team would not tolerate any dissent. Montreal is well-known for the media pressure the team faces daily, and this only made lives more difficult for all involved, discouraging many from wanting to play for the team. It provided an added pressure that no one could thrive in. This iron-fisted approach only added to the issues the team faced as they fell to the bottom of the standings, ending with a third-overall pick (Alex Galchenyuk).
The proof of this terrible approach to personnel management is in the results. Gauthier was fired, and the club brought in someone from outside the organization who was seen as being the exact opposite of him in Marc Bergevin. For several seasons, the club became relevant again, having some playoff success over the next five seasons. The Cammalleri trade is a shining example of how not to manage players or a team.
The failure of the 2017 Trade Deadline wasn’t due to a series of overpaid deals, or that Bergevin didn’t overpay in any way, it’s that he completely missed an opportunity to solidify his team for the playoffs properly. They finished first in the Atlantic Division with 103 points and were matched up in the first round with the New York Rangers. The series was expected to go Montreal’s way, however, because they chose to add larger, slower players instead of scoring — which was their need at the time — they lost that series in six games. This loss led to the team “re-tooling” on the fly.
Bergevin made a series of deals to appease his then-head coach Claude Julien, who had taken over from Michel Therrien after he was fired on Valentine’s Day of that year due to the team’s recent struggles. Bergevin dealt for Andreas Martinsen from the Colorado Avalanche in exchange for Sven Andrighetto. The second deal was adding Dwight King from the Los Angeles Kings in exchange for a 2018 conditional fourth-round pick, then he added Steve Ott from the Detroit Red Wings in exchange for a 2018 sixth-round pick. But there was one more deal.
Perhaps the most surprising move of the deadline saw Bergevin ship out long-time forward and Max Pacioretty’s linemate David Desharnais for defenceman Brandon Davidson. While Davidson was seen as an advanced analytics fit, it wasn’t that aspect that caught Julien’s eye. The overall trend to every move was not speed or offensive skill, but rather about size and grit. It was an instance of a GM giving in to demands from his coach to get players he liked. There was no overall plan to roster construction or style of play. The assets that Bergevin dealt away in those trades weren’t high-value picks, and didn’t impact the franchise negatively. However, none of the trades addressed Montreal’s one glaring need at that time, the need for a top-six scoring forward.
The club was never able to recover from that collapse in the playoffs. They went from a 103-point season in 2016-17 to a dismal 71-point finish. This led to the Canadiens’ management to begin a retool. They did their best not to crush the fanbase’s spirit by admitting the team would suffer through several lean seasons, but fans knew they were in for some dark times.
The Canadiens’ rebuild continues, and the deadline deals Hughes executes will hopefully be in line with what will help make this team a Stanley Cup contender within the next couple of years.
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