The Montreal Canadiens’ Worst Trade Deadline Deals of This Century

The Montreal Canadiens have one of the most storied franchises in NHL history, with 24 Stanley Cup championships and a legacy that few teams can match. However, even the most celebrated organizations make mistakes, and the Habs have had their share of regrettable decisions at the trade deadline over the past two decades. While some trades are made with the best intentions—adding depth for a playoff run or positioning for the future—others have proven to be costly missteps that set the franchise back for years.

The trade deadline is arguably the most critical time of the season for NHL general managers. It’s a high-stakes period where teams must decide whether to buy, sell, or stand pat. For the Canadiens, several deadline deals made since 2000 have left fans wondering what could have been. These transactions either moved away future assets for underwhelming returns, failed to address glaring needs, or were executed in ways that damaged the team’s culture and reputation around the league.

Trading away Cristobal Huet instead of strengthening the roster

The 2007-08 season was one of the Canadiens’ best regular-season performances of the century. Finishing first overall in the Eastern Conference with a roster led by Alexei Kovalev’s offensive resurgence, Montreal looked poised for a deep playoff run. Kovalev recorded more than one point per game that season, becoming the last Canadiens player to achieve that feat. Combined with near career-best performances from Tomas Plekanec, Mark Streit, and Andrei Kostitsyn, the team boasted one of the league’s most potent offenses and power-play units.

Instead of capitalizing on this momentum and adding pieces for a championship push, then-general manager Bob Gainey made the puzzling decision to become a seller at the 2008 trade deadline. According to reports, the Canadiens traded starting goaltender Cristobal Huet to the Washington Capitals for just a second-round draft pick. Huet had been stellar for Montreal that season, posting a 21-12-4 record with a .916 save percentage. The French netminder provided stability and veteran leadership in net, qualities that are invaluable during playoff runs.

The rationale behind the move was that the Canadiens had two promising young goaltenders waiting in the wings: 20-year-old Carey Price and 22-year-old Jaroslav Halak. While both would go on to have excellent careers, asking them to carry a team with Stanley Cup aspirations in the middle of a season was a questionable strategy. The trade provided no immediate benefit to the roster and actually weakened it by removing a proven playoff performer. It has since been confirmed that Montreal nearly acquired Vincent Lecavalier from the Tampa Bay Lightning, but the deal fell through, leaving the team without any significant additions.

The Capitals, meanwhile, benefited greatly from Huet’s excellent play down the stretch. The second-round pick Montreal received was eventually bundled with a third-round selection and traded to the Atlanta Thrashers for 39-year-old defenseman Mathieu Schneider, a rental who failed to make a significant impact. The Huet trade remains one of the most head-scratching moves of the century, as it demonstrated a lack of conviction in a team that had genuine championship potential.

The disrespectful Michael Cammalleri trade that damaged the franchise’s reputation

Few Montreal Canadiens worst trade deadline deals of this century were as poorly executed as the Michael Cammalleri trade in January 2012. Not only was the return below market value, but the manner in which the deal was conducted showed a stunning lack of respect for a player who had been integral to the team’s success just two years prior. Cammalleri was a critical member of the Canadiens squad that made an improbable run to the Eastern Conference Final in 2010, providing offensive firepower and leadership when the team needed it most.

By the 2011-12 season, both Cammalleri and the Canadiens had fallen on hard times. Following a disappointing loss, Cammalleri criticized his teammates’ attitude, reportedly saying the team prepared and played with a losing mentality. While there has been dispute over the exact wording of his comments, the sentiment was clear: he was frustrated with the team’s direction. Then-general manager Pierre Gauthier took offense and decided to make an example of the sniper.

During a game against the Boston Bruins, Cammalleri was pulled from the bench mid-game and informed he had been traded to the Calgary Flames. The main piece in return was power forward Rene Bourque, along with prospect Patrick Holland and a second-round pick in the 2013 Draft. The Canadiens also sent goaltender Karri Ramo and a fifth-round pick to Calgary. While Bourque would have some productive moments in Montreal, he never matched Cammalleri’s offensive output or impact.

The real damage from this trade wasn’t the return on the ice—it was the message it sent throughout the hockey world. Gauthier’s iron-fisted approach and public humiliation of Cammalleri created an environment where players, prospects, and coaches felt they couldn’t speak honestly about the team’s issues. In a market like Montreal, where media scrutiny is already intense, this only made things worse. The franchise’s reputation suffered, and many players became reluctant to waive no-trade clauses to come to Montreal.

The proof of this disastrous personnel management is evident in the results. The team collapsed to the bottom of the standings, finishing with just 78 points and earning the third-overall pick in the 2012 Draft. Gauthier was fired shortly after, and the organization brought in Marc Bergevin from outside to restore stability and rebuild the team’s damaged reputation. For anyone looking at similar organizational failures, the Montreal Canadiens’ worst free agent signings since 2000 provides additional context for the franchise’s struggles during this era.

The complete failure of the 2017 trade deadline

Sometimes the worst Montreal Canadiens trade deadline deals of this century aren’t about what was done, but about what wasn’t done. The 2017 trade deadline perfectly exemplifies this concept. After finishing first in the Atlantic Division with 103 points, the Canadiens appeared to be legitimate contenders. However, instead of addressing the team’s most glaring need—offensive firepower—then-GM Marc Bergevin made a series of puzzling acquisitions that prioritized size and grit over skill.

Bergevin had recently fired head coach Michel Therrien on Valentine’s Day and replaced him with Claude Julien, a coach known for preferring physical, defensive-minded players. In what appeared to be an attempt to appease his new bench boss, Bergevin went on a shopping spree for bigger, slower players. He acquired Andreas Martinsen from the Colorado Avalanche in exchange for Sven Andrighetto, a skilled offensive player who would go on to have success elsewhere. He then added Dwight King from the Los Angeles Kings for a conditional fourth-round pick and Steve Ott from the Detroit Red Wings for a sixth-round pick.

The most surprising move came when Bergevin traded long-time forward David Desharnais, Max Pacioretty’s linemate, to the Edmonton Oilers for defenseman Brandon Davidson. While Davidson was viewed favorably by advanced analytics, Julien seemed more interested in his size than his statistical profile. None of these moves addressed Montreal’s critical need for top-six scoring depth, which would prove to be their undoing in the playoffs.

The Canadiens faced the New York Rangers in the first round and lost in six games, largely because they couldn’t generate enough offense. The collapse was swift and severe. The team went from 103 points in 2016-17 to a dismal 71-point finish the following season, plummeting from first place to the draft lottery. The “retool on the fly” became a full rebuild, and the franchise entered a period of darkness that would last several years.

This deadline disaster illustrates how a GM can make multiple moves without actually improving the team. The assets Bergevin gave up weren’t particularly valuable, but the opportunity cost was enormous. By failing to add the scoring help the team desperately needed, he wasted a season where the Canadiens were genuine contenders. The disconnect between the roster’s needs and the moves made remains one of the most frustrating chapters in recent franchise history.

The Thomas Vanek rental that produced minimal returns

Another entry among the Montreal Canadiens worst trade deadline deals of this century came in 2014 when Marc Bergevin acquired veteran winger Thomas Vanek from the New York Islanders. On paper, the move made sense: Montreal needed offensive help for a playoff push, and Vanek was a proven 40-goal scorer with playoff experience. However, the price paid was steep, and the return was minimal, making it one of the more regrettable rental acquisitions of the Bergevin era.

The Canadiens sent a second-round pick in 2014 and prospect Sebastian Collberg to the Islanders for Vanek. While this doesn’t seem excessive for a player of Vanek’s caliber, the context matters. Vanek was a pure rental—a pending unrestricted free agent with no interest in re-signing with Montreal long-term. He played just 22 regular-season games for the Habs, recording a respectable 15 points, but failed to make a significant impact when it mattered most.

In the playoffs, Vanek managed just three points in 17 games as the Canadiens reached the Eastern Conference Final before falling to the New York Rangers. His inability to produce in crucial moments raised questions about whether the acquisition was worth the cost. When July 1st arrived, Vanek signed a three-year deal with the Minnesota Wild, leaving Montreal with nothing to show for their investment except a brief playoff run that fell short of the ultimate goal.

What makes this trade particularly frustrating is that Collberg, while never panning out as hoped, represented organizational depth that was traded away for a short-term rental. The second-round pick could have been used to acquire a different player or to draft a prospect who might have contributed to the team’s future. Instead, Bergevin gambled on a player who couldn’t deliver when it counted. While not as catastrophic as some of the other deals on this list, the Vanek trade serves as a reminder that deadline rentals don’t always pay dividends, even when the player’s resume looks impressive. Much like the trades examined when analyzing the Toronto Maple Leafs’ worst trades of all time, sometimes the cost outweighs the benefit, regardless of the player’s reputation.

The Petry extension that turned into an albatross contract

While not technically a trade deadline deal, Jeff Petry’s contract extension in 2015 deserves mention in any discussion of Montreal’s questionable transactions during this period because of how it later impacted the team’s flexibility at future deadlines. Acquired from the Edmonton Oilers at the 2015 trade deadline for a second-round pick and a conditional pick, Petry initially looked like an excellent addition. He played well during his first stint with the team and helped the Canadiens reach the second round of the playoffs.

Impressed by his performance, Bergevin signed Petry to a six-year, $33 million contract extension that would kick in for the 2015-16 season. For the first several years, the deal looked reasonable as Petry was a steady top-four defenseman who could play in all situations. However, as he aged and the team’s fortunes declined, the contract became increasingly problematic. By the time the Canadiens were rebuilding under new GM Kent Hughes, Petry’s declining performance and hefty cap hit made him difficult to move.

The situation worsened when Petry expressed his desire to leave Montreal, citing family reasons and the team’s lack of competitiveness. This put Hughes in a difficult negotiating position at the 2022 trade deadline and beyond. The GM eventually traded Petry to the Pittsburgh Penguins in the summer of 2022, but had to retain 50% of his salary and accept a minimal return to make the deal work. What started as a successful deadline acquisition and subsequent extension became a cautionary tale about how long-term contracts can hamper a team’s ability to maneuver at future deadlines.

The Petry situation highlights an important aspect of deadline management: every move has long-term consequences. While the initial acquisition was smart, the extension locked the Canadiens into a contract that eventually required salary retention to escape. It limited the team’s cap flexibility during crucial rebuilding years and prevented them from using that money to add younger, more affordable talent.

Learning from past mistakes and looking toward the future

The Montreal Canadiens’ worst trade deadline deals of this century serve as valuable lessons in roster management and organizational decision-making. From the Huet trade that weakened a contending team to the Cammalleri debacle that damaged the franchise’s reputation, from the failed 2017 deadline that wasted a 103-point season to rental acquisitions that produced minimal returns, these moves have had lasting impacts on the organization.

What ties many of these mistakes together is a failure to properly assess the team’s true needs and competitive window. The Huet trade demonstrated a lack of conviction in a genuinely competitive roster. The Cammalleri move showed how poor player relations can poison an organization’s culture. The 2017 deadline revealed the dangers of making moves to appease a coach rather than addressing actual roster deficiencies. And various rental acquisitions highlighted the risks of mortgaging the future for short-term gains that may never materialize.

Current GM Kent Hughes has taken a markedly different approach since assuming control of the franchise. Rather than making splashy deadline moves for questionable fits, he has focused on accumulating draft picks and prospects while carefully managing the team’s cap situation. His patient, process-oriented strategy stands in stark contrast to some of the impulsive decisions made by his predecessors. The Canadiens’ rebuild is ongoing, but the lessons learned from past deadline disasters have clearly informed the current management’s philosophy.

As the Canadiens continue building toward their next competitive window, these cautionary tales remain relevant. They remind us that trade deadline deals—whether buying or selling—must align with the organization’s long-term vision and competitive reality. The pressure to make moves in a hockey-mad market like Montreal is immense, but the worst decisions have often come when GMs acted rashly or without clear strategic purpose. With a talented young core developing and a management team committed to sustainable success, Habs fans can hope that future trade deadlines will produce far better results than some of the regrettable deals that have haunted the franchise throughout this century.