In a shocking twist that could reshape the NHL landscape, the 2025 season has already seen its share of disastrous trades that threaten to haunt franchises for years to come. As teams gear up for the Stanley Cup playoffs, several general managers have made critical miscalculations that could cost them dearly. Here are the top five worst trades of the season, each one a potential nail in the coffin for playoff hopes and team futures.
Kicking off our countdown at number five, the Edmonton Oilers’ ill-fated acquisition of Jake Walman from the San Jose Sharks stands out as a glaring misstep. In a desperate bid to shore up their porous defense, GM Stan Bowman traded away a 2026 first-round pick and promising prospect Carl Bergland for a player who is, essentially, a duplicate of what they already have. Walman, an offensive defenseman, does nothing to address the Oilers’ glaring need for a shutdown presence on the blue line. With Conor McDavid’s prime slipping away and last year’s devastating Game 7 loss still fresh, this trade exemplifies poor management at a critical juncture.
At number four, the Detroit Red Wings’ lack of action has proven to be just as damaging as any trade gone wrong. With over $10 million in cap space and a legitimate shot at their first playoff appearance since 2016, GM Steve Yzerman made only a minor move, trading for aging players Peter Morazz and Craig Smith. This passive approach sends a clear message: the Red Wings lack faith in their current roster. As rivals strengthened their teams, Detroit’s inaction could cost them dearly, undermining both their playoff aspirations and the confidence of their star players.
The Nashville Predators land at number three for a series of blunders that showcase a troubling trend of asset mismanagement. Under new GM Barry Trotz, Nashville traded away defenseman Luke Shen and forward Tommy Novak to Pittsburgh for Michael Bunting and a fourth-round pick. Hours later, Shen was flipped to Winnipeg for a second-rounder, leaving many to wonder why Nashville didn’t capitalize on that opportunity themselves. The Predators’ failure to maximize value during a critical trade deadline could significantly hinder their competitive timeline.
In the number two spot, the Carolina Hurricanes executed a masterclass in mismanagement with their handling of Miko Rantanen. Just weeks before the deadline, Carolina traded for the star center, only to fail to secure a contract extension. They subsequently flipped him to Dallas for unproven prospects and draft picks, effectively trading away proven talent for uncertainty. This series of miscalculations has weakened their roster at a time when they were expected to contend for the Cup, leaving fans and analysts alike scratching their heads.
Finally, the Boston Bruins’ franchise-altering fire sale takes the top spot as the worst trade of the season. In a frantic 24-hour period, the Bruins traded away cornerstone players Brad Marchand and Brandon Carlo, among others, in a move that reeks of panic rather than strategy. Retaining salary for Marchand while receiving a mere conditional second-round pick in return is a staggering misjudgment. With the Bruins still in playoff contention, these trades not only weaken their team but also signal a troubling internal dysfunction that could haunt the franchise for years to come.
These five disastrous trades share common threads: misjudged player value, failure to maximize returns, and decisions that contradict team timelines. As the playoffs loom, the repercussions of these trades will be put to the ultimate test. For some GMs, these blunders could cost them their jobs, while others may watch former stars hoist the Cup in different uniforms. In a salary cap league where championship windows close quickly, these trades serve as a stark reminder: sometimes, the most critical moves are the ones left unmade. The Stanley Cup picture is shifting, and the stakes have never been higher.
