5 NHL Trade Fails That Will Keep Haunting Teams During the 2025-26 Season
Trading players is part of the business of the NHL. Finding the right deals isn't easy despite what some fans and pundits might think, especially within the constraints of today's salary-cap world.
It's made no easier when roughly 30 percent of the league's 861 players have some form of no-trade protection.
That creates additional pressure on the general managers of the NHL's 32 teams to get it right when they make trades. Failure can sometimes have serious consequences that can haunt a team long after the deal is done.
Most times, a trade is made to improve a team's chances of becoming a playoff contender or a Stanley Cup champion. Sometimes, a logjam at a position requires moving out a player. At times, a swap of players of comparable age and talent takes place that seems favorable for both clubs.
However, not every trade pans out. It could be because the player isn't the right fit within the roster. The team that moved out an extra player may have traded the wrong one. A deal that was supposed to favor both teams ends up lopsided.
Some of those factors are among the five NHL trade fails we're examining here. We're focusing on deals that occurred since 2023.
Follow along and see if you agree with our assessments.
Detroit Red Wings Trade Jake Walman to San Jose Sharks
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On June 25, 2024, the Detroit Red Wings traded Jake Walman and a 2024 second-round pick to the San Jose Sharks for future considerations.
The move raised eyebrows as the Wings appeared to give away a good defenseman who had played well enough to earn a three-year contract extension the year before.
After the trade, The Athletic's Max Bultman reported the move appeared to have been made to free up salary-cap space and to clear some space on a crowded blue line. Rumors later emerged claiming Walman had a rocky relationship with the coaching staff, frowning on his "extracurricular activities" during stoppages of play.
Walman, 29, had a good season with the last-place Sharks, earning a team-leading 23:11 of ice time per game and tallying a career-high 32 points in 50 games. On March 6, the rebuilding club flipped him to the Edmonton Oilers, where he had eight points in 15 regular-season games while logging 21:26 of ice time.
Considering how well Walman played with two different teams last season, the fact that the Red Wings gave him away (and included a 2024 second-round pick in the deal) was not one of general manager Steve Yzerman's finest moves.
Their ongoing need for another top-four defenseman makes it even worse.
Tyler Toffoli Traded by New Jersey Devils to Winnipeg Jets
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Nearly a year after a franchise-best 112-point performance in 2022-23, the New Jersey Devils were on the verge of missing the 2024 playoffs.
They went into sell mode, and one of the players moved was Tyler Toffoli, as the winger was shipped to the Winnipeg Jets for two draft picks by the March 8 trade deadline.
Toffoli was slated to become an unrestricted free agent that summer. According to Devils general manager Tom Fitzgerald, the two sides couldn't agree to a new contract because they disagreed over the length of the deal.
At the time of the trade, Toffoli had a team-leading 26 goals, along with 44 points in 61 games. After netting 11 points in 18 games with the Jets, he signed a four-year contract with the rebuilding San Jose Sharks as an unrestricted free agent on July 1, 2024.
Toffoli had a strong performance with the young Sharks, leading the club with 30 goals and sitting third in points (54) while skating alongside promising forwards like Macklin Celebrini and William Eklund.
Meanwhile, the Devils rebounded by clinching a playoff berth with 91 points. However, with star center Jack Hughes sidelined by a knee injury, they were eliminated in the first round by the Carolina Hurricanes.
According to James Nichols of New Jersey Hockey Now, the Toffoli trade left a void among the Devils' top-six forwards that management has failed to address. He's advocated for the club to look into reacquiring the 32-year-old winger, but his pleas appear to have fallen on deaf ears.
Colorado Avalanche Ship Bowen Byram to Buffalo Sabres for Casey Mittelstadt
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The Colorado Avalanche trading star winger Mikko Rantanen last January to the Carolina Hurricanes in a three-team, multi-player blockbuster could become a regrettable move for the Avs if winger Martin Necas fails to pan out or if he prices himself out of their market.
However, a move they made before the 2024 trade deadline has had a more negative impact thus far. On March 8, 2024, they shipped defenseman Bowen Byram to the Buffalo Sabres for center Casey Mittelstadt.
At the time, we felt this trade would help both teams. We gave the Avalanche a higher grade (A) than the Sabres (B+), based on Mittelstadt's production that season and Byram's injury history.
A year later, Byram enjoyed a career-best 38-point performance with the struggling Sabres, earning the 24-year-old defenseman a two-year contract with an average annual value of $6.3 million.
As for Mittelstadt, he was traded to the Boston Bruins at the 2025 trade deadline.
Parting with Byram for Mittelstadt was meant to address the Avalanche's need for a reliable second-line center. They even inked the 25-year-old center last June to a three-year contract with a $5.75 million AAV. However, he struggled to fill that role, leading to his trade to the Boston Bruins for center Charlie Coyle.
The Avalanche also acquired Brock Nelson from the New York Islanders before the trade deadline to fill that second-line center position. He had a respectable 13 points in 19 regular-season games, but only four assists in seven playoff games. Nevertheless, the Avs re-signed him to a three-year deal with an AAV of $7.5 million.
Nelson turns 34 on Oct. 15, and there's no certainty he'll be able to fill that second-line center role throughout the duration of his contract. Coyle, meanwhile, was traded with winger Miles Wood to the Columbus Blue Jackets on June 30 in a cost-cutting move.
Had Mittelstadt panned out as hoped, the Avalanche would have had a young second-line center with an affordable contract in his playing prime. Instead, they now have an older, more expensive option who might not be able to suitably fulfill that role throughout the duration of his contract.
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J.T. Miller Traded by Vancouver Canucks to New York Rangers
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Coming off a 109-point performance in 2023-24 that was the third-best in franchise history, the Vancouver Canucks entered last season expected to become a dominant club in the Western Conference.
Instead, injuries and turmoil hampered them throughout the season as they missed the 2025 playoffs.
By midseason, a long-simmering rift between centers Elias Pettersson and J.T. Miller reached the point where it became untenable for the franchise. Following weeks of trade speculation, Miller was shipped to the New York Rangers in a multi-player trade on January 31.
The deal failed to improve the struggling Rangers, who also missed the 2025 playoffs. However, it did address their need for reliable depth at center among their top two lines, enabling them to move a struggling Mika Zibanejad to the wing.
Miller also performed at over a point-per-game pace (35 points in 32 games) for the Rangers last season. His rugged, two-way style of play and intensity could be what they need to get back on track in 2025-26. He's also under contract through 2029-30 with an AAV of $8 million.
The Canucks received oft-injured center Filip Chytil, promising defenseman Victor Mancini, and the Rangers' 2025 first-round pick in the deal. They subsequently included that first-rounder in a trade for defenseman Marcus Pettersson with the Pittsburgh Penguins.
Pettersson will bolster the Canucks blue line right away, and Mancini could turn into a reliable top-four defenseman in the future. However, Chytil rarely saw second-line minutes during his tenure with the Rangers, and his concussion history is a concern.
The deal did little to suitably fill the void left at center by Miller's departure. His absence will continue to be felt by the Canucks during this season, which could prove difficult to overcome.
Pittsburgh Penguins Acquire Erik Karlsson from San Jose Sharks
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On Aug. 6, 2023, the Pittsburgh Penguins swung a blockbuster, multi-player trade involving the San Jose Sharks and Montreal Canadiens for defenseman Erik Karlsson from the Sharks.
Karlsson was coming off a career-best 101-point performance with the rebuilding Sharks in 2022-23, winning the James Norris Memorial Trophy for the third time. With the Penguins missing the playoffs for the first time in 16 seasons, the addition of the Swede was supposed to help them bounce back.
It was also the first significant trade by new general manager Kyle Dubas, and to date, it remains his biggest move. Coming over from the Toronto Maple Leafs, the Karlsson acquisition was seen as Dubas putting his stamp on the Penguins.
Two years later, the Karlsson trade remains an ongoing failure for the Penguins. His production over each of the last two seasons was roughly half of what he put up in his final season in San Jose. Meanwhile, the Penguins moved deeper into a rebuild after missing the playoffs in each of the last two seasons.
Karlsson has two years remaining on his contract, with the Penguins carrying $10 million of his $11.5 million average annual value. He also has a full no-movement clause, but that hasn't stopped him from regularly appearing in trade rumors this year.
Perhaps Karlsson will waive his clause for a chance to play for a contender where his production could improve, provided the Penguins are willing to retain part of his cap hit. For now, the trade that brought him to Pittsburgh remains an expensive mistake that continues to haunt the Penguins and Dubas.
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