The Most Regrettable NHL Trades of the Last 3 Seasons

When an NHL team acquires a player via the trade market, it's with the hope that the player will improve the roster.

Sometimes those moves can pan out, even succeeding beyond their wildest dreams.

A recent notable example is the Florida Panthers acquiring and signing power forward Matthew Tkachuk from the Calgary Flames on July 22, 2022 .

He led the Panthers to the 2023 Stanley Cup Final and was a key part of their 2024 Cup run this spring.

Sometimes, however, a significant move fails to pan out as hoped.

The player could struggle to adjust to this new club.

He could also have a year on his contract and prefer playing elsewhere when it expires.

A major trade can sometimes have consequences that haunt a general manager.

He could trade away a quality player for a return that doesn't meet expectations.

He could also make a move that ends up costing him his job.

Here's our look at the most regrettable trades from 2021-22 to 2023-24.

Feel free to express your views on our picks in the app comments below.

The Vegas Golden Knights' attempt to move Evgenii Dadonov to the Anaheim Ducks before the 2022 NHL trade deadline would end up costing the Ottawa Senators dearly.

This story begins with the Senators trading Dadonov to the Golden Knights in July 2021 for defenseman Nick Holden and a 2022 third-round pick.

However, they failed to disclose to the Golden Knights that Dadonov's 10-team, no-trade list was still in effect.

Fast forward to March 2022 when the Golden Knights shipped Dadonov to the Ducks in order to gain some salary-cap flexibility to reactivate sidelined winger Mark Stone and defenseman Alec Martinez as they battled for a playoff berth.

On March 23, however, the league invalidated the trade because it didn't comply with the forward's no-trade clause.

Last fall, the NHL launched an investigation into Ottawa's role in the botched trade.

On Nov.

1, 2023, the league announced the Senators would forfeit a first-round pick in one of the 2024, 2025 or 2026 drafts.

This was because Sens general manager Pierre Dorion gave the Golden Knights the wrong information about Dadonov's no-trade clause.

The same day, the Senators announced they had parted ways with Dorion, who had held the GM job since April 2016.

The Dadonov trade started out as the Golden Knights' attempt to make a cost-cutting move.

It ended up becoming a deal that had significant consequences for the winger's former club.

Approaching the 2021-22 season, then-Ottawa Senators general manager Pierre Dorion stated his team's rebuild process was over .

He believed his club was ready for the next step when they would start to win and push toward playoff contention.

That step failed to materialize, as the Senators finished with the seventh-worst record in the league in '21-'22.

That prompted Dorion to make a bold move entering the first round of the 2022 NHL Draft.

On July 7, 2022 , he shipped three draft picks (including the seventh-overall pick) to Chicago for winger Alex DeBrincat.

Then 24, DeBrincat was a two-time 41-goal scorer and a year away from restricted free-agent status with arbitration rights.

However, Chicago GM Kyle Davidson was in the middle of a major roster rebuild and lacked first-round picks in the 2022 draft.

DeBrincat was the only player who could fetch a return containing a first-rounder high in the selection order.

Dorion was confident he'd get DeBrincat signed to a long-term extension.

A year later, however, the winger informed Senators management he wasn't interested, forcing Dorion to trade him to the Detroit Red Wings for winger Dominik Kubalik, prospect defenseman Donovan Sebrango, a conditional 2024 first-rounder, and a 2024 fourth-rounder.

DeBrincat had 66 points in 82 games during his sole season in Ottawa but the Senators still failed to improve.

Dorion gave up a high-quality first-rounder as part of the return to land him and was forced to accept a lesser return to send him to Detroit.

Failing to ensure DeBrincat would sign with the Senators before acquiring him from Chicago was a big blunder on Dorion's part.

He ultimately made a series of moves that did nothing to improve his club over the next two seasons.

On May 5, 2021, the New York Rangers promoted Chris Drury to team president and general manager.

Among hisfirst moves as GM was shipping Pavel Buchnevich to the St.

LouisBlues for forward Sammy Blais and a 2022 second-rounddraft pick.

Buchnevich, then 26, was coming off abreakout performance during the COVID-shortened 2020-21 season.

Theright winger tallied a then-career high of 20 goals and 48 points injust 54 games skating alongside left wing Chris Kreider and centerMika Zibanejad.

The Rangers acquired Blais to addsize and physicality to their checking lines, but he would last lessthan two seasons in New York before getting traded back to St.

Louis .

They would trade away the second-rounder from the Blues to theWinnipeg Jets on March 21, 2022, as part of the return in the AndrewCopp deal .

Writing about the Buchnevich trade ayear later, The Athletic's Arthur Staple explained it was done to make room for young forwards Kaapo Kakko, Vitali Kravtsovand Alexis Lafreniere.

However, Kakko has struggled to meetexpectations while Kravtsov now skates in the KHL.

Lafreniere hasemerged as a scorer after struggling to adjust to playing his off-wing.

Buchenevich blossomed into a star with theBlues.

He reached a new career-high of 30 goals and 46 assists for 76points in 2021-22 and followed up with 67 points in 63 games in2022-23 and 63 points last season.

On July 2, 2024, he signed asix-year, $48 million contract extension .

The Rangers, meanwhile, struggled tofind a suitable replacement.

Patrick Kane, VladimirTarasenko, and Frank Vatrano have come and gone while Kakko is theongoing subject of trade speculation .

Their depth at right became a contributing factor in their difficulty getting past theEastern Conference Final in 2022 and 2024.

Drury has made several trades sinceshipping Buchnevich to the Blues.

That move could be his biggest regret as Rangers GM.

The Los Angeles Kings finished 2022-23with 47 wins and 104 points, marking the second-best regular-seasonperformance in franchise history .

However, they were eliminated fromthe first round of the playoffs by the Edmonton Oilers for the secondstraight season.

Kings general manager Rob Blake made a major move to bolster his depth at center.

On June 27,2023, he acquired Pierre-Luc Dubois from the Winnipeg Jets in exchangefor forwards Alex Iafallo, Gabriel Vilardi, Rasmus Kupari, and a 2024second-round pick.

Dubois also signed an eight-year contract with anaverage annual value of $8.5 million.

Blake praised Dubois as "an elite two-way center with a unique skillset," citing his ability to "contribute to all facets of the game." He added how excited the organization was to have Dubois join the club and commit to a long-term deal.

Nearly a year later, Blake and theKings were no longer excited about Dubois.

On June 19, they shippedhim to the Washington Capitals for goaltender Darcy Kuemper.

Meanwhile, Iafallo, Vilardi and Kupari helped the Jets finished lastseason with the second-best regular-season record (52 wins, 110points) in franchise history .

Dubois was a disappointment in Los Angeles, managing only 40 points in 82 games after back-to-back seasons of 60 or more points with the Jets.

He saw mostly third-line center duty and even spent some time on their fourth line.

The 6'4", 225-pounder managed just one goal in five playoff games as the Oilers again eliminated the Kings from the first round.

Blake took the blame for Dubois'struggles, saying he didn't do a good enough job integrating him intothe right roles on the team.

He managed to shed the big center'shefty contract shipping him to Washington for Kuemper, who has threeyears left on his deal with an AAV of $5.3 million but alsostruggled during his two seasons with the Capitals.

This move was among several thisoffseason that raised questions about Blake's management of theKings.

Already on the hot seat entering this season, he could risklosing his job if they fail to improve.

On June 1, 2023, the PittsburghPenguins hired former Toronto Maple Leafs general manager Kyle Dubasas president of hockey operations.

Two months later, he also took over therole of Penguins GM.

It was apparent from the start thatDubas was trying to bolster the roster depth around aging starsSidney Crosby, Evgeni Malkin and Kris Letang to give them one lastshot at a championship run.

He acquired winger Reilly Smith from theVegas Golden Knights and added checking-line forwards Lars Eller andNoel Acciari.

Dubas then made the biggest splash ofthe 2023 offseason, acquiring Erik Karlsson on Aug.

6 from the SanJose Sharks in a multi-player deal involving the Montreal Canadiens.Karlsson, then 33, was coming off a career-best 101-point performancewith the lowly Sharks, earning the James Norris Memorial Trophy forthe third time in his career.

Pittsburgh also took on $10million of Karlsson's $11.5 million average annual value through2026-27 .

Still, with one of the league's best puck-moving defensemenon their blue line, the Penguins seemed poised torebound from missing the playoffs in 2023, which ended a postseason streakthat began in 2007.

Instead, the Penguins failed to qualify for the second straightseason.

Karlsson wasn't expected to have another season close to his2022-23 stats, but his production dropped to 56 points in 82 games.Respectable for most offensive rearguards but not what was expectedfor a player joining what was supposed to be a playoff contender.

Dubas has spent this offseason adding younger players to his roster like Cody Glass,Blake Lizotte and Anthony Beauvillier, and restocking his prospectpipeline.

Meanwhile, Karlsson's hefty cap hit limits attempts toadd significant talent to the Penguins roster and likely led to Dubas trading pending free agent winger Jake Guentzel to Carolina inMarch.

Karlsson might bounce back this seasonafter a year of adjusting to a new city and team.

However, he'sapproaching the stage of his career when performance declines.

Adding him to a roster already loaded with aging, expensivestars could become increasingly burdensome for the Penguins over theremaining years of his contract.

A three-time Stanley Cup champion between 2009-10 and 2014-15, Chicago's championship window was closing by the summer of 2021.

Since 2015-16, they'd reached the playoffs three times and were eliminated from the opening round in each series.

Stars like Patrick Kane and Jonathan Toews were aging.

Salary-cap constraints led to cost-cutting trades that depleted their roster.

Defenseman Duncan Keith was traded to the Edmonton Oilers at his request to be closer to his family, leaving Chicago without a blue-line linchpin.

Then-general manager Stan Bowman saw an opportunity to address Keith's departure.

On July 23, he acquired Seth Jones from the Columbus Blue Jackets, sending them young defenseman Adam Boqvist and three draft picks.

He also signed Jones to an eight-year, $76 million contract .

Then 26, Jones had been a blueline stalwart with the Blue Jackets, logging big minutes while posting a career-best 57 points in 2017-18 and 46 points the following season.

He played a crucial role in the best stretch of the Blue Jackets history , helping them reach the playoffs in four straight seasons from 2016-17 to 2019-20.

Acquiring Jones, however, wasn't enough to turn Chicago's drained roster into a contender again.

They changed management in 2021-22 and under new GM Kyle Davidson have been engaged in a major roster rebuild.

Toews and Kane are no longer with the team, leaving Jones as their highest-paid player.

Now 29, Jones has played well throughout the roster changes, tallying 37 points in 2022-23 and 31 points in 67 games last season.

Nevertheless, he will be past his playing prime by the time Chicago's rebuilding roster is ready to become a contender in four or five years.

Jones' contract is considered to be among the league's worst .

His $9.5 million average annual value takes up considerable cap space and could hamper their efforts to re-sign promising young players like Connor Bedard.

It also makes him difficult to trade, as does his full no-movement clause.

On July 20, 2022, The Athletic reported Matthew Tkachuk informed the Calgary Flames that he wouldn't sign a new contract with them.

Two days later, they traded the restricted free-agent winger to the Florida Panthers for left wing Jonathan Huberdeau and defenseman MacKenzie Weegar.

This swap worked out great for the Panthers.

Tkachuk signed an eight-year contract and swiftly became one of their top stars.

He led them to the 2023 Stanley Cup Final and helped them win their first Cup earlier this spring.

It also seemed like a great return for the Flames at the time.

Huberdeau was coming off a career-best 115-point performance and was considered among the league's best playmakers.

Meanwhile, the puck-moving Weegar reached a then-career-best 44 points in 80 games.

Both signed lucrative long-term extensions with the Flames later that year.

Weegar fit in well on the Flames blueline, tallying a career-best 20 goals and 52 points last season.

Huberdeau, however, has struggled since going to Calgary.

He managed 55 points in 79 games in 2022-23.

It didn't get any better for the 31-year-old winger last season, netting 52 points in 81 games.

The decline in Huberdeau's production coincided with the Flames' difficulties adjusting to the loss of Tkachuk and linemate Johnny Gaudreau, who signed with the Columbus Blue Jackets in 2022 as a free agent.

After a 111-point season in 2021-22 (the second-best record in franchise history), the Flames missed the playoffs the next two seasons.

Huberdeau isn't primarily to blame for the Flames' decline, which resulted in management, coaching, and roster changes.

Nevertheless, his offensive woes were a contributing factor.

He's now entering the second season of his eight-year contract with an average annual value of $10.5 million and a full no-movement clause for the duration of his deal.

Given his age, Huberdeau's best seasons are likely behind him.

If so, the Flames have a declining asset with a long, expensive contract that is nearly impossible to move taking up a big chunk of their cap space until 2031..

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