<p>With less than two months until the 2025 NHL Trade Deadline on March 7, we’re delivering at least one deadline-focused story every day at Daily Faceoff.</p>



<p>Today, in honor of the Quarter Century celebration happening around the NHL, we evaluate the worst trades of the past 25 years, a few of which happened at the Trade Deadline.</p>



<h2 class="wp-block-heading">2025 NHL Trade Deadline Countdown: 40 days</h2>



<p>A quarter century in the books already? Wow. For older millennials like me, Gen Xers and Boomers, it feels like yesterday we were dreading the Y2K bug. But here we are in 2025 already. It’s a nice juncture to look back on the past 25 years – which is what the NHL is doing, unveiling Quarter Century Teams for each franchise and, next month, holding a fan vote for the all-NHL Quarter Century Team.</p><div class="injected-ad injected-video" data-nn-ad-tech-injection-count="0" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="131"></div>



<p>Across the Nation Network, we’ve been reflecting on the quarter century, too, including some team-centric breakdowns of the worst trades. Since we cover all 32 teams at Daily Faceoff, let’s join in and examine the worst trades across the NHL in the past 25 years. Chances are, you’ll <em>feel </em>something as soon as you see each of these, especially if you cheer for one of the victimized teams. “Worst” is also a matter of perception; every one of the deals in this story could crack a “best” list if viewed through the eyes of the team that won the deal.</p>



<h2 class="wp-block-heading">Honorable mentions</h2>



<p>I strongly considered these trades for the list, but they narrowly missed the cut</p>



<p>– The Danny Briere/Chris Gratton trade (2003)<br>– Jaromir Jagr for Anson Carter (2004)<br>– The Blues’ Ryan Miller trade deadline flop (2014)<br>– Phillip Danault to Montreal (2016)</p><div class="injected-ad" data-nn-ad-tech-injection-count="1" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="140"></div>



<h4 class="wp-block-heading"><strong>10. <a href="https://www.dailyfaceoff.com/teams/montreal-canadiens/line-combinations">Montreal Canadiens</a> trade Ryan McDonagh, Chris Higgins and Pavel Valentenko to <a href="https://www.dailyfaceoff.com/teams/new-york-rangers/line-combinations">New York Rangers</a> for Scott Gomez, Tom Pyatt and Michael Busto: June 20, 2009</strong></h4>



<p>Trades sting the most when both ends of the deal go the other team’s way, with the marquee piece you sent away flourishing while the piece you receive flops. McDonagh, the prized prospect in the package that went New York’s way, was a staple on the Rangers’ blueline for eight seasons, churning up minutes as one of the league’s best two-way defenders and leaders and helping them reach the 2013-14 Stanley Cup Final. Gomez wasn’t terrible as a playmaking center in his first season with the team but couldn’t come anywhere close to justifying his albatross contract, which carried a cap hit of $7,357,143. He went from adequate to subpar by his second season with the Habs, and they ended up using a compliance buyout on him before the 2012-13 season. Montreal had fashioned itself a contender at the time of the Gomez trade and was trying to put itself over the top but set itself back years instead.</p><div class="injected-ad" data-nn-ad-tech-injection-count="2" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="159"></div>



<h4 class="wp-block-heading"><strong>9. <a href="https://flamesnation.ca/">Calgary Flames </a>trade Matthew Tkachuk and a 2025 fourth-round pick to <a href="https://www.dailyfaceoff.com/teams/florida-panthers/line-combinations">Florida Panthers</a> for Jonathan Huberdeau, MacKenzie Weegar, a 2025 first-round pick and Cole Schwindt: July 22, 2022</strong></h4>



<p>Too soon? Not when the trade yielded such tangible results already. Tkachuk was knocking on the door of superstardom when he requested his trade out of Calgary in summer 2022, resulting in this unprecedented blockbuster that included two 100-point scorers swapping addresses. As a Panther, Tkachuk immediately cemented his status as one of the best power forwards of his generation. He was a Stanley Cup and Hart Trophy finalist in Year 1 with the team and a Stanley Cup champion in Year 2. It doesn’t get any better. Huberdeau has played decently this year after a rough first two seasons as a Flame, and Weegar is a rock-solid two-way defenseman, but that doesn’t take away the fact a first-place Calgary team had to give away difference maker on Tkachuk’s level. Then-GM Brad Treliving did not have much leverage and got what looked like a solid return at the time, but I’m grading these trades on the results, not how we perceived them in the moment.</p><div class="injected-ad" data-nn-ad-tech-injection-count="3" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="165"></div>



<h4 class="wp-block-heading"><strong>8. <a href="https://www.dailyfaceoff.com/teams/philadelphia-flyers/line-combinations">Philadelphia Flyers </a>trade Patrick Sharp and Eric Meloche to <a href="https://www.dailyfaceoff.com/teams/chicago-blackhawks/line-combinations">Chicago Blackhawks</a> for a 2006 third-round pick (traded to MTL: Ryan White) and Matt Ellison: Dec. 5, 2005</strong></h4>



<p>Who could’ve had the foresight to understand what Philadelphia was giving up? Sharp was about to turn 24. He’d bounced between the AHL and NHL, looking like a Quad-A player or depth forward at best. But the Blackhawks and then GM Dale Tallon saw something in his speed and skill and cemented a crucial component of their dynasty with this seemingly throwaway December deal. The late-blooming Sharp delivered four 30-goal seasons and eclipsed 20 goals eight times as a Hawk. He played on all three Stanley Cup teams between 2009-10 and 2014-15. His 42 playoff goals place him seventh in franchise history, and he was even named to Chicago’s Quarter Century First Team last month over Hall of Famer Marian Hossa. As for White and Ellison: If you’re asking “Who?” that sums it up. White did play more than 300 NHL games as a checking forward.</p><div class="injected-ad" data-nn-ad-tech-injection-count="4" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="146"></div>



<h4 class="wp-block-heading"><strong>7. <a href="https://theleafsnation.com/">Toronto Maple Leafs </a>trade the rights to Tuukka Rask to <a href="https://www.dailyfaceoff.com/teams/boston-bruins/line-combinations">Boston Bruins</a> for Andrew Raycroft: June 24, 2006</strong></h4>



<p>Anthony Stolarz and Joseph Woll have been so appreciated in Toronto this season because the team hasn’t had a reliable goaltender since Ed Belfour more than 20 years ago. They <em>could’ve </em>had one in probable future Hall of Famer Rask, but they traded him in a kneejerk move from GM John Ferguson Jr. after the Leafs missed the playoffs coming out of the lockout in 2005-06. It’s not like Rask was an unknown project; the Leafs had taken him in him the <em>first round </em>a year earlier. They tried to paper over their goaltending problem with a buy low on Raycroft. He struggled as a Leaf and the franchise plunged into one of its darkest, least competitive eras.</p>



<h4 class="wp-block-heading"><strong>6. <a href="https://flamesnation.ca/">Calgary Flames</a> trade Jean-Sebastian Giguere to <a href="https://www.dailyfaceoff.com/teams/anaheim-ducks/line-combinations">Anaheim Ducks</a> for a 2000 second-round pick (traded to WSH: Matt Pettinger): June 10, 2000</strong></h4>



<p>This one feels a little unfair. How could the Flames have known what they had in Giguere when they punted him to the Ducks for a second-rounder? Then again, he’d posted the highest save percentage of any Calgary goalie in 1999-00 at .914, so he was already flashing plenty of potential. Then-GM Craig Button sent him to Anaheim in favor of bringing aging veteran Mike Vernon back. Vernon couldn’t recapture his old Stanley Cup magic in his second stint with the Flames, and Giguere became the greatest goalie in Ducks history. His performance in the 2002-03 postseason was so legendary that it earned him the Conn Smythe Trophy on a team that lost Game 7 of the Final, and he backstopped Anaheim to its first championship in 2006-07. ‘Jiggy’ remains the franchise leader in wins and shutouts.</p><div class="injected-ad" data-nn-ad-tech-injection-count="5" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="255"></div>



<h4 class="wp-block-heading"><strong>5. <a href="https://www.dailyfaceoff.com/teams/columbus-blue-jackets/line-combinations">Columbus Blue Jackets </a>trade Jeff Carter to<a href="https://www.dailyfaceoff.com/teams/los-angeles-kings/line-combinations"> Los Angeles Kings</a> for Jack Johnson and a 2013 first-round pick (Marko Dano): Feb. 23, 2012</strong></h4>



<p>Some Trade Deadline deals yield a high-impact player who keys a championship run that season. Others bring in a player who becomes an important part of the franchise’s fabric for <em>many</em> seasons. The Carter trade did both. Sure, he punched up 2011-12 Kings’ scoring, led the post-season with eight goals and three game-winners and helped them become the first No. 8 seed to win a Stanley Cup. But Carter was also a pillar on the 2013-14 Cup team and ended up playing 10 seasons with the Kings. He ranks 10<sup>th</sup>&nbsp;in franchise history in goals. It’s amazing to think that, given Jack Johnson’s struggles, the Kings and GM Dean Lombardi got the disgruntled Carter from Columbus for almost nothing.</p>



<h4 class="wp-block-heading"><strong>4. <a href="https://www.dailyfaceoff.com/teams/washington-capitals/line-combinations">Washington Capitals</a> trade Filip Forsberg to <a href="https://www.dailyfaceoff.com/teams/nashville-predators/line-combinations">Nashville Predators</a> for Martin Erat and Michael Latta: April 3, 2013</strong></h4>



<p>The staggering thing about this trade: it was a foresight 20/20 situation, not hindsight. Most hockey pundits immediately lambasted Capitals GM George McPhee for sacrificing one of his best young forward prospects in a desperate rental deal for middling playmaker Erat. He was a horrific bust in Washington, delivering two goals and 27 points in 66 games between the regular season and playoffs in parts of two seasons. As for Forsberg? He’s the Predators franchise leader in goals.</p><div class="injected-ad" data-nn-ad-tech-injection-count="6" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="196"></div>



<h4 class="wp-block-heading"><strong>3. <a href="https://www.dailyfaceoff.com/teams/new-york-islanders/line-combinations">New York Islanders</a> trade Roberto Luongo and Olli Jokinen to <a href="https://www.dailyfaceoff.com/teams/florida-panthers/line-combinations">Florida Panthers</a> for Mark Parrish and Oleg Kvasha: June 24, 2000</strong></h4>



<p>“The trade is two for two” would’ve fit nicely had social media existed in 2000.&nbsp;It’s not just that Luongo went on to have a Hall of Fame career and sit fourth on the all-time wins list, or that, a quarter century later, Jokinen still sits third on the Panthers’ career goals and points lists. It’s that the Isles and GM Mike Milbury made this trade specifically because they were committing to supposed prodigy netminder Rick DiPietro with the No. 1 overall pick. The next two picks in that draft: Dany Heatley and Marian Gaborik. So think of this trade as Luongo, Jokinen and Heatley for Parrish, Kvasha and DiPietro. Devastating.</p>



<h4 class="wp-block-heading"><strong>2. <a href="https://www.dailyfaceoff.com/teams/boston-bruins/line-combinations">Boston Bruins</a> trade Joe Thornton to <a href="https://www.dailyfaceoff.com/teams/san-jose-sharks/line-combinations">San Jose Sharks</a> for Marco Sturm, Brad Stuart and Wayne Primeau, Nov. 20, 2005</strong></h4>



<p>How staggering does this deal look almost 20 years later? Well, Thornton is the only player to win the Hart Trophy as MVP for a season during which he was traded. The Bruins had re-signed him on a three year deal going into 2005-06, but the relationship between him and the team was strained, his leadership called into question. Thornton went off for 92 points in 58 games post-trade that year to capture the Art Ross Trophy. He led the NHL in assists in each of his first three seasons as a Shark. He helped them reach the 2016-17 Stanley Cup Final. He’s their all-time assists leader, and he ranks seventh in NHL history in assists and 14<sup>th</sup> in points. What stands out the most about this trade is that the Bruins didn’t even receive a single pick. They traded Stuart and Primeau the following season, landing a member of their 2011 Stanley Cup team in Andrew Ference in the process. That doesn’t come close to justifying the fact Boston gave up one of the greatest players ever for a pu pu platter.</p><div class="injected-ad" data-nn-ad-tech-injection-count="7" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="293"></div>



<h4 class="wp-block-heading"><strong>1. <a href="https://www.dailyfaceoff.com/teams/new-york-islanders/line-combinations">New York Islanders</a> trade Zdeno Chara, Bill Muckalt and a 2001 first-round pick (Jason Spezza) to <a href="https://www.dailyfaceoff.com/teams/ottawa-senators/line-combinations">Ottawa Senators</a> for Alexei Yashin</strong></h4>



<p>Milbury is lucky this list cuts off in the year 2000. He “only” landed two trades on it but would have more if we looked into his 1990s deals. The Islanders paid for their aggressive Yashin trade for years to come and in more ways than one. It was painful enough to give up a future Hall of Fame defenseman, then more of a project, in Chara. But they also surrendered the pick that would yield Ottawa its top scoring center in franchise history in Spezza. To squeeze extra lemon juice into the wound: the Isles signed Yashin to a 10-year, $87.5 million contract after acquiring him, bought him out by 2007 and kept paying him north of $2 million a year until 2015. Yashin had some respectable years as an Isle, but Ottawa absolutely cooked New York on this transaction, even if the Sens would fumble Chara in free agency five years later.</p><div class="injected-ad" data-nn-ad-tech-injection-count="8" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="154"></div>



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Nashville Predators left winger Filip Forsberg