By Steven Papadopoulos, The Hockey News intern
It’s the 2025 NHL trade deadline week, the perfect time to reminisce on some of the biggest moves in recent memory.
Adam Larsson and Taylor Hall (Perry Nelson-Imagn Images)
A massive trade already happened this season with Mikko Rantanen heading to the Carolina Hurricanes, and there’s media speculation about whether he gets moved again.
Some of these trades paid off in the long run with a Stanley Cup, while others were worth the attempt, even if the team didn’t end up winning it all.
From most recent to oldest, here are some eye-catching trades over the last 10 years.
Jan. 24, 2025: Colorado Avalanche trades Mikko Rantanen to Carolina Hurricanes in a three-team deal
Most people expected Mikko Rantanen to stay in Colorado for at least the rest of the season, as his contract expires in the summer. But that was not the case in the late hours on Friday, Jan. 24, when the Hurricanes acquired the right winger and Taylor Hall.
The Avalanche received centers Martin Necas and Jack Drury, and the Chicago Blackhawks got a third-round pick for retaining 50 percent of Rantanen’s $9.25-million cap hit.
The trade came as a complete surprise to the hockey world. It’s too early to pick a winner in this trade, but the Hurricanes now have a top-10 player in the NHL in Rantanen, a solid veteran in Hall, and a former Hart Trophy winner. Carolina is the early winner of this deal if it can re-sign Rantanen before the deadline or the end of the season.
Feb. 28, 2023: Chicago Blackhawks trade Patrick Kane to New York Rangers
For the longest time, nobody expected that Chicago would trade Kane. A former face of the franchise did everything you could dream of in the NHL. He’s a three-time Stanley Cup champion, scoring the game-winning goal in 2010 to give the Blackhawks their first Cup in 49 years, and he won the Ted Lindsay Award, Hart Trophy, Art Ross Trophy, Calder Trophy and a Conn Smythe Trophy, all with the Blackhawks.
It was hard to believe when the rumors began that Kane might leave Chicago. But on Feb. 28, 2023, Chicago moved Kane in a three-team deal with the Rangers and Arizona Coyotes. Chicago ultimately received a second-round pick, a 2025 forth-rounder, Andy Welinski and Vili Saarijarvi. The Rangers received Kane and Cooper Zech.
The day Kane was traded signified the end of the most successful era in Blackhawks history. However, it allowed Kane to reunite with former teammate Artemi Panarin and possibly have a chance at another Cup. Ultimately, that didn’t happen, as the Rangers lost in seven games to their rival, the New Jersey Devils, in the first round. Even though he was there briefly, seeing ‘Showtime’ on the Broadway Blueshirts was cool and weird.
Feb. 17, 2023: Ryan O’Reilly traded to Minnesota Wild by St. Louis Blues, then flipped to Toronto Maple Leafs
It was all or nothing for the Leafs in the 2022-23 season as then-GM Kyle Dubas – who was in the final year of his contract – made several deals before the trade deadline ended. This was the biggest one of the bunch.
The Maple Leafs received O’Reilly and Noel Acciari. The Blues received Mikhail Abramov, Adam Gaudette, a 2023 first-rounder, 2023 third-rounder and a 2024 second-rounder.
O’Reilly got to live out a childhood dream of playing for the Leafs. In 24 games (regular season and playoffs combined), he had seven goals and 20 points.
Even though he did not re-sign with the Buds, it was fun while it lasted, and he’ll be remembered as one of the players who helped the team break its 19-year first-round playoff curse.
July 25, 2022: Florida Panthers trade Jonathan Huberdeau and MacKenzie Weegar to Calgary Flames for Matthew Tkachuk
Matthew Tkachuk did not want to sign a long-term contract with the Flames in 2022, and arbitration for the pending RFA was scheduled for August. That led to a trade that stopped NHL fans in their tracks.
Florida traded Huberdeau fresh off a career-high 115-point season and an effective two-way defeseman in Weegar for Tkachuk, who agreed to an eight-year contract.
It was a massive risk that paid off. The Panthers made the Cup final in the two seasons afterward, winning the Cup in 2024. Tkachuk had a career-high 109-point season in 2022-23 and had 22 points in 24 games en route to the Cup.
Huberdeau, meanwhile, had 55 points in 79 games in his first season with the Flames and 52 points in 81 games the year afterward. He currently has 44 points in 60 games in 2024-25. Weegar set a career high in points last season, with 52 in 82 games. It hasn’t been a total loss for the Flames, who got a massive return for a player who didn’t want to be with them for the long term.
Nov. 4, 2021: Jack Eichel traded to Vegas Golden Knights
The Eichel and Buffalo Sabres saga ended when the team sent their former captain and No. 2 overall pick to Vegas, along with a third-round pick in the 2023 draft. Going to the Sabres from Vegas were forwards Peyton Krebs and Alex Tuch, a top-10-protected first-round pick in the 2022 draft and a second-round pick.
Eichel could have the surgery he wanted to fix a herniated disk in his neck. This was the root of the problem between him and the Sabres organization, as the team did not feel comfortable with the procedure.
In the end, this trade went very well for the Golden Knights, as they won the Stanley Cup the season after Eichel arrived in Sin City. During the 2023 post-season, Eichel had 26 points in 22 games. Vegas clearly won this deal.
Feb. 25, 2019: Mark Stone traded to Vegas
Ottawa dealt Stone and Tobias Lindberg to the Golden Knights for Erik Brannstrom, Oscar Lindberg and a 2020 second-round pick.
The Senators fully committed to a rebuild after trading other key players ahead of the 2019 trade deadline.
Stone immediately became a key player for the Golden Knights and remains one to this day, even being named the first captain in franchise history on Jan. 13, 2021. He was a key piece to the Knights winning the Stanley Cup in 2023, becoming the third player in NHL history to score a hat trick in a Cup-clinching win. Stone had 24 points in 22 playoff games en route to Vegas’ first championship.
Five Years Later: 2019 Trades of Mark Stone and Matt Duchene Did Nothing to Help the Ottawa Senators Rebuild Duchene scored in double overtime to send the Dallas Stars to their second straight NHL Western Conference Final.
Sept. 13, 2018: Erik Karlsson traded to San Jose Sharks
Karlsson getting traded to San Jose virtually began the Senators’ rebuild. The year before Karlsson was traded, the Sens made it to the Eastern Conference final and were one goal away from going to the Stanley Cup final. But in 2017-18, things went downhill in the standings.
By the fall of 2018, Ottawa sent Karlsson to the Sharks with Francis Perron for Josh Norris, Chris Tierney, Dylan DeMelo, Rudolfs Balcers, San Jose’s first-round pick in the 2020 draft, a 2019 second-round pick and two conditional picks.
Karlsson’s time in San Jose went well for the most part. In his first season in San Jose, they went all the way to the Western Conference final but lost to the St. Louis Blues, which ended up winning the Cup that year. Karlsson dealt with injuries during his days in San Jose, but he also claimed his third Norris Trophy and his first and only 100-point season to date before being dealt again to Pittsburgh.
The Sens have a strong center in Norris, who has been a key piece for Ottawa when healthy. The first-round pick in the trade ended up being Tim Stutzle, one of Ottawa’s shining stars who has shown he can be dangerous in the NHL.
June 23, 2017: Artemi Panarin traded to Columbus Blue Jackets by Chicago
Panarin was looking to be the next great thing in Chicago, coming off of back-to-back seasons with more than 70 points and being a season removed from the Calder Trophy. Things couldn’t have been going better for him.
That is, until June 23, 2017, when the Blackhawks dealt him, center Tyler Motte and a 2017 sixth-round pick to the Columbus Blue Jackets in exchange for center Brandon Saad, goalie Anton Forsberg and a 2018 fifth-round pick.
This trade happened right before Chicago’s down years, which eventually led to the beginning of a painful rebuild.
Columbus won this trade, even though Panarin was only there briefly before going to the Rangers. He was a key reason the Blue Jackets made the playoffs and swept the heavily favored Tampa Bay Lightning in 2019.
June 29, 2016: Taylor Hall traded to New Jersey Devils by Edmonton Oilers for Adam Larsson
Then-Oilers GM Peter Chiarelli surprised fans by trading their former franchise player to the Devils for Larsson, who is a solid two-way defenseman.
The winner of this trade is Taylor Hall. He had his best season in New Jersey in the 2017-18 campaign, where he racked up 39 goals and 93 points. He also won the Hart Trophy and helped the Devils make their first playoff appearance since 2012.
June 29, 2016: Montreal Canadiens trade P.K. Subban to Nashville Predators for Shea Weber
June 29, 2016, is considered one of the craziest days in the NHL’s Modern Era. The Hall and Larsson trade took place on that day. Steven Stamkos decided to stay put in Tampa Bay by signing an eight-year, $68-million contract extension.
But that wasn’t it.
The Canadiens sent Subban to Nashville in exchange for Predators captain Weber. Both were in the prime of their careers, and both fan bases were shocked by the news. (By the way, all three of these moves – Hall/Larsson, Stamkos’ contract and Subban/Weber – transpired in just 23 minutes.)
Subban was a key piece of the Preds making it to the Stanley Cup final in 2016. Weber was named captain of the Canadiens in 2018 and guided the team to the Cup final in 2021. Both players couldn’t win it all.
This trade worked out well for both teams in the end. Subban is retired, while Weber hasn’t played since the 2021 Cup final. The Utah Hockey Club have his contract, which expires after next season.
Former Preds GM David Poile Reflects on Shea Weber Trade: “I Wish It Never Happened” Retired Nashville Predators GM David Poile spoke honestly about the deal that was the most difficult for him to make — trading Shea Weber for P.K. Subban.
July 1, 2015: Phil Kessel traded to Pittsburgh
For many Canadians, July 1 means two things: Canada Day and the first day of NHL free agency. But for Leafs fans in 2015, it was bittersweet.
On that day, Toronto traded Kessel, Tyler Biggs, defenseman Tim Erixon and a 2016 second-round pick to Pittsburgh. In return, the Leafs got center Nick Spaling, right winger Kasperi Kapanen, defenseman Scott Harrington and first- and third-round picks in 2016.
Kessel went on to win two Cups with the Pens and was a part of one of the highly successful ‘HBK Line’ with Carl Hagelin and Nick Bonino.
Which other massive trades come to mind in the last 10 years? Let us know in the comments on THN.com.
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