7 Biggest Trades in NHL History, Ranked

Nothing shakes up the hockey odds market quite like teams swapping players, including the Quinn Hughes trade and Tristan Jarry trade in late 2025. 

That was the case when Wayne Gretzky was traded from the Edmonton Oilers to the Los Angeles Kings in what is inarguably the biggest deal in the history of the NHL.

Check out more about that deal and more on my list of the seven biggest trades in NHL history.

1. Wayne Gretzky, Marty McSorley, Mike Krushelynski for Jimmy Carson, Martin Gelinas, three first-round picks, and $15 million 

Known as “The Trade” in hockey circles, no trade has had a bigger impact on the NHL – and the sport of hockey – than the deal that saw Wayne Gretzky get traded from the Edmonton Oilers to the Los Angeles Kings on Aug. 8, 1988.   

Gretzky won four Stanley Cups in Edmonton and established himself as the best player of his generation, but the Oilers were in some financial trouble and couldn’t risk The Great One leaving for nothing at the end of his contract. 

The trade not only changed the power dynamics of the league, but Gretzky’s tenure in Los Angeles significantly impacted the sport’s growth in California and the rest of the United States. 

2. Eric Lindros for Peter Forsberg, Ron Hextall, Mike Ricci, Chris Simon, Kerry Huffman, Steve Duchesne, two first-round picks, and $15 million

Eric Lindros was one of the biggest prospects in NHL history, but he became just as polarizing when he made it known that he would not play for the Quebec Nordiques, who drafted him first overall in 1991.

Knowing they needed to move Lindros before he was eligible to reenter the draft in 1993, the Nordiques struck a deal with the Philadelphia Flyers for a haul that included Peter Forsberg, Mike Ricci, and a couple of first-round picks.

The trade worked out well for both franchises, as Lindros became an icon in the City of Brotherly Love, while Forsberg was a massive part of the dominant Colorado Avalanche (the Nordiques relocated to Denver in 1995) teams in the late 1990s and early 2000s. 

3. Patrick Roy and Mike Keane for Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko 

Speaking of those dominant Avalanche teams, it was another blockbuster trade that put them over the top. 

With star forwards like Joe Sakic, Forsberg, and Claude Lemieux leading the way, the Avs felt they just needed to shore up their goaltending to make a run at the Stanley Cup in 1995-1996.

They addressed that issue by acquiring all-time great Patrick Roy from the Montreal Canadiens for Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko. 

Roy and the Avs would win the Stanley Cup five months later.

4. Joe Thornton for Marco Sturm, Brad Stuart, and Wayne Primeau

Joe Thornton looked like he was on his way to becoming an all-time great in Boston, but things changed dramatically in 2005. 

The Bruins were off to an uninspiring start in 2005-2006, and Thornton was turned into something of a scapegoat despite posting 33 points in 24 games. The Bruins decided to shake up their roster by trading Thornton to the San Jose Sharks rather than go down the path of signing him to a contract extension.

While Sturm, Stuart, and Primeau all had decent NHL careers, Thornton is a shoo-in for the Hall of Fame and is one of the best players in Sharks’ history.

The upshot for the Bruins is that the Thornton trade did pave the way for the signing of Zdeno Chara in the summer of 2006.

5. Wendel Clark, Sylvain Lefebvre, Landon Wilson, a first-round pick for Mats Sundin, Garth Butcher, Todd Warriner, and a first-round pick 

Looking back on this trade, it seems like a sensible deal. But back in June 1994, it shocked the hockey world.

Wendel Clark was considered the heart and soul of the Toronto Maple Leafs, so fans were beside themselves when it was announced that he was being dealt to Quebec for Mats Sundin.

Little did anybody know back then that Clark, then the captain of the Leafs and one of the most beloved players in team history, was being traded for a player who would fill both of those roles a few years later.

6. Matthew Tkachuk for Jonathan Huberdeau, MacKenzie Weegar, Cole Schwindt, and a first-round pick 

Perhaps the most impactful trade over the last decade, Matthew Tkachuk’s arrival in Florida completely changed the fortunes of the Panthers, who won their first Stanley Cup in 2024, largely thanks to Tkachuk.

Not too long ago, the Cats were considered one of the weaker organizations in the sport, and they were always dealing with rumours of relocation, financial stresses, and attendance issues. 

Those issues have completely evaporated since Tkachuk’s arrival.

7. Mikko Rantanen for Martin Necas, Jack Drury, a second-round pick, and a fourth-round pick

The jury is still out on who won this trade, but it certainly shook up the 2024-2025 NHL season.

The Hurricanes saw their Stanley Cup odds shortened considerably when they acquired Rantanen, who had eclipsed the 100-point mark in the previous two campaigns and had 64 points in 49 games with the Avalanche at the time of the deal.