Skip to main content

On anniversary of Gretzky trade, look back at five most shocking deals since

It's been 29 years since Wayne Gretzky was traded to Los Angeles, and while no trade will ever be quite as shocking, look back on five deals that have stunned the hockey world in the years following "The Trade."

On August 9, 1988, 29 years ago today, the single most shocking trade in NHL history took place as the Edmonton Oilers, only months removed from winning their fourth Stanley Cup in five seasons, dealt Wayne Gretzky to the Los Angeles Kings in an absolute blockbuster of a deal.

The swap with the Kings, which landed the Oilers Jimmy Carson, Martin Gelinas, three first-round picks and $15 million, was made all the more amazing by the fact that they were getting Gretzky not as his career was winding down, but arguably as he was set to enter his prime. He had just turned 27, was only two campaigns removed from a run of three-consecutive 200-point seasons and already had eight Hart Trophies, seven Art Ross Trophies and five Lester B. Pearson Awards to his name, not to mention he had just won the Conn Smythe Trophy for the second time with 12 goals and 43 points in 19 post-season games.

It is worth noting that the league was no stranger to notable deals at the time, with big name players moving with almost amazing frequency compared to the modern era, but to this day there stands only one swap that can simply be summed up as “The Trade.” Ask an Oilers fan about The Trade, and they’ll know exactly what you’re talking about. Likewise, a Kings fan would conjure up images of Gretzky pulling on Los Angeles’ silver and black for the first time. There’s not another trade in league history that can be summed up with those two words, though.

However, that’s not say there hasn’t been some shocking deals in the years since Gretzky was dealt, seemingly out of nowhere, to the Kings. Here are the five most shocking trades that have come in the 19 years since The Trade:

THE LINDROS TRADE — June 30, 1992

Philadelphia Flyers acquire: Eric Lindros

Quebec Nordiques acquire: Ron Hextall, Steve Duchesne, Kerry Huffman, Mike Ricci, Peter Forsberg, Chris Simon, 1993 first-round pick, 1994 first-round pick, $15 million

When Gretzky was moved along for a massive package of players and cash, it made perfect sense. After all, Gretzky, then nine seasons into his NHL career, already had 1,669 points to his name. But the same couldn’t be said for Lindros, who, when dealt from the Quebec Nordiques to the Philadelphia Flyers, commanded an awfully similar level of return. In fact, one could argue the return for Lindros was much greater.

Of course, Lindros proved to be worth it, and three seasons into his career captured dual MVP honors by winning both the Hart and the Pearson. Injuries would end up hampering Lindros’ career, however, and his time in Philadelphia came to a close following the 1999-00 season. Lindros only played another 274 games in the NHL, retiring following the 2006-07 season. He was inducted into the Hall of Fame in 2016.

As shocking as the package for Lindros, though, is that one of the trade pieces hit equally big for the Nordiques, who later became the Colorado Avalanche. Forsberg won the Calder Trophy in 1994-95, was a Hart and Art Ross winner by 2002-03 and helped guide the Avalanche to two Stanley Cups. Forsberg entered the Hall of Fame two years earlier than Lindros, earning his induction in 2014.


Colorado Avalanche acquire: Patrick Roy, Mike Keane

Montreal Canadiens acquire: Jocelyn Thibault, Martin Rucinsky, Andrei Kovalenko

The trade that saw Roy depart from the Canadiens could have been seen coming, but it didn’t make the deal any less shocking.

What set the trade into motion was a horrendous outing in early December in which Roy was left in goal as Montreal was absolutely pounded by the Detroit Red Wings. Across 32 minutes of work, Roy faced 26 shots from Red Wings attackers and surrendered nine goals against, and it took until midway through the second period for coach Mario Tremblay to take Roy out of the game. When arriving at the bench, Roy was visibly angry and told then-team president Ronald Corey that he was finished in Montreal.

Some believed the situation could be worked out, the relationship between Roy and the team smoother over, but four days after getting shelled against Detroit, Roy was headed to the Avalanche in a five-player deal that included Canadiens captain Keane and three players from Colorado, including starting goaltender Thibault.

We all know how it worked out, too. In his first post-season in Colorado, Roy led the Avalanche to the franchise’s first Stanley Cup and would later win his third — and third Conn Smythe — in 2000-01 to solidify his spot as one of the greatest goaltenders to ever play the game.


San Jose Sharks acquire: Joe Thornton

Boston Bruins acquire: Wayne Primeau, Brad Stuart, Marco Sturm

With the lockout over and the 2005-06 season underway, the Bruins were led by a 26-year-old Thornton who had scored 36 goals and 101 points only three seasons earlier. He was a Hart contender, the undoubted MVP of the Bruins and the captain of a team that was attempting to continue a streak of three-straight playoff appearances.

And then, all of a sudden, they weren’t.

Little more than one-quarter of the way through the campaign, Thornton, who had already put up nine goals and 33 points in 23 games, was traded to the Sharks in a head-scratching, blockbuster deal. It was a bizarre trade, one few saw coming, and that includes NHL GMs. In 2009, Pierre LeBrun reported that “a number of NHL GMs” said they had no idea Thornton was even on the trade block at the time. 

There was some instant regret on the Bruins’ side, too. Thornton finished out the campaign by posting another 20 goals and 92 points, winning the Art Ross and becoming the first and only player in NHL history to win the Hart in a season in which he played for two teams.

As for the return, none of the three players were on Boston’s roster at the time of the 2010-11 Stanley Cup victory, though later trading Primeau and Stuart did land the Bruins defenseman Andrew Ference, who would play a role in the title run.


Dallas Stars acquire: Tyler Seguin, Rich Peverly, Ryan Button

Boston Bruins acquire: Loui Eriksson, Reilly Smith, Joe Morrow, Matt Fraser

There’s no intention here of picking on Bruins’ fans, but we have to go from one of Boston’s most infamous trades to the next, as the Seguin trade is the only deal keeping the Thornton swap from being the absolute most shocking move the Bruins have made in the modern era.

At the time of the trade, Seguin was, undoubtedly, still a work in progress and the Bruins didn’t know exactly what they had on their hands. Seguin had played well for stretches, including a 29-goal, 67-point sophomore campaign, but his playoff performances, especially a disappointing stretch in 2012-13, left much to be desired. That said, deciding to ship Seguin out following that playoff run was, shall we say, ill-advised, and it was certainly a move that caught many by surprise.

Seguin had potential, loads of it, that seemed untapped, and it didn’t take long for him to make the Bruins regret the deal. In his first season in Dallas, Seguin notched 37 goals and 84 points, finishing fourth in both points and Hart voting, and over the four years he’s spent as a Star, Seguin has registered 133 goals and 306 points, the eighth- and fifth-most in the league over that span, respectively.

Making matters worse for Boston is that Eriksson is really the only player who panned out, but that ended with his eventual departure as a free agent in July 2016. As for Smith, he was later dealt to the Panthers, Fraser ended up on waivers and Morrow’s contract expired only for him to sign with the rival Montreal Canadiens.


Montreal Canadiens acquire:
P.K. Subban

Nashville Predators acquire: Shea Weber

It feels as though the Subban-Weber deal only happened yesterday, and it’s going to take a long while for Canadiens fans to forget the trade, no matter how well Weber might play.

In Montreal, Subban was already beyond simple fan favorite status. An on-ice marvel, Subban was already a one-time Norris Trophy winner and two-time finalist, consistently among the team’s highest scorers and one of the most exciting players not just on the Canadiens, but in the entire league. He was worth the price of admission. Beyond that, Subban was an integral part of the community and, in September 2015, pledged $10 million to the Montreal Children’s Hospital.

But that didn’t stop rumors from swirling that Subban could be dealt, and days before free agency was set to open, that’s exactly what happened in a mind-blowing one-for-one swap for then-Nashville Predators captain Weber.

Both Weber and Subban had great years in their respective new homes this past season, and while some would argue Weber had the far better regular season, few will deny that Subban’s overall impact may have the Predators ahead in the deal. Subban logged monster minutes in the post-season, helping guide Nashville to a Western Conference championship and the Stanley Cup final.

And while it’s no Gretzky trade, it’s likely the most shocking one-for-one swap the league will see for years to come.

Want more in-depth features and expert analysis on the game you love? Subscribe to The Hockey News magazine.


Red Dutton and Eddie Shore

From the Archives: How the Amerks Almost Ruled New York

The New York Americans came before the Rangers, but the newer New York team had the success. Stan Fischler looks at the attempts to improve the Amerks.

Connor Bedard

Bedard and Friends Enjoy Homecoming at CHL/NHL Top Prospects Game

British Columbia is well represented at the 2023 CHL/NHL Top Prospects Game, including people who played with and against Connor Bedard growing up.

Rick Rypien

Hockey World and Beyond Remembers Importance of Mental Health

Adam Proteau remembers those we lost to mental illness, the supports to help those currently struggling and how there can be more strides to improve help.