9 Worst NHL Trades in League History, Ranked

Every season there are dozens of trades consummated in the NHL. It’s part of the business. 

While some of those deals will be forgotten, others will go down in history as blockbuster deals that alter the landscape of the entire league and shake up the Stanley Cup odds.

In this countdown, I’ll focus on the deals that will live in infamy as the nine worst in the history of the NHL.

Worst NHL Trades in League History

1. Wayne Gretzky, Marty McSorley, Mike Krushelynski for Jimmy Carson, Martin Gelinas, Three First-Round Picks, and $15 Million 

The biggest trade in NHL history is also the most lopsided. There were extenuating circumstances that led to the Edmonton Oilers’ decision to send Wayne Gretzky to the Los Angeles Kings. Still, there is no denying that Edmonton came up way short in getting an appropriate return for the best player in league history.

Jimmy Carson ended up being the best part of the package that Edmonton received, but he only played two seasons with the Oilers. 

Gretzky, meanwhile, registered 918 points in 539 games with the Kings.

2. Mark Messier for Louie DeBrusk, Bernie Nicholls, and Steven Rice

The Oilers also take the second spot on this list for the package they got in return for Gretzky’s sidekick, Mark Messier. 

Like with the Gretzky trade, there were some financial stresses that put the Oilers in a tough spot, but the return for one of the best players – and captains – in NHL history just needs to be better than what Edmonton received.

That’s especially true when you consider that Messier would become a legend in New York and he led the Rangers to the 1994 Stanley Cup, ending a 54-year drought. 

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

It looked like Joe Thornton was well on his way to becoming an all-time great with the Boston Bruins in the early 2000s. Thornton averaged more than a point per game during a four-season span between 2000-2001 and 2003-2004, and he put up 33 points in his first 23 contests of the 2005-2006 season.

But the Bruins saw things differently. With the team in a malaise, the B’s decided to shake things up by dealing their best player to the San Jose Sharks for Marco Sturm, Brad Stuart, and Wayne Primeau.

All three had solid, if unremarkable, NHL careers, while Thornton captured the Hart Trophy in the season he was traded.

Thornton is considered one of the best players in the history of the Sharks and is a shoo-in for the Hockey Hall of Fame. 

4. Brett Hull for Rob Ramage and Rick Wamsley

Brett Hull had a remarkable career, but things weren’t straightforward for “The Golden Brett” in his early years. Hull went undrafted, twice, before the Calgary Flames selected him in the sixth round of the 1984 NHL Entry Draft.

Hull became a regular with the Flames in the 1987-1988 season, but he was traded to St. Louis in exchange for defenceman Rob Ramage and goaltender Rick Wamsley. The Flames cited concerns over Hull’s conditioning, despite the fact that Hull posted 50 points in 52 games as a rookie.

Rather than work with the young scorer, Calgary cut ties and moved on.

Hull moved on, too. He moved on to become one of the best offensive players of his generation and still holds the record for most goals in the history of the Blues.  

5. Teemu Selanne and Marc Chouinard for Chad Kilger, Oleg Tverdosky, and a Third-Round Pick

Teemu Selanne took the NHL by storm with a 76-goal rookie campaign for the Winnipeg Jets in 1992-1993. It looked like the Jets, who were in dire financial straits, had a star to build around.

But Selanne’s contract became too rich for the Jets, who also were paying big money to a pair of other forwards, Keith Tkachuk and Alexei Zhamnov. 

So the Jets decided that the financially prudent move would be to trade Selanne to the Anaheim Mighty Ducks. 

The deal would go on to completely change the fortunes of the Ducks, who needed a jolt after the expansion novelty wore off. Selanne delivered that by becoming the face of the franchise along with Paul Kariya.

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

Patrick Roy’s storied career in Montreal came to a dramatic end when he requested a trade because he felt he was humiliated by head coach Mario Tremblay. 

The trade request ended with Roy getting dealt to the Colorado Avalanche, in what would eventually go down as one of the most lopsided trades in NHL history.

Roy led the Avalanche to two Stanley Cups and was a five-time All-Star with the Avs. 

7.  Gary Leeman, Alexander Godynyuk, Jeff Reese, Michel Petit, and Craig Berube for Doug Gilmour, Jamie Macoun, Ric Nattress, Kent Manderville, and Rick Wamsley

Just three years after trading Hull, the Flames dealt another offensive dynamo, Doug Gilmour, to the Toronto Maple Leafs in a 10-player swap.

Gilmour rose to stardom in Calgary and helped the Flames capture the 1989 Stanley Cup, but a bitter contract dispute pushed him to request a trade in the middle of the 1991-1992 season. 

The Flames obliged his request and Gilmour was sent to the Maple Leafs in a massive swap. 

The trade changed the fortunes of both clubs. Gilmour quickly became an icon in Toronto and pushed the Maple Leafs to within one game of the 1993 Stanley Cup Final, while the Flames struggled for much of the next decade. 

8. Marcel Dionne and Bart Crashley for Dan Maloney, Terry Harper, and a Second-Round Pick

Marcel Dionne looked like he was going to join the likes of Gordie Howe, Red Kelly, and Ted Lindsay as an all-time great for the Detroit Red Wings. 

Instead, Dionne would end up monopolizing the record books for the Los Angeles Kings.

Dionne holds the record for most points in franchise history and was inducted into the Hockey Hall of Fame in 1992. 

9. Zdeno Chara, Bill Muckalt, and a First-Round Pick for Alexei Yashin

This trade would go down as a massive coup for the Ottawa Senators, but there was logic to why the Islanders made the deal at the time.

After spending a decade near the basement of the NHL, the Isles’ new owners wanted to make a splash and targeted Alexei Yashin, a dynamic offensive force who was in the middle of a contract dispute with Ottawa.

To get Yashin, the Isles sent Zdeno Chara and a first-round pick that the Senators used to draft Jason Spezza.

Yashin helped resuscitate the Islanders, but Chara and Spezza turned the Sens into a powerhouse that regularly boasted the shortest hockey odds to win the Stanley Cup during their tenure.

What Is the Biggest Trade in NHL History?

There is no question that “The Trade” is the biggest trade in NHL history.

Wayne Gretzky’s move from Edmonton to Los Angeles completely changed the trajectory of both franchises, the league, and even the entire sport.

With Gretzky in Los Angeles, hockey’s popularity rocketed in California and the United States. 

The date of the deal, Aug. 8, 1988, is still considered one of the most important in the history of the NHL.