The 10 Worst NHL Trades of All Time

Why do we do this, anyways? Is it because everyone likes to play “backseat GM” and claim that we wouldn’t make these poor executive decisions? Is it because we are gluttons for punishment and like to torture ourselves by remembering the dark times? Regardless, it doesn’t matter how many trade deadlines the league goes through, there always comes that time when the hockey-viewing populous reminisces over the worst transactions made.

The NHL is about turn 100 years old, which means there is plenty of time for front offices to fudge a trade decision at least once. But no matter how many transactions occur, everyone still looks back on Adam Oates making Red Wings history. Or Eric Lindros being swapped for half a roster. Or, everyone’s favorite, The Great One jetting off to California.

What makes these trades so bad isn’t necessarily the trades themselves, but the aftermath of them. Here are the NHL’s top 10 all-time worst trades in no particular order.

1. Marian Hossa

Los Angeles Kings goaltender Jason LaBarbera deflects a shot by Marian Hossa of the Atlanta Thrashers | Kirby Lee/NHLImages

Los Angeles Kings goaltender Jason LaBarbera deflects a shot by Marian Hossa of the Atlanta Thrashers | Kirby Lee/NHLImages

The trade: The Atlanta Thrashers traded Marian Hossa, along with winger Pascal Dupuis, to the Pittsburgh Penguins for Colby Armstrong, Angelo Esposito, Eric Christensen, and a first-round draft pick.

The aftermath: Here is a textbook “bad trade.” Before they moved up to Manitoba to be the Winnipeg Jets, the now-debunked Thrashers lost a lot, but had a chance to give itself a makeover. So they shipped star player Hossa to Pittsburgh. That plan didn’t work in their favor however, as Atlanta’s takeaway from the trade didn’t evolve into anything substantial.

Hossa’s future was significantly brighter. He was part of the Stanley Cup-contending Pens and Detroit Red Wings before winning two championships during his current lengthy tenure with the Chicago Blackhawks. Even though the scoring Slovak is pushing 40, he continues to churn out points (515 career goals, 597 career assists) and climb the NHL all-time goals list.

2. Roberto Luongo

Roberto Luongo of the Florida Panthers looks on from his crease | Jeff Vinnick/NHLI via Getty Images

Roberto Luongo of the Florida Panthers looks on from his crease | Jeff Vinnick/NHLI via Getty Images

The trade: The Florida Panthers traded Roberto Luongo, Lukas Krajicek, and a sixth-round pick to the Vancouver Canucks in exchange for Todd Bertuzzi, Alex Auld, and Bryan Allen. (2006)

The aftermath: Oh yes, Luongo’s first stint in net for Florida. That stretched ended with quite well for the netminder, who headed to Vancouver to become a pillar for the competitive Canucks team we know so well from the early 2000s.

In return for the goalie and company, the Panthers got a troubled Bertuzzi, who only lasted a handful of games before being shipped off to Detroit, (and then Anaheim, and then Calgary, and then back to Detroit.) Luongo has since returned to Florida and has been bit by the injury bug on a couple occasions. But back in 2006, he came out on the good end of a bad trade for the Panthers.

3. Jaromir Jagr

Right wing Jaromir Jagr of the Washington Capitals skates on the ice | 2001 NHLI\Doug Pensinger/Getty Images

Right wing Jaromir Jagr of the Washington Capitals skates on the ice | 2001 NHLI\Doug Pensinger/Getty Images

The trade: The Pittsburgh Penguins traded Jaromir Jagr, along with defenseman Frantisek Kucera, to the Washington Capitals for Kris Beech, Michal Sivek, Ross Lupaschuk, future considerations, and cash (2001).

The aftermath: Once upon a hockey, a 29-year-old Czech superstar named Jagr decided that he wanted a trade from the Penguins’ team that he had won a couple Stanley Cups with. While both parties are doing just fine now, there was no happy ending immediately after the trade. Pittsburgh’s return for the league’s leading goal scorer produced 13 goals, 10 of which came from Beech.

Jagr on the other hand, was signed to a huge seven-year contract for the Capitals and continued registering points at an alarming rate — although it was pretty well-known how unhappy he was in Washington. They traded him to the New York Rangers in 2004.

4. Adam Oates

Center Adam Oates of the Edmonton Oilers waits on the ice | Elsa/Getty Images

Center Adam Oates of the Edmonton Oilers waits on the ice | Elsa/Getty Images

The trade: The Detroit Red Wings moved Adam Oates, along with Paul MacLean, to the St. Louis Blues for Bernie Federko and Tony McKegney (1989).

The aftermath: This was called, by many outlets, the worst trade in Red Wings history. Federko retired after a year, and McKegney only lasted 14 games amid some serious character issues in Detroit’s dressing room.

Oates was reportedly devastated by his trade. While his departure from St. Louis a couple years later was incredibly messy, his time with the Blues will forever be a highlight of his Hall of Fame career. He notched 90 assists in the 199091 campaign, most of those registered as the step-up for Oates’ hockey partner in crime, Brett Hull. The success of the dynamic duo left plenty to wonder whether or not Oates could have reached those numbers in a Red Wings sweater, instead of in St. Louis with the Golden Brett.

5. Brett Hull

Brett Hull of the St. Louis Blues skates against Brian Bellows of the Montreal Canadiens in the '90s at the Montreal Forum | Denis Brodeur/NHLI via Getty Images

Brett Hull of the St. Louis Blues skates against Brian Bellows of the Montreal Canadiens in the ’90s at the Montreal Forum | Denis Brodeur/NHLI via Getty Images

The trade: The Calgary Flames trade young stud Hull, along with Steve Bozek, to the St. Louis Blues for veterans Rob Ramage and Rick Wamsley (1988).

The aftermath: The trade for the other half of the “Hull and Oates” duo is quite interesting. On one hand, the Flames hoisted Lord Stanley’s Mug in 1989. On the other hand, that followed a downward trend while Hull scored 72 goals in 80 games in during the 198990 season, and 86 goals in 78 games the following season. Of course, that 199091 season marks the debut of Hull teaming up with Adam Oates to become one of the best duos that the game has ever seen.

How many of those many goals for the Blues would Hull have scored for Calgary? How many records would he have set for the Flames? Like the number of licks it takes to get to the center of the Tootsie pop, the world may never know.

6. Marcel Dionne

Marcel Dionne of the Los Angeles Kings skates against the Toronto Maple Leafs in 1984 | Graig Abel Collection/Getty Images

Marcel Dionne of the Los Angeles Kings skates against the Toronto Maple Leafs in 1984 | Graig Abel Collection/Getty Images

The trade: The Detroit Red Wings traded Dionne and Bart Crashley to the LA Kings for Terry Harper, Dan Maloney, and a secondround draft pick in 1976 (1975).

The aftermath: How does a player get traded after a 121point season? The team they play for doesn’t like said player’s contract demands and ships them off. Such was the case for Dionne, as a contract dispute punched his ticket out of Detroit.

Harper and Maloney faired okay over the course of the next few season. But they didn’t make the mark that Dionne made, with five consecutive 100point seasons over a decade of service in a Kings’ sweater.

7. Cam Neely

Cam Neely shows his ring during his induction into the Hockey Hall of Fame in 2005 | Bruce Bennett/Getty Images

Cam Neely shows his ring during his induction into the Hockey Hall of Fame in 2005 | Bruce Bennett/Getty Images

The trade: The Vancouver Canucks shipped Neely and their first-round pick to the Boston Bruins for Barry Pederson (1986).

The aftermath: In the wide world of lopsided trades, the Cam Neely trade is one of the best recognized. (Although it isn’t as uneven as the Eric Lindros acquisition, but more on that later.)

It’s a simple tale. Before the trade, Pederson’s numbers were superior to those of young British Columbia product Neely. After the trade, all of that changed. Pederson’s number dropped during his tenure in Vancouver. Neely’s career flourished tallying both goals and penalty minutes and he went on to have a Hall of Fame career, star in a couple movies, and eventually be president of the Bruins.

8. Phil Esposito

Boston Bruins Phil Esposito celebrates after scoring a goal against the Chicago Blackhawks goalie Tony Esposito | Heinz Kluetmeier/Sports Illustrated/Getty Images

Boston Bruins Phil Esposito celebrates after scoring a goal against the Chicago Blackhawks goalie Tony Esposito | Heinz Kluetmeier/Sports Illustrated/Getty Images

The trade: The Chicago Blackhawks traded Phil Esposito, along with Ken Hodge and Fred Stanfield, to the Boston Bruins in exchange for Gilles Marotte, Pit Martin, and Jack Norris.

The aftermath: For as much as Esposito didn’t fit the program in Chicago, this ended up being one heck of a steal for Boston. He led the NHL in scoring five times during his tenure with the Bruins and established himself as a key cog in the B’s roster.

In fact the whole trade was profitable for Boston, with Stanfield putting up regular points and Hodge registering a couple 100-plus point seasons.

9. Wayne Gretzky

The Edmonton Oilers' Wayne Gretzky celebrates with the Stanley Cup trophy | David E. Klutho/Sports Illustrated/Getty Images

The Edmonton Oilers’ Wayne Gretzky celebrates with the Stanley Cup trophy | David E. Klutho/Sports Illustrated/Getty Images

The trade: The Edmonton Oilers traded Wayne Gretzky, along with Marty McSorely and Mike Krushelnyski, to the Kings in exchange for Jimmy Carson, Martin Gelinas, three first-round picks, and $15 million. (1988)

The aftermath: Depending on what listicle you look at, this is rated as the worst trade ever to occur in the kingdom of hockey. No doubt because it is one of, if not the, most emotional trade to date. The fact that the Oilers won a Cup after the trade doesn’t even make a difference.

Canada’s greatest athlete and celebrity was shipped off to Hollywood, and Edmonton did not take it well. Like, Oilers’ GM Peter Pocklington received death threats because Oilers fans could not except it. It’s still a hot discussion topic whether or not the Gretzky trade was the first move in disassembling the unstoppable Oilers dynasty. Jari Kurri and Mark Messier departed just a couple seasons later, and others followed through the early ’90s. While The Great One returned up north and his No. 99 was retired and raised in Edmonton, there is no doubt that the trade of ’88 still stings.

10. Eric Lindros

Eric Lindros of the Philadelphia Flyers leaves the ice after playing against the New York Rangers during the 2012 Bridgestone NHL Winter Classic Alumni Game | Jim McIsaac/Getty Images

Eric Lindros of the Philadelphia Flyers leaves the ice after playing against the New York Rangers during the 2012 Bridgestone NHL Winter Classic Alumni Game | Jim McIsaac/Getty Images

The trade: The Quebec Nordiques traded Eric Lindros to the Philadelphia Flyers for Steve Duchesne, Peter Forsberg, Ron Hextall, Kerry Huffman, Mike Ricci, and Chris Simon, as well as two draft picks and $15 million (1992).

The aftermath: Eric Lindros was supposed to be the next big thing, a winning combination of every great player to ever inhabit the NHL. He didn’t want to play for the Nordiques, who drafted him first overall in 1991, and Philadelphia saw an opportunity. Lindros was a spectacle for a hot minute for the Flyers. Then injuries bogged him down and hampered his career. He never brought the Cup to Philly.

The pack of juggernauts that the Flyers sent to the Nordiques, on the other hand, was the roster makeover that Quebec needed. The new-fangled squad moved from Quebec to Colorado, and became the Stanley Cup winning Avalanche in 1996 and 2001.

Statistics courtesy of ESPN and NHL.com.