NHL: Bad Deals and Great Steals—Unlucky 13 Worst Trades of All-Time

The glass is either half empty or half full.

Lopsided and bad trades are often great steals for the other team involved, while at other times transactions aren’t beneficial for either side.

Young prospects shipped out prematurely, disgruntled stars traded ill-advisedly, proven champions and seasoned veterans moved grudgingly or lost on a gamble.

Damage in bad trades may be immediate or can haunt the loser long-term; losing leadership, massive point production, or even Stanley Cups.

This is a look at the 13 worst trades all-time in the National Hockey League.

The Constitution of A Bad Trade

The order of the countdown is determined both quantitatively, in terms of stats produced and seasons played, and by interpretation of quality.

The ranking method employed, seeks to unveil primarily the winners and losers according to players' career longevity and their offensive numbers (markedly, the majority of trades involve high profile forwards), as well as the long term effects on the players' old and new teams.

Scenarios where bad acquisitions came at the expense of later successful draft picks or of entirely untested rookies are largely avoided owing to the intangible element that hindsight affords in assesing movement of unknown commodities.

Otherwise, surely Toronto's swap of Scott Niedermayer's draft rights for Tom Kurvers would figure on the list. As would their trade of, amongst others, prospect Brad Boyes for Owen Nolan.

The Sharks would be on the hook for their cheap release of Miikka Kiprusoff for a conditional pick, leaving the Blackhawks equally guilty of their exchange of Dominic Hasek for Stephane Beauregard.

But that is the privy of hindsight.

Another case of exception: The 1995 trade sending Joe Nieuwendyk to Calgary for Corey Millen and rookie Jarome Iginla who had yet to play in the League may appear lopsided in the long run given the outstanding tenure of the Flames captain.

Yet the trade short term was as much a win for the Stars who Nieuwendyk helped carry to a Cup championship in 1998-99.

Thus the transaction served the purpose of both clubs, one immediate, the other in the future, and as such escapes the Top 13.

13. Yash’in Burn

2001-June 23 Traded from Ottawa Senators to New York Islanders for Bill Muckalt, Zdeno Chara and round 1 pick (Jason Spezza)

At first glance this trade draws parallels to the Niewendyk-Iginla exchange since it brought a productive veteran, and future captain, Alexei Yashin
(119 G, 290 Pts) to Long Island for five seasons.

But even with Yashin, the Islanders did not achieve any great honors.

And though the deal included the as yet unknown commodity that is now superstar Jason Spezza, it centered on the young but already seasoned giant blue-liner.

Zdeno Chara, whose offensive output exploded upon arrival in the Canadian capital, has since become a household All-Star in the League as the Boston Bruins captain.

12. Lindros Loss

1992-June 30 Traded from Quebec Nordiques to Philadelphia Flyers for Chris Simon, Mike Ricci, Kerry Huffman, Ron Hextall, Peter Forsberg, Steve Duchesne,, round one pick (Jocelyn Thibault) and $15,000,000 cash

This trade looks lopsided if only for the number of players dealt to the Nordiques. Yet it has to be remembered that the Flyers were thought to be the winners of this transaction.

Philly gained a young phenom whose career gradually dwindled as his string of concussions grew. But the franchise player and longstanding captain nevertheless amassed 290 goals and 659 points as a Flyer, leading the team to the Stanley Cup Finals.

His achievements, however, are challenged by those of the oft-injured Peter Forsberg and the ragtag bunch that were dealt along with him, principally Simon and Ricci, securing the base of the newly-moved Colorado Avalanche who won the Stanley Cup twice in six seasons.

11. Where You Headed Joe?

2005-November 30 Traded from Boston Bruins to San Jose Sharks for Wayne Primeau, Brad Stuart, and Marco Sturm.

Although the trade might not be as uneven as many presume, the Bruins still sacrificed their franchise player in the deal. Thornton has since found his niche in San Jose.

His passing abilities have raised the team’s offensive production as he finds himself atop the League’s production tables. In his fourth season, the big center has 260 helpers and 339 total points with the Sharks.

Boston, in return, received a B-cast bundle. The under-performing Primeau was quickly shipped to Calgary alongside Stuart in return for Andrew Ference and Chuck Kobasew, who along with Marco Sturm now log decent, though far from spectacular, numbers for the Bruins.

10. Sundin Saga; In the Days When the Destination Was Chosen For Him

1994-June 28 Traded from Quebec Nordiques with Garth Butcher, Todd Warriner and round one pick to Toronto Maple Leafs for Wendel Clark, Sylvain Lefebvre, Landon Wilsonone, and round pick

If the Nordiques won the previous one, they blew it with Mats.

The main return chip was Wendel Clark who, though he was coming off a record year for the Buds, played only 37 games in a Nordiques jersey before being shipped out soon thereafter for Claude Lemieux.

And while Lemieux was a positive pick up, even his productive tenure with the Avalanche paled in comparison with the impact that the longtime Maple Leafs captain had in Toronto.

Shouldering the club for 13 seasons, he netted 420 goals and 1122 points, the most in franchise history, and was a nine-time All-Star in the process.

9. Sunny Day! Big Bert Leaves New York

1998-February 6 Traded from New York Islanders with Bryan McCabe and round three pick (Jarkko Ruutu) to Vancouver Canucks for Trevor Linden

As if the Chara and Spezza swap for Yashin wasn’t enough, enter another one of "Mad" Mike Milbury’s blunders. The common joke has it that Milbury makes trades that are rejected on EA NHL Live.

And this one wasn’t the last either.

In exchange for the then current-Olympian Linden, the Canucks received a future Canadian representative and All-Star who tallied 188 goals and 449 points.

Even when things went sour following the Moore ordeal, Bertuzzi was the key chip in the exchange that saw Luongo head West.

Meanwhile, Trevor Linden played a total of 107 games on the Island before being traded to the Habs for Branislav Mezei (one goal in 66 games as an Islander before his demotion to the AHL).

8. Happy Gilmour—No More!

1992-January 2 Traded from Calgary Flames with Jamie Macoun, Kent Manderville, Ric Nattress, and Rick Wamsley to Toronto Maple Leafs for Craig Berube, Alexander Godynyuk, Gary Leeman, Michel Petit, and Jeff Reese.

In the largest trade in NHL history, ex-Calgary, and newly appointed Toronto GM Cliff Fletcher, succeeded in reacquiring Gilmour.

In six campaigns with the Leafs, the “C”-bearing Gilmour potted 133 goals with a side of 334 assists and won the Selke Trophy as the best defensive forward in 1992-93.

That same year he established a club record with 127 points scored, earning All-Star appearances that year and the next.

The payoff for Calgary was dismal, as the mixed bag five-player acquisition played a cumulative total of 378 games in Flames colours before reaching different ends with the club.

7. So Long Selanne

1996-February 7 Traded from Winnipeg Jets with Marc Chouinard and round four pick to Anaheim Mighty Ducks for Oleg Tverdovsky, Chad Kilger, and a third round pick.

The financially troubled Winnipeg Jets were shedding salary and dropped the ball on Selanne, losing the 10-time All-Star without any significant prospects or compensation in return.

Selanne went on to clinch the league’s scoring titles in 1998 and 1999 and registered 225 goals with 482 points in 394 games over six years in his first stint as a Duck.

In return, the Winnipeg Jets/ Pheonix Coyotes claimed Tverdovsky and Kilger who combined for 30 tallies during their short stops with the system.

6. Needy for Neely

1986-June 6 Traded from Vancouver Canucks with round one pick (Glen Wesley) to Boston Bruins for Barry Pederson.

The hometown kid from B.C. left a glaring hole in his wake when he left Vancouver, becoming Boston’s leading scorer in his first full year.

The Hall of Famer, though often injured, shone for the Bruins, collecting 344 goals and 590 points over 10 seasons, three times netting 50 scores or more.

Wesley complemented him well over seven years with a respectable total of 77 goals and 307 points.

Pederson meanwhile, broke off from his goal-scoring ways and mananged only 60 notches with 197 points in the four years he spent as a Canuck.

5. That’s All She Oates

1989-June 15 Traded from Detroit Red Wings with Paul MacLean to St. Louis Blues for Bernie Federko and Tony McKegney.

Though MacLean was a respectable addition, it was Oates who put up 58 goals and had 286 helpers during his three years with the Blues.

Part of the "Hull & Oates" tandem, he was the intrinsic element behind the success of Brett Hull.

Hull never repeated the numbers that he had playing along his center. With Oates by his side he averaged 76 goals per year (scoring at a rate of 0.98 goals a game).

In the eight years remaining in St Louis without Oates, Hull averaged 37 goals per season (0.58 per game).

In return, the Motown gang received a total of 57 and 3 points from Federko and McKegney respectively. The first played only one season, the second logged even less, ending his tenure with the Red Wings after 14 games.

4. Off the Mark, Naslund Goes West

1996-March 20 Traded from Pittsburgh Penguins to Vancouver Canucks for Alek Stojanov.

The anonimity of Stojanov, who dressed for a total of 45 games for the Penguins before being demoted in perpetuity to the minors, speaks volumes.

Naslund went on to play a dozen seasons with the ‘Nucks, sport the captaincy, and rack up 346 goals along with 410 assists.

* The move is not unlike (other than in its longevity) the Canadiens acquisition of Alex Kovalev from the NY Rangers in exchange for Jozef Balej who played only 13 games with the Blue Shirts, and only one more in the NHL altogether. Kovalev in 296 matches with the CH has 225 pts, equalling a 0.84 pt./game production, just shy of Naslund’s 0.86.

3. Rob’bed, Twice!

A: 2000- June Traded from the New York Islanders with Olli Jokinen to Florida Panthers for Oleg Kvasha and Mark Parrish.

This blunder was one for the ages, even with Mike Milbury’s resume.

B: 2006-June23 Traded from Florida Panthers with Lukas Krajicek and a sixth-rounder to Vancouver Canucks for Todd Bertuzzi, Bryan Allen, and Alex Auld

In the Sunshine State they don’t like too much of a good thing.

Having acquired the young stars, the failing franchise was pressured to release both. Three years prior to this year’s trade of Jokinen to the Coyotes, Roberto returned to Canada.

GM Mike Keenan gambled on the trouble-case that was Todd Bertuzzi ,who was injured to boot, and shipped out the star keeper to land him.

Today, Allen is the only one still a Panther. Bertuzzi stayed for seven games while Auld played only 20 games more.

Luongo has since become the Canucks team captain, face of the franchise and continues to be one of the elite goalies in the NHL.

2. The Oil Spring A Leak, Pt. III: Oilers Take A Coffey Break

1987-November 24 Traded from Edmonton Oilers with Dave Hunter and Wayne Van Dorp to Pittsburgh Penguins for Dave Hannan, Chris Joseph, Moe Mantha, and Craig Simpson.

Paul Coffey deserves a mention in the disintegration of the Oilers, though his exit did not scar the Edmonton squad as deeply as could be imagined as they continued to exercise their League dominance.

An incredibly offensively gifted D-man, Coffey was at financial odds with Edmonton’s management and was shipped out. Though he never equalled his output from the Oiler days, Coffey enjoyed 15 successful post-trade years, winning his fourth Cup with the Pens in 1991.

(2). The Oil Spring A Leak, Pt. II: What A Mess!

1991-October 4 Traded from Edmonton Oilers with future considerations to New York Rangers for Louie DeBrusk, Bernie Nicholls, and Steven Rice.
An All-Time great, Messier would find his second home in Manhattan, effectively dropping the curtain on the Oiler glory days.

In his first six year run with the Rangers he tallied 183 goals and 518 points, and would add 67 and 173 more respectively, in his later four year return.

Known even more for his leadership and passion, the Moose famously guaranteed a playoff victory and delivered with a hat-trick in the semi-finals, thus shouldering the Rangers to a Stanley Cup victory in 1994.

(2). The Oil Spring A Leak, Pt. I: The Great Goodbye

1988-August 9 Traded from Edmonton Oilers with Mike Krushelnyski and Marty McSorley to Los Angeles Kings for Jimmy Carson, Martin Gelinas, round one pick in 1989 (Jason Miller), round one pick in 1991 (Martin Rucinsky), round one pick in the 1993 (Nick Stajduhar) and $15,000,000 cash.

Hailed by most as the greatest player ever, Gretzky’s feats need not be heralded, nor the transaction balance assessed.

The trade that shocked the hockey world remains at number two only because the Oilers still won another title following his departure, only to be ultimately broken by Messier’s exit to Broadway.

1. Au Rev-Roy Patrick!

1995-December 6 Traded from Montreal Canadiens with Mike Keane to Colorado Avalanche for Andrei Kovalenko, Martin Rucinsky, and Jocelyn Thibault.

As shocking as Gretzky’s departure was, Roy’s was the more devastating.

The catalyst of the trade was the infamous game were Patrick’s embarrassing performance against the Red Wings (and the coach’s refusal to pull him) prompted him to heatedly inform the Team President that he had just played his last game for Montreal.

For the Canadiens, it was the beginning of a decade long downwards spiral from which they have only managed to slowly climb back from a decade later.

Shipped out along with then-team captain Mike Keane, Roy went on to win two more Stanley Cups (his first that very same year) as well as his third Conn Smythe Trophy in 2001, backstopping his way to becoming the all-time winningest goalie in NHL history.