More data and analytical tools for evaluating talent have pretty well served to make it harder than ever to truly screw up as an NHL executive. Sure, bad contracts are still handed out and draft fails happen, but few talent-for-talent trades nowadays are so bad as to be considered entirely one-sided in nature. The transition has helped maintain some degree of competitive balance while ensuring for at least relatively competent club management across the league, but if we’re being honest here, it has also taken some of the fun out of trade evaluation.

But fear not – past executive mistakes continue to reverberate around the NHL and are even still felt within the league’s current power structure. One-time hapless organizations like the Toronto Maple Leafs and the New York Islanders aren’t giving away first round picks like they may have in the past, but they still have to endure the sins committed by forebearers like John Ferguson Jr and Mike Milbury. Whether the average general manager has grown smarter or not, bad trades will still happen and, in the meantime, we still have the physical proof of past one-sided transactions across the league.

The thing about a one-sided trade is that it can stick with your club, for better or for worse. Time passes and players move on, but a losing gamble that results in an albatross contract, a missed opportunity or a costly talent loss can linger just as long as adding a star on the cheap can provide a major boost for your team. Whether these trades bring back fond memories or open up old wounds, here are 15 lopsided deals that involve players who are still plying their trade in the NHL.

15. Ben Bishop for Cory Conacher

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Other than the 11 inch height difference between the 6’7″ Ben Bishop and the 5’8″ Cory Conacher, the trade between the Ottawa Senators netminder and Tampa Bay Lightning forward seemed pretty even when it was made. At the time, Bishop was a 26-year-old just beginning to find his way as an NHL starter while Conacher was a 23-year-old rookie who had netted nine goals and 24 points over his first 35 career games. Tampa Bay even threw in a fourth rounder to further balance things out.

The two main players in the trade quickly went in opposite directions. Starting with his first full season in Tampa, Bishop emerged as a franchise goalie, earning two Vezina nominations in three seasons and backstopping the Lightning all the way to the 2015 Cup Finals. Conacher, meanwhile, quickly went about proving his red hot start for be a fluke. Since the trade, he has played 121 more games with just 13 goals to show for it. He’s now back in Tampa, albeit on a two-year, two-way deal.

14. Patrick Sharp for Matt Ellison

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Back in 2006, Philadelphia Flyers GM Bobby Clarke had the kind of problem that most general managers would kill to have: he had too much depth down the middle. Indeed, it was hard to find enough minutes to go around with Peter Forsberg, Jeff Carter, Mike Richards, RJ Umberger and Patrick Sharp on the roster. It was a 24-year-old Sharp who was ultimately the casualty, shipped to Chicago in a package for the supposedly more versatile Matt Ellison.

Ellison may have been able to play multiple forward spots, but unfortunately he didn’t play any of them well enough to remain employed in the NHL. He played just seven games in Philly and now plies his trade in the KHL. Sharp, meanwhile, did switch positions with the Blackhawks and wound up doing a serviceable job at left wing. He has scored over 250 goals and won three Stanley Cups over 13 seasons since leaving the Flyers.

13. Alex Steen for Lee Stempniak

Billy Hurst-USA TODAY Sports

The basic notion of trading prospects for proven talent in a bid to win now seems entirely reasonable. Theoretically, you are sacrificing potential for a proven commodity that will better serve your present needs. But not all prospects are created equal, nor are veteran players. For the Toronto Maple Leafs, a 24-year-old Alex Steen – not to mention another former first round pick in Carlo Colaiacovo – was a steep price to pay for a slightly above average Lee Stempniak.

Steen ultimately became a victim of the pressure and expectations of playing for the Leafs, where averaging 16 goals over your first three seasons prompts criticism instead of praise. He would enjoy a fresh start in St. Louis, one that has now spanned 10 seasons and counting, four of which have produced 20 goals or better. Stempniak, on the other hand, produced 25 total goals over 123 games before being dealt to Phoenix for a whole lot of nothing.

12. Dustin Byfuglien for Marty Reasoner

Stan Szeto-USA TODAY Sports

One day, the Chicago Blackhawks of this generation will be remembered only in the most glowing terms. Led by Jonathan Toews and Patrick Kane, it was this group that snapped a half century Stanley Cup drought and then repeated as champs two more times. At present time, however, it’s difficult to not at least acknowledge the club’s falling victim to their own success and struggling to keep their team together amidst the pressure of the salary cap.

Thought just one of the many examples, Dustin Byfuglien might represent the most damaging financially-motivated departure for the Blackhawks. Just 25 and already emerging as a formidable defensive force, Big Buff simply wasn’t going to fit under the cap with a new contract forthcoming. While GM Stan Bowman should be commended for getting assets back rather than losing him for nothing, the club came away with the pretty underwhelming return of Marty Reasoner and an assortment of spare parts. Even as he’s been forced to sell off valuable parts, Bowman has seldom been fleeced quite like this.

11. Ryan McDonagh for Scott Gomez

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In the summer of 2009, the Montreal Canadiens were hoping to develop a one-two punch down the middle by acquiring Scott Gomez to compliment Tomas Plekanec. Unfortunately, the only one-two punch that the six-player Gomez deal produced was the double whammy of repercussions it carried for the Habs. First came the burden of carrying the hefty contract of the under-performing Gomez, then came the emergence of the outgoing Ryan McDonagh. When a trade produces problems with what you’ve acquired and what you’ve lost, odds are it isn’t a great swap.

Gomez arrived in Montreal having averaged 68 points over his previous five seasons, but was getting paid accordingly. Along with Gomez, the Habs assumed his contract, with five years and over $35 million remaining on it. After 59 points in his first season with his new club, the Alaska native saw his production plummet and would never top 38 points again. Burning a significant chunk of money on a diminishing asset isn’t ideal, but wouldn’t have been so bad were it not for McDonagh turning into the New York Rangers captain and defensive cornerstone.

10. Filip Forsberg for Martin Erat

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It takes a special collection of talent to post six 100-plus point seasons over the past nine, a stretch that has included three President’s trophies. Indeed, the Washington Capitals have been chockful of elite skill with Alex Ovechkin leading a deep group of forwards and Braden Holtby providing outstanding goaltending. Unfortunately, NHL success is measured through the lens of the elusive Stanley Cup and Ovechkin, Holtby and co still haven’t brought one to the nation’s capital.

For as long as the franchise continues to tease greatness and fall short, the infamous 2013 trade of Filip Forsberg for Martin Erat and Michael Latta will likely stand as a painful reminder of what could have been. Yes, Washington once had the Swedish sniper who has most recently posted back-to-back 30-goal seasons for the Nashville Predators, all before the age of 24. In fact, Forsberg has already served as an offensive anchor on a Finals-bound Preds team, which surely stung a Caps franchise that hasn’t reached the Cup Finals since 1998.

9. Tuukka Rask for Andrew Raycroft

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In the lowly but plentiful history of trades that badly backfired on the Toronto Maple Leafs, their dealings with the Boston Bruins are best (worst?) remembered for the Phil Kessel trade. But even though it cost the Leafs a chance at Tyler Seguin and Dougie Hamilton, it at least brought in Kessel’s 181 goals and a playoff berth that would not have been possible without the skilled US winger. It was, however, another deal with the Bruins that would prove more costly with even less of a return.

The Leafs were enjoying the luxury of two highly touted goaltending prospects – Justin Pogge and Tuukka Rask – and opted to use that surplus to improve their present club. Unfortunately, GM John Ferguson Jr. made two evaluation mistakes, first betting on Pogge over Rask and targeting a recent Calder trophy winner in goaltender Andrew Raycroft. Instead of trading Pogge, he of seven career NHL games, Ferguson unloaded a future Vezina winner. And while the acquisition of Raycroft might have seemed like a savvy play, Boston seemed eager to unload the 26-year-old coming off of a disappointing follow-up to his successful rookie campaign.

8. Brent Burns for Devin Setoguchi

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We tend to view bad trades through the overly simplistic lens of a team that didn’t know what they were giving up until the player starred for someone else. Sometimes, though, even the engineer of a bad deal deserves more credit than that. Minnesota Wild GM Chuck Fletcher certainly didn’t intend to hand a future Norris trophy winner to the San Jose Sharks, but also recognized Brent Burns as a special talent when he traded him back in 2011.

While Fletcher valued the 26-year-old blue liner who had finished the previous season as the club’s No. 1 defenseman, he also realized that the Wild needed a new plan coming off of their third of four consecutive seasons out of the playoffs. They felt they could work towards a fresh start by acquiring a package that included Devin Setoguchi, Charlie Coyle and a first round pick used on Zach Phillips. Coyle is still just 25 and has a 20-goal campaign under his belt, but Setoguchi spent just two seasons in Minnesota and Phillips still has yet to touch NHL ice. Going the other way was Burns, who has gone onto greater success than perhaps anyone expected, growing into the bearded face of the talented Sharks.

7. Wayne Simmonds and Brayden Schenn for Mike Richards

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Trading a 26-year-old center coming off of four seasons in which he averaged 28 goals and 70 points hardly seems like a recipe for success. But after six seasons in Philadelphia that were so productive that they handed him the ‘C’, Mike Richards quickly proved that he wasn’t cut out for La La Land after a trade to the Los Angeles Kings. Despite having been captain of the Flyers, Richards lacked the maturity to keep his focus on hockey. He developed a reputation as a partier and was eventually arrested for possession of oxycodone, just as his on-ice production took a nosedive.

As bad as things got between Richards and the Kings, a relationship that ended with a messy lawsuit over the club’s attempt to terminate his massive contract, it didn’t keep the franchise from winning two Stanley Cups with the former Kitchener Ranger in tow. What really made the 2011 trade a costly one, then, was surrendering young forwards Wayne Simmonds and Brayden Schenn. Simmonds is coming off back-to-back 30-goal seasons and Schenn collected nearly 250 points over six seasons in Philly before being flipped to St. Louis this past summer.

6. Roberto Luongo for Todd Bertuzzi

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It is a credit to the longevity of Roberto Luongo that, even though he was the second-oldest player traded in the 2006 six-player mega-deal that sent him to Vancouver from Florida, he remains the only trade participant still active. Now back with the club who traded him 11 years ago, Bobby Lou’s current contributions to the Florida Panthers at 38 years of age still doesn’t change how badly the original deal worked out for the club.

After being traded for a package headlined by Todd Bertuzzi, Luongo became a franchise icon in Vancouver. He backstopped the Canucks to six postseason appearances over parts of eight seasons, including coming one game shy of Stanley Cup glory in 2011. Bertuzzi, who Vancouver was anxious to get rid of after the infamous Steve Moore incident, spent just seven games in the Sunshine State before being flipped to Detroit for a package of young talent that never really developed into much. You could actually go back further for Luongo and count the 2000 deal that saw him and Olli Jokinen leave Long Island for Mark Parrish and Oleg Kvasha on this list, as well.

5. Jakub Voracek and Sean Couturier for Jeff Carter

John E. Sokolowski-USA TODAY Sports

June 23rd, 2011 should be a celebrated date in the annals of Philadelphia Flyer history. Two big trades made by the Flyers that day helped firm up the future core of the club. And all that Philly had to do was to bid farewell to one of the NHL’s biggest bromances, the duo of Mike Richards and Jeff Carter. We already talked about how the club turned Richards into Wayne Simmonds and Brayden Schenn, but the Carter deal may have been even more of a heist.

Carter remains in the league and even posted a 32-goal campaign last season, but the productivity he’s enjoyed in LA wasn’t anywhere to be seen during a short stint in Columbus. For the price of future top six forwards Jakub Voracek and Sean Couturier, the Blue Jackets got all of 15 goals in 39 games and a -11 from Carter. He was quickly flipped (again) to the Kings for Jack Johnson and Marko Dano.

4. Tyler Seguin for Loui Eriksson

Jerome Miron-USA TODAY Sports

This probably isn’t the Tyler Seguin swap that most fans expected to see on this list, but I’ve already explained how Brian Burke and the Toronto Maple Leafs’ side of the Phil Kessel-for-Seguin trade can be easily defended, given Kessel’s contributions to the blue and white. Less defensible is what the Boston Bruins were thinking when they gave up on the promising 21-year-old center after just three seasons, shipping him off to Dallas for an underwhelming package headlined by Loui Eriksson.

Despite the fact that the deal took place just four years ago and was heavy on future talent for the Bruins, the book has already closed on Boston’s side of the trade. Every piece of the trade return for Seguin and Rich Peverley has reached a dead end, either through waivers or free agency. Even the subsequent trade of Reilly Smith for Jimmy Hayes failed to produce anything of consequence. A 30-goal season from Eriksson in Beantown was at least something, but pales in comparison to the 150 goals and over 300 points that Seguin has scored – before the age of 26, mind you – with the Stars.

3. Joe Thornton for Brad Stuart and Marco Sturm

Stan Szeto-USA TODAY Sports

When it comes to the Seguin deal, you would think that the Bruins would have learned their lesson long before about trading a franchise center entering his prime. It was eight years prior that the club’s relationship with 1998 No. 1 overall pick Joe Thornton grew icy amid public scrutiny of the 26-year-old’s play and leadership. With both sides seeking a fresh start, Jumbo Joe was dealt to San Jose for the trio of Marco Sturm, Brad Stuart and Wayne Primeau.

The B’s probably didn’t expect this one to still haunt them 12 years on, more than two seasons since any of the three acquired players last suited up in the NHL. At 38 years of age, Thornton is a sure-fire Hall of Famer and ranks second to Patrick Marleau in franchise history in both games played and points. Although the Bruins have won a Stanley Cup in the years since the deal, their respectable 17 playoff series post-Thornton still don’t measure up to the 22 series the Sharks have competed in with the big man.

2. Jaromir Jagr for Kris Beech, Ross Lupaschuk and Michal Sivek

Bruce Fedyck-USA TODAY Sports

That we have to go all the way back to 2001 to find this lopsided trade for a still-active NHLer serves as further illustration of the remarkable longevity enjoyed by the iconic Jaromir Jagr, who might just hold on long enough in the NHL to play in a fifth decade. The Pittsburgh Penguins were in rebuild mode and looking to move on from the costly 28-year-old when they sent Jagr to Washington for the prospect trio of Kris Beech, Ross Lupaschuk and Michal Sivek.

So how did that one work out for the Pens? The three men tallied 28 total goals in the NHL (with 25 coming from Beech) and were completely out of the league by 2008. The ageless Czech winger, on the other hand, topped 28 goals on his own in five different seasons since the deal and is still kicking around with the Calgary Flames as he approaches his 46th birthday. Adding insult to injury and illustrating the danger in sending a star player to a rival team, Jagr has now scored 25 goals against Pittsburgh in a whopping 57 games since the deal.

1. Zdeno Chara and Jason Spezza for Alexei Yashin

Sergei Belski-USA TODAY Sports

For all of the bad GM’s represented on this list, it seems fitting that long-time New York Islanders GM “Mad” Mike Milbury takes the top spot here. It was Milbury who made the decision to go all-in on a trade for Russian star scorer Alexei Yashin, who was coming off of back-to-back 40-goal campaigns in Ottawa but had fallen out of favor with the Senators following multiple contract holdouts and public squabbles. While Milbury and the Isles appeared to have more leverage given Yashin’s position with the Sens, the club still sold the farm to get him.

To bring Yashin to Long Island on draft day in 2001, the Isles packaged their No. 2 overall pick with winger Bill Muckalt and a tall, gangly defenseman by the name of Zdeno Chara. The draft pick became highly touted center Jason Spezza, forming the core of the up-and-coming Senators in the years following. Chara is now well into his tenure with the Boston Bruins and Spezza has spent the past few years in Dallas, both continuing to perform at a high level. As for Yashin, Milbury promptly showered him with a 10-year, $87.5 million. He would, however, never live up to the contract, scoring 32 goals in his first season with his new club and failing to top 28 goals in any season thereafter.

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