15 Embarrassing NHL Trades That Will Haunt These Teams For A Long Time

Who doesn’t love a good blockbuster trade?

Humans love drama, and in the sporting world it doesn’t get much more dramatic (off the playing surface, that is) than a blockbuster deal. Fans rush to online message boards to discuss who won or lost the trade, and these debates can rage on for days, weeks, or even years after the trade.

It usually does take a few years to fairly evaluate any deal, as players tend to progress or regress over time. A trade that perhaps seemed fair at the time may in fact turn out to be lopsided a few years later.

Today’s list looks at the 15 most lopsided trades in the NHL that involve active NHL players. Some of these trades looked fair the day they happened but time has proven otherwise, and some looked lopsided on the day, and that hasn’t changed.

There were a surprising amount of very good hockey players involved in these trades. Can you think of any others that should have made the cut? Read on:


15 Islanders Trade Roberto Luongo And Olli Jokinen To Panthers For Oleg Kvasha And Mark Parrish

Robert Mayer-USA TODAY Sports

Honestly, all three of the trades Roberto Luongo has been involved in could have appeared on this list, but this one is definitely the most lopsided. This occurred way back on June 24, 2000, making it the oldest trade on the list. Luongo is the only player still active, and the Islanders saw him as expendable on account of them having just drafted goalie Rick Dipietro first overall.

It’s well documented that Dipietro is one of the bigger busts of all time, while it’s also well documented that Luongo went on to become one of the best goalies of his generation. Luongo is obviously in the twilight of his career at 38 years old, but his win count could hit 500 by the time it’s all said and done, which would make him just the third goalie ever to reach the plateau (Martin Brodeur and Patrick Roy).

14 Flyers Trade James Van Riemsdyk To Toronto For Luke Schenn

John E. Sokolowski-USA TODAY Sports

This trade occurred on June 23, 2012, which was right in the heart of some dark days in Toronto. The team’s management was in shambles, and they were certainly losing more deals than they were winning. Credit where it’s due though, this trade was grand larceny on the part of GM Brian Burke. James Van Riemsdyk is a solid first-line player in this league, whereas Schenn is a fringe defenseman.

At the time of the deal it seemed like a somewhat fair deal. Sure, Van Riemsdyk had progressed ahead of Schenn a little, but that’s to be expected considering that JVR is a forward and Schenn a D-man. Since the day of the trade though, Van Riemsdyk has blossomed into a star, whereas Schenn has stagnated—and that’s probably a nice way of putting it.

13 Leafs Trade Alexander Steen And Carlo Colaiacovo To Blues For Lee Stempniak

James Guillory-USA TODAY Sports

As mentioned above in #14, the Leafs have had terrible management for most of this third millennium. On Nov. 24, 2008, the Leafs sent Alexander Steen and Carlo Colaiacovo to the Blues for Lee Stempniak. Let’s ignore Colaiacovo here, as the major reason this was such a terrible trade was giving up on Steen so early in the promising young forward’s career.

Stempniak and Steen were similar players (position, production, and age-wise) at the time. In fact, Stempniak had the best season to date, enjoying a 27-goal, 52-point campaign with the Blues in 2007-08. That said, Steen was a former first rounder who was still getting better, and Stempniak shot nearly double his career average shooting percentage in his 27-goal campaign. At the time it looked sketchy, and now nearly a decade later it looks embarrassing for interim GM Cliff Fletcher.

12 Canadiens Trade Ryan McDonagh, Chris Higgins, Doug Janik And Pavel Valentenko To Rangers For Scott Gomez, Tom Pyatt And Michael Busto

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That list of players above is a lot to take in, so let’s narrow it down to that actual impact players: Ryan McDonagh (and Chris Higgins, I guess) for Scott Gomez. At the time Gomez was the best player involved in the deal, and as the old adage goes, “whoever gets the best player wins the trade.” So, at first, it looked as though Montreal did alright here. That said, McDonagh hadn’t played an NHL game yet.

This trade occurred on June 30, 2009, and it wasn’t long after that the tides started to turn on this deal. Gomez had just one decent season in Montreal before basically falling off the proverbial cliff, and we all know that Ryan McDonagh has risen to the captaincy in the Big Apple and is their #1 defenseman. The Habs have basically been depleting their blue line since this trade, proving they’ve learned nothing.

11 Canadiens Trade P.K. Subban To Predators For Shea Weber

Sergei Belski-USA TODAY Sports

This will be one of the more polarizing entries on the list, but I stand by it. When Marc Bergevin dealt franchise defenseman P.K. Subban to Nashville in exchange for other franchise defenseman Shea Weber straight up, he was trading a young defenseman in the heart of his prime who was already locked up for the remainder of his best years, for an over-the-hill rearguard who’s getting slower and comes with an endless contract.

I understand that Weber is a heck of a player, but the Canadiens will be paying him beyond his 40th birthday, and that’s tough for a team that has depleted the rest of its D corps over the past few seasons/decade. Subban helped the Preds to the Stanley Cup Final last spring, while the Habs look to be like a lost franchise these days.

10 Bruins trade Blake Wheeler And Marc Stuart To Thrashers For Rich Peverley And Boris Valabik

Charles LeClaire-USA TODAY Sports

If a superstar player gets dealt for peanuts on the dollar, it’s a pretty safe bet that Peter Chiarelli was the GM who traded the star. As of the time of writing, four of the top 30 current NHL scoring leaders have been traded by Peter Chiarelli at some point. Considering that only six of the top 30 have been traded in their careers, that’s noteworthy.

This deal, which occurred on Feb. 18, 2011, is one of the worst deals Chia made as GM of the Bruins. Blake Wheeler is an elite offensive player in the NHL, today, and Mark Stuart was probably the second-best player in this deal so what does that tell you about it? Chiarelli really boned this one up, and it certainly would not be the last time he commits such an error.

9 Leafs Trade Tuukka Rask’s Rights To Bruins For Andrew Raycroft

Greg M. Cooper-USA TODAY Sports

Back in 2006, the Maple Leafs had top goalie prospect Justin Pogge already in the system, so obviously Tuukka Rask became expendable. Toronto held the rights to Rask, but hadn’t even signed him to a contract when they decided to send his rights to Boston in exchange for 2004 Calder Trophy winner Andrew Raycroft.

This trade occurred at the 2006 draft, and history has shown it to be one of the most lopsided deals this millennium. Rask worked his way into the Boston backup role in 2009, won the Cup behind Tim Thomas in 2011, and has since controlled the Boston crease and collected one Vezina Trophy as the league’s best goalie. Raycroft had two very underwhelming seasons in Toronto. Oh, and that Pogge kid never panned out.


8 Oilers Trade Taylor Hall To Devils For Adam Larsson

Ed Mulholland-USA TODAY Sports

Another Peter Chiarelli special here! It was no secret that the Edmonton Oilers were desperate for defensemen in the summer of 2016, and making a trade from a place of desperation almost never works. Nonetheless, Chiarelli wasted no time in pulling the trigger on a deal that saw him deal a top 5 LW for a (maybe) top 50 defenseman.

I like Adam Larsson for the player he is, and that’s a one-dimensional, stay-at-home, second-pairing defenseman. He can play on a top-pairing for sure, but his D partner better be able to bring some offense from the back end if that’s the case. I’m certain Chiarelli knew he was giving up the better player here, so why wasn’t he able to at least grind a second-round pick out of Jersey in addition? Did he even ask? This truly is a terrible trade, and I don’t care what anyone says.

7 Oilers Trade Jordan Eberle To Islanders For Ryan Strome

Nicole Sweet-USA TODAY Sports

The third (and, believe it or not, NOT the last) Chiarelli entry on this list goes to one of his most recent moves. In the 2017 offseason, Chia Pete decided that Jordan Eberle’s two points in 13 postseason games was not enough, and he dealt the talented winger for a much less talented winger in Ryan Strome.

Again, much like the last entry wasn't an indictment of Larsson, this is not an indictment of Strome. Strome is who we thought he was, and there wasn’t any reason to expect any different. Blind Chiarelli supporters point to this move as a salary dump, but all it takes is a quick glance at the Cap Friendly home page to see that the Oilers indeed have cap space in spades. The may have needed to clear his contract for 2018-19 when McDavid’s $12.5 AAV contract kicks in, but with reports that the cap may go up to $82M, they probably could have squeezed Ebs in. This trade is pathetic on Chia’s part.

6 Flyers Trade Patrick Sharp And Eric Meloche To Blackhawks For Matt Ellison And A 3rd Rounder

Dennis Wierzbicki-USA TODAY Sports

Patrick Sharp played a key role in three Stanley Cup Champion Chicago Blackhawks teams. In 2013-14 he even led the team in regular season scoring with 78 points, and that was a team with Patrick Kane, Marian Hossa and Jonathan Toews on it, so there was plenty of competition on the roster. With all that in mind, it’s worth looking at how the Hawks acquired Sharp.

On Dec. 5, 2005, the above trade happened, and oh my lordy does it ever look bad today. I’ve never heard of Matt Ellison before, but he did in fact play in 43 NHL games (just seven of them with the Flyers, though). If you add in Meloche’s games, the pair combined to play just 20 for the club that traded Sharp for their services. The third round pick was moved to Montreal, so the Flyers really have nothing to show for Sharp.

5 Predators Trade Devan Dubnyk To Canadiens For Future Considerations

Brace Hemmelgarn-USA TODAY Sports

This trade occurred on March 5, 2014, and it came during what was probably the most tumultuous year of Devan Dubnyk’s life. While it was David Poile who pulled the trigger here, I don’t necessarily see this as a big screw-up on his part. He already had Pekka Rinne in the starter’s crease and depth in the system, so Dubnyk was definitely expendable, let alone his confidence level was at rock bottom.

About eight months after this trade, Dubnyk was sent from Arizona (where he was backing up Mike Smith) to Minnesota, and by season’s end he was one of the three Vezina Trophy finalists. It’s pretty rare that a player will be traded for future considerations one day, and then just over one year later be named as a finalist for a major NHL award, but it happened here.

4 Flyers Trade Sergei Bobrovsky To Blue Jackets For A 2nd Rounder And Two 4ths

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This one would be hilarious if it weren’t so tragic. The Flyers hadn’t really had a legitimate starting goaltender since current GM Ron Hextall retired, but they did have a promising young prospect by the name of Sergei Bobrovsky in the system. However, the Flyers sold the farm on an offer sheet for a different Russian netminder, Ilya Bryzgalov.

After the duo shared the crease for 2011-12, the Flyers had to trade Bob (Bryz was already untrade-able at this point), so they sent Bobrovsky to Columbus for three depth draft picks. How’d that work out for them? Well, Bobrovsky won the Vezina Trophjy as top goalie THAT SEASON, and he is your current reigning Vezina champion as well. On top of that, he’s your front-runner for 2017-18. Bryz of course received the compliance buyout.

3 Bruins Trade Tyler Seguin, Rich Peverley, And Ryan Button to Stars For Loui Eriksson, Reilly Smith, Joe Morrow, And Matt Fraser

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The fourth and final Peter Chiarelli muck-up shows up here at number three on our list. Reportedly fed-up with the 21-year-old's propensity to drink, party, and possibly have sex with women (very unusual for a 21-year-old, I know), Chiarelli decided to pull the trigger and he sent Seguin to the Dallas Stars, along with Rich Peverley and Ryan Button, for Reilly Smith, Loui Eriksson, Joe Morrow and Matt Fraser.

What’s incredible to me in all these Chia deals is that there wasn’t a single one in which he acquired a draft pick, and he was giving up the best player in the deal—by far—in each of them. I’m not sure what this means—does Chia see no value in depth draft picks? Most of the players he’s received back in these deals were at one point depth picks, so I simply don’t know what the deal is here. Does he ask? Who knows.

2 Islanders Trade Zdeno Chara, Bill Muckalt And A 1st Rounder To Senators For Alexei Yashin

Christopher Hanewinckel-USA TODAY Sports

Wow. I actually find it hard to believe that this trade even happened, but it certainly did. Let’s ignore Bill Muckalt here and focus on the other three assets involved. If this deal were simply Chara for Yashin straight up, it might still find its way onto this list. But, the fact that the first round pick involved turned out to be a 2nd-overall, and that 2nd-overall turned out to be Jason Spezza, really drives this deal up the list.

It’s not that Yashin didn’t have some good seasons with the Islanders, at least on a personal level. However, the Isles’ superstar center failed to take the club past the first round of the playoffs during his tenure there. Sure, Chara never reached incredible heights as a member of the Senators (though he was very good), but when he signed in Boston as a UFA in 2006, he really hit his stride. He won a Norris in '09, and led the B’s to a Stanley Cup in '11.

1 Bruins Trade Joe Thornton to Sharks For Marco Sturm, Wayne Primeau And Brad Stuart

Stan Szeto-USA TODAY Sports

I still can’t believe this actually happened. While the vast majority of the trades on this list were at least somewhat balanced on the day of the deal, this one was more crooked than a politician the day it happened. Joe Thornton was a former first overall pick and was amid a season in which he would eventually win the Art Ross Trophy as the NHL's leading scorer and the Hart Trophy as the league MVP.

I could go through all things that Marco Sturm, Wayne Primeau, and Brad Stuart contributed to the Bruins during their respective times with the Bruins (Sturm was the only one still there two years later), but I think we can all agree it pales in comparison to what Thornton has done as a Shark (he’s scored 958 points with the franchise in his 943 games with the club to date).


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