Top 15 Recent NHL Trades Teams Are Already Regretting

As sports fans, we love a big blockbuster trade. As soon as news of one breaks, we’re all quick to analyze it at first glance — whether it's breaking down which team won or lost the trade or vilifying one GM while praising another as some sort of magician.

While most trades made in the league today are fairly even given the fact that no one likes to get fleeced on a deal, there are still some outliers that make you scratch your head and think “what the heck was that GM thinking?”

Within the past calendar year, there have been 85 trades in the NHL, many of which were minor deals that you may not have even heard of. About half of those trades did immediately impact clubs, although it’s too early to tell who the winner of most of those deals was. Today, we’re going to look at some of the deals made recently that one team is likely already starting to regret.

Some of the deals here on the list would be classified as blockbusters, whereas others are smaller deals that could turn out to have major impacts down the road. Either way, most of these deals must have been pretty tough to make, and I bet some of these GMs are either publicly or secretly regretting these trades already.

15 Nail Yakupov for a 3rd round pick and Zach Pochiro

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The most recent trade to appear on our list here was made between the Edmonton Oilers and St. Louis Blues back on Oct. 7. The Oilers sent former 1st overall draft pick Nail Yakupov to St. Louis for a conditional 3rd round pick and prospect Zach Pochiro. It’s not likely Pochiro ever plays in the league, and the condition on the 3rd rounder is it turns into a 2nd is Yak scores 15 goals this season.

The Oilers probably already regret this deal, although they spent the last three seasons whittling down the young Russian's trade value, so they really had no choice here. Any way you look at it, if you trade a first overall pick for a 3rd round draft choice just four years after selecting him, you’re pretty much knowingly cutting your losses.

14 Mikkel Boedker for Alex Tanguay, Conner Bleackley and Kyle Wood

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Back at the 2016 trade deadline, the Colorado Avalanche sent Alex Tanguay, Conner Bleackley, and Kyle Wood to the Arizona Coyotes for Mikkel Boedker. Boedker was a rental for the Avs, but the problem here is that Colorado didn’t even really come close to making the postseason while forfeiting two solid prospects in Bleackley and Wood—and that’s not to mention that Tanguay was probably just as good as Boedker last season anyway.

The only positive here for Colorado is that they didn’t use any picks. But Wood, however, is a former 3rd rounder who has recently been showing some positive signs in his development. While the ramifications of this trade are minimal today, you can bet GM Joe Sakic is nervously eyeing Bleackley’s and Wood’s development.

13 Jared McCann, a 2nd round pick and a 4th round pick for Erik Gudbranson and a 5th round pick

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The Vancouver Canucks paid a king’s ransom to acquire Erik Gudbranson from the Florida Panthers, forfeiting a 2nd, a 4th, and prospect Jared McCann for the rearguard and a 5th. McCann’s rumored poor attitude may have contributed to this trade from Canucks GM Jim Benning’s standpoint; but nonetheless, this is already a loss from Vancouver’s view.

Gudbranson hasn’t developed into the star defenseman he was projected as, and it’s unlikely he takes further steps at the age of 24. One cool distinction that Gudbranson has is that he is the youngest player in the league without a visor, as the rule to grandfather it in came into effect after he made his big league debut. Sure, that doesn’t really help the Canucks on the ice, but it’s something. No?

12 Kris Russell for Jyrki Jokipakka and Brett Pollock

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The Dallas Stars gave up two promising prospects for a rental in Kris Russell at the 2016 NHL trade deadline. You always overpay for rentals, but what’s curious here is that the Stars basically gave up a defenseman (Jyrki Jokipakka) who was already as good as Russell but many years younger with a higher ceiling.

The other prospect Calgary received (Brett Pollock) is a former 2nd round pick who is only 20 and could still develop into a bottom-six NHL forward. When you factor in the fact that the Stars were ousted in the 2nd round and were unable to retain Russell (or simply didn’t want to keep him—tough to say for sure), this trade could come back to bite Dallas in the near future. They still have some unanswered questions on the blueline.

11 Marko Dano and a 1st round pick for Andrew Ladd, Jay Harrison and Matt Fraser

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The Chicago Blackhawks made one of the bigger splashes heading into the 2016 trade deadline by acquiring Andrew Ladd, Jay Harrison and Matt Fraser from Winnipeg for Marko Dano and a 1st round pick. This was a classic rental overpay, but that’s to be expected.

The unfortunate part is Ladd didn’t really contribute much in the way of offense when the playoffs rolled around, pitching in just two points in Chicago’s first-round series against the Blues, which they lost in seven games. I can’t be too sure, but I imagine GM Stan Bowman would take this one back if he could, as the trade didn’t even help the defending champs win a playoff series. Ladd signed with the New York Islanders in the offseason, essentially making this a trade with no value whatsoever for the Hawks.

10 David Perron and Adam Clendening for Carl Hagelin

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Back in January — about a month before the 2016 trade deadline — the Anaheim Ducks decided that Carl Hagelin wasn’t a fit for their system and they sent him to Pittsburgh in exchange for David Perron and Adam Clendening. Hagelin, of course, went on to play a key role in the postseason for the Stanley Cup winning Penguins, whereas Perron continued his tough season in Anaheim and Clendening never played a game for the Ducks.

Hagelin pitched in 16 points in 24 games during Pittsburgh’s Cup run, mostly playing on a line with Phil Kessel and Nick Bonino. At times, this was Pittsburgh’s best line. Perron, meanwhile, posted a meager three points in Anaheim’s seven-game first round exit. Today, Hagelin remains a Penguin and neither Perron nor Clendening are a part of Anaheim’s system.

9 Patrick Maroon for Martin Gernat and a 4th round pick

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Oilers GM Peter Chiarelli will feature on this list in a negative light a little later, but for now, we’ll heap a little praise on him for this deal. At the 2016 trade deadline, the Oilers sent prospect Martin Gernat and a 4th round pick to Anaheim in exchange for Patrick Maroon. Maroon has enjoyed some success during his early days in Edmonton and looks to be a player who can help Edmonton out of the basement. Gernat will likely never develop into an NHL regular, and 4th round picks rarely play in the league.

What’s particularly puzzling is that Anaheim is currently paying for half his salary. I’m not too sure why Anaheim saw the need to chase Maroon out of town at all costs, especially considering how he’d enjoyed success (albeit sporadically) playing on a line with Ryan Getzlaf and Corey Perry.

8 Andrew Shaw for two 2nd round picks

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If you ask me, the Montreal Canadiens paid a pretty high price for the services of Andrew Shaw. Now, if Shaw came coupled with a reasonable contract this wouldn’t be so bad, but instead, he arrived as an RFA without a contract. Montreal was essentially forced to match the demands he was making in Chicago, which were frankly quite high for a player of his caliber.

Shaw’s cap hit is $3.9 million, and in a cap world that’s too much for a forward whose career high in points is 39 (which he scored three seasons ago). There are no guarantees that the two picks Chicago made (winger Alex DeBrincat and defenseman Chad Krys) will ever turn into anything, but Montreal is starting to look like a team that will be saddled with crappy contracts if these trends continue.

7 Rob Scuderi for Trevor Daley

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There was a time when Rob Scuderi was a solid rental pickup; he would provide solid veteran depth to blue lines and could be relied upon when your team’s main objective was to keep the puck out of the net. Well, Chicago didn’t even keep Scuderi long enough for the playoffs, whereas Trevor Daley made contributions in Pittsburgh all season long, including in the postseason before he went down with an ankle injury.

Why Daley never fit into Chicago’s system will remain a mystery to me. He’s a decent puck mover, so there’s no reason to believe he wouldn’t succeed in a role feeding the biscuit to Patrick Kane, Marian Hossa, Jonathan Toews and others, but who knows. For whatever reason the Hawks took a pass, and now Daley is a Stanley Cup champion because of it.

6 Eric Staal for two 2nd round picks and Aleksi Saarela

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Every season at the trade deadline, teams overpay for rentals players who end up disappointing. In 2016, perhaps the best example of this was when the New York Rangers sent Aleksi Saarela and two 2nd round draft choices to Carolina in exchange for six weeks of Eric Staal. Forget the fact that Staal was in the middle of his least productive season, but the Rangers knew they wouldn’t be able to re-sign him.

In 20 regular season games, Staal recorded just three goals and six points with New York, and in the playoffs he was even worse, registering nothing in the Rangers’ early exit at the hands of the Penguins. As expected, Staal moved on from New York in the offseason and signed a contract with Minnesota, and the Rangers have absolutely nothing to show for that deal today.

5 Griffin Reinhart for a 1st round pick and a 2nd round pick

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Oilers GM Peter Chiarelli has proven since arriving in Edmonton—and prior to that, frankly—that he’s not afraid to pull the trigger on a big deal. He’s recently proven that he’s also not afraid to lose a big deal. One of the worst deals he’s made since coming to Edmonton is when he acquired Griffin Reinhart at the 2015 draft from the New York Islanders in exchange for two draft picks (the 16th and 32nd overall picks in a very deep draft class).

The Oilers needed help on defense to be sure, but perhaps actually acquiring a player who was already an NHL defenseman would have been a smarter move. Instead, they got Reinhart, who’d only played eight games in the league when he came to Edmonton, and he still isn’t good enough to crack the Oilers roster.

4 Ryan Johansen for Seth Jones

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The Columbus Blue Jackets really kamikazed the Ryan Johansen situation. It all started with the holdout after his ELC expired and it ended with a trade that the Jackets, quite frankly, got fleeced on. That’s not to say that Seth Jones isn’t a solid hockey player, but Johansen is a legitimate first line center who deserved to get paid more than Nick Foligno; the Jackets management team didn’t really see it that way, however.

Now the Nashville Predators have that number one center they have long coveted (since they came into the league, really), while Columbus’ best pivots are Brandon Dubinsky and Alexander Wennberg. Not to disparage those names, but I’m sure even they would admit that they aren’t Ryan Johansen.

3 The Dion Phaneuf Blockbuster

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Everyone assumed that Toronto was stuck with the Dion Phaneuf contract and that they were either going to have to buy him out or patiently wait until, like, 2035 for the deal to expire. Toronto shocked the hockey world last February by sending Phaneuf, along with Matt Frattin, Casey Bailey, Ryan Rupert, and Cody Donaghey to Ottawa for Jared Cowen, Colin Greening, Milan Michalek, Tobias Lindberg, and a 2nd round pick.

That’s a lot of moving parts, but in the end, you really do wonder what Ottawa was thinking. They gave up a handful of fairly useful assets in exchange for an aging, declining defenseman on a terrible contract. The former Leafs captain is patrolling the second unit in Ottawa, and he’s making more money than Erik Karlsson, which would piss me off if I was Karlsson.

2 Taylor Hall for Adam Larsson

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Although I personally think that the Griffin Reinhart trade was worse than this one in many ways, at least Peter Chiarelli and the Oilers didn’t give up a top-five LW in the Reinhart deal. He did when he sent Taylor Hall to New Jersey in exchange for Adam Larsson. Larsson is a fine hockey player, but he’s not even a top 20 player in his position in the league. Heck, he might not even be top 50.

With the Oilers off to a fairly hot start, I don’t imagine they’re missing Hall all that much—especially considering the fact that they have Connor McDavid fulfilling their offensive needs now. However, I would bet my life that even Chiarelli looks at this deal 10 years from now and wonders just what the heck he was thinking.

1 P.K. Subban for Shea Weber

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The Montreal Canadiens management team has the reputation of being just a bit stubborn, so I’d be willing to bet that Marc Bergevin and co. actually don’t openly regret this trade yet. But, from and unbiased and reasonable standpoint, they certainly should.

They won’t necessarily feel the wrath of this move for a few more seasons but keep in mind that Weber’s contract carries him through 2026 and comes with a cap hit of over $7.8 million. He’ll be 42 when the Canadiens are finally no longer responsible for paying his exorbitant salary. P.K. Subban, meanwhile, is in the prime of his career and is on a contract that is slightly more expensive, sure, but at least it expires when Subban is 32 and not 42.

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