Every NHL Team's Most Regretful Move Of The Past Year

They say it’s better to live life without regrets, but I’ve never fully agreed with that sentiment. If you don’t have regrets, how are you supposed to learn from your mistakes?

I think identifying something as a regret can help you avoid future mistakes of a similar nature. With that in mind, it might not be a terrible idea for the general managers of NHL teams to take a look at today’s list, as it points out the most regretful roster move of each team from the past year.

It should be noted that a few of these list items are very minor regrets. That’s because some teams simply haven’t screwed up too badly over the past year, so it was tough to find a move to qualify for the list. Losing a player to the expansion draft, for instance, is unavoidable in most cases, yet it can still be a regretful event.

Many entries on the list were fully earned by GMs, though. A few GMs had so many regretful decisions just from the past 12 months that I had trouble picking. One thing I learned from this little exercise is that the Oilers, Senators, and Canadiens should probably get new general managers.


30 Anaheim Ducks: Losing Shea Theodore

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The Anaheim Ducks are a team that hasn’t really made any noticeably poor decisions from a roster construction standpoint over the past year, but they did unfortunately lose a pretty darn good defensive prospect to expansion. It was clear the Ducks were set to lose a valuable piece, as they were (and still are) incredibly deep on the blue line.

Officially, the Ducks actually lost Clayton Stoner to expansion, but that was thanks to an earlier trade that sent Shea Theodore to Vegas in exchange for the promise to not touch Josh Manson when it came time to pick a player off the Ducks. While this move is not the fault of GM Bob Murray, it’s fair to say that the Ducks are regretful they lost a prospect like Theodore for nothing.

29 Arizona Coyotes: Acquiring Niklas Hjalmarsson For Two Prospects

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Arizona Coyotes GM John Chayka was a mover and a shaker this offseason, making substantial changes to his goaltending, defense, and forwards. One of those deals saw the ‘Yotes send two pretty good prospects to Chicago (Laurent Dauphin and Connor Murphy) in exchange for veteran defenseman Niklas Hjalmarsson.

Any team would of course welcome a three-time Stanley Cup champion to the fold with open arms, but so far the returns on Hjalmarsson have left much to be desired. Perhaps he doesn’t have the top-end shelter in Arizona that he had in Chicago, but whatever the case is he’s not getting it done for the Coyotes. He’s playing only the fourth most among D-men in the desert this season, and has missed time to injury.

28 Boston Bruins: Firing Claude Julien

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The Bruins were another team in which I was hard-pressed to find a clear-cut mistake over the past year. The closest I could find technically isn’t really even a roster move, but it directly affects the roster so I’m sticking with it. Claude Julien is a great coach, and the Bruins fired him after 10 years at the helm. Now, this entry isn't based on the firing, but more the opportunity to give a division rival a chance to hire him.

That’s exactly what happened. As soon as Julien shook loose, the Canadiens saw an opportunity and jumped, turfing Michel Therrien to open the head coach spot for Julien. Not that the Canadiens have a roster that even the best coach could make into a winner, but it’s still a kick in the teeth that they have to face their former coach at least four times a season for the foreseeable future.

27 Buffalo Sabres: The Jack Eichel Extension

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The Sabres brass has made a handful of questionable decisions over the past five years or so, but they’ve actually cleaned it up when talking about over just the past year. The club signed face-of-the-franchise Jack Eichel to an eight-year contract extension at the start of the season. The deal comes with a $10M cap hit and lasts eight seasons, starting in 2018-19.

Honestly, this deal probably isn’t so bad, but I had to choose something so this is where I landed. This season Eichel has gotten off to a less-than-ideal start for the Sabres, and the team as a whole has been a general disappointment (thanks for the phrase, Pete Chiarelli). If Eichel gives this level of performance in Buffalo over the next decade, the Sabres are getting ripped off.

26 Calgary Flames: The Travis Hamonic Trade

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Brad Treliving has made a lot of fine decisions as head of the Calgary Flames, and I’d be the first to admit that I was at first supportive of this trade. Sure, a 1st and 2nd-round pick is a steep price to pay, but you’re getting a top-pairing defenseman back, right? Well, unfortunately for the Flames, it looks as though Travis Hamonic’s 2016-17 off-year is repeating itself.

Perhaps most frustrating for Calgary is that the two picks they sent to New York are actually for the 2018 draft. Unless Hamonic turns around his thus far dreadful season, Treliving and co. will be forced to watch the Islanders select some high picks off the board that originally belonged to the Flames. This illustrates that Calgary thinks they're in a win-now mode… but are they, really?

25 Carolina Hurricanes: Not Enough Term For Teravainen

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Albeit overall a somewhat inactive club, the ‘Canes haven’t made too many obviously poor decisions in the past year. In fact, I couldn’t even find one. That’s why I’m criticizing the specifics of an otherwise great deal made by the Hurricanes, which is when they signed young forward Teuvo Teravainen to a two-year contract extension.

It’s not the dollar value I have a problem with—quite the opposite, actually. The $2.9M cap hit is rather friendly for the ‘Canes, actually. No, it’s the two-year term that I’m critical of. Teravainen was just waiting to break out, and early returns on 2017-18 show this is probably the year it happens. How much is he going to cost the club at the end of 2018-19? More term and more money would have been the bright move.

25. Chicago Blackhawks: Trading Artemi Panarin Too Soon

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I fully understand that the Chicago Blackhawks pretty much need to purge talent every season in order to remain cap compliant, but I still don’t understand why they traded Artemi Panarin to the Blue Jackets for Brandon Saad this past offseason. The full deal was Panarin, Tyler Motte, and a 6th-rounder for Saad, Anton Forsberg, and a 5th-rounder, but the accoutrements don’t move the dial for me in this deal.

If this trade was made in the summer of 2019, I would have totally gotten it. Panarin is locked in for two more years (including this one) at a $6M cap hit, which is identical to Saad’s deal (except he’s locked in for two more years beyond Panarin). If you think Panarin is going to get a fat raise, fine—but why rush to a trade? I feel like there’s more to this deal we don’t know, but nonetheless it’s GM Stan Bowman’s worst move of the past year.

24 Colorado Avalanche: Keeping Duchene Around To Start The Year

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The fact that Matt Duchene wanted out of Colorado—his favorite team growing up—was the worst-kept secret around the NHL for the past 10 months or so. GM Joe Sakic was reportedly trying to find a dance partner at the trade deadline, but no dice. He was also unable to find a suitable deal during the summer, so in the end they started the 2017-18 campaign with Duchene on the roster.

He’s since been dealt, and there’s no question that the Avalanche did well on this deal. Here’s the issue, though: the Avalanche got little immediate help in the deal, and the club was off to a surprisingly decent start. Now the team that burst out of the gate with Duchene in the top six has to find a way to stay afloat without the star winger. This could have been avoided with a summer blockbuster, and I have trouble believing his trade value changed much from August to November.

23 Columbus Blue Jackets: Losing William Karlsson To Expansion

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The Jackets have been savvy on the management front for a few seasons now, and their biggest mistakes were made years ago (yet they’re still waiting on a few of those contracts to expire). That said, they can’t be thrilled about losing 24-year-old center William Karlsson to expansion. Karlsson was no offensive dynamo during his time in Ohio, but he had definitely shown promise.

We’re now one-quarter of the way through 2017-18, and it’s safe to say that Karlsson is having that breakout year on a Vegas team that has surprised many pundits. He's on pace for about 65 points this season. Obviously a slight regression can be expected, but Karlsson looks legit and the Jackets have nothing to show for the asset.

22 Dallas Stars: Too Much Money For Martin Hanzal

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In a salary cap world, it’s extremely important that you don’t hand out contracts irresponsibly. Martin Hanzal is a consummate professional who’s played nearly 650 games, putting up 329 points along the way. On a good NHL team, he is a solid third line center who can probably play on your second power play unit.

The Dallas Stars are a team that has some pretty good players in the middle of the prime of their careers, so they need to be going for it. The three-year deal they signed Hanzal to in the summer was a little bit rich for my blood, as it has a $4.75M AAV. This won’t be a major issue until year three, when Tyler Seguin will need a new contract and likely a huge raise on his $5.75M cap hit—at which point it becomes a somewhat major issue.

21 Detroit Red Wings: Tatar Contract Too Generous

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The Detroit Red Wings weren’t a playoff team last year, yet they still find themselves right up against the cap ceiling. That’s unfortunate, but when you look at some of the recent signings GM Ken Holland has made, you start to find out why. Take, for instance, the four-year contract extension he inked Tomas Tatar to back in July. Why make him your second-highest paid forward by giving him a $5.3M AAV?

While Tatar has shown flashes of elite potential, he still hasn’t been able to fully breakout since recording 56 points in 2014-15. So far the results in 2017-18 for Tatar have revealed much of the same as the past two seasons, where he’s posted point totals of 45 and 46 points. Actually, he’s pacing for less than that this season, making the extension a little concerning.

20 Edmonton Oilers: The Jordan Eberle Trade

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Poor Oilers fans. I had trouble finding poor managerial decisions for almost a third of the league’s teams, but when it came time to pick Edmonton’s I had trouble deciding which disastrous decision to go with. I could have definitely gone with the Kris Russell extension ($4M x four years?!?!), and I could have even pointed to the Benoit Pouliot buyout as a pretty major error – they did not need the cap space this season, and now he’s on the books for four seasons instead of just two had he been bought out next summer instead.

Alas, I ended up going with the Jordan Eberle trade, as it is one of the most pointless things I’ve seen in a long while. Some say it was a salary dump, but let me reiterate: the Oilers have plenty of cap space remaining this season. The Oilers got Ryan Strome back, and they are reportedly underwhelmed by him thus far. How about you don’t trade for a forward who’s put up back-to-back seasons of 28 and 30 points and then expect him to be something else?

19 Florida Panthers: Reilly Smith Trade

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The Florida Panthers seemed to be on the right track there a few seasons ago, but now it appears they’re back to their same old tricks. One questionable move they made came back at the expansion draft when they dealt forward Reilly Smith to the Golden Knights for a measly 4th-round draft pick. Oh, and they also lost Jonathan Marchessault.

Look, I get it, Florida. You were a little choked that Reilly only put up 37 points in 2016-17 after a 50 point campaign the year before. Also, he had a new $5M AAV contract about to kick in. Well, Smith has been a pretty important part of that surprising Golden Knights squadron, averaging close to a point per game. The Panthers sit in the bottom tier of their division and could definitely use some scoring depth—which is exactly what Smith provides.

18 Los Angeles Kings: Cammalleri Signing

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This is the first entry on the list in which the offending team has already righted the wrong (sort of). The Kings signed Michael Cammalleri to a one-year, $1M contract in the offseason, and while the gamble didn’t pay off, it seemed like a decent risk. Cammalleri had just been bought out by the Devils, making the 35-year-old a UFA.

It turns out Cammalleri is too slow for today’s NHL at his advanced age, so the Kings found a dance partner in the Oilers and swapped underperforming veterans. The Kings now have Jussi Jokinen instead of Cammalleri, and let’s face it, that’s a lateral move. Nonetheless, the fact that a one-year deal to a veteran is the worst move the Kings have made over the past year, they should consider themselves lucky.

17 Minnesota Wild: Trading For Martin Hanzal

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I really don’t mean to be piling on Martin Hanzal in this article, but perhaps I’m just curious as to what information these general managers are using to valuate him. With the information available, I see Hanzal as a third line center on a good team and a second line center on a bad team. At last season’s trade deadline, just nine months ago, the Minnesota Wild sent a 1st and 2nd round pick, along with Grayson Downing, to Arizona for Hanzal, Ryan White, and a 4th.

The Wild were and are a good team, so Hanzal was never slotted to play above the third line in Minny. Hanzal actually performed decently down the stretch in the State of Hockey, notching 13 points in his 20 games. That said, the Wild lost to the Blues in the first round and today have nothing to show for the deadline deal.

16 Montreal Canadiens: Trading Sergachev/Overall Depletion Of D

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Rather than picking one move over the past year, I sort of had to go with the gradual dismantling of the defense in Montreal. The biggest move was of course the trade that sent Mikhail Sergachev and a conditional 2nd-round pick to Tampa for Jonathan Drouin and a conditional 6th. It looks as though the conditions won’t be met for the picks to be exchanged (if Sergachev plays 40 games, no picks are swapped).

While this trade in and of itself is just fine, the fact that GM Marc Bergevin has been so willing to deal away his defensemen for pennies on the dollar of late has put the Habs in a tough spot. They also traded Nathan Beaulieu to the Sabres for a 3rd-round pick so that they wouldn’t lose him for nothing in expansion, but the end result is an atrocious Montreal blue line.

15 Nashville Predators: Bonino Signing

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How do I say anything bad about Nashville? GM David Poile was crowned GM of the Year last season for his daft work that got the Nashville Predators to the Stanley Cup Final. He’s the league’s longest-serving general manager, and there’s good reason for that. Over the past year, there hasn’t really been a single bad move to be found on Poile’s resume.

That said, this list promised the worst move for each team over the past year, so I guess I’ll go with the Nick Bonino signing. Bonino is a solid third line player in this league, and that’s where he’s playing in Nashville. I guess what I’m trying to say is a $4.1M cap hit for Bonino is a bit high? No, what I’m actually trying to say is Poile has been flawless over the past year. Leave him alone.

14 New Jersey Devils: Stafford Signing

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New Jersey is not a team that throws money around at players, so it was pretty difficult to find a signing that is egregiously bad over the past year. Ditto for trades, as the moves they’ve made in that regard have been either wins or lateral moves. That said, they took a chance on reclamation project Drew Stafford and signed him to a one-year deal worth a measly $800,000.

Look, I’m not saying it was a terrible move, nor was it a move that had any major consequences. But Drew Stafford is too slow for today’s NHL, and it shows whenever you tune in to watch him play. That said, he's still producing goals this season, but I stand by my evaluation of the player: too slow, and he’s bound for either Europe or retirement after this year.

13 New York Islanders: Clutterbuck Extension

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In a salary cap world, it’s very important that you don’t pay depth players too much. It’s the best players who drive your team, and you need to pay them what they deserve and then build around them. Islanders GM Garth Snow has been decent at managing his cap space over the past five years or so, but the long-term extension of Cal Clutterbuck he signed in December 2016 raises some eyebrows.

Clutterbuck is a great fourth-liner or an okay third-liner, and nothing more really. The way I see it, if you spend north of $2M on those players, you can find yourself in some trouble. Clutterbuck’s contract not only comes with a $3.5M cap hit, but it lasts for the next five (!!!) years. That could come back to bite the Isles when it comes time to extend John Tavares, among others.

12 New York Rangers: Trading Antti Raanta And Derek Stepan

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The New York Rangers are in the powerhouse Metropolitan Division, so they were always going to have an uphill climb to the playoffs. They’re already a little behind the eight ball, as they’ve played roughly .500 hockey for the first few months of the season—not good enough. They brought in a few valuable pieces, but they did trade Derek Stepan and Antti Raanta away with no immediate help coming back, and that’s hurting them.

Stepan had sort of been filling the No. 1 center role in New York before his departure, and his absence has left a noticeable void down the middle in the Big Apple. Raanta, of course, was just playing backup to Henrik Lundqvist, but he was reliable and Hank is getting old. Can he keep playing as much as he has so far in 2017-18? They better hope so, because Ondrej Pavelec is no Raanta.

11 Ottawa Senators: Trading Away Jonathan Dahlen

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Despite being nominated for GM of the year last season, and despite his club’s Cinderella run to Game 7 OT of the Eastern Conference Final, I truly believe Pierre Dorion is out to lunch. Ottawa is not a great team, and it’s sort of hard for me to believe they’re a playoff team, let alone a franchise that’s ready to contend for a Stanley Cup.

Dorion disagrees though, and that’s evident through the deals he’s made over the past year. The recent Matt Duchene acquisition was a steep price to pay for what I view as a slight upgrade over Kyle Turris, but for his worst move of the past calendar year I’m going with the Alex Burrows/Jonathan Dahlen trade. Dorion is mortgaging the Sens future for today, but the problem is that they’re not real today.

10 Philadelphia Flyers: Trading Away Brayden Schenn (As Soon As He Got Good)

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This trade sort of flew under the radar for me, but today it looks egregious on the Flyers part. Brayden Schenn had been a part of the Flyers system ever since arriving from Los Angeles in the Mike Richards trade. It took some time, but he developed into a legit number one center, and he had back to back seasons in Philly where he recorded 59 and 55 points.

That’s lower-tier first line center numbers, but they decided to part ways with Schenn and get Jori Lehtera and a 1st-round pick for him. Lehtera has found himself in the press box with a clean bill of health a few times already, while Schenn is terrorizing the league on the NHL’s best line (no disrespect to Tampa’s top unit) with Jaden Schwartz and Vladimir Tarasenko.

9 Pittsburgh Penguins: Acquiring Ryan Reaves

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Excuse me for a moment, but on what planet is Ryan Reaves worth a 1st round draft pick? Reaves’ player type is heading towards extinction fast, as the need for clubs to employ “protectors” dwindles by the day. Back in June, the Pens sent Oscar Sundqvist and a 1st rounder to acquire Reaves. They also received a 2nd round pick in return, but that’s still not good enough for me.

The game has gotten fast and it’s getting faster, and rosters without speed throughout the lineup are getting exposed in 2017-18. The Penguins are still winning—despite brutal 5-vs-5 goal shares and an abysmal goal differential—but if they want to continue their reign at the top, they should avoid acquiring players like Reaves from here on out.

8 San Jose Sharks: Trading Goldobin

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Much like the Senators did with the Dahlen/Burrows trade, the Sharks were going for it at the trade deadline last year when they sent Nikolay Goldobin and a 4th-rounder to Vancouver for the services of veteran Jannik Hansen. While I get the thought process behind this move, the Sharks were bounced by the Oilers in round one, making the pickup more or less useless.

Hansen at least had an extra year left on his contract, so at least they have the services of the veteran winger for this season as well. That said, I’d bet there’s a pretty good chance that GM Doug Wilson would take this one back if he could. If scouts are to be believed, Goldobin is going to be a heck of a player one day.

7 St. Louis Blues: Patrik Berglund Extension

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Here’s another club that simply has not made an error over the past year. For the Blues I combed over every single move made by Doug Armstrong, and the worst thing I found was, I guess, the Patrik Berglund contract extension. Berglund’s deal is five years long and comes with a cap hit of $3.85M per season.

Honestly, it’s not really a terrible contract so I don’t want to pile onto the guy too much. That said, Berglund’s career has been riddled with injuries, and he's been riddled with them early in the 2017-18 season because of that. When he does dress he’s a reliable third liner, but even so I’d argue that a cap hit of just under $4M is a steep price for that player type.

6 Tampa Bay Lightning: Tyler Johnson Contract Extension

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The Tampa Bay Lightning are terrorizing the NHL this season after missing the postseason in 2016-17. All eyes are on Steven Stamkos and Nikita Kucherov, who sit at the top of the league scoring through the first quarter of the season, and the club has them locked up at a combined cap hit of about $13M per season—not bad.

However, there are a few other contracts that may give them issues in a few years when it comes time to re-sign Kucherov, and one of those was signed this past summer. GM Steve Yzerman inked Tyler Johnson to a seven-year extension worth $5M per season, and I’d argue that’s a lot of money AND term for the center. He has been skating on the fourth line recently, after all.

5 Toronto Maple Leafs: Marleau Signing

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The Toronto Maple Leafs front office has been mighty good since the most recent shakeup, so it was really hard to find a mistake made by them over the past year. I might take some flak for my Toronto entry here, but I had to go with the three-year, $18.75M contract they signed with Patrick Marleau.

Look, I actually think this contract would be solid if it was for just two years, but I anticipate some serious cap issues in Toronto when it comes time to re-sign Mitch Marner and Auston Matthews. They’re already a cap team, and Matthews will likely earn north of $10M per season on his next deal, and Marner will probably make just shy of $10M. Do you think the Leafs will want to have to pay a 40-year-old Marleau $6.25M at this juncture?

4 Vancouver Canucks: Tryamkin Ditches Town

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For a few years there it looked like Jim Benning was one of the league’s worst GMs. Make no mistake, he hasn’t righted all of his wrongs, but he has cleaned up his act a bit. Over the past year I found some savvy moves, and nothing egregiously awful. So, rather than crapping on Benning, I’m saying the most regretful roster change occurred when defenseman Nikita Tryamkin decided to leave the NHL for Europe.

Tryamkin never really adapted to the Vancouver lifestyle, and after his departure he spoke candidly to a Russian media outlet, complaining about the nasty drug culture in the city along with a dirty street that he doesn’t name, but one we can assume is the infamous East Hastings St. In any case, the Canucks lost a promising D prospect (for now, at least).

3 Vegas Golden Knights: Too Many D-Men

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How am I supposed to criticize moves made by the Vegas Golden Knights to this point? An expansion team that sits in first place in their division at the quarter-mark? Their underlying possession numbers are solid too, so it looks as though they may even be the real deal. Unfortunately I have to find something bad to say though, so I’ll go with their strategy of stocking up on D at the expansion draft last June.

I actually saw this as a sound strategy at the time, but it sort of backfired on GM George McPhee and the Golden Knights. The market wasn’t as hot for D as they anticipated, and now they’re stuck with an influx of defensemen and not enough roster spots to play them all. Not a terrible problem to have, but Vegas simply doesn’t have any terrible problems today.

2 Washington Capitals: Acquiring Kevin Shattenkirk

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When it became clear that the St. Louis Blues were going to be unable to extend offensive defenseman Kevin Shattenkirk, the auction was on. Conventional wisdom stated that the Washington Capitals were one Kevin Shattenkirk away from having all the requisite pieces of a championship team, so they sold the farm for the rental at the deadline, giving up a first-round pick (among other assets) for Shatty.

Well, Shattenkirk and the Capitals met an all-too-familiar fate in the 2017 postseason, falling yet again in the second round to yet again their rival Pittsburgh Penguins. Shattenkirk proceeded to hit the open market and he ended up signing with the Rangers, leaving the Caps with nothing to show from the deal. Has the Capitals' window closed? If not, it is at least starting to close.

1 Winnipeg Jets: Bryan Little Extension

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The Winnipeg Jets finally look to be putting things together. It’s felt like they’ve had one of the best top-six forward groups for years now, but they’ve never had reliable goaltending and its cost them some seasons. They have great young pieces coupled with great veterans on some pretty decent contracts. That said, they signed Bryan Little to a six-year extension back in July that doesn’t even kick until next season when he’ll be 31.

Little is a solid player, but this was a lot of term for a player on the wrong side of 30, and it doesn’t really look like they saved money by giving more term. Little’s new deal will carry a cap hit of nearly $5.3M, which is about market value for a player of his caliber. The question is: will Little still be of this caliber in three years? Four?

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