6 NHL Teams Already Regretting Their 2021 Offseason Pickups

Franklin Steele@SteeleOnIceFeatured Columnist IIIDecember 3, 2021

6 NHL Teams Already Regretting Their 2021 Offseason Pickups

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    Stanley Cup winners aren't built during free agency. Contending teams can go fishing in the NHL's offseason waters in hopes of rounding out their squad. But, by and large, successful organizations build from within and use trades or free agency to fill perceived gaps and shore things up around the margins.

    Yet we still see general managers go bonkers every time free agency opens to bid against each other. This past summer, against the backdrop of a pandemic that supposedly ravaged the league's financial landscape, teams spent over half a billion dollars during the first day of free agency alone.

    Some of those trades and signings have a better chance of working out than others. We liked the New Jersey Devils getting Dougie Hamilton at a surprisingly decent cap number ($9 million AAV), for example. 

    Ditto for the Detroit Red Wings' gamble on goaltender Alex Nedeljkovic. The Calder Trophy finalist from a year ago is carrying a 7-3-3 record through early December and has stolen a few games for Detroit. Like this ridiculous outing recently against the Boston Bruins, where he stopped 41 shots and propelled the Red Wings to victory despite the offense managing just 16 shots.

    Everything doesn't come up roses all the time, though, and there are a handful of teams around the league that should already be sweating the moves they made this past offseason.

New York Islanders

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    It was easy to get caught up in the narrative of what the New York Islanders did this past summer. Adding Zach Parise and Zdeno Chara was fun in all the right ways.

    Parise's father was an important player for the Isles in the late 70s, yet New York passed on the opportunity to draft his son with the 15th overall pick in 2003. So when it became clear that the veteran would be joining the Islanders to chase a Stanley Cup, takes such as this one—that the Islanders were fixing an 18-year-old mistake—pretty much wrote themselves.

    Chara returning to Long Island had a similarly wistful feeling about it. He was famously part of the doomed trade that brought Alexei Yashin to the Islanders. It's frequently cited as one of the worst trades in the history of the NHL, with New York giving up the future Norris Trophy winner along with Bill Muckalt and a first-round pick that turned into Jason Spezza for Yashin.


    They appeared to be the perfect complementary pieces for an Islanders team that has Stanley Cup aspirations. New York's season has been derailed by injuries, however, and head coach Barry Trotz has decided to use Chara way more than was anticipated when he was signed.

    The presence of the 6'9" defenseman caused Trotz to inexplicably break up the pairing of Adam Pelech and Ryan Pulock—a duo that had become one of the best in the NHL, according to both the eye test and from a stats perspective

    Parise has also had to take on way more of a minutes load than was intended due to the mounting injuries. Neither longtime player has managed to handle his larger-than-expected workload well either. 

Vancouver Canucks

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    It could be argued that no team in the NHL was busier than the Vancouver Canucks this past offseason. The number of moves they made was simply staggering, as they tried to retool their big league roster while giving the relocated Abbotsford Canucks one of the stronger groups in the minors.

    Things haven't worked out for either team in either league, though. Both versions of the Canucks are dwelling at the bottom of their respective divisions, and this could be a franchise that's staring down another reset.

    Analysts at multiple outlets, such as The Athletic and TheHockeyWriters.com, are calling for Jim Benning's firing, and it's easy to see why with how his team has performed in 2021-22.

    Benning and his team should be praised for turning bad contracts into usable assets. Getting out from under Nate Schmidt's contract, for example, shout be applauded. The buyouts of Braden Holtby and Jake Virtanen were necessary as well.

    But taking on Oliver Ekman-Larsson's behemoth contract, even though it meant also adding Conor Garland and getting rid of three bad deals for bottom-of-the-roster players, wasn't a good bit of business. It's a deal that's very focused on the short term, especially when you consider that all three crummy contracts Vancouver moved will expire after this season.

    Meanwhile, Ekman-Larsson is on pace for seven goals and 14 points this season. And while it's true he's been solid in a shutdown role for the Cancucks, you're hoping for more out of the defenseman considering he's signed through the 2026-27 season. 

    This is what it looks like when NHL teams try to take shortcuts and end up in the wrong part of town because their GPS dropped at just the wrong time.

Boston Bruins

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    Unlike the Canucks, whose entire offseason plan could realistically be called into question, the Boston Bruins had a solid summer overall. Re-signing Taylor Hall after he clicked so well seemed like a no-brainer, and all of their recent internal transitions, such as moving to Charlie McAvoy as the No. 1 blueliner instead of Chara, have been flawless.

    That is, of course, until this season. Boston appears to be missing Tuukka Rask more than most pundits would have guessed. This past summer, it wasn't clear if the veteran netminder would be returning for one more shot at the Stanley Cup with Boston.

    So the Bruins inked Linus Ullmark to a surprising four-year contract worth $20 million. The logic seemed sound at the time. If Ullmark was able to look solid with the lowly Buffalo Sabres, then surely joining a team like the B's would be a boost for him.

    The Sabres played incredibly conservatively last year though, which might have inflated Ullmark's value. He's been unable to fend off rookie Jeremy Swayman for playing time, with neither goalie really taking the crease and running with it.

    Boston now faces the reality that Rask could be looking to return in January, making the Ullmark bet look even less likely to pay off. He's just nine games into his career as a Bruin, so it's too early to write off the 28-year-old goalie entirely. Still, it's fair to wonder if the Bruins are already kicking themselves for this commitment. 

Vegas Golden Knights

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    This past offseason was always going to be difficult for the Vegas Golden Knights. They've evolved from an island of misfit toys post-expansion draft to one of the most aggressive, trigger-happy and freewheeling teams in the NHL.

    However, acquiring seemingly every shiny new toy that hits the trade block comes with a cost. We understand why the Golen Knights needed to trade Marc-Andre Fleury. Moving him was gutwrenching for the fanbase, to say the least, but it was a business decision.

    Sometimes, those kinds of calls are difficult to make. But to see the team turn around and burn the cap space that trading Fleury cleared up on Evgenii Dadonov was mind-boggling. When healthy, Vegas' top-six wingers are more or less locked in, meaning that the forward was always going to be plugged in on the third line.

    That's an odd place for a declining finisher in Dadonov, who has seen his point totals drop in three consecutive seasons. And a change of scenery hasn't helped. He's got five goals and nine points through 22 games.

    The Golden Knights' cap situation is now a mess following the acquisition of Jack Eichel. If the entire lineup was healthy, they'd be more than $7 million over the salary cap, according to Jason Chen of The Hockey News.

    It's a scenario that could have been avoided by hanging onto cleared cap space when it was there. Vegas is a team that's all-in on winning a Stanley Cup, and it seems that goal has made them a bit impatient. We aren't saying Fleury should still be a Golden Knight, but Vegas clearly could be managing its cap situation a bit more effectively. 

Seattle Kraken

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    We all understand what Philipp Grubauer was supposed to be for the Seattle Kraken. The netminder was supposed to be their version of Marc-Andre Fleury—a franchise-settling goalie that could safely be counted on and built around.

    After going 30-9-1 with the Colorado Avalanche last year and finishing third in the Vezina Trophy race, he seemed like just as good a bet as any for general manager Ron Francis. But the organization's approach to cap management has been somewhat baffling to this point, and it's illustrated by adding Grubauer.

    Seattle's approach leading up to and during their expansion draft seemed clear: put together a competent team while hanging onto valuable cap space. The Kraken passed on some talented yet expensive pieces while building their inaugural roster, after all: Carey Price, Vladimir Tarasenko and Eichel, to name a few.

    Then free agency opened, and the Kraken decided to make a splash, signing Grubauer after the NHL rejected their initial contract for violating rules regarding front-loaded deals. They eventually settled on a six-year pact worth $35.4 million, and the netminder hasn't been able to play up to those standards.

    He hasn't really even been all that close, and it's fair to wonder just how much Grubauer was propped up by a stellar Colorado team.

    The netminder has long-time viewers of his wondering if he's ok while he continues to be one of the NHL's least effective goalies. His minus-10.6 GSAA across 18 appearances is the worst number in the league, with the second-worst coming from Alexandar Georgiev's minus-7.7 mark with the New York Rangers.

    If there were a shadowy inverse version of the Vezina Trophy, Grubauer would be running away with it.

Chicago Blackhawks

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    Chicago Blackhawks fans should be familiar with this song and dance by now. The on-ice moves the organization made over the summer raised serious eyebrows, but at least games hadn't been played yet, so the Hawks could maintain a "just you wait" mentality.

    Their 2021-22 campaign has been a disaster for so, so many reasons. We're just going to be examining their roster moves in this space. For more on the off-ice situations, our own Abbey Mastracco tackled them in late October with vigor.

    Chicago trading for Fleury was a solid roll of the dice for the organization. He cost them nothing but minor league forward Mikael Hakkarainen, after all, and the Blackhawks weren't exactly awash with NHL-caliber starters.

    We've knocked teams in this post for making bad bets, so we'll at least give Chicago credit for taking a shot with the defending Vezina Trophy winner. He hasn't panned out in the Windy City, though, and now there's speculation that he could be traded again in the coming weeks.

    There was a good chance Flower would be able to play up to the standards that trading away nothing for him created. That isn't the case for Seth Jones, who has virtually no chance of living up to an eight-year, $78 million contract extension that doesn't kick in until next year.

    Mike Kelly of Sportsnet did a fantastic job explaining why this is the case in detail in July. Distilling his analysis down to a tl;dr version is easy: Jones hasn't been worth this kind of contract for three years now, and given his age, he is unlikely to elevate to the kind of play this contract needs to make sense.

    It's a deal that will saddle the Blackhawks for nearly a decade, and we'll all wonder what Chicago was thinking when they made this deal in the summer of 2021.


    Stats appear courtesy of Stathead, NHL.com and Natural Stat Trick and are accurate through games played on Dec. 1.