Analyzing Every NHL Team's Worst Contract

Franklin Steele@SteeleOnIceFeatured Columnist IIIOctober 24, 2021

Analyzing Every NHL Team's Worst Contract

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    When casually taking a stroll down CapFriendly, an NHL analyst's version of taking a random walk down Wall Street, it's generally pretty easy to pick out each team's worst contract. Typically, that deal will belong to an aging member of the organization's core who once stood as a pillar of its success.

    Some contracts age more gracefully than others, of course. How often do we see these human beings compared to wine?

    Consider the Chicago Blackhawks' deals for Patrick Kane and Jonathan Toews. On July 9, 2014, when these matching megadeals worth $84 million over eight years were announced, it seemed like both forwards were on similar trajectories.

    Kane and Toews were key pieces for a Blackhawks team that spent a solid decade flirting with becoming a dynasty. One could argue that Chicago actually was one, and we wouldn't quibble.

    As important as both forwards have been in the Windy City, their contracts haven't quite aged the same.

    Toews is only three seasons removed from scoring 81 points in 82 games, but after sitting out the entirety of 2020-21 because of "chronic immune response syndrome," it's fair to wonder what the 33-year-old has left in the tank. His health is obviously the primary concern here, but out on the ice, Toews might not be able to live up to his $10.5 million cap hit over the next two seasons.

    Meanwhile, Kane has been a point-per-game player over the past three seasons, finishing 2020-21 tied for fifth in scoring. Kane turns 33 in November, illustrating just how differently two identical contracts can play out over time.

    All of this is to say that NHL teams and players don't agree to contract terms in a vacuum. There are multiple angles to consider, especially when we have hindsight at our disposal.

Anaheim Ducks: Cam Fowler

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    Year Signed: 2017

    Seasons Remaining: Five

    Cap Hit: $6.5 million

    A recent trend has seen NHL teams jump at the opportunity to lock up their young, up-and-coming defensemen. Over at The Athletic, Pierre LeBrun recently broke down the unique financial landscape that is encouraging players and organizations alike to commit to long-term deals.

    Younger defenders have seemingly been signing eight-year extensions every third day over the past few months.

    When the Anaheim Ducks and Cam Fowler agreed to terms on this eight-year pact, it made sense on many levels. He was coming off of his age-25 season, had already appeared in nearly 500 games and broken the 30-point barrier in three of the previous four campaigns. The Windsor, Ontario, native had draft pedigree, going 12th overall in 2010, and the $6.5 million cap hit seemed like a safe bet for the Ducks.

    While Fowler hasn't exactly fallen off of a cliff in terms of his play, his production has dwindled in each season since the deal began in 2018. He was particularly bad in 2020-21, with an expected-goals-for percentage of 36.5.

    Sure, the Ducks aren't a great hockey team right now, but Fowler hasn't been part of the solution for Anaheim. His cap hit isn't unmanageable, but he's entering his age-30 season, and the defenseman isn't likely to be worth $6.5 million for the next half-decade.

Arizona Coyotes: Clayton Keller

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    Ross D. Franklin/Associated Press

    Year Signed: 2019

    Seasons Remaining: Seven

    Cap Hit: $7.15 million

    It's here with the Arizona Coyotes that we first need to make this distinction: "worst" doesn't necessarily mean bad or hopeless for all of these teams. It just means that, as the rosters are constructed, these individuals are the ones who haven't been able to or are the most likely to underperform relative to their cap hits.

    Enter Clayton Keller, who has just started his age-23 season. While he isn't a $7.15 million player yet, the Coyotes took a calculated risk on the former seventh overall selection by skipping a bridge deal entirely. After all, these are the kinds of players rebuilding teams need to lock down at reasonable cap hits.

    That's what Arizona did with Keller.

    The forward had an outstanding rookie campaign, posting 65 points in 82 games in his age-19 season, finishing third in Calder Trophy voting. From a points-per-60 perspective, Keller has taken a step back since then.

    In his first year, he produced 3.2 points per 60. Over his past two seasons, Keller has been putting up points at a lower 2.3-per-60 clip. Those are solid numbers, but his production has fallen short of the expectations that come along with a cap hit north of $7 million.

    He's one of just a handful of legit NHL talents on the league's most stripped-down roster, however. If Arizona can rebuild over the next few years, Keller will have more talent around him and should be able to grow into his contract.

Boston Bruins: Charlie Coyle

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    Year Signed: 2019

    Seasons Remaining: Five

    Cap Hit: $5.25 million

    The Boston Bruins ice one of the most well-constructed rosters in the NHL. Their core is starting to age a bit, so they aren't in the shape they were two or three years ago. But Brad Marchand and David Pastrnak are on two of the best deals in the sport, while almost everyone else on the roster is at least supplying average value retaliative to their cap hits. No cap sheet is blemish free, though, and in Boston, said pockmark is Charlie Coyle.

    On paper, Coyle looks like the kind of player who has traditionally been associated with the Bruins. He's big, plays hard and isn't easy to knock around in the offensive zone.

    That's why it made a lot of sense when the Bruins traded for the former San Jose Sharks first-round pick in February 2019. The contract he signed ahead of 2020-21 made a bit less sense.

    Players are worth more to teams than simply how many points they can put on the board, especially in Boston, where the team's vaunted first line is arguably the best in the NHL. Coyle is making a lot of money to post just 0.31 points per game, though. The Bruins' expected goals for/against also took a hit when the forward was on the ice in 2020-21.

    It's tough to use that truncated season—the majority of which was played without fans in arenas—as a barometer, but as he enters his age-29 season with half a decade left on his deal, it's fair to wonder whether Coyle will ever be worth north of $5 million to the B's.

Buffalo Sabres: Jeff Skinner

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    Year Signed: 2019

    Seasons Remaining: Six

    Cap Hit: $9 million

    Sometimes teams go off the rails for reasons that are hard to figure out. Hockey is, by and large, a game that is heavily influenced by random events that are difficult to control.

    Still, when organizations are bad for as long as the Buffalo Sabres have been, there's a reason for it. It starts at the top, with consistently poor decision-making by the front office trickling its way down on to the ice on a nightly basis.

    Case in point: Jeff Skinner.

    The Sabres traded for him, bolstering their forward core in the process. He clicked with (former) franchise center Jack Eichel to the tune of 40 goals and 63 points in his first full campaign with Buffalo. They rewarded Skinner with a monster eight-year deal worth $72 million before splitting up him and Eichel, leading to 26 fewer goals for Skinner.

    It's almost like the Sabres should have known who was driving the bus for the line, right?

    They now have one of the most untradeable contracts in the league and possibly in league history. The contract was misguided in the first place and isn't going to look better as Eichel is done in Buffalo and Skinner is 29.

Calgary Flames: Milan Lucic

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    Mark J. Terrill/Associated Press

    Year Signed: 2016

    Seasons Remaining: Two

    Cap Hit: $6 million

    The Calgary Flames aren't responsible for the terms of Milan Lucic's contract. However, they willingly traded for him, so he is designated as the team's worst contract. As already discussed, all of these deals weren't made in a vacuum. There are circumstances at play for everyone in the NHL, and this case is no different.

    Lucic isn't the runaway worst contract in Calgary, and few would argue that the Flames would be better off with James Neal in the lineup on a nightly basis. Those forwards were dealt for one another (with Lucic arriving with a conditional third-round pick). One could easily argue that Calgary did the best it could by turning a fading Neal into Lucic, who, at the very least, is zero fun to play against. 

    He had a bit of a bounce-back campaign a year ago, putting up 10 goals and 23 points across 56 contests. Lucic still isn't worth his $6 million cap hit, but considering Neal is just barely hanging on at the NHL level, the Flames did just fine in this trade.

    Still, on a roster full of tough choices to make on various players over the next few years, Lucic has the worst deal for Calgary. Stay tuned to see whether that remains the case a year from now.

Carolina Hurricanes: Brady Skjei

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    Year Signed: 2018

    Seasons Remaining: Three

    Cap Hit: $5.25 million

    Teams in the NHL always seem to get hung up on pedigree. If you got selected in the first round within the past few seasons and don't have any off-ice issues associated with you, odds are good that a team looking for a bargain will think it can get something out of you that no one else has been able to.

    When the Carolina Hurricanes traded for Brady Skjei in February 2020, it seemed like that is what they were trying to do. It's not like 6'3", 210-pound blueliners grow on trees, after all.

    Skeji wasn't all that great for the Canes following the deal, though, and he took a pretty big step back in 2020-21. We'll say it over and over again: It's tough to judge any player for what they did or didn't do during that pandemic-affected season, but we can't simply throw it out, either.

    At 27, could Skjei evolve into a player who is at least closer to being worth his $5.25 million cap charge? It's possible. Maybe he has an opportunity to shine now that Dougie Hamilton is no longer with the Hurricanes. The fact is that he hasn't panned out in Carolina just yet.

    Until he finds his game or his contract expires, Skjei has the worst contract for a generally well-run organization.

Chicago Blackhawks: Seth Jones

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    Patrick McDermott/Getty Images

    Year Signed: 2021

    Seasons Remaining: Eight, but the extension hasn't even kicked in yet!

    Cap Hit: $9.5 million

    Hey there, Chicago Blackhawks fans. Are you tired of hearing about how awful Seth Jones' contract is even though he only signed it at the end of July? Then the next nine years are going to be even worse, because this is a deal that isn't going to age well.

    The massive extension Jones received before pulling on a Blackhawks sweater over his head raised eyebrows among some of the team's best beat reporters. And even if he plays like a $9.5 million defenseman in 2021-22, his new deal doesn't kick in until next year.


    Half of Jones' contract will take place during his early 30s, and NHL players just don't typically improve as they creep toward 35.

    There are exceptions, but organizations usually aren't betting $76 million that a player will prove to be a special case.

    Chicago ignored the fact that Jones has been on a downward trajectory for three straight seasons. The Blackhawks ignored the fact that a bad Columbus Blue Jackets was better in terms of expected-goals-for percentage when their perceived No. 1 defenseman wasn't on the ice for them. The red flags surrounding this deal are numerous and real.

    We hope Jones can live up to his megadeal. The odds just aren't in his or Chicago's favor.

Colorado Avalanche: Erik Johnson

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    David Zalubowski/Associated Press

    Year Signed: 2015

    Seasons Remaining: Two

    Cap Hit: $6 million

    The Colorado Avalanche have the cleanest cap sheet in the league. Darren McCarty and the rest of the '97 Detroit Red Wings would even take a glance at Colorado's salary situation, quietly nod in approval and move on with their days.

    That is to say that even the biggest Avalanche detractor has to look at what they have built over the past several seasons and respect it. If the Tampa Bay Lightning are the latest threat to become an actual dynasty, Colorado's turn is coming.

    Possibly as soon as this season.

    As such, they don't have any glaringly awful deals that they have to contend with. Any player can fall off at any time for numerous reasons, but as far as what we can guess at, the Avalanche haven't exposed themselves to much risk because they have extended their core out for the foreseeable future.

    So the "worst" contract designation goes to Erik Johnson, who just barely isn't worth his $6 million cap charge. Yeah, it's a great time to be a fan of the Avalanche.

Columbus Blue Jackets: Zach Werenski

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    Kirk Irwin/Getty Images

    Year Signed: 2021

    Seasons Remaining: Six

    Cap Hit$9,583,333

    From a public relations and club pride standpoint, we 110 percent understand why the Columbus Blue Jackets inked Zach Werenski to this contract. The club has done all it can to bring talent to Ohio, only to see players bolt for more attractive cities via free agency or forced trades.

    Even the Jackets' own first-round draft picks have taken to forcing their way out of town before having much leverage to do so.

    So when a player of Werenski's caliber and pedigree decides to call Columbus home for six years, well, it matters more to the organization from a "statement" standpoint than an on-ice one. Still, if we go after Chicago for making a statement for acquiring Jones, we have to hold the Blue Jackets similarly accountable.

    Werenski is only 24, so he could well grow into this deal. This one definitely falls under the not hopeless heading. But this isn't a player who has established himself as an elite defenseman. And his cap hit will be higher than both Cale Makar's and Charlie McAvoy's once this extension kicks in. Who would you honestly rather have if you're a Blue Jackets fan?

    This is a player who's never received a single first-place Norris Trophy vote making more than two defenders who finished last year second and fifth in voting, respectively. Can he live up to the nearly $10 million cap hit? 

    Maybe. Until he does, though, this is Columbus' most questionable contract.

Dallas Stars: Tyler Seguin

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    Jeffrey McWhorter/Associated Press

    Year Signed: 2018

    Seasons Remaining: Six

    Cap Hit: $9.85 million

    This kind of $10-ish million cap hit is starting to become a trend as we break down the worst contracts across the NHL. Preferably, you would be in a position similar to Columbus or Colorado, where you have a skater who could grow into their cap hit or is coming off of the books relatively soon.

    With Tyler Seguin, the Dallas Stars aren't in either comparably enviable position.

    This is a forward coming off of an illness that limited him to three games in 2020-21. This is also a player who scored 30 fewer points in his most recent full season (2019-20) compared to the year prior (2018-19). That isn't the kind of track you want someone like Seguin to be taking.

    Yet here we are, just three years into an eight-year contract that could end up being a pretty massive anchor on Dallas' books. Seguin is being paid like one of the NHL's elite forwards. He's expected to do a lot of things for the Stars, but as he enters his year-30 season, it's unlikely that he will find the nearly point-per-game pace he enjoyed in his mid-20s.

    We don't make the rules. Nor do we control players' hour glasses or the effect Father Time has on their play. We just know what's happened in the past, and skaters in Seguin's position haven't generally gotten better as they have gotten closer to 35. 

Detroit Red Wings: Danny DeKeyser

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    Carlos Osorio/Associated Press

    Year Signed: 2016

    Seasons Remaining: One

    Cap Hit: $5 million

    A few seasons ago, the Detroit Red Wings were in cap hell. Straight up. For all the proof you need, revisit the trade that got Pavel Datsyuk off of the books. Did Detroit know it would cost them a chance at drafting Jakob Chychrun? Probably not, but the trade still, in effect, did exactly that.

    And for a team that needs every bit of talent it can get, losing out on a shot at someone like the 6'2", 220-pound blueliner stings. Regardless, the Red Wings largely find themselves on the periphery of cap hell. Or at least, in a different circle of it, where they don't have enough skilled players worth paying to fill up their books.

    So for their worst contract, we'll go with Danny DeKeyser. With one year remaining, it's hard to rip on this contract too much now. Swap him out for Marc Staal if you want. We would even entertain commentary on Dylan Larkin's $6.1 million AAV until 2023 making him slightly overpaid.

    In terms of who's simply making more money than they are worth, though, DeKeyser (or Staal) grades out as the worst deal in Detroit. But his and Staal's pacts are up at the end of 2021-22, limiting the negative impact they will have in the coming seasons.

Edmonton Oilers: Darnell Nurse

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    Michael Dwyer/Associated Press

    Year Signed: 2021

    Seasons Remaining: Eight

    Cap Hit: $9.25 million

    You could safely revisit the Blue Jackets slide concerning Werenski, add an extra two years' worth of age for Darnell Nurse and arrive at a lot of the same concerns.

    Except—and this is a huge except—Werenski hasn't spend the past few years of his career skating with the best hockey player on Earth in Connor McDavid. Thinking that doesn't make Nurse look at least a little better than he is would be naive.

    There's no other way to put it, and in a universe where the Oilers don't roster McDavid, Nurse doesn't get this $74 million extension.

    We're not trying to say that he isn't a solid defenseman. But, again, this is a defenseman who's received zero first-place Calder Trophy votes through his eight-year NHL career. That means not a single member of the NHLPA's voting body has thought that Nurse was the best blueliner in the league for even a single season.

    Yet the Oilers are paying him as if he's a perennial best defenseman candidate. Nurse isn't even involved in those conversations, though. Assuming he continues to skate with McDavid, the former seventh overall pick will likely continue to put up gaudy numbers.

    It won't be him driving play, though.

Florida Panthers: Sergei Bobrovsky

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    Lynne Sladky/Associated Press

    Year Signed: 2019

    Seasons Remaining: Five

    Cap Hit: $10 million

    Evaluating goalies is difficult, to the point we're almost uncomfortable including any on this list of worst contracts in the NHL. Every season, we see an under-the-radar netminder seemingly pop off for big numbers out of nowhere while some former All-Star or Vezina Trophy winner's game tanks.

    Age doesn't affect goalies like it does forwards or defensemen, either, making projections for the position even more difficult.

    Despite all that, we're confident that Sergei Bobrovsky has the worst contract on the Florida Panthers for two reasons. First off, this is a well-constructed hockey team. Besides Bob, value-wise, they don't have any contracts that grade out as below average.

    Secondly, well, even if Florida were a mid-range organization, cap-sheet wise, this megadeal isn't likely to start to look better than it has over the past two campaigns. Yes, we've heard all about how Bobrovsky is ready for the fresh start that 2021-22 will afford him.

    The reality is that even when the netminder was at his best in Columbus, he still wasn't worth a $10 million cap hit. One could make the argument he might have been worth it in 2016-17, when he won his second Vezina Trophy and finished third in Hart Trophy voting.

    Expecting any player to maintain that level of output for seven years is unreasonable, though. And Bobrovsky is just as close to the end of his deal in Florida as he is to his best season. That doesn't bode well for the Panthers and their ability to get $10 million performances from their No. 1 netminder.

Los Angeles Kings: Drew Doughty

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    Harry How/Getty Images

    Year Signed: 2018

    Seasons Remaining: Six

    Cap Hit: $11 million

    Let's preface this analysis by acknowledging that Drew Doughty was a solid top-pairing defenseman for the Los Angeles Kings last season. It was a nice bounce-back campaign for a blueliner who was once one of the most feared in the league, back when the road to the Stanley Cup Final out of the West generally went through California.

    Unfortunately for Doughty and the Kings, 2020-21 likely represented the new ceiling for the 31-year-old. Eight goals and 34 points in 56 games is nothing to sneeze at, and again, he wasn't bad.

    It's just that solid top-pairing defenseman and wasn't bad aren't expressions you want to hear tossed around about a player who's hitting the cap for $11 million a year for the next six. Just being a good No. 1 defenseman isn't enough for Doughty. Not with what he's making.

    That kind of cap hit demands a capital-E elite level of play, and as the defenseman enters his age-32 season, we have to wonder whether he'll return to the heights that saw him finish second in Norris Trophy voting in 2017-18.

Minnesota Wild: Dead Money

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    OK, so this one is a little different, but when examining the Minnesota Wild's cap situation, it's the only conclusion that makes any sense. They don't have any awful contracts on the books for players who are, you know, still playing in the State of Hockey.

    The decision to buy out both Ryan Suter and Zach Parise during the offseason was interesting, to say the least. We're even prepared to call the moves confounding while stopping just short of calling the choice bad. At least how things stand for now. 

    It's hard to ignore the fact that Minnesota is going to have a whole lot of cap space tied up in two players who are skating for other teams until 2026-27, however. Look at how much dead cap these buyouts will create for the Wild in the coming seasons and try to explain it away as anything besides ugly.

    2021-22: $4,743,588 in dead cap space

    2022-23: $12,743,588 in dead cap space (!!)

    2023-24: $14,743,588 (!!!)

    2024-25: $14,743,588 (!!!)

    2025-26: $$1,666,666

    2026-27: $1,666,666 (and it's over)

    It's hard to figure out just how much nearly $15 million in dead money will hurt the Wild in the coming seasons, but it's safe to assume they won't be going in on any big-name free agents in the near future. And that will also hamstring their ability to give big-money extensions to any younger players who emerge between now and 2025.

Montreal Canadiens: Josh Anderson

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    Minas Panagiotakis/Getty Images

    Year Signed: 2020

    Seasons Remaining: Six

    Cap Hit: $5.5 million

    The contract Josh Anderson signed with the Montreal Canadiens basically carries the same issues that Milan Lucic's does. There's an aspect to the forward's game that is difficult to drill down through analytics, and we aren't going to ignore that.

    Opponents don't enter games with the Habs looking forward to contending with this 6'3", 226-pound forward. He threw 139 hits last season and has never been afraid to throw the gloves even though that isn't his calling card.

    Skill drives play in the NHL across long sample sizes, though, and Anderson's impact at both ends of the ice makes it hard to justify his cap hit. He found the back of the net 17 times a year ago, and there probably isn't a general manager in the NHL who wouldn't take him on their team.

    Still, with a physical playing style and the back half of this contract taking place during Anderson's early 30s, it might not be long until this is a detrimental deal. If he can flirt with 20 goals and maintain his physical presence over the next six years, then fine. Montreal probably isn't regretting the $5.5 million cap hit.

    That's a pretty big if, though, and if Anderson's body begins to break down or he can't match last year's 13.6 shooting percentage, this could become a problem for Montreal between now and 2027. Especially since the Canadiens gave Anderson a modified no-trade list that kicked in this year.

Nashville Predators: Ryan Johansen

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    Mark Humphrey/Associated Press

    Year Signed: 2017

    Seasons Remaining: Four

    Cap Hit: $8 million

    For a handful of seasons there, the Nashville Predators had what we will call light Stanley Cup aspirations. Even the 2016-17 version of this team that made the Stanley Cup Final did so as the eighth seed. As it turns out, Ryan Johansen was stellar in that playoff run, posting 13 points in 14 contests, averaging more than 20 minutes a night.

    The center inked an extension that July, and it seemed like a solid deal for both player and team. Johansen played like (or at least close to like) an $8 million center through the first two years of this deal, posting 118 points in 159 games from 2017-18 to 2018-19.

    He's regressed noticeably since, to the point the Predators signed another center, Matt Duchene, to a big-money deal in 2019 to try to offset the decline. Duchene's contract has aged poorly too, though, leaving Nashville saddled with two of the worst contracts in the league.

New Jersey Devils: P.K. Subban

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    Jared Silber/Getty Images

    Year Signed: 2014

    Seasons Remaining: One

    Cap Hit: $9 million

    During his heyday, few players in the NHL could bring fans to their feet like P.K. Subban. He was an electric skater and always felt like a threat to make something happen when the puck was on his stick. This is a defenseman who notched at least 30 points a season for nine straight years, from 2011 with Montreal to 2019 with the Predators.

    Subban has been a shell of that player since landing in New Jersey via trade two years ago, however. New Jersey didn't exactly sell the farm to land him, and he's at the point that he only has only this season left on his contract. The Devils are fine here.

    Still, the team doesn't have that many long-term commitments to compete with Subban and his $9 million cap hit for worst deal on the books. He has virtually no chance of playing up to that level in 2021-22, and it will be interesting to see whether New Jersey manages to move him as a rental at the trade deadline, assuming it is out of the playoff race by then.

New York Islanders: Jean-Gabriel Pageau

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    Mike Stobe/Getty Images

    Year Signed: 2020

    Seasons Remaining: Five

    Cap Hit: $5 million

    This is another situation where the "worst" contract on the books for a team isn't all that bad. Jean-Gabriel Pageau provides the New York Islanders with solid all-around play while he's on the ice during the regular season and then seems to turn into a different player once the playoffs roll around.

    Sometimes NHL teams can overpay for clutch players, but Pageau's cap hit is probably just a million or so off of what it should be, so it's not hampering the Islanders too badly at this point. 

    What could cause New York some stress is that mostly everyone up front not named Mathew Barzal is at least a little overpaid. Is Pageau nuking the Islanders' cap situation by being mildly overpaid? No, but combine that with slightly pricey deals for other forwards like Brock Nelson ($6 million cap hit over the next four seasons) and Anders Lee ($7 million for the next five campaigns) and things start to add up.

    Would you rather have five or six players making a bit too much, combining for a decent lump sum, or one player hurting the cap sheet? It seems clear that New York prefers the former approach.

New York Rangers: Barclay Goodrow

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    Claus Andersen/Getty Images

    Year Signed: 2021

    Seasons Remaining: Six

    Cap Hit$3,641,667 million

    It would be fair to characterize Barclay Goodrow as a hockey player's hockey player. He does all the little things that inspire teammates and that coaches love. He isn't afraid to block shots, play hurt or throw his body around to make an impact.

    He finished just among of the NHL's most prolific hitters in 2020-21 and has a few Stanley Cup rings from his time with the Tampa Bay Lightning to boot.

    This has been talked about to the point of nausea with the moves made in New York over the summer, but it still holds true: Toughness for the sake of it doesn't win hockey games. Physicality isn't useless, but it is if there isn't more being brought to the table.

    We aren't saying that Goodrow doesn't bring anything else besides sandpaper and a few Cup rings, but it isn't much else. Tampa generally had a tough time holding on to the puck when the forward was on the ice, and one has to wonder who was driving play for the Lightning's vaunted third line of 2020-21.

    Let's give Goodrow the benefit of the doubt and say that it was him. Would it still make sense for the Rangers to give a player renowned for physical play who turns 29 in February a six-year deal? Especially since they were only bidding against themselves at the time the pact was inked?

    We'll let you sell it to us in the comments section, but we won't be buying any of it.

Ottawa Senators: Thomas Chabot

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    Icon Sportswire/Getty Images

    Year Signed: 2019

    Seasons Remaining: Seven

    Cap Hit: $8 million

    General managers in the NHL are usually playing a game of damned if you do, damned if you don't when it comes to locking up members of a promising-looking core. Wait too long, and a player can establish their value, perhaps taking another million or two to the bank following a bridge deal.

    We're more and more frequently seeing situations like the one between Thomas Chabot and the Ottawa Senators, however. He's not even the first example of this kind of contract on this list, and we have a feeling he won't be the last.

    Right now, Chabot simply isn't an $8 million-a-year defenseman. There are bars that need to be cleared for players to be worth that kind of money, and expecting a 24-year-old to suddenly develop into a borderline elite defenseman is a big ask.

    There's no denying that the 18th overall pick in 2015 has a ton of offensive talent. He showcased that in 2018-19, when he scored 14 goals and added 41 assists across just 70 games. That's the kind of player Ottawa is paying Chabot to be. He wasn't close to the top three, but he still got Norris Trophy votes that year.

    He plays a ton, but can the Senators hope to win a championship when they can't start their highest-paid defender in the defensive zone? Chabot could grow into this deal a bit over the next season or two, and we're prepared to eat crow if he does.

    For now, though, he's Ottawa's biggest question mark on the cap sheet.

Philadelphia Flyers: Kevin Hayes

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    Len Redkoles/Getty Images

    Year Signed: 2019

    Seasons Remaining: Five

    Cap Hit$7,142,857 million

    This contract was eye popping the moment it was announced, and it hasn't aged any better over the two seasons since it was signed.

    There's no denying that, when healthy, Kevin Hayes can be a steady offensive producer for the Philadelphia Flyers. Since breaking into the league with the New York Rangers in 2014-15, the forward has been a consistent threat to score roughly every fourth game while adding a steady diet of assists to boot.

    He had the best season of his career the year before signing this deal with the Flyers, though—funny thing, that—and it's that campaign that Philadelphia decided to pay him for.

    In 2019-20, Hayes found the back of the net 23 times and was a penalty-killing machine. And assuming he fully recovers from offseason surgery, he could well be a threat to approach those numbers again.

    So what's the problem, then? The issue is that Hayes is making more than $7 million a year, which makes him one of the league's 30 highest-paid centers. That naturally implies that he's a No. 1 pivot. Good as Hayes is, he isn't built to be the top center on a contending team.

    But that is what the Flyers are paying him like he is, which is why this contract is the worst in Philadelphia. Besides, you know, Ben Simmonds'.

Pittsburgh Penguins: Brock McGinn

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    Icon Sportswire/Getty Images

    Year Signed: 2021

    Seasons Remaining: Four

    Cap Hit$2.75 million

    Brock McGinn and his $2.75 million cap hit won't haunt the Pittsburgh Penguins until 2025, when the deal expires. We just aren't exactly sure what the forward did to warrant that kind of term. And it's the length that makes this deal a head-scratcher.

    He's been a serviceable bottom-six grinder since entering the league six years ago, but McGinn is three years removed from his career high in goals (16) and points (30). As we've stated several times to this point, there's more to players and the game of hockey than points.

    But offensive talent and/or upside is generally what gets forwards paid in the NHL. Grinders are free to ply their trade across bottom-six roles whenever the need arises, but it isn't like there's a jump ball for their services every year when free agency opens.

    McGinn seems to be fitting in just fine in Pittsburgh, which is good since he has the team's second-longest deal among forwards.

San Jose Sharks: Yikes! (But Erik Karlsson)

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    Ezra Shaw/Getty Images

    Year Signed: 2019

    Seasons Remaining: Six

    Cap Hit: $11.5 million

    No team in the NHL is in worse cap shape than the San Jose Sharks. And there's nothing this once-proud organization can do besides wait out these awful contracts and hope that they get some help via early retirements or moves to LTIR.

    As it stands, Erik Karlsson has arguably the worst contract in the sport. It's a toss up between him and Doughty, who at least is giving the Kings some value.

    Only three players in the league have a bigger cap hit than Karlsson's $11.5 million. He might have been worth that kind of dollar amount when he was posting 70 or 80 points a year, but the last time he did that was in 2016-17. In his age-31 campaign, this one is only going to get uglier for the Sharks.

    It's been sad to watch one of the league's most electric players slowly lose the skating stride that once made him such a threat.

Seattle Kraken: Alex Wennberg

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    Bruce Bennett/Getty Images

    Year Signed: 2021

    Seasons Remaining: Three

    Cap Hit: $4.5 million

    Finding centers is a difficult thing for any franchise to do. For the Seattle Kraken, though, finding talent down the middle of the ice was almost impossible during their expansion draft in July. They had some middle-six options to choose from, but teams don't generally start making Stanley Cup Final appearances without legit No. 1 and No. 2 pivots.

    Just ask the Vegas Golden Knights.

    So it wasn't all too surprising when general manager Ron Francis needed to overpay a bit during free agency to fill out his center ranks. This contract for Alex Wennberg is far from the kind that can cripple a team's cap sheet. It isn't an anchor like Karlsson's.

    And the reality is that Seattle knows exactly what it is getting from Wennberg over the next three years. They just had to pay a bit more than he is worth to get that talent in the lineup.

St. Louis Blues: Justin Faulk

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    Michael Martin/Getty Images

    Year Signed: 2019

    Seasons Remaining: Seven

    Cap Hit: $6.5 million

    Let's forget for a second that the St. Louis Blues might have been able to keep captain Alex Pietrangelo if not for extending Justin Faulk before he had even played a game for the club. We've been trying to consider all circumstances surrounding every one of these contracts that we've labeled the worst.

    For Faulk, though, that simply isn't possible. We just don't have enough space here, so let's just get down to it: The Blues are paying the 29-year-old to be a legit No. 1 defenseman, and he isn't one. Full stop. He isn't even a top-pairing blueliner.

    One could even argue that the former Carolina Hurricane has never been a true No. 1 or No. 2 during his career. Faulk always put up decent point totals in Carolina, but it was never worth the roller-coaster ride in the defensive zone.

    The Blues, before even seeing what he looked like in their sweater (or, more importantly, system) gave him a huge extension, and it's one that will be dragging down the team's cap situation until 2027.

Tampa Bay Lightning: Ryan McDonagh

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    Scott Audette/Getty Images

    Year Signed: 2018

    Seasons Remaining: Five

    Cap Hit: $6.75 million

    Even the smartest organizations in the NHL don't have the ability to see the future. General managers and their brain trusts do their best to project a player's worth based on a multitude of factors. Sometimes they get it right. The Tampa Bay Lightning usually do.

    The Ryan McDonagh extension is one that they simply whiffed on. Still, we understand why they made the deal at the time.

    In 2018-19, the defenseman played well enough to garner some Norris Trophy votes. He posted a new career high in points (46) and seemed like a safe enough bet for the Lightning to make. So they handed him a seven-year deal worth north of $47 million. There's no question that McDonagh earned this kind of money during his time with Tampa Bay.

    But he's simply not worth that kind of money now. As the Lightning continue to churn through talent to keep on top of a salary-cap crunch, it's tough not to turn a sour eye toward this $6.75 million cap hit and wonder what Tampa Bay could have done with that money elsewhere.

Toronto Maple Leafs: John Tavares

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    Mark Blinch/Getty Images

    Year Signed: 2018

    Seasons Remaining: Four

    Cap Hit: $11 million

    John Tavares is here as the worst contract on the Toronto Maple Leafs as a byproduct of the many excellent deals they have on the books. We worry that the captain won't be worth $11 million by the last year or two of this deal, but that was a known risk when Toronto took on Tavares.

    To this point, he's been nearly a point-per-game player, and if he had stayed healthy during last year's playoffs, who knows what would have happened with this talented Maple Leafs team.

    That's going to be the hang-up when analyzing any team that has Stanley Cup aspirations as consistently as Toronto has, however. If Tavares only scored five empty-net goals and notched 24 secondary assists but caught fire and helped the Maple Leafs earn a championship parade, no one in Toronto would care.

    Tavares has been an outstanding player in Toronto. Every bit as good as advertised. We can just see the bottom dropping out on this deal by the time 2025 rolls around and he's 34.

Vancouver Canucks: Oliver Ekman-Larsson

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    Icon Sportswire/Getty Images

    Year Signed: 2018

    Seasons Remaining: Six

    Cap Hit: $8.25 million

    This one might be the most baffling we list here because the Vancouver Canucks went out and traded for this terrible contract. How the Coyotes managed to only retain $990,000 of Oliver Ekman-Larsson's contract is beyond us.

    So is the fact that an NHL general manager thought that six seasons of this entirely washed defenseman would actively benefit their team.

    Ekman-Larsson was a pillar for the Coyotes during times when nothing else surrounding the franchise seemed stable. No one will take that away from him, but there's simply no denying that he's been getting caved in at even-strength for the last half decade.

    Arizona hasn't been a good hockey team, but no one can honestly argue that Ekman-Larsson has looked like part of a possible solution since his best season six years ago. And the Canucks essentially said, "Yep, give us that 30-year-old defenseman until 2027."

    Vancouver now has not one, not two but three remarkably overpaid defenders, and it'll have a hard time icing a legit contender as long as that remains the case.


Vegas Golden Knights: Evgenii Dadonov

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    Ethan Miller/Getty Images

    Year Signed: 2020

    Seasons Remaining: Two

    Cap Hit: $5 million

    Evgenii Dadonov is another player who isn't going to tank his team's cap situation for any real amount of time. It's just that the Golden Knights have done a relatively good job of paying players what they are worth or getting them to take a bit less to be a part of something special in Vegas.

    He's mostly here because we aren't sure why the Golden Knights didn't simply hang on to the cap space that trading away Marc-Andre Fleury created. Dadonov was an effective goal scorer over his final three seasons with the Panthers.

    He found the back of the net 81 times in 225 games played from 2017-18 to 2019-20, scoring at least 25 goals in each of those campaigns. Upon joining the Senators in 2020, the wing fell off to the tune of 13 goals in 55 contests, and we aren't sure why Vegas decided to roll the dice on him rediscovering his scoring touch as a 32-year-old.

    Plus, Vegas is already a high-octane offensive team. Dadonov's cap hit isn't overly brutal, but the Golden Knights could have made a bigger, more important splash later in the season with that space.

Washington Capitals: Evgeny Kuznetsov

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    Icon Sportswire/Getty Images

    Year Signed: 2017

    Seasons Remaining: Four

    Cap Hit: $7.8 million

    Another intriguing contract to examine as we wind down our list. Evgeny Kuznetsov's situation is unique when compared to mostly every other player we have discussed. He's not a former All-World talent on the wrong side of 30 with virtually no chance to live up to his cap hit.

    Nor is he a young defenseman, looking to blossom into the player his cap hit implies that he is. 

    He's a 29-year-old center who, during the prime of his career with the Washington Capitals, was a near-lock for 70-plus points despite not seeing much ice time with Alexander Ovechkin. Can simply getting back to enjoying the game be enough to reinvigorate his career?

    Maybe. And if Kuznetsov can return to that 70-point plateau, his cap hit of nearly $8 million will be much easier to stomach. He still won't be worth every cent, but there would be many more overpaid players in the league.

Winnipeg Jets: Josh Morrissey

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    Chris Carlson/Associated Press

    Year Signed: 2019

    Seasons Remaining: Seven

    Cap Hit: $6.25 million

    Eight years is a long time to figure out exactly what kind player you have on your hands. That's essentially what the Winnipeg Jets committed to doing when they handed this $50 million pact to Josh Morrissey.

    When he went from skating with Jacob Trouba to being asked to haul around random replacement-level defenders, his on-ice contributions took a massive hit. While his cap hit doesn't suggest that he should be a No. 1 blueliner, it does imply that he should be a strong No. 2.

    Is that what the Jets have here?

    After beefing up their backend over the summer, Winnipeg will have its answer by this time next year. As of now, though, Morrissey has been routinely crushed by his tough assignments. While we feel for him because of the various situations he's been placed in, the truth is that he simply hasn't been up to the tasks at hand.


    All salary-cap information appears courtesy of CapFriendly and is accurate through October 20, 2021.


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