Every NHL Team’s Worst Contract

In the modern NHL, contract and salary cap management may be more critical than ever. With the cap kept flat due to the financial consequences of the COVID-19 pandemic, teams need to be thinking not only about the here and now, but about the long-term implications of any contract they sign. General managers who can minimize bad contracts will likely be the GMs who find the most success.

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However, every team in the league has a contract on the books that is questionable, no matter how good their GM is. This article will take a look at each team’s worst contract, with two things in mind: first, contracts evolve. In most of these cases, the team would likely not sign the same deal knowing what they know now. So we will attempt to establish why these contracts were signed when they were signed.

Second, and in the same line, these deals tend to become albatrosses because of injury, reduced performance, or aging. So all of these opinions are written with due respect to the players who, for the most part, were once-great NHL players who earned these contracts at the time.

Sergei Bobrovsky, Matt Duchene, Erik Karlsson Every NHL Teams's Worst Contract
Sergei Bobrovsky, Matt Duchene, Erik Karlsson (The Hockey Writers)

(The bolded text below each player name displays the term remaining on the contract, including the 2020-21 season, as well as the AAV and any no-trade clauses (NTC) or no-movement clauses (NMC) the deals contain.)

Anaheim Ducks: Adam Henrique

(Three years, $5.825 million, with M-NTC)

The Anaheim Ducks are deep in the process of a rebuild that could be painful, and they are likely to finish as one of the bottom-five teams in the league unless a trade for Jack Eichel materializes. One thing that hasn’t helped is general manager Bob Murray’s tendency to sign aging players to lengthy contracts. As such, the Ducks have a few candidates for worst contract, including Jakob Silfverberg (30, four years, $5.25 million AAV) and Cam Fowler (29, six years, $6.5 million AAV).

But Adam Henrique takes the nod here by an edge, especially after the Ducks waived him last season. Henrique is a perfectly fine middle-six center who has managed seven consecutive forty-plus point seasons. But those just aren’t numbers that justify a price tag that nears $6 million and, as the waiver attempt makes clear, the Ducks have been unhappy with that production. Especially with the flat cap, contracts like that are troublesome, and they’ll be hard-pressed to unload it.

Arizona Coyotes: Clayton Keller

(Seven years, $7.15 million, with NTC starting in 2024, NMC beginning in 2026)

Relatively new Arizona Coyotes general manager Bill Armstrong has been making moves and clearing cap space in the desert, hoping to accelerate a rebuild for the recently homeless franchise. In that process, he managed to trade former captain Oliver Ekman-Larsson to the Vancouver Canucks. It was an impressive feat that rid him of one of the more burdensome contracts in the league (spoiler alert: we’ll return to Ekman-Larsson later). But a few questionable contracts still remain on his books: Nick Schmaltz, who has five years remaining at $5.85 million, and Clayton Keller, with seven years at $7.15 million left. We’ll focus on the longer, richer contract for this article.

Clayton Keller Arizona Coyotes
Clayton Keller, Arizona Coyotes (Jess Starr/The Hockey Writers)

Keller is currently, for lack of a better candidate, the face of the Coyotes, especially if the team indeed moves on from Phil Kessel before the season or at the trade deadline. Arizona paid top dollar to keep the young player after he scored 114 points in his first 167 career NHL games. But the 65 points in 82 games from his rookie season is looking like more and more of an anomaly. Keller is just 23 and has plenty of time to redeem himself. Moreover, the Coyotes need central players and have to hit the cap floor, so this contract is hardly crippling. But it’s a serious overpay for the production he’s shown in the two seasons since signing the deal, and the Coyotes would love to see him pick it up now that he’s the clear centerpiece of the team.

Boston Bruins: Charlie Coyle

(Five years, $5.25 million, with M-NTC, NMC)

Charlie Coyle’s contract is hardly one of the worst in the NHL, but on a team that has very few notable bad contracts, his still stands out a bit. The Massachusetts native hasn’t reached the 40-point threshold in any of the last four seasons but was a huge contributor in the team’s run to the Stanley Cup the season he came over from the Minnesota Wild. Unfortunately, it was that recency bias that influenced his contract early in the next season. Coyle is still a fine player and a solid contributor in Boston’s middle six. But a $5.25 million annual commitment to a player who isn’t regularly adding 40 points is a stretch, and on a team with very strong contract management overall, it’s a deal that stands out.

Buffalo Sabres: Jeff Skinner

(Six years, $9 million, with NMC)  

Some contracts feel like a stretch the moment they are signed. Some contracts look fatal because of the early returns after they are signed. Jeff Skinner’s contract with the Buffalo Sabres falls into both categories. Skinner scored 40 goals in his first season with Buffalo, and as a pending-Unrestricted Free Agent (UFA), then general manager Jason Botterill felt like he had to keep his star winger. But the eight-year, $72 million deal he signed always seemed like a steep price tag whose career high was 63 points (which he hit three times).

Jeff Skinner Buffalo Sabres
Jeff Skinner, Buffalo Sabres (Amy Irvin / The Hockey Writers)

Unfortunately, Skinner’s performance hasn’t justified the deal he’d signed. He managed just 23 points the following season in 59 games, with a minus-22 rating. His results in 2020-21 were even worse, finishing with 14 points in 53 games. Skinner’s repeated early-season healthy scratches helped spark head coach Ralph Krueger’s ouster in March. there’s no obvious solution for Skinner’s future in Buffalo, and, as the team seems mired in a perpetual rebuild, contracts like his will continue to be an albatross that holds them back.

Calgary Flames: Milan Lucic

(Two years, $5.25 million, with NMC)

Milan Lucic’s contract with the Calgary Flames is a bit unique, in that the Flames knew they were acquiring a cumbersome deal when they swapped James Neal for Lucic in 2019. Both veteran players had worn out their welcome with their clubs and carried bad contracts, and each franchise thought a change of scenery might be the best solution. Lucic played his 1,000th career game and celebrated it as a Flame. He provides the veteran leadership and grit he always has, but the offensive contributions are a thing of the past. Still, unless Lucic retires, Calgary will have to ride out the rest of this deal.

Carolina Hurricanes: Jake Gardiner

(Two years, $4.05 million, with M-NTC)

There are those who would argue that signing Anthony DeAngelo as a free agent made his the worst contract for the Carolina Hurricanes. But that really isn’t in keeping with the spirit of this article. The Hurricanes have few truly bad contracts, and there are two main contenders for “worst deal.” Jordan Staal, though he is the team’s captain, makes $6 million a season, and doesn’t produce like that kind of player anymore. But given his importance to the team, not to mention a fairly significant resurgence last season, Jake Gardiner’s two years remaining at just over $4 million will edge him out. Gardiner isn’t a terrible asset. But he was signed to be a point-producing blueliner like he had been with the Toronto Maple Leafs. And he simply hasn’t been. Last season, he scored eight points and only managed 26 games. It’s not a devastating deal, but general manager Don Waddell would likely prefer to have it off his books.

Chicago Blackhawks: Brett Connolly

(Two years, $3.5 million)

There are several contenders for the worst contract on the Chicago Blackhawks, even after the contracts of Brent Seabrook and Duncan Keith are finally off the books. Tyler Johnson’s three remaining years at $5 million per season could be a problem, but he is looking for a fresh start in Chicago and still has the potential to be a productive middle-six forward. Calvin De Haan is making $4.55 million, but only for one more season. There is even an argument for giving Seth Jones the “honors” after the former Columbus defenseman signed an eight-year, $76 million extension before playing a single game in the Windy City. But because he hasn’t debuted, he deserves a chance to prove his worth with his new team. So, for the time being, we’ll give the nod to Brett Connolly.

Brett Connolly Florida Panthers
Brett Connolly, Florida Panthers (Amy Irvin / The Hockey Writers)

The Blackhawks traded for Connolly knowing he was on a bad deal. He was part of the return in a big trade deadline deal that sent Lucas Wallmark and Lucas Carlsson to the Florida Panthers and brought back Connolly, Riley Stillman, a 2021 seventh-round pick, and the rights to Henrik Borgstrom. The last name is the one this deal hinges on. The Helsinki, Finland native is a former first-round pick (23rd overall in 2016), and some evaluators believe he has the talent to become an impact forward in the NHL. But his path to playing time was non-existent in Florida, so the Blackhawks, who must think highly of Borgstrom, made him the price for taking a bad contract off Florida’s hands. If he blossoms into a star, no one in Chicago will worry about two years of a bad Connolly contract. But until we see that, the deal will be a headache for the Blackhawks.

Colorado Avalanche: Erik Johnson

(Two years, $6 million, M-NTC/NMC)  

Erik Johnson, when healthy, could still be a stalwart defenseman for the Colorado Avalanche. But health has been harder to come by for the defenseman, who managed only four games last season. He waived his no-movement clause for the expansion draft last season, preventing one of the biggest potential consequences of this deal, but he remains in Colorado, a salary-laden team trying to stay under the cap. This contract isn’t too terrible, but it puts the team in a vulnerable position, and it remains a significant obstacle for general manager Joe Sakic.

Columbus Blue Jackets: Gustav Nyquist

(Two years, $5.5 million)

Gustav Nyquist is still a fine NHL player, assuming he can recover from the torn labrum surgery that forced him to miss the 2020-21 season. He managed 42 points in 70 games in his first season with the Columbus Blue Jackets. But one can’t fully escape the feeling that he was a panicked free agent signing for a franchise in a pinch.

Gustav Nyquist Columbus Blue Jackets
Gustav Nyquist, Columbus Blue Jackets (Amy Irvin / The Hockey Writers)

When the Blue Jackets signed Nyquist, the franchise had just lost two stars and several deadline acquisitions to free agency. Artemi Panarin and Sergei Bobrovsky were gone, and while the team’s decision to load up for one final playoff run did result in their first-ever trip to the second round, the team’s core dismantled immediately after. Nyquist was a UFA and willing to come to Columbus, so they signed him to a four-year, $22 million contract. The team has plenty of cap room still, but the Nyquist deal still feels like a knee-jerk reaction to trying circumstances.

Dallas Stars: Ben Bishop

(Two years, $4.9 million, with M-NTC/NMC)

One could argue that Dallas Stars goalie Ben Bishop has done nothing to deserve appearing on this list. When healthy, he’s been among the best goaltenders in the league. The issue is, he’s been healthy less and less in recent seasons. And his injuries seem to occur frequently at critical times. His absence late in the 2018 season may have cost the Stars a playoff berth. He played injured in the 2019 playoffs (though no one can question his performance in their Game 7 loss in the second round) and missed the entire following postseason run to the Stanley Cup Final. Now, he’s missed the entire 2020-21 season and doesn’t look to be ready for the 2021-22 season. Though the team can bury his cap hit on the Long-Term Injured Reserve (LTIR), it still hurts that he can’t play. Even as good as Anton Khudobin has been, the Stars are better with Bishop healthy.

Detroit Red Wings: Danny DeKeyser

(One year, $5 million, with M-NTC)

The Detroit Red Wings used to be a tangled web of terrible contracts, but through patience and the careful maneuvering of general manager Steve Yzerman, they are in the final years of most of their worst deals. Given that the team is rebuilding, and probably more concerned with hitting the cap floor than staying under the cap ceiling, none of the deals remaining on the books are especially hindering. But even so, Danny DeKeyser’s year left at a $5 million AAV isn’t ideal.

Danny DeKeyser Red Wings
Danny DeKeyser, Detroit Red Wings, December 20, 2017 (Amy Irvin / The Hockey Writers)

DeKeyser has played 488 games with the Red Wings entering the 2021-22 season but has never quite lived up to the hype he had coming out as a college free agent when he originally signed with the team. He played just 18:06 per game in the 2020-21 season, despite being paid like a top-pairing defenseman. And he finished with 12 points in 47 games. He’s not a bad player, and he can provide value to the team, but at a $5 million cap hit, he’s certainly overpriced.

Edmonton Oilers: Zack Kassian

(Three years, $3.2 million)

The Edmonton Oilers traded for Duncan Keith over the summer, bringing in an expensive deal that carries a $5.54 million cap hit for two more seasons. While Keith’s contract had been named as Chicago’s worst contract in previous editions of this article, the Oilers traded for it for a reason and knew the costs when they got involved. They want his veteran presence and took the cap hit willingly, so, for the time being, we will look elsewhere for Edmonton’s worst deal.

Zack Kassian’s four-year, $12.8 million contract looked dubious from the very start. Sure, he signed it during what would become his second-consecutive 15-goal campaign with the Oilers, a team desperate for secondary scoring beyond that provided by Connor McDavid and Leon Draisaitl. But Kassian was a journeyman grinder who had shown no ability to score consistently at that level. The bruising forward celebrated his new deal by incurring a seven-game suspension just weeks after signing it, and things haven’t gotten much better since. In 2020-21, Kassian was invisible, with just five points in 27 games. Three more seasons of this contract isn’t an exciting prospect, but GM Ken Holland has no one to blame but himself.

Florida Panthers: Sergei Bobrovsky

(Five years, $10 million, with NMC)

Sometimes, you take a big swing in free agency, and sometimes, it just doesn’t pay off. Sergei Bobrovsky was the top goaltender to hit UFA status in many years when the Florida Panthers signed him prior to the 2019-20 season, and they paid top dollar to pair him with new head coach Joel Quenneville. But, even while the Panthers have improved to become a top team in the league, the two-time Vezina Trophy center has been mediocre at best in his two seasons so far.

Sergei Bobrovsky Florida Panthers
Sergei Bobrovsky, Florida Panthers (Amy Irvin / The Hockey Writers)

Bobrokvsy’s numbers weren’t horrendous in the 2020-21 season, as he finished with a .906 save percentage (SV%) and a 2.91 goals-against average (GAA), with minus-1.9 goals saved above average (GSAA). Unfortunately, Chris Driedger was a revelation behind him and carried a 2.09 GAA and .927 SV%. Bobrovsky’s NMC forced Florida to expose Driedger to the expansion draft, whereupon the Seattle Kraken gladly took him. Now, it appears top prospect Spencer Knight is ready for the NHL. But Bobrovksy’s hefty contract likely means he will continue to earn playing time above the youngster. Knight is still the future, but the road to get there could be a rocky one with Bobrovsky between the pipes.

Los Angeles Kings: Drew Doughty

(Six years, $11 million, with NMC)  

Some might view this as a controversial choice, but they shouldn’t. No one is questioning Drew Doughty’s career contributions to the Los Angeles Kings, nor his Hall of Fame resume in the future. But at this point in his career, he is not producing anywhere near what he should for someone who carries a cap hit tied for fifth-highest in the league (and the second-highest amongst defensemen. Spoiler alert: the one defenseman who surpasses him will also appear in this article).

Doughty had 34 points in 56 games this season, which is still fine. He logged 26:23 on average, which is among the highest numbers in the league. But his point share, which measures a player’s contribution to his team’s place in the standings, is down to 5.2, from career highs in the double digits for three consecutive seasons. Those numbers are fine, they just aren’t elite. And an $11 million cap hit is far too high for anyone who is no longer elite. As the Kings approach the end of their rebuild, Doughty’s number could be a roadblock to their making the most of the years ahead.

Minnesota Wild: Mats Zuccarello

(Three years, $6 million, with NMC)

Let there be no mistake: in many ways, the worst contracts on the Minnesota Wild are still the twin contracts given to Zach Parise and Ryan Suter in July 2012. Though GM Bill Guerin finally took the plunge and bought both players out, those contracts will haunt the team for years to come, especially between 2022-2025, when they carry combined dead cap hits of roughly $12.6 million (2022-23) and $14.6 million (2023-24, 2024-25) that will effectively cripple the team in free agency, the trade market, and contract extension talks.

Minnesota Wild Zach Parise Ryan Suter

But, a bought-out contract isn’t officially in the spirit of this article, so for the worst active contract, we turn to Mats Zuccarello, who signed a five-year, $30 million contract in 2019. It’s not that Zuccarello has been particularly bad for the Wild — he hasn’t. In fact, he’s had 72 points in his first 107 regular season games with the Wild. His inclusion here has more to do with his age, 34, and the $6 million free agency premium the team is paying him. Zuccarello may be the greatest-ever Norwegian NHL player by a country mile, but he’s aging and expensive, and with those two buyouts on the books, the Wild cannot afford even an ounce of fat on their books. Guerin would likely be thrilled to trade Zuccarello to a team with excess cap space, given the chance, and may look to do that after the 2021-22 season. Of course, the unnecessary NMC his predecessor gave Zuccarello could prevent even that.

Montreal Canadiens: Carey Price

(Five years, $10.5 million, with NMC)  

Though Carey Price maintains a reputation as one of the best goaltenders in the NHL, the reality is, his numbers haven’t shown it lately. He’s had negative GSAA three of the last four seasons, and his SV% has remained sub-.910 for two straight campaigns. Yes, his workload is intense. But whether it’s age or exposure, he isn’t the goalie he once was. Even after last season’s remarkable playoff run, general manager Marc Bergevin still thought Price’s contract was burdensome enough to ask him to waive his NMC for the expansion draft, which he did. As this list shows time and again, AAV’s greater than $10 million simply do not work out often for older players approaching or within unrestricted free agency, and Price is no exception.

Nashville Predators: Matt Duchene

(Five years, $8 million)

The Nashville Predators have a pair of $8 million cap hit contracts for their two top centers, both of whom are severely underperforming. But, Matt Duchene’s deal is one season longer, and his performance last season was abysmal, so he clearly takes the nod here.

Matt Duchene Nashville Predators
Matt Duchene, Nashville Predators (Jess Starr/The Hockey Writers)

A lot of teams have made big mistakes in the pursuit of a true number one center, and Duchene’s seven-year, $56 million contract certainly seems to have been one. The speedster and former two-time 70-point scorer hit UFA status as one of the hottest free agents in years, especially coming off a strong showing with the Blue Jackets after having been acquired at the trade deadline. Despite the hype, the country music fan’s marriage with Nashville seemed inevitable. Unfortunately, the results have been more “Heartbreak Hotel” than “I Like It, I Love It.” He recorded just 42 points in his first season and dropped to just 13 in 34 games last season. Unless Duchene turns it around, the Predators are stuck with one of the roughest contracts in the league.

New Jersey Devils: P.K. Subban

(One year, $9 million)

P.K. Subban is still a star personality in the NHL, but he is far from the elite, Norris-caliber defenseman he was in Montreal, or even with the Predators. When the Devils acquired him for almost nothing in 2019 (ironically to free up cap space for the Predators so they could sign Duchene), they hoped he could be a veteran influence on a young team with two first-overall picks in Nico Hischier and the then-incoming Jack Hughes. Only the players can know whether he’s served that purpose, but he’s not the player he once was on the ice. And with limited bad contracts on the Devils, Subban was a clear choice for this list.

New York Islanders: Matt Martin

(Three years, $1.5 million)

When general manager Lou Lamoriello managed to move Andrew Ladd’s contract to the Arizona Coyotes, he cleared himself of his biggest headache as far as the salary cap is concerned. But there remains one deal on his roster that is just hard to explain, and that is the four-year, $6 million contract Matt Martin is currently in the second season of. Martin is an enforcer, and this is the second unnecessarily long contract Lamoriello has given him, having signed him to a four-year deal with the Toronto Maple Leafs as well. It’s not that Martin doesn’t bring something to the room. It’s that his role isn’t one a team needs to commit to for four years at a time. The AAV is low, so the damage is minimal. But the Islanders’ accounts are pretty clean right now, so Martin will take the heat for now.

New York Rangers: Jacob Trouba

(Five years, $8 million, with NMC)

The New York Rangers traded for Jacob Trouba after a career season in which he had 50 points in 82 games. Trouba was well known at the time to want a trade and even rumored to prefer the Rangers, so it made perfect sense; however, New York gave up Neal Pionk and a first-round pick (that became Ville Heinola) to acquire the defenseman. They then signed him a month later to a seven-year, $56 million contract before he ever played a game with the team, a classic mistake but one a general manager can’t always avoid.

Jacob Trouba New York Rangers
Jacob Trouba, New York Rangers (Jess Starr/The Hockey Writers)

Trouba has been fine with the Rangers, he just hasn’t been extraordinary. And as one of just 13 defensemen in the NHL to make $8 million a season or more, extraordinary should be the expectation. He’s had just 39 points in 108 games since joining the Rangers and is minus-9 in that time. Meanwhile, teammate Adam Fox has blossomed into a superstar, winning a Norris Trophy last season. To compound matters, Pionk has looked like arguably the more reliable defenseman, though he makes over $2 million less per season, and Heinola is believed to be a future top-four centerpiece. With Fox, Vitali Kravtsov, and Kaapo Kakko all needing extensions after the season (not to mention Alexis Lafrenière after next season), Trouba’s deal will be an obstacle. It’s not that he’s a bad player. He’s just a replaceable player being paid too much. And that can be a disaster in the flat-cap NHL.

Ottawa Senators: Matt Murray

(Three years, $6.25 million)

The Ottawa Senators traded for Matt Murray and signed him to a four-year, $25 million contract extension betting that he would return to form as the two-time Stanley Cup winner that he once was. But early returns are not promising. In his first season, he had an .893 SV%, a 3.38 GAA, and minus-11.0 GSAA. He actually delivered a quality start in more than half of his games but also had eight games defined as “really bad starts” (RBS) with a SV% below .850. The Senators are a young, rebuilding team who need to hit the salary cap floor, so Murray’s contract really doesn’t damage them terribly. But it is the worst of a few bad deals.

Philadelphia Flyers: Kevin Hayes

(Five years, $7.142 million, with NMC)

The Philadelphia Flyers had one of the busier offseasons of any team in the NHL, and in the process rid themselves of the troublesome contracts of Shayne Gostisbehere and Jakub Voráček. They still have several questionable deals on the books, though, and with due respect to a beloved player, none is more suspect than the one given to forward Kevin Hayes.

Kevin Hayes Philadelphia Flyers
Kevin Hayes, Philadelphia Flyers (Amy Irvin / The Hockey Writers)

The Flyers signed Hayes to a seven-year, $50 million contract as a pending UFA by first trading for his rights. The price tag of over $7 million per season immediately felt like an absurd stretch for a player who had only just passed the 50 point mark for the first time in his career, especially since the club tacked on a NMC. Hayes actually has fit in well in Philadelphia and is a beloved, heart-and-soul type player admired around the league. But that cap hit is still too much, especially in a flat-cap era. Plus, as a 6-foot-5, 216 pound, physical forward, his game isn’t likely to age gracefully. Some Flyers fans may disagree, but over time, Hayes’ contract is likely to look worse and worse.

Pittsburgh Penguins: Mike Matheson

(Five years, $4.875 million)

In trading Patric Hornqvist for Mike Matheson, the Pittsburgh Penguins offloaded a troublesome contract, but they brought one back as well. Matheson is a fine young defenseman, but he doesn’t offer any contribution substantial enough to justify a $4.875 million annual contract. He is middle of the pack on the team in on-ice xGF%, and in the bottom third in on-ice CF%. And with 107 points in 343 career games, he isn’t a point producer, either. Matheson isn’t a terrible player by any means, but his contract is too much and too long and will hinder an already cap-strapped team.

San Jose Sharks: Erik Karlsson

(Six years, $11.5 million, with NMC)

Erik Karlsson was once the best offensive defenseman in the NHL, and, in his prime, was among the best point-generating blueliners in the history of the game. But those days are gone, and the many remaining years on his contract are not.

San Jose Sharks Erik Karlsson
San Jose Sharks defenseman Erik Karlsson (AP Photo/Jeff Chiu)

Athletes are inevitably paid for past production rather than future production, but Karlsson may be the worst case in the league. His skating seems lost, and he’s collected just 107 points in his first 161 games in San Jose. He’s middle of the team in on-ice CF% and xGF%. Karlsson would still be a valuable player on the right contract. But with the fourth-highest cap hit in the league, his is a devasting deal that has helped force the Sharks into a rebuilding phase.

Seattle Kraken: Brandon Tanev

(Four years, $3.5 million, with M-NTC)

On a brand new team with very few original contracts, it’s unfair really to choose any deal, but we’ll finger Brandon Tanev’s four years remaining with a $3.5 million AAV as the worst contract on the Seattle Kraken. He’s an okay middle-six player but his career-high of 29 points doesn’t justify committing either as much time or as much money to him as he’s earning now. Obviously, the Kraken were comfortable taking his deal in the expansion draft, so they can’t be too concerned with it, and at present, they’re not in any danger of hitting the cap ceiling, but someone had to earn this spot on the list.

St. Louis Blues: Vladimir Tarasenko

(Two years, $7.5 million, with NTC)

No entry better portrays how quickly things change in the NHL than Vladimir Tarasenko’s presence on this list. Just two years ago, he would have been considered the best value on the St. Louis Blues’ roster, or many other rosters, for that matter. But serious injuries and strife with the team have left him a shell of his former self, and a discontented player who wants out of town. The summer saw the Blues try to trade him and fail to find any interested parties who would take on his contract (without salary retention), and now he’s entering the season playing for a team he no longer feels comfortable on. It will be his chance to prove his value and his health and potentially earn his trade, but until he’s gone, his contract will be a $7.5 million logjam on the books.

Tampa Bay Lightning: Ryan McDonagh

(Five Years, $6.75 million, with NTC)

Can the perfect NHL franchise and two-time Stanley Cup champion really have a bad contract? Barely. The Tampa Bay Lightning have been notoriously precise with the salary cap, and their latest deal, bringing in Seabrook’s contract to manipulate the LTIR and trading Johnson in the process, left them without one obvious choice for this ignoble distinction. The two remaining options who are remotely deleterious to their overall contract situation are captain Steven Stamkos (merely because of injury) and defenseman Ryan McDonagh, due to term and role. We’ll choose McDonagh by a hair.

Ryan McDonagh, Tampa Bay Lightning
Ryan McDonagh, Tampa Bay Lightning (Amy Irvin / The Hockey Writers)

McDonagh is a perfectly fine top-four defenseman. But on a team where every dollar counts and a team that produces future talent like the Hoover Dam produces electricity, a five-year deal for an aging defenseman could be more cumbersome over time. The team doesn’t rely on him for point production, but he has just 24 points in his last 100 regular-season games. In spite of that, they’ve won two Stanley Cups, and no one in Tampa has any hard feelings toward McDonagh. But somebody has to hold down this spot, and he’s the most obvious answer right now.

Toronto Maple Leafs: John Tavares

(Four years, $11 million, with NMC)

There’s no question that John Tavares remains one of the premier centers in the NHL, but he didn’t rank among the top 10 in a recent front office ranking organized by ESPN. He carries the sixth-highest cap hit in the NHL (though his teammates Auston Matthews and Mitch Marner rank third and seventh). The narrative for signing the hometown kid who was the most coveted free agent in recent memory was obvious. And Tavares currently has 198 points in 201 games for the Toronto Maple Leafs. So he hasn’t really done anything to earn derision.

The problem with Tavares’ contract is his circumstances. The deal undoubtedly drove up the value and the temperature in negotiations with Matthews, Marner, and even William Nylander. And now Tavares is approaching the end of his prime, likely to decrease in output substantially over the next several seasons. When the Maple Leafs need to re-sign Matthews after the 2023-24 season, they’ll need to navigate the final season on Tavares’ contract to do it. One could easily pick on Alexander Kerfoot’s deal as the worst in Toronto, given the high cap hit for a bottom-six forward. But Tavares’ deal has haunted the Maple Leafs already, and those unfortunate circumstances are likely to continue.

Vancouver Canucks: Oliver Ekman-Larsson

(Six years, $7.26 million (Arizona retains $990,00 per season) with NMC)

By trading Jay Beagle, Loui Eriksson, and Antoine Roussel to the Coyotes, Vancouver Canucks GM Jim Benning rid himself of three small headaches. But he arguably packaged them to trade for one big headache, the long and expensive contract of Oliver Ekman-Larsson.

Ekman-Larsson may have something valuable to offer a team at the right price tag. But there’s no question that over $7 million a season for seven more seasons is not the right price. His offseason production has dropped off, from a career-high of 23 goals in 2014-15 down to just three last season. And while defense was never the best part of his game, it seems to have gotten worse in recent seasons. The Canucks are gambling that a fresh start and some salary cap relief will make Ekman-Larsson a more viable defender, but given the difficulties they are having signing Elias Pettersson and Quinn Hughes to contract extensions, Ekman-Larsson’s deal is already an obstacle for his new franchise.

Vegas Golden Knights: Alex Pietrangelo

(Six years, $8.8 million, with NMC)

Is it too early to condemn Alex Pietrangelo’s one-year old new contract with the Vegas Golden Knights? Maybe. But on a team that was already among the best in the NHL, signing the top free-agent defenseman always felt like something of an extravagance. The Vegas front office has earned a reputation for impatience and tinkering, and Pietrangelo is the prime example: bringing in another huge contract despite consistent playoff success. Plus, they traded Nate Schmidt for peanuts and upset their locker room to make the deal fit.

Pietrangelo is a top-line right-handed defenseman, and those should cost a premium. But he struggled to stay healthy in his first season in Vegas and finished with 23 points in 41 games. He was a standout player in the Golden Knights’ postseason run, but that didn’t get them any farther than they had been in previous runs. It’s not that he isn’t still a fantastic player. It’s that the Golden Knights are committing to him through his age decline on a backloaded deal as a luxury on a team that was already very good. Vegas could live to regret this signing in a flat-cap era.

Washington Capitals: T.J. Oshie

(Four years, $5.75 million, with M-NTC) 

T.J. Oshie is still a skilled top-six player at this point in his career. He was a major factor in the Washington Capitals’ Stanley Cup run, scoring 21 points in 24 games. He’s also a fan favorite and a U.S. Hockey legend, with his incredible shootout performance in the Sochi Olympics. There’s no questioning why the Capitals wanted to keep Oshie around for the long haul.

T.J. Oshie Washington Capitals
T.J. Oshie, Washington Capitals (Jess Starr/The Hockey Writers)

But in this case, the haul was a few years too long. He will be 37 by the end of his current deal, and there’s no reason to believe his level of play will hold up that long. At almost $6 million per year, that’s a big gamble for Washington. The Capitals are still a dangerous team, but as they age, Oshie’s contract is likely to look worse and worse.

Winnipeg Jets: Adam Lowry

(Five years, $3.25 million, with M-NTC)

Before we criticize too quickly, let’s be clear that the Winnipeg Jets have one of the cleanest contract sheets in the league, and choosing a “worst” contract wasn’t easy (especially as Bryan Little’s deal will likely be buried on LTIR in perpetuity). But in signing Adam Lowry to a five-year, $16.25 million contract extension last spring, GM Kevin Cheveldayoff made the classic mistake of signing an average-but-popular player to too friendly a contract. Lowry’s never passed 30 points in a season, and his metrics aren’t especially friendly, either. He’s a fine player. But not the kind of player you need to commit to for five seasons. Everyone knows the struggles Winnipeg faces to acquire free agents or keep players with expiring contracts, so this might be an overpay to prevent another departure. It’s not a disastrous deal, it’s just a little too rich for a bottom-six player.

Spending Never Stops

Many speculated whether the flat-cap era would lead to a new and more cautious approach to contracts, but a quick look at the dealings this offseason makes it clear that won’t be the case. GMs signed several contracts that will almost certainly appear on this list in future seasons, and money flew around on free agency day with wreckless abandon. Some things never change, and bad contracts in the NHL fit right in alongside death and taxes.