In a salary cap world, having a bad contract on your roster can absolutely cripple your GM. Expensive deals on low-impact players can inhibit a club’s ability to make trades, and sometimes it can mean that they can’t chase high-profile UFAs.

It’s safe to say that, behind closed doors, every GM in the league regrets at least one contract he currently has on the books—for some of them there are probably a few that are causing ulcers.

When you look at the salaries across the league today, it’s interesting to note that it’s not just the bad teams that have bad contracts on record. Indeed, some of the perennial contenders are anchored with bad deals, and some of those bad deals were signed as a direct product of the success they’ve had.

Today we take a look at the 15 worst contracts across the league. Although the GMs won’t admit it publicly, I’d bet that each of these contracts keep them up at night as they rue the day they signed these deals (or in some cases, traded for them). You’ll find most of the deals on this list have term attached to them (with a few notable exceptions), as term is really what hinders a GM’s ability to move and shake in the market.

Here are the Top 15 Current NHL Contracts Teams Are Seriously Regretting, starting with a few double entries. Enjoy:

15. Daniel/Henrik Sedin

Marc DesRosiers-USA TODAY Sports

With just one year left on their identical $7M AAV contracts, the Sedin brothers won’t be crippling the Vancouver Canucks for too much longer, but today they’re really inhibiting the club’s ability to move into full-on rebuild mode. The Swedish twins are still fine players, but far removed from the elite level they were at when the contracts were signed.

If only one player of the Sedins’ ilk was on a payroll at $7M, it wouldn’t be such a huge deal. With their full no-move clauses, they would have to approve of any trade before it happens. Judging by how well they do in the Vancouver community and the fact that their families are firmly situated in Van City, it’s unlikely the Sedins leave Vancouver any time soon.

14. Jonathan Toews/Patrick Kane

Dennis Wierzbicki-USA TODAY Sports

Our second and final “double-entry” on the list is the duo of Jonathan Toews and Patrick Kane in Chicago. Look, these are two of the league’s best forwards. Kane’s offensive ability is among the best in the NHL, and Toews is no slouch himself, and it’s universally agreed that the captain brings with him an elite two-way game and a basket full of intangibles.

However, having $21M tied up between two forwards for eight seasons is a pretty good way to ensure that you’ll have trouble finding a reliable support cast moving ahead. This issue hasn’t come to roost for the Blackhawks yet, but they’ll be feeling it three or four years down the road. This entry could also include Brent Seabrook as well, as with his salary, the three of them take up nearly $30M in cap space.

13. Andrew MacDonald

Kim Klement-USA TODAY Sports

Andrew MacDonald is currently in year three of the six-year deal he signed with the Flyers in 2014. The contract comes with a $5M cap hit, and when you consider that the defenseman played 43 games with the Leigh Valley Phantoms last season, it’s obviously a pretty bad deal for Philly. He’s bounced back to become at least a regular in the lineup this season, but sorry, that’s not enough.

What makes it worse is that Philly is almost always a cap team, meaning they have very little wiggle room to make moves. GM Ron Hextall would probably sleep a lot better and breathe a lot easier if he could trim that pesky MacDonald contract off the books. The 30-year-old is under contract until 2020 though, so that’s a pipe dream at this point.

12. Jori Lehtera

Billy Hurst-USA TODAY Sports

Finnish center Jori Lehtera decided to make the move to North America a little later than most, as he came over to St. Louis as a 26-year-old in 2014. His rookie season was a little up and down, but he did produce 44 points and showed promise as a legitimate two-way forward prospect. The Blues decided they’d seen enough from Lehtera and inked him to an extension in the 2015 offseason—a three-year deal that comes with a $4.7M cap hit and didn’t start until this season.

Lehtera’s sophomore season was a step back offensively, as he scored 10 fewer points in a few more games. The Blues were hoping this was just the dreaded sophomore slump, but Lehtera is actually scoring at an even lower rate so far this season. I bet the Blues were wishing that they didn’t have that contract on the books, as maybe they’d be able to retain the services of Kevin Shattenkirk beyond this season.

11. Shea Weber

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Shea Weber burst out of the gate at the start of this season, re-energized by the change of scenery. He was blasting power play goals in from the point at an impressive rate, and fans in Montreal were finding it easy to forget that the acquisition cost them P.K. Subban. Weber has come back to Earth since, and is actually producing five-on-five offense at a worryingly low rate.

Pair these points with the fact that Weber is 31 years old (prime time to begin a regression) and is under contract through his 40th birthday. That contract also comes with a hefty $7.9M cap hit, which is a somewhat reasonable price for the rearguard now, but how about in 2020? And if it still looks good then, will you feel confident that it will also look good in 2023?

10. Johnny Boychuk

Kim Klement-USA TODAY Sports

Sometimes players will catch fire for a few months straight, and if they do this at the right time it can earn them a sweet contract. That’s pretty much what happened with Johnny Boychuk and the Islanders back in March 2015. The Edmonton native was having the best season of his career and was a pending UFA; Garth Snow signed him to a seven year deal that came with a $6M cap hit.

This contract isn’t absolutely terrible today, but it will be soon. Boychuk has already celebrated his 33rd birthday, and he’ll be 38 by the time his contract expires. I’ve said it a few times before, but early 30s is the common age for a player of any position to begin his regression. It’s puzzling to me how many teams are willing to pay premium prices for players who have already peaked.

9. David Backes

Bob DeChiara-USA TODAY Sports

The 2016 offseason had its share of high-profile signings, and one of them was the contract the Bruins inked former Blue David Backes to on July 1. The deal is five years long, and it comes with a cap hit of $6M. If what Backes has done so far this season in Beantown is any indication of what is to come, then the Bruins are probably already sweating this deal.

Backes is on pace for the lowest point total of his career since 2007-08 (not including the lockout year). It’s not like he’s completely fallen off the face of the Earth like a few other guys you’ll read about later on in the article, (he’s notched 12 goals and 26 points in his 50 games thus far), but the drop off in production has to have fans worrying at least a little bit.

8. Dion Phaneuf

Sergei Belski-USA TODAY Sports

This entry comes with an asterisk, as former Sens GM Bryan Murray actually traded for the contract that is currently hampering GM Pierre Dorion and the Ottawa Senators blue line. Dion Phaneuf was acquired in a blockbuster just over a year ago, and I often wonder what Murray was thinking here. Was he not aware of the term attached to the contract? Because it’s a major issue.

The deal comes with a $7M annual cap hit, and it carries through 2020-21. Phaneuf impressed a lot of people when he broke into the league as a rookie in 2005-06, scoring 20 goals in his first year in the league. He was great pretty much the whole time he was in Calgary, but his regression began when he was traded to Toronto.

7. Frans Nielsen

Kim Klement-USA TODAY Sports

The Red Wings made a free agent splash last summer by signing Frans Nielsen to a six year contract that comes with a $5.25M cap hit. The Wings are currently experiencing the downside of paying premium dollars to an aging, regressing player in Henrik Zetterberg, so it’s curious as to why they added a second contract that has equal capability to anchor the team moving forward.

It’s not that Nielsen is having a terrible season with the Wings or anything. His 27 points in 56 games so far is only slightly below is career average, but it is well below his career high of 58, set in 2013-14. That’s why it’s safe to say that Nielsen is over the hill, and the Red Wings will be paying the Danish center a pretty decent wage to be mediocre (at best) for five more seasons after this one.

6. Mikkel Boedker

Isaiah J. Downing-USA TODAY Sports

The San Jose Sharks are a great team, but as I said earlier even great teams sign bad contracts every now and then. In the 2016 offseason San Jose signed veteran winger Mikkel Boedker to a four year contract that pays the Dane $4M per season. He earned this deal by finishing strong in Colorado last season, recording 12 points in 18 games after being traded from Arizona at the deadline.

The Sharks probably should have looked at Boedker’s career as a whole rather than the last 18 games of one season. Had they done that, they’d realize that 30-40 points is what they should reasonably expect from Boedker. In a cap league, $4M is a lot of money to be paying a guy who scores rarely AND doesn’t bring much else to the table (he doesn’t figure in on the club’s special teams much).

5. Loui Eriksson

Anne-Marie Sorvin-USA TODAY Sports

Loui Eriksson came to the Vancouver Canucks in the offseason with fans hoping they’d finally found the right winger to play with the Sedin twins. The list of “best wingers to ever play with the Sedins” is topped-off by Alex Burrows and Anson Carter, so needless to say they haven’t had their dream winger quite yet. Unfortunately, so far it looks like Eriksson isn’t the answer.

The real problem for the Canucks here is term. Eriksson is set to make $6M/season through 2021-22. Conventional wisdom tells us that the Canucks should be shifting gears into full rebuild mode—the Sedins have one year left on their deals, and Vancouver’s playoff odds sit at about 2.3% according to Sports Club Stats—so this is not a great contract to have on the books.

4. Bobby Ryan

Sergei Belski-USA TODAY Sports

Bobby Ryan is Ottawa’s highest paid player, which wouldn’t be a huge problem if not for the fact that he’s producing points at a rate slower than six forwards and two defensemen on his own team so far this year. It also wouldn’t be such a huge problem if he were, say, heading into the final year of the deal that pays him $7.3M per season, but alas that is not the case either.

The Sens are on the hook to pay Ryan for five more seasons beyond the present one, meaning that they are basically saddled with an immovable contract through 2021-22. When depth forward Zach Smith and sophomore Ryan Dzingel are outscoring you and you’re Bobby Ryan, you know there might be a problem.

3. Ryan Callahan

Kim Klement-USA TODAY Sports

The Tampa Bay Lightning were heading into the season as favorites to win the Atlantic Division, but things have gone sideways for Tampa. An early season serious injury to captain Steven Stamkos derailed them, and they haven’t been able to stay in the race. Their highest paid forward (aside from Stamkos) is Ryan Callahan, and that’s a problem not only because he’s not all that productive, but because it also has a no-move clause attached.

Callahan will count as $5.8M towards the Lightning cap until the end of 2019-20, so three more seasons after this one. Expansion causes a whole other problem for Tampa, as they are now forced to use a protection spot on Callahan. This means that, in all likelihood, they’ll be forced to leave a superior forward unprotected—perhaps even Alex Killorn, whose value is much higher than Callahan’s today and in the future.

2. Milan Lucic

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Things are going pretty well in Edmonton these days, something I haven’t been able to say in over 10 years. Connor McDavid and Cam Talbot have led the club to, as of now, appears to be a sure playoff berth for the first time since 2006, and they could even take a run at the Pacific Division title with a strong finish. However, the elephant in the room is the lack of five-on-five production from Milan Lucic.

GM Peter Chiarelli signed Lucic to a seven-year deal in the offseason that comes with a cap hit of $6M. When the deal broke, most people assumed that the deal would become a problem at some point during the seven years, but figured they’d get a good three or four years out of the hulking winger. Lucic is producing five-on-five offense at a rate similar to that of Jack Skille and Ryan Reaves. So, yeah.

1. Dustin Brown

Kirby Lee-USA TODAY Sports

Dustin Brown will always be a legend in Los Angeles, as he captained the club to its first two championships in 2012 and 2014. That first performance earned him a fat contract that will pay him $5.8M through 2021-22, and that’s really a shame because his game has taken a fast nose-dive. Brown has lost the captaincy to Anze Kopitar, and is awkwardly playing out the remainder of his deal in L.A.

Brown is the second-highest paid Kings forward after Kopitar. He signed the extension in the 2013 offseason, at which point his offense essentially disappeared completely. Although he’s producing at a slightly higher rate this season than the past few, the winger has averaged 27 points since his deal kicked in, whereas he was around the 55 point mark prior to the start of the contract.

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