Worst contracts signed in 2023 NHL free agency so far

Free agency has always been looked at as the time for teams to make some adds without having to give up assets in a trade or use the draft picks and in-house resources required to develop prospects. It’s like someone else put all the work into that player for you, and you just have to open the wallet to have them on your team.

Except in a salary cap world, spending money can also cost you. All the trades we’ve seen where a third team is involved to retain some salary for a draft pick, or a team takes on a bad contract along with assets for nothing in return, have proven that cap space is just as big of an asset. That makes it all the more important to spend it wisely, and there are plenty of opportunities for a team to do the exact opposite.

I’m looking at those opportunities, listing off some of the worst contracts handed out so far in free agency. Some come at absurdly high cap hits and some come much longer than they should, but all of them are easy to see aging poorly. I did a prediction of which players would get bad contracts this year before free agency started, and four of them ended up on this list, which just goes to show how easy it is to see coming, and how easy it should have been to avoid them.

To start, here are a few honorable mentions, deals that aren’t quite as bad as other contracts given out but could still cause problems for their teams.

Ivan Barbashev, Vegas Golden Knights ($5M x five years) – I highlighted Barbashev in my buyer beware article last month, and while I do think the contract is a bit lengthy and bit pricey, my biggest concern was that he plays better on the wing than down the middle. By re-signing with Vegas, he likely avoids that because they’re set down the middle with Jack Eichel, William Karlsson, Chandler Stephenson, and Nicholas Roy, with all but Stephenson signed for at least the next three seasons. And if Barbashev’s contract does become a problem, we know Vegas will have no issue moving on from it.

Justin Holl, Detroit Red Wings ($3.4M x three years) – I don’t hate Holl as much as a lot of other people who’ve watched him regularly seem to, but I was surprised to see him get this much considering the playoff performance he was coming off of. He’s a solid defender that can play in a shutdown role with a good defenseman in a pinch, but it just feels like way too much for him at age 31. And as I’ll get into another Red Wing contract, it feels like it will just get in the way of their incoming young talent.

Tristan Jarry, Pittsburgh Penguins ($5.375M x five years) – Jarry was probably the best goaltender on the market, but the biggest concern for him has always been health, so it’s bold to bet Sidney Crosby’s, Evgeni Malkin’s, and Kris Letang’s final Stanley Cup aspirations on Jarry finally staying healthy. It certainly could work, and Pittsburgh doesn’t really care about the final couple of years being a hindrance for their cap anyways. It is a weird contract to see Kyle Dubas hand out, considering the most term he’s given to a goalie prior to this that wasn’t an entry-level contract was Petr Mrazek and Joseph Woll at three years.

Ryan Reaves, Toronto Maple Leafs ($1.35M x three years) – The fact that this contract can end up as only a $200,000 cap hit if it’s buried in the minors saves it a bit, but giving a 36-year-old three years is rarely a good idea, nevermind to a big, slow enforcer who’s already seen his play fall off. The cap hit is minimal regardless, but the big factor will be if he ends up taking away ice time from better players down the road if he becomes a coaching blind spot, which in turn keeps him up in the NHL and the cap hit $1.15M more, all as the Leafs need to penny pinch with the Core Four’s contracts coming up in the next few years.

J.T. Compher, Detroit Red Wings

Five years, $5.1M AAV, 10-team no-trade clause

Look, I understand why this contract is what it is. I addressed it last month in my article predicting which players might get overpaid on the market. There weren’t a lot of quality centers in this year’s free agency class. It slightly improved from when I wrote that piece due to some of the buyouts, but even then it was still slim pickings. That alone was going to see Compher get an overpayment, never mind the fact that he put up a career year and positioned himself as one of the best centers in that weak market. He’s a fine player, and if he can stay at the level he played at this past season, this contract won’t be that bad, although it’s still a big bet.

That almost convinced me to not include this contract, but what keeps it on the list is the fact that it just doesn’t make sense for Detroit. They made a similar signing last season with Andrew Copp, so while that gives them a reliable 1-2-3 punch down the middle with those two behind Dylan Larkin, neither is a strong No. 2 option. The back-and-forth decisions from the Red Wings also have me questioning the Yzerplan, as GM Steve Yzerman jumped the gun signing veterans who weren’t game-breakers last season for a team not ready to take that next step, backtracked later in the year when it failed, and is now doing it again this season.

Compher is a solid player, but the Wings now have eight forwards who are 26 or older, and only one is a high-end talent in Larkin. The rest are solid players who would help surround a playoff team, not a rebuilding team, and all they do now is just block the young talent they’ve assembled from developing in the NHL and actually getting playing time.

Pierre Engvall, Scott Mayfield, & Semyon Varlamov, New York Islanders

Pierre Engvall: Seven years, $3M AAV, 16-team no-trade clause
Scott Mayfield: Seven years, $3.5M AAV, Full no-trade clause 2023-24 to 2026-27, 16-team no-trade clause 2027-28 to 2029-30
Semyon Varlamov: Four years, $2.75M AAV, Full no-trade clause first two years, 16-team no-trade clause final two years

There’s another team that has multiple entries on here, but I decided to group this trio of signings by the Islanders because they all share one thing in common: too much term. I always remember a Steve Simmons tweet of him thinking back to something Lou Lamoriello once complained about with most big contracts and how it’s always too much money and too much term, and it’s ironic because Lamoriello is one of the worst for giving out too much money for too much term, and this is a fantastic example of the latter.

In a vacuum, I don’t mind these deals. Semyon Varlamov has been a quietly solid goalie behind Ilya Sorokin (who also got a big extension at the same time as these three, but on a much better contract), Scott Mayfield is a great top-four defender, and while Pierre Engvall gets a lot of hate for being a big body that doesn’t hit, there’s a lot of things he does well.

They’re all good players, and I’d take them at those cap hits right now, but not in the later years. Engvall is the youngest of the bunch and he’ll be 34 when his contract expires, and Mayfield will be 37 when his expires. And Varlamov is 35 now! Giving goalies terms is never a good idea, never mind when they’re approaching their twilight years. These three contracts have the potential to age very poorly and I’m intrigued to see what happens with them.

Radko Gudas, Anaheim Ducks

Three years, $4M AAV, Full no-trade clause year one, 16-team no-trade clause year two, 10-team no-trade clause year three

When Gudas signed his three-year deal with the Florida Panthers in 2020, I remember it being something that drew a couple of red flags, mostly just due to the term, the fact that he was 30, and his physical style of play being something that could cause his game to fall off a cliff very quickly. I ended up being wrong, as he was quite solid throughout the deal, but now he’s three years older and his body has more miles on it, so giving him term again is a bit risky. Not only did the Ducks give him the same term as the Panthers did, but he also got a $1.5M raise on top of that.

He’ll certainly add a steady presence on their defense and essentially replaces Kevin Shattenkirk as the veteran on the blueline, but that’s still a steep price for Gudas. If you’re going to overpay for a physical stay-at-home defenseman, Gudas is one of the few that actually brings the play to back it up, but at his age, it could get worse in a hurry.

It certainly doesn’t help a rebuilding team in the Ducks either when he’s going to essentially block a roster spot for the numerous defensive prospects in Anaheim, especially when that cap hit is going to complicate things even more when their young players get off their entry-level contracts and the Ducks can’t afford all of them.

Alex Killorn, Anaheim Ducks

Four years, $6.25M AAV, Full no-trade clause first two years, 15-team no-trade clause final two years

This contract had the second-largest cap hit among non-extension contracts this summer, and… it just doesn’t really make sense to me. I get why; hockey teams can’t help themselves from drooling all over experienced veterans, and he is coming off a career year. But I figured both his age and the fact that he was playing alongside Steven Stamkos and Anthony Cirelli for most of the past two seasons was going to scare some teams off, so he was maybe going to end up with an overpayment on either term or money on this deal, but I was not expecting both.

Killorn is an excellent player, but it’s also quite clear that the traits that made his market value as high as $6.25M were partially a product of his environment. I like Trevor Zegras as much as the next guy, but he is no Stamkos or Nikita Kucherov or Brayden Point right now, so you likely aren’t going to get that same level of success that he got in Tampa Bay.

He’ll definitely be a great mentor for the young group coming up, but $6.25M for four years is a high price to pay for that, especially when, like Gudas, that cap hit is going to block a few young guns when they get off their entry-level contracts in the next few years.

Joonas Korpisalo, Ottawa Senators

Five years, $4M AAV, 10-team no-trade clause

This deal isn’t so bad as much as it is a huge gamble. Korpisalo had a solid season with the Columbus Blue Jackets and stepped up his play a bit more behind a much better Los Angeles Kings team. He even had a good start to the playoffs when the Kings had the 2-1 series lead, with the other three being games to forget, but you can only slow down Connor McDavid and Leon Draisaitl for so long. If last year was a new Korpisalo, this is a solid addition for a Sens team in desperate need of consistent goaltending.

The problem is that Korpisalo’s career hasn’t been consistent. This season was one of just three in his eight-year career where he finished above a .905 save percentage and one of three where he had a positive 5v5 goals saved above expected, so you can’t just blame the team in front of him either. On top of that, he hasn’t started more than 39 games in a season, so if the Sens are looking to give him a starter’s workload, that’s going to be an adjustment.

Basically, this signing is gambling a lot on a career year being more than a career year, or that the Senators defense is good enough to cover up his mistakes, which it might not be just yet. And of course, giving term to any goalie that isn’t consistently elite is never a good idea, and Korpisalo has been a perennial backup for most of his career. This could be a decent add, but it’s a bit too high-priced to be a safe bet, and all previous signs point to this not turning out well.