These Mid-Season Contract Extensions Have Not Aged Well

This year has been unique for in-season contract extensions, as a rising salary cap put pressure on teams to lock up their pending free agents before they could even sniff the open market. What once looked like a promising free-agent class in the summer of 2026 quickly turned into a very thin market void of big names and impact players. Some of those extensions were signed with players who had thrived in previous years and/or started the season well, but faltered after signing their big new contract, leaving teams in a tough spot heading into the summer. Here are five contracts that the signing teams would presumably like to have back.

The first player on our list could very well turn things around next season, and that is Dallas Stars defenseman Thomas Harley. The 24-year-old inked an eight-year, $84.7MM contract extension at the end of October ($10.587MM AAV), and it made perfect sense at the time, as Harley was the 15th-highest-scoring defenseman in the NHL over the previous three seasons, with 105 points in 166 games, and played a solid defensive game as well. However, he struggled this past season, posting his lowest offensive numbers in three years and struggling to drive play. Harley lacked a solid partner for much of the year, but given his new salary cap hit, the hope would be that he could overcome that obstacle, especially considering Dallas doesn’t have the cap space to really look at upgrades on their back end. Harley has plenty of time to turn things around, and he likely will, but Stars management has to be a little nervous about the deal they inked and the long-term ramifications if Harley can’t get his game back next season.

Sticking with Western Conference defensemen, Jake Walman of the Edmonton Oilers was a colossal disaster after signing his seven-year, $49MM extension with the team. The 30-year-old had been terrific after a trade from the San Jose Sharks, but after signing his extension in October, Walman began to struggle and never returned to his form for most of the season. Walman’s signing was made because Oilers management believed he was a good fit for the team’s style, with his solid first pass and heavy shot. But many of the warts in Walman’s game became evident as the season went on. He isn’t physical, he turns the puck over too much, and he doesn’t play a full season. These issues aren’t exactly unique, but for a player being signed to a $7MM AAV, you’d hope he would give you more than 21 points a season, something Walman has done just once in his NHL career. A big issue for the Oilers and Walman is that his contract will take him from his age 30-37 seasons, and at this point he is a finished product. It’s clear Edmonton overpaid to retain his services.

Moving up front, the Winnipeg Jets were quick to re-sign their captain Adam Lowry to a five-year, $25MM contract extension in late November. The deal looked fine at the time, though there were concerns about his age, as he was 32 at the time of signing, and five years is a long time for a player who plays the way he does. Lowry remains a solid shutdown center who can skate, outwork his opponents, and tilt the ice in the Jets’ favor. But given his age and style of play, it’s fair to wonder how much longer he can serve as a Jets top-nine center before his body breaks down and he is relegated to fourth-line duties. It’s a tough spot for Winnipeg because Lowry is a heart-and-soul player, but five years for him is a long time, and it’s a contract the Jets would probably like to renegotiate. Given the history with Lowry, the Jets would no doubt love to keep him in the fold, but at a lower cap rate.

Another late-October extension (two years, $12MM) was New Jersey Devils goaltender Jacob Markstrom, who had a decent first season with the Devils but was awful in his second year. The timing of this one was particularly peculiar, as Markstrom was off to a very slow start in October 2025, posting a 5.13 GAA and a .830 SV% in just four appearances. He was also coming off a lower-body injury and was 35 years old at the time, making the timing of the signing even stranger. Obviously, the Devils were concerned he might go on a heater and raise the price tag, but that never happened as Markstrom struggled through much of the year, finishing with a 3.07 GAA and a .883 SV%. Those numbers are clearly concerning, but the silver lining is that Markstrom has a history of struggling through a season and bouncing back the following year to get into Vezina Trophy contention, so a bounce-back season in 2026-27 can’t be discounted. However, for now the Devils must be looking at Markstrom’s $6MM AAV and wondering how much lower the number could have been or whether they should have gone in a different direction.

Finally, we have Detroit Red Wings defenseman Ben Chiarot, who inked a three-year extension this past January worth $3.85MM per season. The 35-year-old has his strengths, as he is reasonably good at skating and can move the puck. He’s also incredibly physical, playing on the edge much of the time and displaying a high level of orneriness in the defensive zone. But that is where his strengths wear off, and his weaknesses are becoming more glaring as he ages. Chiarot has been a drain on whoever he is paired with, particularly on the possession front, and he has posted the worst Wins Above Replacement score for two consecutive regular seasons (as per hockeystats.com). Chiarot can still be an effective defenseman in the NHL, but not in the top four, and that’s where Detroit may need to deploy him once again next season.

None of these contracts are going to be especially crippling to a team, but they do show how quickly the shine can wear off a high-priced extension and how much pressure teams are under to extend their players, thanks to a rising salary cap and many teams’ possession of additional cap space, chasing a few available players.