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.
Oilers Activate Tristan Jarry, Jake Walman
The Edmonton Oilers are nearly back to full force. According to a team announcement, the Oilers have activated goaltender Tristan Jarry and defenseman Jake Walman from their long-term injured reserve.
The moving parts don’t end there either. In the same announcement, Edmonton shared that they’ve moved veteran forward Adam Henrique to the long-term injured reserve, and have converted netminder Connor Ingram‘s emergency recall into standard one.
Despite being acquired a month ago, the Oilers have seen very little of Jarry. In only his third game with the team, Jarry left the contest with a lower-body injury and hasn’t played since.
Throughout his brief intro to the team, he played relatively well, being credited for three wins in his three starts. However, much of that had to do with the performance of the team in front of him, as Jarry only managed an .887 SV%, 3.08 GAA, and -0.7 Goals Saved Above Average (GSAA).
It is still too small a sample size to accurately predict his future performance in Edmonton. Before the trade, Jarry had managed a 9-3-1 record in 14 games with the Pittsburgh Penguins with a .909 SV%, 2.66 GAA, and 4.8 GSAA.
Meanwhile, the Oilers will get a major boost to their defensive core with the return of Walman. The 29-year-old blueliner hasn’t played since late November due to a lower-body injury, missing the team’s last 23 games.
Before the injury, Walman was his typically steady self, scoring three goals and 10 points in 17 games while averaging more than 20 minutes per game. Still, Edmonton will want more stability from him on the defensive side of the puck, as he’s only managed an 85.4% on-ice SV% at even strength this season.
On the other side of the transaction, the Oilers have expectedly moved Henrique to the LTIR. The 16-year veteran suffered an undisclosed injury on January 6th and isn’t expected to return until after the Olympics.
Lastly, Edmonton will surprisingly move forward with three netminders on the active roster. Despite having a disastrous performance with the AHL’s Bakersfield Condors, Ingram has provided some stability in net for the Oilers of late. In his first year with the organization, he has managed a 4-2-1 record in seven games with a .904 SV% and 2.70 GAA. If he continues his success, fellow netminder Calvin Pickard‘s days with the team could be numbered.
Edmonton Oilers Reassign Riley Stillman
The Edmonton Oilers have shedded one of their depth defenseman off the active roster. According to a team announcement, the Oilers have reassigned Riley Stillman to the AHL’s Bakersfield Condors.
Stillman, 27, has been with Edmonton for nearly a month. He was recalled on December 12th, and has been enjoying his time as the team’s seventh defenseman since. Despite being on the team for that long, he has only appeared in four games, scoring zero points while averaging just over 12 minutes of ice time per game.
He’ll return to a Condors club where he’s already registered 22 games on the season. Still, it’s been a fairly disappointing first year with the team, scoring two goals and seven points with a -8 rating. Still, if he continues on his current pace when he returns to the lineup, he’ll reach double-digit point totals for the second time in his AHL career.
It’s been some time since Stillman was a consistent player in the NHL. During the 2021-22 and 2022-23 campaigns, Stillman skated in 102 games between the Chicago Blackhawks, Vancouver Canucks, and Buffalo Sabres, scoring three goals and 20 points with a -21 rating, averaging 14:51 of ice time per night.
Since the Oilers didn’t make a corresponding roster move, it gives credibility to the idea that Jake Walman will return to the team soon. Mark Spector of Sportsnet hinted as much today, indicating that Walman is expected back in the near future.
Walman, who is one year away from beginning his seven-year, $49MM extension in Edmonton, hasn’t appeared in a game since November 20th when he went down with a lower-body injury. He skated in 17 games before the injury, scoring three goals and 10 points in 17 games with a -3 rating, with a 49.0% CorsiFor% at even strength.
Oilers Recall Max Jones, Place Clattenburg, Roslovic On IR, Walman To LTIR
Earlier today the Edmonton Oilers announced that Max Jones has been recalled from AHL Bakersfield, while fellow forwards Connor Clattenburg and Jack Roslovic have been placed on injured reserve. Finally, as was speculated yesterday, defenseman Jake Walman has landed on long-term injured reserve. The moves come in advance of tonight’s game versus Detroit.
Jones, a familiar face to Anaheim fans, was a first round pick by the Ducks in 2016. Now 27, he was once a potential top-six power forward, but was never able to pan out. Now an AHLer, Jones has a career high of 19 points at the NHL level, in 284 games so far. Injuries were a huge factor in his stunted development, especially as the Michigan native suffered a torn pectoral in 2021, which was a crucial year to prove himself in Anaheim.
After a stop in Boston, Jones made his way to Edmonton as an add-in from the Trent Frederic trade. He skated in 19 games as an Oiler last season, but has spent all of 2025-26 in the AHL so far. Jones has just seven points in 17 games with the Condors, but with 49 penalty minutes, he is trying to lean more into a grinder role at this point.
Edmonton has brought in other former first rounders who have been solid role players, such as Kasperi Kapanen and Vasily Podkolzin, and Jones may have an opportunity with the team’s numerous injuries, although he is not expected to play tonight.
Roslovic got off to a dynamite start to his Oilers tenure with 18 points in 23 games, prior to going down in late November. He is listed as week-to-week with an undisclosed injury, and may have his sights on a return by the New Year.
Clattenburg, just 20, brought needed energy in his first five NHL games. He has missed the team’s last two contests after an apparent eye injury. With just two points in the AHL this season, the winger brings limited skill, but at 6’2” he could be an eventual fixture on the Oilers’ fourth line, proving to be a nice find in the fifth round of the 2024 draft.
The headline of long-term injured reserve for Walman may cause concern, but the main motivation for such a designation is likely salary cap motivated. With his $3.4MM off the books for now, Edmonton can finally carry a full roster as they soon head off for a five-game road trip. The defenseman has dealt with multiple injuries after inking a seven-year extension at the start of the season. As he has already missed the last seven, Walman only has to miss three more games to meet the LTIR requirements. Similar to Roslovic, his ailment is also unknown, but a return before January would be a surprise.
Currently holding the second Wild Card spot, Edmonton is thankful to have most of their marquee talent healthy, however, their depth will be put to the test, a common theme throughout much of the McDavid/Draisaitl era in which the team has had a top-heavy construction. Their road trip ahead could be a turning point if the team can return to their true potential, and push for another deep run in the spring.
Oilers Likely To Move Jake Walman To LTIR
The Oilers have been dealing with a tight salary cap situation all season long, primarily using LTIR in order to keep cap-compliant. At the moment, they have two forwards on there in Kasperi Kapanen and Noah Philp but even with that, they are only able to afford to carry a minimum-sized roster of 12 forwards, six defensemen, and two goalies.
That could soon be changing, however. Jason Gregor of Sports 1440 indicates (Twitter link) that the Oilers will likely move defenseman Jake Walman to LTIR over the next couple of days. In doing so, they’ll add his $3.4MM AAV to their LTIR pool which will be enough to call up an extra forward and defenseman as they get set to embark on a five-game road trip that begins on Saturday in Toronto.
Walman is in his first full season with Edmonton after being acquired from San Jose at the trade deadline back in March. He made a big impact after joining the team and that has carried over to this season, at least when he’s healthy enough to be in the lineup. Through 17 games, Walman has three goals and seven assists along with 31 blocked shots while averaging a little over 20 minutes a night of playing time. His early performance with the Oilers earned him a seven-year, $49MM extension back in October.
Walman missed five games with an undisclosed injury earlier in the season and has been out with another undisclosed injury since leaving Edmonton’s game on November 20th. If the Oilers do indeed move Walman to LTIR, they will be able to backdate the placement to that time with the 10-game, 24-day requirements being calculated from there. Considering he’s already missed seven games, this is a safe procedural move that would make a lot of sense for the Oilers to make.
Injury Notes: Roslovic, Hartman, Foegele
Oilers Head Coach Kris Knoblauch shared several updates, as reported by Jason Gregor of Sports 1440; most notably, Jack Roslovic is set to miss multiple weeks. Kasperi Kapanen will be out at least one week, possibly longer, and Jake Walman is making progress, in time for a possible return next week.
Just yesterday it was thought that Roslovic could be just questionable for Saturday’s game, so the week-to-week diagnosis is a surprise. The forward has been a tremendous fit in Edmonton, with 10 goals and 18 points in 23 games, and will be sorely missed as the team faces mounting pressure to get on track. 21-year-old Matthew Savoie will have an opportunity to step up offensively, as the Oilers will desperately fight for a strong December. Roslovic left last Tuesday against Dallas after blocking a shot.
Meanwhile, Kapanen was back in practice yesterday after a five-week absence, but appeared to re-aggravate the injury, and was visibly frustrated leaving the ice. Walman has been out since November 20th, avoiding the IR, and will be eager to return to the lineup to prove his worth after inking a major long-term extension in October.
Elsewhere across the league:
- Ahead of their hosting of Colorado this afternoon, the Minnesota Wild announced that Ryan Hartman has been activated from injured reserve, and Nicolas Aubé-Kubel has been reassigned to AHL Iowa in a corresponding move. Hartman, thought to be week-to-week with a lower-body injury earlier in the month, is a welcome addition especially with Marcus Foligno set to miss time. Hartman, 31, has seven points in 20 games, a far cry from his 34-goal output four years ago, but the South Carolina native remains a solid third line center for the club. Meanwhile, Aubé-Kubel was called up just yesterday, but is headed back to Iowa without yet appearing for Minnesota this season.
- Zach Dooley, Manager of Editorial Content for the Los Angeles Kings, shared that forward Warren Foegele will not play this afternoon in Anaheim. Foegele, a fixture of the Kings’ bottom six, left practice yesterday with an apparent injury. The 29-year-old has four goals in 18 games this year, after setting a career high 24 in his first season with the black and silver in 2024-25. In his absence, fellow 29-year-old Jeff Malott enters the lineup, bringing major size and physicality in a fourth line role.
Pacific Notes: Oilers, Walman, Poehling, Parekh
It has been a consistently inconsistent season for the Oilers who have shown flashes of dominance at times and have struggled mightily at others. The end result has been a middling 9-9-5 record to start the campaign. Despite that, Pierre LeBrun of TSN and The Athletic suggests (Twitter link) that management isn’t quite ready to start making moves yet and would like to get closer to the 30-game mark which would allow them to ideally have a healthier roster to help them better assess what they need to do. More specifically, the better assessment might be what they can afford to do as they’ve been operating in LTIR all season and will have very limited cap space when the team is fully healthy, putting them in a money-in, money-out situation when it comes to the trade market.
More from the Pacific:
- Still with the Oilers, defenseman Jake Walman is listed as day-to-day with an undisclosed injury, notes team reporter Tony Brar (Twitter link). Head coach Kris Knoblauch suggested that the blueliner should be back within a week, meaning an IR placement is unlikely. Walman is in his first full season with Edmonton after being acquired near the trade deadline last season and has been impactful, collecting 10 points in 17 games while logging a little more than 20 minutes per night of ice time.
- Ducks center Ryan Poehling took to the ice today for the first time since suffering an upper-body injury a week and a half ago. However, it will still be a little while before he’s cleared to return as head coach Joel Quenneville told reporters, including Derek Lee of The Hockey News, that the earliest that Poehling could return is next weekend. The 26-year-old is in his first season with Anaheim and had a goal and five assists in 16 games prior to the injury.
- Flames defenseman Zayne Parekh has resumed skating as he works his way back from an upper-body injury, relays Flames Nation’s Ryan Pike (Twitter link). He has missed the last couple of weeks due to the injury and even if he’s cleared to return sooner than later, he won’t be with the team for long as he has already been confirmed to be going to the World Juniors if healthy by then. Parekh is in his first full professional season after recently surpassing the nine-game threshold and has an assist in 11 outings so far while averaging a little less than 15 minutes per night of playing time.
Oilers Activate Jake Walman From IR
The Edmonton Oilers have activated defenseman Jake Walman from injured reserve. He missed the start of the season due to an undisclosed injury that landed him on injured reserve one day into the regular season.
Walman joined the Oilers at the 2025 Trade Deadline, with a 2026 first-round pick and forward prospect Carl Berglund headed back to the San Jose Sharks. He played through 15 games and racked up a productive eight points through the end of Edmonton’s regular season. That earned him a core role in the team’s postseason lineup, setting him up to deliver 10 points in 22 games through the Oilers’ push to a Stanley Cup Final loss.
Walman only managed to appear in one preseason game before sustaining his latest injury. That gives the Oilers a 38-game sample of what the puck-moving defender can offer the team. He averaged over 21 minutes of ice time in his limited sample with the Oilers last season – a light respite after he averaged 23 minutes of ice time through 50 games with San Jose to start the year. It was the first season that Walman averaged north of 20 minutes of ice time, though he came close to that mark with the Detroit Red Wings in both 2022-23 and 2023-24.
Small sample size aside, there seems to be little doubting that Walman will soon slot back into his role alongside Darnell Nurse. The duo outscored opponents eight-to-two through the end of the 2024-25 season. Nurse has spent the start of this season rotating between minutes with Troy Stecher, Alec Regula, and Brett Kulak. Despite the heap of change, none of Nurse’s pairings have been on the ice for an even-strength goal yet. That has left a heavy load for Edmonton’s other D-pairings – a load that the team should be able to mitigate with the return of Walman.
The Oilers have lose their last three games, after starting the year 2-0-1. Much of that struggle can be attributed to their measly 1.6 goals-for-per-60 average – fourth-worst in the NHL so far. With an average of 12 goals and 34 points per 82 games played since 2023, Walman could be the exact piece Edmonton needs to turn their fates around. Walman is expected to make his season debut in Tuesday’s matchup against the Ottawa Senators.
Pacific Notes: Oilers, Sherwood, Kings, Golden Knights
The Edmonton Oilers, who were hit by the injury bug out of the gate, have a number of players expected back soon. Mark Spector of Sportsnet shared today that Head Coach Kris Knoblauch “hopes” that Mattias Janmark and Alec Regula are set to return this weekend, Jake Walman next Thursday, and finally, Zach Hyman’s November 1st estimated return is still on track.
Hyman originally suffered a very untimely major wrist injury in last year’s Western Conference Finals. Meanwhile, newcomer Andrew Mangiapane is off to a hot start with 2 goals, in the coveted seat of Connor McDavid’s wing. It will be interesting to see how the Oil work Hyman back into the lineup, along with the recent addition of Jack Roslovic.
Walman and Janmark have both been out with undisclosed injuries not thought to be serious. Regula has appeared in both of the Oilers’ games to start the season, but is out tonight with yet another undisclosed injury. The 25-year-old was claimed off waivers from Boston last year, offering imposing size and a right handed shot, filling a bottom-pair role perhaps missed by the team since the departure of Vincent Desharnais.
Elsewhere across the division:
- In an article published by The Fourth Period earlier today, referencing word from their own David Pagnotta, Kiefer Sherwood and the Canucks have not begun contract discussions yet. A late-bloomer who established himself as a full-time NHLer with Nashville, Sherwood signed with Vancouver last season on a two-year deal and took another step, posting 40 points, and most notably, breaking the NHL single-season record for hits. Sherwood is a prototypical fourth liner in today’s game, and perhaps the club is feeling out his performance this year before they take next steps toward a considerable pay increase.
- The Kings have updates of their own; as Elliotte Friedman of Sportsnet shared on today’s episode of the FAN Hockey Show, that star Adrian Kempe wants to stay. Friedman said that talks had been in the $9-10MM range, but now, given the market explosion, it could go higher. The 29-year-old broke out in a steal of a 4-year deal at $5.5MM which finally ends this season. Additionally, David Pagnotta of The Fourth Period also shared that the team is in no rush with an extension for young standout Brandt Clarke, as published today. Given such huge contracts given out to Luke Hughes and Lane Hutson, the Kings will be content to play the long game and see how Clarke’s season unfolds.
- SinBin.vegas noted tonight from the Golden Knights Insider Show, that forward Brett Howden will be out of tonight’s game in Calgary, and Cole Reinhardt will make his Vegas debut. It is not clear if it is an injury or scratch for Howden, who has one goal in the team’s first three games. Reinhardt signed a two-year deal coming over from the Senators, where he spent most time in the AHL, but notched two points in 17 games for the big club last year.
Oilers Place Jake Walman On Injured Reserve
The Oilers announced that defenseman Jake Walman is headed to injured reserve after sitting out last night’s season opener with an undisclosed injury. They’ll use his vacant spot to officially register forward Jack Roslovic‘s contract and add him to the active roster after announcing his signing last night.
Walman suffered a setback in his recovery from the injury on Monday, according to the team’s Tony Brar. That was hours after the club announced a seven-year, $49MM extension for the pending unrestricted free agent, in addition to locking up captain Connor McDavid for another two years after this one. He hasn’t played since logging over 21 minutes of ice time in Edmonton’s preseason opener against the Flames on Sep. 21, so his IR placement will be backdated to then, and he’ll be eligible for activation at any time.
A 2014 third-rounder, Walman is entering his first full season with the Oilers and his seventh NHL campaign overall. He’s coming off a breakout campaign that earned him that extension and saw him average almost 23 minutes per game across 65 appearances with the Sharks and Oilers, posting a 7-33–40 scoring line and +4 rating. If he’d not been banged up for nearly 20 games last year, he was on pace for a 50-point campaign in 82 games, ranking 22nd in the league in points per game.
It’s still not clear when Edmonton expects Walman to make his season debut. The lefty was widely expected to play mostly on his off side this season and round out Edmonton’s second pairing with Darnell Nurse. Alec Regula filled that spot last night in the Oilers’ shootout loss to the Flames, and it didn’t go very well. While the pairing controlled 63.8% of expected goals at 5-on-5, he ended up being a -2 on the night.