


On the ice from Long Island
Sign up for Inside the Islanders by Ethan Sears, a weekly Sports+ exclusive.
The clock on Josh Bailey’s future begins with the end of the Stanley Cup Final, meaning the first domino of the Islanders’ offseason should fall within the next couple of weeks.
The NHL’s buyout period starts Thursday, and runs until 5 p.m. on June 30.
Presuming the Islanders want to go into free agency on July 1 with as much cap space as possible available to them, that also functions as a window within which they must either find a trade partner for Bailey or take what savings they can in a buyout.
For a general manager who is famously opaque, Lou Lamoriello was quite clear about his intentions in speaking to reporters last week.
The priority is re-signing the Islanders’ own free agents — Pierre Engvall, Scott Mayfield, Zach Parise and Semyon Varlamov. Lamoriello also acknowledged the same uncomfortable reality Bailey did on the team’s breakup day a month earlier: The team’s longest-tenured player is unlikely to be with them next year.
“In Josh’s case, it looks like maybe it’s near the end for here in our situation,” Lamoriello said. “Josh and I have, I think, a man-to-man relationship as far as honesty, and we will work with him to help him. But my priority is doing what’s best for the team.”
Bailey does not have a no-trade clause, so he cannot pick his destination. The 33-year-old still has value as a locker-room presence, particularly on a young team, though it’s hard to see him as anything more than a bottom-six piece given that he struggled throughout last season, scoring just eight times and getting healthy-scratched for the entire first round of the playoffs.
If a trade is going to happen, though, it seems like the pool would be limited to teams with young rosters and cap space, where development would be prioritized over winning and where getting a draft pick as part of a deal to take on Bailey’s $5 million hit would be considered a win.
That would be the Arizonas, Chicagos, Anaheims and San Joses of the world.
The Islanders don’t have a first- or third-round pick to dangle in a trade, at least for the upcoming draft, having spent their first-rounder to get Bo Horvat and their third to dump Andrew Ladd in 2021.
They also don’t have next year’s third-rounder, which went to Toronto in the Pierre Engvall deal.
And it would be tough to imagine them giving up their 2023 second-round pick because that would mean they won’t pick in this draft until the fourth round — which feels unpalatable even for a team that puts as little emphasis on their farm system as the Islanders do.
Even so, the difference between a trade and a buyout could be the difference between re-signing all four of the Islanders’ pending UFAs or not, let alone another player.
If the Islanders buy out Bailey, they’ll save $2.33 million against the cap this season at the cost of $1.16 million in 2024-25, when the cap is projected to spike.
There is about a $2.66 million difference between a Bailey trade and buyout — a not-insignificant percentage of the potentially available cap dollars for the Islanders, which would total approximately $11.13 million if Bailey is dealt with no players coming back.
Remember, in addition to the four unrestricted free agents, Oliver Wahlstrom and Samuel Bolduc are due new contracts. Parker Wotherspoon is a Group 6 unrestricted free agent, too, though unlikely to be worth more than the league minimum if the Islanders bring him back.
The math is going to get tight very, very fast — even if the Islanders can move Bailey’s entire cap hit.
That makes it all the more imperative to get something done as soon as possible.
A smaller part of Lamoriello’s presser last week that stuck out nonetheless was his defensive response regarding Noah Dobson’s season, particularly given the expectations put on the 23-year-old by Lamoriello just under a year ago when signing the defenseman to a three-year, $12 million extension.
“First of all, I think too much criticism has been of Dobson,” Lamoriello said. “Look at his point production — very similar to last year. And I think that we put a lot of high expectations on him. Maybe I did in signing him to a contract. But it’s your second year, your sophomore year, so to speak. And people look at him and give him a little more attention.
“I’ve spent some time with him postseason as recently as today. And he’s in a great mindset. He knows what he can do to be better, and will do that. And I have high expectations for him. I think he’s gonna be one of your elite scoring defensemen in this league before his career is over.”
Good on Lamoriello for acknowledging that foisting expectations on the defenseman was an error, though a large chunk of the hype came from Dobson’s own 2021-22 season as much as anything else.
It’s not particularly true, however, to suggest that similar point production means he had a similarly good season in 2022-23 — the stagnation on the defensive side of his game was evident, and he struggled to quarterback a power play that had ranked 12th in the league a season prior.
But this is the right kind of approach to take for a player who still is early in his development and could grow into a star.
There is no reason to doubt Lamoriello’s assessment that Dobson will eventually be an elite scoring defenseman right now, though next season will be telling.
Let’s say for the sake of argument that the Islanders manage to bring back everyone.
Now answer me this: Where is Simon Holmstrom on the depth chart as of opening night?
Unless there are mitigating factors in the form of injury or Holmstrom putting together an exceptional training camp, it is not all that easy to find a place for the 22-year-old, who played 50 games last season, but was healthy-scratched during the playoffs.
Remember, it is not just the players who made up the lineup in the postseason whom Holmstrom would need to beat out, but also Wahlstrom, who will return from a knee injury.
That situation has the potential to get complicated quickly for the former first-round pick.