Islanders trade Josh Bailey to Blackhawks in salary cap crunch

The writing was on the wall for the Islanders and Josh Bailey. And finally on Thursday morning, the longest-tenured athlete in New York was moved away from the city.

The Islanders traded Bailey to the Blackhawks, with a 2026 second-round pick attached, in exchange for future considerations, allowing the team to offload $5 million in cap space without giving up any of their already-limited picks in the 2023 draft. 

Chicago wasted no time in placing Bailey on waivers in order to buy out his contract.

It counts as a painful-but-necessary step for general manager Lou Lamoriello, who acknowledged earlier this month that Bailey was “near the end” with the Islanders.

In order to bring back Pierre Engvall, Scott Mayfield, Semyon Varlamov and Zach Parise — all of whom are unrestricted free agents — along with restricted free agent Oliver Wahlstrom, the Islanders had no choice but to move Bailey, who became expendable last season when he struggled to produce and was a healthy scratch in the playoffs.

The Islanders are now set to enter free agency on Saturday with $10.3 million in cap space, enough that bringing everyone back is feasible, but not so much that it will be easy.

Doing so still might hinge on one or more of Mayfield, Engvall or Varlamov taking a discount to play on Long Island.

That is not inconceivable, especially given the strong preference of both Mayfield and Varlamov to stay, but it is a precarious spot to be in nonetheless.

If Parise returns, it is expected to be on the minimum salary. Lamoriello said Tuesday that the 38-year-old is still deciding whether to play another year.

Bailey, one of just three players in franchise history to have played over 1,000 games in blue and orange, hit a roadblock right before he hit the 1,000-game milestone last season.

Coach Lane Lambert made him a healthy scratch in what would have been his 998th career game, ensuring that he would celebrate 1,000 on the road instead of at home, in a high-profile match against the Rangers. 

Though he refused to make a public stink at the time, Bailey acknowledged on breakup day that it didn’t sit right with him, and that a return to Long Island was unlikely.

“I think as far as where my role is, obviously if I’m gonna be sitting in the stands a lot, that’s not something I want to do,” Bailey said.

Even so, seeing Bailey — an Islander since 2008 and a member of the leadership group — in a different sweater will be jarring.

“I came here as a teenager. Got married, all our kids were born here, all our roots are here,” Bailey said on breakup day. “This is where we plan on living when hockey’s all said and done, regardless. So 15 years has been a pretty good run. I’m very proud of that.”

Bailey is behind only Bryan Trottier and Denis Potvin on the franchise games played list, and ranks seventh all-time in points.

“I feel like I’ve been here a while. He’s been here longer and had a pretty big impact on the team, in the community,” Brock Nelson said on breakup day. “He’s a great guy that goes out there, nothing really seems to faze him. … The way he handled himself was awesome, but at the same time, you definitely miss him. Just how much he’s impacting the group and the camaraderie you have down the stretch.”