New York Islanders player Josh Bailey talking to reporters on...

New York Islanders player Josh Bailey talking to reporters on May 1, 2023 at Northwell Health Ice Center in Eisenhower Park. Credit: Newsday/Alejandra Villa Loarca

NASHVILLE, Tenn. — Josh Bailey is no longer the longest-tenured Islander. He may be the shortest-tenured player in Chicago history.

Chicago acquired Bailey on Thursday shortly before the second round of the NHL Draft began at Bridgestone Arena along with a second-round pick in 2006 in exchange for future considerations, giving the Islanders much more flexibility under the $83.5 million salary-cap ceiling to either try and re-sign their own free agents or pursue other roster improvements.

“Well, that was the key,” Islanders president and general manager Lou Lamoriello said. “That gives us more flexibility right now to do some things that we’d like to do.”

But Bailey was almost immediately placed on unconditional waivers for the purpose of buying out the final season of his six-year, $30 million deal, which will make him an unrestricted free agent when the market opens Saturday at noon.

“I have great respect for Josh’s career and him being a vet in this league,” Chicago general manager Kyle Davidson told the media. “Didn’t necessarily see a clear path to a role for us. So better to give him the opportunity to find that elsewhere than kind of be in and out and not have a true role with us.”
That’s what happened to Bailey in his 15th and final season with the Islanders.

He was a frequent healthy scratch, playing 64 games with eight goals and 17 assists, and then was a healthy scratch for all six games of the Islanders’ first-round playoff loss to the Hurricanes. Bailey, 33, made clear at the Islanders’ breakup day on May 1 he would prefer to play elsewhere if he was not going to have a regular role.

“If I’m going to be sitting in the stands a lot, it’s not something I want to do,” Bailey said.

He played 1,057 games for the Islanders, the third most in franchise history, after being selected ninth overall in 2008 and making his NHL debut that year. He compiled 184 goals and his 396 assists are the fourth most in franchise history.  His 580 points rank seventh.

“I spoke to Josh this morning,” Lamoriello said. “He’s in Europe. He and his group of [now ex-] teammates went on a golfing trip. It’s certainly a difficult conversation. But he knew that this potentially could come about. Our conversation was very positive.”

Lamoriello said there was nothing preventing the Islanders from re-signing Bailey as a free agent but added that wasn’t something Islanders were planning to do.

He did not reveal whether he or Bailey had any forewarning Chicago would be buying out Bailey. But Lamoriello said that was a good thing for Bailey.

“That was their decision to make and it’s in Josh’s benefit to make any decision right now for his future,” Lamoriello said. “I don’t think it could have worked out any better under the circumstances and I’m delighted that it worked out this way so that he can get an opportunity of where he’d like to go.”

The additional $5 million in cap space leaves the Islanders with approximately $73.2 million allocated to 19 players.

Defenseman Scott Mayfield, who should earn a substantial raise over his $1.45 million cap hit from last season, left wings Pierre Engvall and Zach Parise and goalie Semyon Varlamov are the team’s unrestricted free agents and Lamoriello repeated it’s still a priority to re-sign them. Parise has yet to decide whether to play next season and Lamoriello said it’s too soon to say whether any will re-sign before Saturday.

He did have a lengthy conversation with Varlamov’s agent, Paul Theofanous, prior to Wednesday night’s first round.

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