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Josh Bailey’s Islanders tenure ends quietly because of course it does

The man who saw everything as an Islander leaves a lasting legacy of quiet competence.

New York Islanders v Edmonton Oilers Photo by Lawrence Scott/Getty Images

Josh Bailey could be infuriating. At many points during his 15 seasons with the Islanders, watching him was frustrating, baffling, confusing and rankling. On his trip to No. 7 on the Islanders all-time scoring list and third on the team’s all time games played list, he also led all post-Dynasty Islanders in fan trade proposals, calls for benchings or waivings, and directives to be launched into the deepest reaches of space.

The Draft Day trade that sent Bailey to the Chicago Blackhawks along with a second round pick in 2026 for “future considerations” (aka absolutely nothing) came out of nowhere.

Like many, I did not expect Lou Lamoriello to bite whatever bullet he needed to to get Bailey’s $5 million cap hit off of the Islanders’ books. The need to move Bailey wasn’t something that sprung up recently. It’s been clear for a while that the Islanders needed cap space, and getting rid of a guy making a not-insignificant amount while being an ineffective skater or a healthy scratch was always going to be one of Lamoriello’s top priorities this offseason.

Even the infamously impossible-to-read general manager said as much in his all-too-rare media addresses since the season ended. When Lou just comes out and says something like, “It looks like Bailey is coming to the end here,” you know he’s serious.

What was surprising was that he found a way to make it happen at all. After a season in which he had his lowest full season point total since his age-18 year on one of the worst teams in NHL history, it’s not like teams were beating down Lamoriello’s door to get a piece of Bailey. No amount of “veteran presence” can make up for an eight-goal, 17 assist season in which he was scratched for almost 20 games and an entire playoff series. It was going to take something like a second rounder, or retaining a lot of salary or throwing in a prospect or some other tax to, in Lamoriello’s words, “do right” by the player. Honestly, a second round pick in a draft three years from now isn’t all that bad.

Bailey was never going to be dumped onto one of the league’s landfills like Arizona or Anaheim. Instead he got moved to a “real” team... that promptly announced they were buying him out, making him and unrestricted free agent for the first time in his career. His loyalty to the Islanders, even when you wouldn’t blame him or anyone for leaving, was unique. He grew from a kid to a man to a husband to a dad on Long Island in front of our eyes. All the while, Bailey seemed to he totally ignored outside of his adopted home.

It will be fascinating to watch happens to him this summer. What teams will call his agent? Does he even have an agent? Who will he listen to pitch him on coming to their town? What will other general managers see in him? This is a man whose career on one of the most unstable teams in professional sports was as chaotic as he is restrained. After watching him play on Islanders teams that were at times some of their easiest opponents and at other some of their fiercest, what is their opinion on Josh Bailey?

Because Islanders fan opinions on Bailey are all over the place. To some, he was the team’s most ineffective, overpaid underperformer. To others, he was always a quality NHLer, with a perception skewed by high expectations and a personality so quiet and anonymous you almost wondered if he was a cyborg or a spy. To many, including myself, he was a player who finally found himself later in his career, who came across confidence over time and after experiencing some of the hardest seasons a professional athlete could experience.

That quietness was a key aspect of Bailey. Even the announcement of his trade to Chicago was just a single sentence. Literally.

It wasn’t unusual to wonder if fans of other teams even knew who he was, even a decade and a half into his career. His longstanding slot on the Islanders roster, coupled with his unflashy skillset and lack of any public persona whatsoever almost made him the NHL equivalent of wallpaper. If you noticed him at all, that means something wasn’t right.

But there were many times over his 1,057 regular season and 71 playoff games that he was noticed. His 16-goal second season at age 19 that claimed his spot as a member of the rebuild’s core. That time he embarrassed Martin Brodeur with a uncharacteristically rude shootout spinorama. His only Islander hat trick in Columbus. His 43 assist breakout season at age 27 that silenced a lot of doubters. His All Star season a year later that felt like vindication for the years of criticisms and disappointment.

While his regular season numbers plateaued after that, the years after begat the unexpected era of “Josh Bailey, Playoff Hero.” Goals against the Penguins, Capitals, Bruins, Lightning and others, not to mention a swath of assists on goals by Brock Nelson and Anthony Beauvillier, rewrote the Bailey narrative once again.

He needed only four games to pass Denis Potvin for second all time on the team’s games played list. Had he played 64 games next season, he would have passed Bryan Trottier for first place.

While at first it seems odd to see his name alongside the franchise’s Hall of Fame elite, the truth is that of this team’s post-Dynasty players, Josh Bailey is among the best. He has been an active, important piece of the best seasons and playoff runs the Islanders have had in almost 40 years. Those seasons don’t happen without Bailey. He wasn’t always the most eye-catching player in the NHL, but his standing and status in franchise history are safe. As soon as he’s retired (and assuming they restart it), his name should be immediately added to the Islanders Hall of Fame banner at UBS Arena.

For 15 years, Josh Bailey represented what the Islanders would become - quietly solid, underrated by many, at their best in the playoffs. It would have been nice to see Bailey retire an Islander. But with that not an option, a surprise morning trade with a far off sweetener followed by a quick and unceremonious buyout almost feels appropriate.