How the NY Islanders Josh Bailey trade impacted a NHL pre-draft blockbuster

The New York Islanders weren't involved in Tuesday's blockbuster trade between the Sabres and Blackhawks., but if you look closely enough, there was a tiny little Islanders connection buried inside the deal.

And it all traces back to Josh Bailey.

As part of the trade that sent Bowen Byram and Jordan Greenway to Chicago, the Sabres received the 4th and the 45th overall pick in this weekend's draft. That second-round pick originally belonged to the Islanders.

To find the origin of it, you have to go back to June 2023 when Lou Lamoriello made the difficult, but not unexpected decision to move Bailey and the final year of his contract to Chicago. The Islanders were trying to clear Bailey's $5 million cap hit off the books, and the price for doing that was attaching a second-round pick.

That second-rounder is the same one that now sits in Buffalo's possession.

At the time, it felt like the end of an era on Long Island. “I was in Ireland at the time,” Bailey later said. “I was with Marty, Cal, Pelly was there, Barzy was there… We were on the 18th hole at Royal Portrush, and my caddy, in his Irish accent, said, ‘Hey lad, your phone’s ringing.’ I knew what was going down, but didn’t know exactly. It was my agent, followed by Lou (Lamoriello). It was actually great in the moment, having those guys around me.” 

Bailey spent parts of 15 seasons with the Islanders and played more than 1,000 NHL games. He wasn't always appreciated while he was here, but he became one of the most recognizable players of his generation in Islanders history.

Chicago immediately bought out Bailey's contract. He later earned a professional tryout with Ottawa and, by most accounts, had a solid training camp. It still wasn't enough to earn a roster spot. He never played another NHL game.

Now, almost three years later, a draft pick tied to Bailey's departure has resurfaced in one of the biggest trades of the offseason.

Will anyone remember this years from now? Probably not.

The headline is Byram. The headline is Buffalo acquiring a top-5 pick.

But buried in the details is a small Islanders footnote. One last reminder that even after a player is gone, the ripple effects of those moves can keep showing up years later in places you'd never expect.

Add us as a preferred source on Google

Follow