Josh Bailey Era Over: Islanders trade forward to Blackhawks, for waiver and buyout

The New York Islanders have addressed their biggest salary cap discomfort by trading away their longest-serving forward, Josh Bailey, to the Chicago Blackhawks. The price of removing Bailey’s $5 million cap hit (one season remaining) was not cheap, but it was deferred: the Isles are sending a 2026 2nd-round pick to Chicago to make it happen.

In Chicago, he’ll likely get to play, and join the “veteran mentor” crew for first-overall pick Connor Bedard, which now includes fellow recent acquisitions Taylor Hall and Nick Foligno. UPDATE: The Blackhawks have placed Bailey on waivers for purposes of a buyout. So now he’s a man without a team.

So ends the era with the first major piece of former GM Garth Snow’s rebuild: Bailey was the ninth-overall picNo. 9 pick in the 2008 NHL Draft, Bailey has 580 points (184 goals, 396 assists) in 1,057 NHL games, all with New York, and 50 points (16 goals, 34 assists) in 71 playoff games.

But hints that Bailey’s time was near an end began a summer ago, when he was the subject of trade rumors as Lou Lamoriello attempted to get out of his annual summer cap crunch. Then new head coach Lane Lambert scratched Bailey shortly before his 1,000th regular season game, ensuring that game would not happen on home ice.

Finally, Bailey was a healthy scratch for all six playoff games this spring. In post-season interviews, Bailey made clear he wanted to keep playing, but not as a pressbox occupant. And when Lamoriello came down from the mountain to address media over a month after the season concluded, even he conceded Bailey’s time with the Isles was probably at an end.

The move opens up critical cap space for the Islanders’ professed desire to bring back unrestricted free agents like Semyon Varlamov, Scott Mayfield and Pierre Engvall.

We’ll see how it all shakes out as draft day activity continues.

Good bye, sweet humble prince. We wanna know-oh-oh-oh, will you score a goal.