End of an Era: NY Islanders move Josh Bailey to Chicago with 2026 2nd round pick

It was an elite run.

After 15 seasons and 1,057 NHL games, all in an Islanders sweater, Josh Bailey will play elsewhere for the 2023-24 season. Minutes before day two of the NHL Draft kicked off, the Islanders traded Bailey along with a 2026 second-round pick to the Chicago Blackhawks for future considerations.

Update: Bailey has been put on on unconditional waivers for purposes of a buyout. If he clears, will become an unrestricted free agent.

Bailey was a healthy scratch down the stretch last season, including the entire first round of the playoffs against the Carolina Hurricanes. While it is in ways bittersweet to see Bailey's career not end on Long Island, this trade is mutually beneficial for both the player and the team.

By trading the 33-year-old Bailey, the Isles, and GM Lou Lamoriello were able to unload the entire $5M AAV this season as he tries to re-sign key free agents, including forward Pierre Engvall and defenseman Scott Mayfield. After trading Bailey ($5M), the team has a $10.3M Projected Cap Space with 19 players on the roster (12F/6D/1G). Oliver Wahlstrom is an RFA, while the UFA list includes Engvall, Mayfield, Zach Parise, Parker Wotherspoon, and Semyon Varlamov.

After the first-round exit to the Carolina Hurricanes, Bailey made it known that he didn't wish to ride the bench at this point in his career and watch games from the press box. “If I’m gonna be sitting in the stands a lot, that’s not something I want to do," said Bailey. He still feels he has a lot to give as a player and now will have a new challenge and opportunity to do that with the rebuilding Blackhawks.

Across points of the season, the writing was on the wall that Bailey's time on Long Island was set to come to an end. He was scratched ahead of playing his 1,000th game and it happened consistently after the trade deadline as the team acquired Bo Horvat, Engvall, and got healthier overall. Appearing in 1,057 regular season games, Bailey has played the third most all-time games with the Islanders, trailing only Hall of Famers Bryan Trottier and Denis Potvin.

There is a strong case for Bailey, despite all his limitations and detractors, to be inducted into the Islanders Hall-of-Fame in the future.