Josh Bailey traded: Islanders send veteran winger, ’26 draft pick to Blackhawks in salary dump move

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Josh Bailey Islanders
Josh Bailey is congratulated by his teammates after scoring during the Islanders’ win over the Buffalo Sabres (Photo courtesy of the New York Islanders)

Josh Bailey’s decade-and-a-half-long tenure with the New York Islanders has officially come to an end.

Thursday morning saw the team announce that they dealt the 33-year-old winger to the Chicago Blackhawks, along with a second-round pick in the 2026 NHL Draft, for future considerations. 

Bailey was then put on unconditional waivers for the purpose of a buyout. If he clears, he will become an unrestricted free agent.

The move is purely a salary dump as Bailey carried a $5 million cap hit in the final year of his contract next season. It provides the Islanders with a bit more financial flexibility to make a run at retaining some notable free agents such as defenseman Scott Mayfield, winger Pierre Engvall, or goalie Semyon Varlamov while potentially beginning to work on securing star netminder Ilya Sorokin to a long-term deal.

According to CapFriendly, the Islanders approximately have a projected $9.5 million cap space after dealing Bailey.

The move ends one of the longest tenures in Islanders franchise history. Bailey was drafted ninth overall by New York in 2008 and ranked third on the team’s all-time list in games played at 1,057 behind only Denis Potvin and Bryan Trottier. He recorded 180 goals and 396 assists — which ranks fourth in franchise history — for 580 points, which ranks seventh in team history.

A down 2022-23 campaign saw Bailey record just eight goals and 17 assists for 25 points in his worst season since his rookie year in 2008-09. He was often scratched by first-year head coach Lane Lambert, including a benching on Oct. 22 against the Lightning in Tampa Bay. It ultimately pushed his 1,000th career game from an Oct. 26 matchup at home against the Rangers — which would have allowed him to celebrate the major milestone with his family and the UBS Arena crowd — to a game two nights later down in Raleigh, NC against the Hurricanes.

Josh Bailey Islanders
Josh Bailey (Wikimedia Commons)

“I think looking back on it now, it’s rather telling getting scratched four, five games into the year before my 1,000th game to where we ended up at the end of the season,” Bailey said during his exit interview last month. “It makes a lot more sense now. But it’s all part of the past.”

Bailey was also a healthy scratch for 10 of the final 13 games of the regular season and did not appear in the six-game loss to the Carolina Hurricanes in the first round of the Stanley Cup Playoffs.

During his exit interview, he opined that he would not spend the final year of his contract “sitting in the stands,” to which Islanders president and general manager Lou Lamoriello obliged to move him.

For more on the Islanders and Josh Bailey, visit AMNY.com