Chicago Blackhawks acquire Josh Bailey

The New York Islanders have parted ways with their longest-tenured player, trading forward Josh Bailey and a 2026 second-round pick to the Chicago Blackhawks in exchange for future considerations.

In a pure cap dump deal, the Islanders have essentially traded a future second-round for an immediate $5M in cap space. Bailey had been a consistent middle-six threat for the Islanders throughout a 15-year career there, but after just eight goals and 25 points in 64 games this season and multiple healthy scratches, both the player and organization felt it was time to move on.

Once a high-end playmaker, Chicago is still getting a player that might be effective in their current situation. Bailey was a well-respected leader in the Islanders’ room and has made it to multiple Eastern Conference Finals. Alongside Nick Foligno and Taylor Hall, Chicago is quickly putting together an ancillary group of some veteran skill and leadership to surround yesterday’s first overall pick, Connor Bedard.

It’s worth noting that a buyout for Bailey was rather palatable. Per CapFriendly, buying out the final season of Bailey’s six-year, $30M contract would have cost them $2.67M this season, providing $2.33M in savings. It would have cost them $1.167M against the cap in 2024-25. Instead, they cut ties entirely, although it’s for the cost of a decent draft pick.

This is Chicago’s second significant move to weaponize cap space in the last few days, acquiring Hall and Foligno from the Boston Bruins for a pair of minor-league defensemen.

It’s the end of an era for the Islanders, who selected Bailey with the ninth overall pick in 2008. He would go on to play 1,057 games as an Islander, ranking third in franchise history behind Bryan Trottier and Denis Potvin. In that time, Bailey recorded 184 goals and 580 points.

The Islanders now have close to $10M in projected cap space, per CapFriendly, which could go to re-signing their quartet of notable UFAs in Pierre Engvall, Zach Parise, Scott Mayfield, and Semyon Varlamov.