The Chicago Blackhawks have acquired forward Josh Bailey and a second-round pick in the 2026 NHL Draft from the New York Islanders in exchange for future considerations, the clubs announced Thursday morning.
Bailey, 33, collected eight goals and 25 points in 64 games with the Islanders during the 2022–23 regular season. He’s set to enter the final year of his contract, which carries a $5M cap hit.
The Islanders originally selected Bailey in the first round (No. 9 overall) of the 2008 NHL Draft. Before Thursday’s trade to Chicago, the 6-foot-1 forward had spent his entire NHL career on Long Island.
The Blackhawks now possess three picks (the Islanders’, the Toronto Maple Leafs’, and their own) in the second round of the 2026 NHL Draft.
After clearing out Bailey’s salary, the Islanders now have a little over $9.5M in projected cap space for the 2023–24 season with 20 players on their roster, according to CapFriendly.
Bailey made his NHL debut with the Islanders during the 2008–09 season. The Bowmanville, Ontario product spent the first eight seasons of his career as a bottom-six producer with the team before jumping up to 56 points in 2016–17 and 71 in 2017–18.
Later in his career with the Islanders, Bailey was instrumental in the team finding success deep into the postseason. He scored 20 points in 22 games in the 2020 Stanley Cup Playoffs to help the Islanders reach the Eastern Conference Final; the next year, he racked up 13 points in 19 games as the Isles returned to the third round.
Through 1,057 career games over 15 seasons with the Islanders, Bailey has collected 184 goals and 580 points. He’s added 16 goals and 50 points in 71 career playoff contests.
Bailey is the latest addition to a Blackhawks club that also picked up Taylor Hall and Nick Foligno from the Boston Bruins this week. Of course, the ‘Hawks also picked somebody named Connor Bedard with the No. 1 pick in the 2023 NHL Draft.
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