Grading the Blackhawks’ Trade for Bailey From the Islanders

In terms of why this trade happened, the reasoning is simple. As a contending franchise, the Islanders needed to clear cap space in order to sign players this offseason while setting themselves up for what will likely be a significant raise for star goaltender Illya Sorokin next offseason. For the Blackhawks, they are a rebuilding franchise for at least a few more seasons, and they just so happened to have plenty of cap space available to take on an unwanted contract like Bailey’s.

So, while this trade makes sense, was it a true win-win for both teams?

Islanders Make Space but Lose a Fan Favorite

On paper, this was the right move for the Islanders. While Bailey was drafted by the franchise back in 2008 and spent the last 15 years of his career taking the ice for them as part of the heart and soul of the franchise, his best years are simply behind him. Injuries have greatly reduced his role with the franchise, and the 2022-23 season was his weakest production-wise in nearly a decade.

Simply put, the Islanders aren’t in a position to pay a player $5 million a year who isn’t producing up to that level. They need to keep as much of their core of young players together, and even attempt to add to their roster to compete for a Stanley Cup now. Yes, it really hurts seeing a player leave that is so deeply entrenched with a franchise as Bailey was to New York, but they were going to have to rip this band-aid off sometime soon, whether it was this offseason or next when they likely would have to let him walk in free agency.

As far as the 2026 second-round pick they gave up, that’s about what it costs to clear $5 million off your cap for a year. Unfortunately, Bailey’s value was negative, so it was going to cost something to remove his contract, and in the moment that pick isn’t a bad choice. 2026 is a long way away, so the Islanders likely won’t care about this pick as their core will look vastly different when that player comes to fruition years after the selection is made.

Grade: B

Blackhawks Add Veteran Leadership in Bailey

For the Blackhawks, the acquisition of Bailey is a bit of a win-win. With the addition of young talent like Connor Bedard to their roster, they need to surround those guys with veteran players who can help coach them both on and off the ice. Even if he is unlikely to bring a lot of scoring potential to their roster, Bailey has leadership in spades which will only help Bedard in his transition to the NHL.

Plus, if things go really well and Bailey stays healthy, there’s a chance he could then be flipped at the trade deadline as a pure rental to a contending team, which would give the Blackhawks another chance to add assets for their future.

When you look at the 2026 second-round pick the Blackhawks got back in this deal, that’s a solid value for what is nothing more than the weaponization of their cap space. Don’t be surprised if that pick is traded before Chicago has a chance to use it, as they will likely be pushing to make the playoffs by the time the 2025-26 season rolls around.

Overall, I think this is an excellent move for Chicago, as it adds a veteran leader to their locker room and a future asset for what amounts to, essentially, nothing more than $5 million in cap space for the 2023-24 season. For a rebuilding team, that’s everything you look for in a cap-dump trade.

Grade: A