Waiving Josh Bailey could be the best option for the NY Islanders

When the New York Islanders held exit interviews with the media on May 1st, veteran winger Josh Bailey made it clear that while he acknowledges his future with the team is uncertain, he is certain that he doesn't want to be a regular scratch. “As far as what my role is, obviously, if I’m gonna be sitting in the stands a lot, that’s not something I want to do,” said the 33-year-old lifetime Islander.

"In Josh's case, it looks like, maybe, it's near the end here," GM Lou Lamoriello added on Jun. 6, seemingly acknowledging that it was unlikely that Bailey would be part of the team's NHL roster next season. "Loyalty will never get in the way of impeding progress. We will work with him to help him," said Lamoriello. "My priority is doing what's best for the team."

Why waiving Josh Bailey could be the best option for the NY Islanders

Much of the focus has been on whether the Islanders can move Bailey and his $5M AAV in a trade to a team needing to get to the cap floor or having enough space to take on all or a significant amount of Bailey's salary, provided the Isles part with an asset, likely a draft pick.

The Islanders are already without a 1st and 3rd round pick in this year's draft, and having to move this or next year's second further stunts the team's ability to create organizational depth without first-rounders in each of the last four drafts. Lamoriello will have to weigh trading more draft picks either this year or next with the benefits of creating cap space to sign their own free agents.

A decision to buyout Bailey could come as early as Friday at the end of the league's first buyout window. The Isles could get a second buyout window for Bailey, depending on other factors, meaning more time to deliberate if that is the best option for the team and player. If Lamoriello chooses to go that route, which would make Bailey a UFA and able to pursue other options around the league, the team's cap hit for next season would be $2.67M, a savings of $2.33M. However, the team would need to carry a cap hit of $1.167M during the 2024-25 season.

However, simply waiving Bailey could be the most practical option. It's unlikely a team would claim him given his recent production and cap hit, meaning Bailey would be eligible to be sent down to Bridgeport and play in the AHL next season, burying part of his contract.

Per CapFriendly, teams do not receive full cap relief when a player on a one-way NHL contract is reassigned to the American Hockey League. In the case of Bailey, his salary cap hit ($5M), minus the sum of the minimum NHL salary ($775,000) for the 2023-24 season + $375,000, still counts towards the team's salary cap. That means Bailey's cap hit would be $3.85M next season, a savings of $1.15M.

That's $1.18M less cap space for next season than they would have if they bought out Bailey, but the team would be free of the contract next season. It would undoubtedly be difficult for a proud player like Bailey, who still believes he can play at a high level, to be in Bridgeport, a level he hasn't played since the 2010-11 season. However, not reporting could result in a suspension without pay situation, and Bailey is due $3.5M in base salary next season.

However, if Lamoriello is true to his words, that loyalty won't stop him from doing what's best for the team, waiving the longest-tenured Islander could be the most attractive and practical option - one that doesn't impact their draft capital or salary cap next season.