Weighing the pros and cons of buying out Josh Bailey

The Stanley Cup has been awarded. For one fanbase, it's time to celebrate all summer, but for the rest of us, it's time to turn our attention to next year.

For the New York Islanders, that means signing pending unrestricted free agents Pierre Engvall, Scott Mayfield, Semyon Varlamov, and Zach Parise or signing their replacements in free agency. It'd also be nice to add a scoring threat. But to do that, they need cap space, and they don't have much.

Josh Bailey's contract has a cap hit of $5 million next year. That's a pretty good salary for a top 6 winger, but unfortunately, Bailey isn't a top 6 winger anymore. He was scratched for most of the end of the regular season and didn't play at all in the playoffs. His contract is essentially $5 million of completely wasted cap space. So, can - and should - the Islanders buy him out?

Let's look at the pros and cons.

First, a quick definition. A buyout is a procedure to reduce a player's contract in exchange for paying it for more years. The player becomes a free agent and can sign with any team, even though his former team must still pay him. For example, Parise will earn more than $7 million from Minnesota next year and the year after, even though he's played for the Islanders for two years. For more information on buyouts, check CapFriendly.

Why would the Islanders want to buy out Bailey? Well, it saves them money.

According to CapFriendly's Buyout Calculator, a buyout would mean that $2.67 million of Bailey's contract (instead of the full $5 million) would count against the cap in 2023-24 and only $1.17 million in 2024-25. In other words, they'd save $2.33 million in 2023-24, which could be used for other free agents. Given how difficult it will be to afford everyone they want, this is a very tempting option to essentially create cap space out of thin air.

But, of course, there are downsides too. First, Bailey's contract is set to expire after 2023-24, meaning that in 2024-25, the Islanders won't have to pay him anything. But if they buy him out, they'll be on the hook for $1.17 million that year. That may not sound like a big deal, but every dollar matters, especially because that's the year they'll have to give Ilya Sorokin a big raise.

Also, while saving $2.33 million in 2023-24 is pretty good, it still leaves them on the hook for $2.67 million of completely dead cap, which makes it possible to re-sign the important guys but probably doesn't let them add a big free agent. It would be better to get rid of the entire contract, which would involve a trade - paying someone a draft pick to take Bailey off our hands.

Is that better or worse than a buyout? That depends on whether you value draft picks more than cap space, and it also depends on which draft picks would be required. Personally, I'd rather get rid of the contract entirely, but that's made more difficult by the fact that the Isles don't have a first or third-round pick in this upcoming draft and have already traded their 2024 draft.

All indications are that Bailey won't be back next year. GM Lou Lamoriello admitted as much when he met with the media last week. The only question left is what that departure will look like. A buyout is possible, and depending on the price of a potential trade, it may be the best option.