Islanders Lamoriello Getting Ready To Mimic A Past Trade?

Last season, Islanders general manager Lou Lamoriello traded Josh Bailey to the Blackhawks with a second-round pick to get his $5 million contract off the books. Is Lamoriello about to mimic that deal this summer?

On Day 2 of the 2023 NHL Draft, New York Islanders general manager Lou Lamoriello sent Josh Bailey and his $5 million cap hit and their 2026 second-round pick to the Chicago Blackhawks for future considerations.

That move gave the Islanders the cap flexibility to bring back their pending unrestricted free agents.

Is Lamoriello getting ready to mimic that trade this summer?

On Friday, Lamoriello made a trade you would typically see on draft day:

While the Islanders could use the extra second-round pick to boost their prospect pool or use it as an asset to acquire a top-six forward, Lamoriello could also use it to entice a team to take on undesired contracts. 

And if the Islanders want to bolster their team, they must create additional cap space. 

Before the Islanders re-sign any of their pending free agents, they have just a tad north of $7 million in space, which is not enough to acquire a top-six talent, whether via a trade or during free agency. 

Opposing teams are well aware of the Islanders' situation, and it would likely take a second-round pick attached to one of those contracts to clear a contract. 

Could Lamoriello be looking to move Anders Lee and his $7 million cap hit, which is on the books for the next two seasons?

While the Islanders captain played well down the stretch and was arguably one of, if not New York's best players in the postseason, getting out of that cap hit would do wonders for the Islanders.

Lee has a full no-trade clause, which will become a modified no-trade clause (15 teams) on July 1, day one of NHL free agency.

So, if the Islanders are looking to move Lee, it won't be easy since he'll have a say regardless, but if there is an agreed-upon destination, one of the two second-round picks will join him.

Could Lamoriello attach the second-round pick to move Jean-Gabriel Pageau's $5 million cap hit, which is on the books for another two seasons?

While Pageau may have more value than Lee, given that he plays on both special teams, is a player who goes up against the best the league has to offer night in and night out, and is a face-off specialist, it would still cost a second-round pick to get his contract off the books given the lack of offensive production (11 goals, 22 assists).

Pageau has a modified no-trade clause (16 teams). 

If the second-round pick is going with either Lee or Pageau, the Islanders would likely not have to retain much, if anything, on those deals.

To clarify, it will likely take a second-round pick plus another asset to move either.

Financially speaking, the Islanders would have over $14 million in cap space—before signing their pending unrestricted and restricted free agents—if Lee were moved and around $12 million if Pageau were moved.

The Islanders have two second-round picks, so, in theory, they could move both players, creating around $19 million in cap space. But then they have to fill those two holes in the lineup, with Pageau's being the hardest one to fill given the many hats he wears. 

While the Islanders can move other players to clear up cap space, like Brock Nelson and his $6 million cap hit and Kyle Palmieri and his $5 million cap hit, those two are coming off 30-plus goal seasons; the second-round pick should not be needed.

Nelson has reached the 30-goal mark in three straight seasons and is the most valuable player on the team -- at least amongst players who would be moved. 

He and Palmieri, who are entering the final year of their deals, are eligible to sign extensions on July 1.

With Lamoriello, everything comes as a surprise, as he rarely tips his cap.

His Friday draft-pick move is certainly not one many saw coming and is one that usually occurs on the draft floor.

However, doing things earlier than most is something he's done recently, most notably acquiring Bo Horvat two months before the 2023 NHL Trade Deadline, a player who was going to be a top-three free agent if he didn't re-sign with the Vancouver Canucks -- which wasn't going to happen. 

It's likely that Lamoriello's next move -- which seems inevitable whether it's bringing on players in a package deal or shipping off someone -- comes during the 2024 NHL Draft, which begins June 28 in Las Vegas.

With the potential cap space that could come from unloading contracts, who is Lamoriello looking at, and how much of a difference-maker will that player or players be for a team with some big holes to fill?

All salary cap numbers are courtesy of CapFriendly. 

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