The Isles are not trading Pulock who has a full NMC in year 2 of an 8 year contract, Romanov who Lou just spent a 1st to acquire last year, or want to take on 2 contracts that only have 1 year remaining.

The Isles top 4 of Pelech, Pulock, Dobson and Romanov are not being moved.

They might not be but they should be for a top line forward

The Isles acquired their top line forward last year in Horvat. This year Horvat and Barzal will actually get to play together unless another injury happens.

The Isles will be targeting Tarasenko in UFA, if they cannot get him then it's Engvall and Wood next.

Horvat is more a 2nd liner who was on a shooting bender he’s a 60 point player hopefully Barzal can keep him at least near a point per game but I don’t think so. I don’t think they’ll be able to afford Tarasenko. Engvall is a good middle 6 winger but he’s not going to change the scoring dynamic by a lot. Wood is a decent bottom 6 but again won’t change the scoring issue.

Leafs aren't interested in this trade...

With moving Bailey and his $5M that would open up the room to sign Tarasenko who should be getting right around $5M for 4 years maybe 3.

He can definitely get more I see him signing a 7M x 3

Tarasenko is old and washed and wood is a 13th forward on most playoff teams. Engvall should be the priority

That’s a lot of money for a 3rd liner

His analytics aren’t good but he still is a 60-70 point player teams will offer him around 6.5-7 on a shorter term

Maybe, it’s immediately and albatross contact though

It’s not hard to put up 60 pts getting the ice time and offensive situations he gets put in - but accounting for regression he likely won’t hit 60 points next season.

He made the rangers worse because he’s a negative at 5v5. Without Tarasenko they probably beat the devils

I fail to see how this makes any sense for Toronto..

Bailey is a negative value player, or at best a neutral value, so New York has to add the 2nd round pick to move him just for future considerations (ie nothing). Nylander (assuming he has an extension) by himself is then easily worth Pulock and Romanov (not taking into account that Toronto has no need for Romanov as they’re filled at LHD for the foreseeable future with much better options. & Holmstrom is a bust and nothing more than a AHL scorer at best.

So:
Bailey + 2nd = future considerations
Pulock + more = Nylander
Romanov = nothing
…. Why then is Toronto just giving you 2 good defenceman for no reason at all?

Yes we are would love this

It's bc of Lilly (whom could fetch at least a 1st like Sandin...). In turn, we are giving up:

Nylander+Brodie+1st+ for 2nd+Cap dump+Pulock+Holmstrom+Romanov... Both Calgary and Colorado easily beat this offer and so the Leafs won't make this deal

The Islanders shouldn't do this because one season of Nylander doesn't equal an entire top-4 defensive pairing. (The whole idea of premising a trade on an extension is silly.) The declining Brodie, whom NY would be unlikely to want to re-sign, isn't close to either Pulock or Romanov in value, and one season of Nylander isn't close to the other. Even with an extension, $9 million Nylander isn't worth more than $6 million Pulock. (The idea that Nylander = Pulock and Romanov combined is just laughably uninformed.) The rest of this is kind of a mismash -- Liljegren seems on his way towards being a good NHLer, the jury is out on Holmstrom, Bailey is certainly not someone Toronto wants or needs, and the second is too far in the future to do the Maple Leafs any good. I don't know how interested Toronto would be in this deal (it probably depends on whether or not Nylander is likely to be extended), but the Islanders shouldn't entertain this at all.

Kudos to the OP. Not sure I would do that trade but there is lots of quality going both ways.

Nylander is certainly a player the Isles need. If anyone WATCHED the Leafs this year they would have seen a player engaged that drove play and protected the puck amazingly well. He didn’t slow down in the playoffs either, was probably the Leafs best forward against the Panthers. Unforetunately he was a little snake bit hitting 3 posts one game, but still managed to come up big scoring the tying goal in the last couple minutes of game 5.

When you watch the Isles you see a team that not only lacks offence but the ability to drive play consistently. Dump it out and dump it in unless Barzal is on the ice.