Might be a trade that could work out for both teams-personally I think it's plugging one whole by making another for the Leafs- but I don't see it as a realistic scenario for a few reasons (trade protection, a top pairing defender with term being dealt, requires 3 other trades to make the cap work for next season).

I could see something like Romanov + Pageau (=7.5M) for Nylander+ Timmins/Liljegren (=8.1/8.4M) in terms of NHL roster players (probably a lot of picks would be involved including the ISLES 2024 1st and maybe a waiver-exempt player from NYI + whatever futures are needed to cover Timmins/Liljegren's value).

I agree that it isn't realistic. I just figured I would try to give the isles perspective of a trade like this.

- Romanov isn't the top-pairing defenseman that TOR needs (at least according to fans) but he does add physicality which is what Treliving is looking to do. With Pelech, Pulock, and Mayfield on the team I think the Isles would be open to moving him out and getting a good puck-moving defender like Timmins instead. A potential problem with this is that the Isles would have 4 RHD if Timmins dresses which might not be to their liking. Toronto on the other hand, would only have 2 RHD but that's just the status quo with Brodie playing the right side.

- Pageau would be a solid 3C for the Leafs, they do have Minten who looks like he will be a great 2 or 3C, but I do think he will eventually get sent down after his 9-games. Out of all the players with trade protection in NYI, I think maybe Pageau would be the most likely to waive for TOR/not have them on his list.

-The Leafs might be better served to keep Timmins but perhaps they can just get futures for him now as part of a Nylander trade since he won't have much of a role as a Leafs until Klingberg leaves (if he does). For the Isles, his having the extra year, might make it easier to fit in Nylander's extension which will probably see him getting a 3-3.5M raise along with Sorokin's 4.5M raise next year. Liljegren probably gets a pay bump in the 2.5-3.5M range depending on the term and how he does this year, but the main reason I think it doesn't make much sense to include him is that the Romanov for Liljegren swap doesn't really make too much sense for either side.

-I had Wahlstrom included originally, but I'm a bit on the fence about that. I think the Isles would prefer to keep him, although they might not be able to afford him if he breaks out but at least he's an RFA. The Leafs might want him due to his good shot, but depending on when this trade occurs there might not really be a spot for him on the roster. At the risk of making this a 7+ piece trade, maybe the Leafs could add Robertson if he is included. On the other hand, the Leafs (and the Isles) could just decide to keep their guy, and give Robertson the opportunity to make the team with Nylander's departure assuming Minten eventually gets sent down.


I do think the Leafs are just going to pay Nylander 9.75-10.5M instead of making a trade that weakens them/is not an absolute slam dunk as I proposed, or one that improves their D but weakens their offense like Pulock for Nylander. Nylander is just making it easier for the Leafs to justify giving in to his demands.