I'm not so sure.I can't stress this enough, the Leafs don't have their 1st round pick for the next two seasons. "Rebuilding" and tanking gets you nothing.
If you move Matthews with 2 years left on his deal and Nylander with a bunch of years left on his deal, you're going to get more than a 1st round pick for each of them.
If they have a sell off, they'll collect a bunch of picks and prospects from the rest of their roster. They could try for more prospects instead of picks to help accelerate getting NHL talent on the roster.
BUT that will only happen if Matthews and Nylander with their NMCs want it to happen. Matthews is allegedly already on the fence. Nylander is on the record as not wanting to go through a rebuild. If Matthews goes, Nylander likely follows.
If that happens, they're rebuilding around their 1st pick in 2026.