Is this idea good?

Chicago says yes all day everyday to this deal and every member of the Leafs management who had knowledge of this deal should be fired. Like if the janitor overherd Dubas on the phone talking about this deal while cleaning and did nothing to stop it , id fire him/her aswell

Nylander and Holl and a single high Rd pick would be more fair.

I'm guessing you're missing the $10.5 million retainment. In the past we've seen 1st Rd picks traded away for 1/3 that dollar amount in player trade retainment (ahem Foligno cost the Leafs two 4th Rd picks just to retain LESS than $2.7 million).

I realize all that. I would hesitate to trade Nylander for kane with that same money retained. Nylander scored 34 goals and 80pts last year, kerfoot scored 15 goals and is a 50pt player. Toews has no value to the leafs and would be on waivers today if he was on the leafs with a 5mill cap hit. Its 2022 not 2014 Toews. Kane is certainly better then Nylander but hes not kerfoot holl and all those pics better.