Brady > Nylander and nobody wants that Kerfoot contract the dude is not good that's a cap dump by the Leafs. 2nd rd pick means that the value is bad for the Leafs but the trade makes no sense to begin with since it doesn't help Ottawa at all.
I wouldn't do it either as Ottawa, but your reasoning is just plain bad.
Kerfoot a cap dump?
Completely ignoring N. Robertson?
Just a bad take, to be honest.
Now that I am over that post, Ottawa needs to rebuild it's nucleus. Nylander can be one of those guys, but I wouldn't start with him. Tkachuk and Chabot is a much better starting point. They would win the trade on value but it's extremely difficult to find players like Brady, and I don't think the value is enough to get them really thinking deeply about it.
An equivalent trade would be like trading Tkachuk, Pageau, Batherson and a 2nd for a guy who is an upgrade, but not an organization altering upgrade. Unless you are getting a #1C or a #1D, why bother?