I'm likely getting ahead of myself, but I do wonder if the Leafs should be really trying to go for it this year. It's possible that Simmonds and Thornton are one-and-dones. It's possible we lose one or both of Hyman and Andersen as UFAs. It's possible we lose both Dermott and Lehtonen for different reasons cutting into our defence depth. And last but maybe most important, it's basically guaranteed that these new divisions give us the best path to the Finals that we'll get for the foreseeable future.
I say this in relation to the Leafs being linked to some mystery winger. Fingers crossed regarding injuries, but we likely only have one forward opening on the team so even though Iafallo seems like a decent fit I wouldn't mind trying to aim a little higher.