The thing to remember with Sheary is he'll be 26 this Summer, which isn't old but it's not like, if we traded him, we'd be giving up the best years of his career. They're likely either already gone or we're in the midst of them. It's quite likely that, especially in coming years, we'll all be pretty sour on this contract.
While that's very true... that still doesn't change the fact that he's still our 3rd most skilled winger on the team, and that without him, having a true 3 line attack is going to be very very hard. Unless of course the plan is to put Guentzel with Crosby, Kessel on the 3rd line, and then whatever's left with Malkin. But most of us usually bitch about that when it happens about how whomever suggests it clearly hates Malkin.
I mean if we did a Sheary+ for Pageau (or some other semi comparable C)
Guentzel - Crosby - Hornqvist
XXXXX - Malkin - XXXXX
Hagelin - Pageau - Kessel
Kuhnhackl - Sheahan - Reaves
Rowney
XXXXX = Rust, and someone else. Now if that someone is any good, then it's not a big deal... but I somehow suspect that that person will not be someone we'd be all that happy with, and that at the end of the day, we will see a lineup (the 'ideal' one) closer to the 2016 one vs the 2017 one with regards to the forward lines.