If Sid leaves Pitt, there's a more than good chance he picks Montreal...
I'm sure Dubas will be trying to retool fast enough to ice a competitive roster for Sid's last contract. But if Jarry continues to flame out, it's hard to see them have anything but a lottery team the next few seasons. Too many holes and too many bloated contracts.
By 26-27, we'll be a top ten roster without him, and potentially the cap room to make it work. Not sure there would be much reason to add him before that as the futures it would take are the very asset ammunition you'd want to have on hand to really bolster the cup contention window he'd be signing on to join.
Next summer, maybe a deal around some young assets we don't have room for + a cap dump & 1 first?
Anderson, Strubble, Mesar, Heineman/Farrell, Flames 1st.
Some teams would offer more, but if Sid wants Mtl I could see the Pens honouring him and accepting a quantity deal like that...
Slaf - Suzuki - CC
Laine - Crosby - Demidov
Roy - Dach - Newhook
Xhekaj - Beck - Gally