InfinityIggy
Zagidulin's Dad
I don't see Treliving muddying the relationship by holding out during the regular season. If it's true Gaudreau can't wait to play in the East, you can't dig your heels in this contract and piss him off. You show him respect this go round, pay him a little more than you're prepared to ($7.5m-ish) and hope he's happy enough to stick around for another contract down the road.
Obviously that can't be the primary intention during these negotiations, but it's an important factor to keep in mind. Last thing you want is your best player not happy with playing for your team and asking for a trade 2 years into a new contract.
I think in the unfortunate case he does want to leave, then that is exactly when you have to dig your heels in.
Sign him to a very trade-friendly contract and begin the long, long process of exploring your options to deal him.
Fortunately, I think Gaudreau wants to be here for awhile.