If Machado wants to go to the Yankees, you don't offer $100M more just to "win."
You may strategically overpay, but even then, you have a reservation price above which the deal doesn't make sense (i.e. you could spend the money elsewhere and make more of an improvement to your roster).
There is no one I'd sign in 2019 that I'd allow to block Trout coming home in 2021.
Trout would be a game changer, not just his talent but the excitement he'd bring, Machado and Harper can't touch that.
Middleton is no fool, he'd like to sign one of them, but I think his signal is not for his GM to be stupid, but for his GM to spend without worrying about the owner's financial constraints (which handcuffs many GMs in smaller markets).