A guy like him has to believe he's the best, even if he demonstrably isn't.
He's not taking a discount, never was. The Jays can afford to pay him market value, the trick is getting him to realize his market value isn't higher than Judge, or whatever Soto gets, or even really comparable to them from an AAV standpoint. If he isn't willing to accept that, then they have to part ways. If Vlad thinks he's worth 40 million per season, he has to hit like Judge for more than 2 months.