If I were a Yankees fan, as beloved as Judge is, I'd want the Yankees to spend that $350 million elsewhere. They're loaded with HR hitters. If they can get a decent-fielding RF who can get 80 RBI for a fraction of the price, they'd be much better off. As a Mets fan, it pains me to say that I hope they don't (over)pay deGrom. Sometimes addition by subtraction is the smartest play.
Judge had an historic regular season. He'll never come close to duplicating that. It's likely that no one will. He's also going to be 31-years-old to begin the season next year and 2022 was only the 2nd season in which he didn't miss significant time due to injury.