Yankees can't compete financially with guys like Cohen. Steinbrenner's lifestyle is funded purely by the Yankees, so as much as they want to win (not denying that they do), they want to remain profitable a bit more. Throwing money crazy around for a WS or two might be nice, but 6 years later when you're paying 100 mil a year for dead weight the Steinbrenner's would be sweating it out Christmas time not being able to buy those cars with ribbons on top for the extended family. So they compromise and spend plenty of money (Cole, Stanton, Donaldson) but they're not willing to spend stupid money (Judge AND Ohtani AND a solid catcher AND bullpen help) that a guy like Cohen, who owns the team for fun, might be willing to.