Former New York Yankees player we'll wish stayed: Andrew Benintendi
Obviously, this transaction is more complex. The Yankees weren't choosing between "Andrew Benintendi in 2023" and "Not That". Any Benintendi contract they signed this offseason would be long-term, and the White Sox decided the number to beat was five years. Rumor had it all offseason long that Benintendi preferred the midwest, and once that number appeared in his inbox. rumor swiftly became fact, even if it hadn't been previously.
Sure, Benintendi would be an improvement on the Yankees' current left field situation, but who would you rather manning the spot in 2025? A 31-year-old Benintendi with an inconsistent track record of power, or Jasson Dominguez/Spencer Jones, with far higher ceilings?
That said ... Benintendi would be an obvious improvement over the Yankees' slapdash solution of placing a utility infielder with an electric bat in left field. Add Benny to the current Yankees roster -- basically what they were trying to do last summer, though it never materialized -- and you have a potent lefty bat with contact skills occupying a current semi-hole. The bench looks better. The lineup looks more diverse. It really could've worked, and we never really got to see it play out.
So far ... Benintendi has just an 80 OPS+ and .263 average without a dinger. If those stats never normalize, the Yankees won't regret losing the outfielder so quickly. But something tells us the 2023 Yankees specifically (though maybe not beyond) work better with Benintendi in left. He's got one more year, at least, as a missing piece.