WINNER: Andrew Benintendi
Coming off a disappointing end to his career in Boston, the former top prospect was resurrected in Kansas City and became the Yankees' first option for "left-handed contact hitting" when they (inevitably) needed an infusion of such things at the 2023 deadline.
Though his Yankees career ended too soon thanks to a wrist snap at the wrong time and a hooked bone flying off its track, Benintendi still managed to beat New York's top offer pretty handily in free agency, signing a five-year pact with the Chicago White Sox that (somehow) ranks as that franchise's largest-ever deal. Good on Benintendi, who found probably two years of extra security in the more comfortable midwest.
LOSERS: Yankees, After the Andrew Benintendi Chase
Not saying the Yankees should've matched Benintendi's contract. Not saying that at all. Five years is an awfully long time for someone who didn't show all that much in the Bronx until about a week before he went down. Spencer Jones is coming. Jasson Dominguez is coming. Aaron Judge is locked down. Harrison Bader maybe should be? Outfield spots aren't plentiful.
That said ... come on. Gotta have a better backup plan than "Telling Everyone Aaron Hicks Will Be Good Again." None of the options were ideal, but not securing any of them still makes the Yankees at worst a loser, and at best a "TBD -- See Me at the Deadline."
Entering the season knowing you have a problem to fix under the gun in July probably isn't a fantastic strategy, though. Whither Daulton Varsho?
WINNER: Brian Cashman
Now he's got Brian Sabean and Omar Minaya around! Both experienced baseball executives should help Cashman immediately with championship-level talent evaluation.
And, in the worst-case scenario, he's gained two shiny new Fall Guys! Win-win.