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Winner: Andrew Benintendi

His career in Boston came to a disappointing end, but he made a comeback in Kansas City, and when the 2023 deadline (inevitably) required an injection of such a thing, the Yankees’ “left-handed contact hitting.” became the first choice. .

His Yankees career ended too quickly due to a mistimed wrist snap and a hook bone flying off the track, but Benintendi nevertheless beat New York’s top offers in free agency fairly easily, signed a five-year deal with Chicago White, the Sox that ranks (somehow) as the biggest deal ever for that franchise. bottom.

Loser: Yankees after Andrew Benintendi chase

I’m not saying the Yankees should have matched Benintendi’s deal. Five years is a very long time for someone who didn’t stand out in the Bronx until about a week before he died. Here comes Spencer Jones. Here comes Jason Dominguez. Aaron Judge is trapped. Should Harrison Vader be? Outfield spots are not abundant.

With that said… come on. You need to have a better backup plan than “tell everyone Aaron Hicks will be fine again.” None of the options were ideal, but failing to secure any of them would put the Yankees at worst as losers and at best “TBD — see you by the deadline.”

That said, it’s probably not a great strategy to go into the season knowing you have to sort things out in July. Where’s Dalton Versho?

Winner: Brian Cashman

Now he’s got Brian Sabeen and Omar Minaya! Both experienced baseball executives should immediately assist Cashman with a championship-level talent assessment.

And worst case scenario, he got two shiny new Fall Guys! Win-win.

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