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Yankees Mailbag: A trade deadline postmortem

This week’s mailbag has one goal, and that’s dissecting what went down (and what went wrong) at the deadline.

MLB: New York Yankees at Tampa Bay Rays Kim Klement-USA TODAY Sports

Good afternoon everyone, it’s time to dive back into the mailbag and answer some of your questions. Remember to send in your questions for our weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com.

Ruff Trade asks: My question — could Cashman and Co. have played the deadline any worse?

The overarching theme of this week’s questions all boiled down to this point, so I suppose we should spend some time on this one. The Yankees’ deadline strategy was unclear for weeks leading up to the end — they weren’t clear buyers or sellers and were inconsistent enough on the field to warrant holding either position, and it seems there was some conflicting opinions within the front office about which side of the fence they should land on as well.

In the end, they did make perhaps the worst choice and stayed on the fence. They held out for a reportedly high price on any of their tradeable players, such as Harrison Bader, Wandy Peralta, and Gleyber Torres and didn’t get enough mutual interest, so they pivoted to picking up a reliever at the end in Keynan Middleton (as well as adding on Spencer Howard when the Rangers had to shed a roster spot). There was hardly much left for them to add when they were done waiting out the market — the Angels, Cubs, and Padres had decided to add instead of sell and then picked up pieces that could’ve helped the Yankees.

In a way, even though this outcome was the worst they could’ve chosen it was also the most predictable. The Yankees played themselves into the tightest corner possible and the roster was so full of holes that were obvious from as early as last year that changing it wholesale would be a monumental task even if they had an obvious direction. Thus, they toed the line until the bitter end and will hope for the best when it comes to climbing their way out of the Wild Card pile.

What we know now about Anthony Rizzo only exemplifies the dysfunction going on here. While I don’t want to get too in depth on this specific issue, it’s impossible to ignore how incomprehensible it is for an organization to blatantly miss an ongoing issue with one of their starting players — unless you look around and see the bigger picture of how the Yankees have mishandled so much of this core.

lidbit asks: Of all the player personnel decisions made late last year and this year, how highly ranked is the continued disuse of Oswald Peraza?

Peraza’s plight is a confusing one, which again ties into the theme at hand. It’s certainly near the top, as he’s got the top prospect shine still firmly attached from just a year ago and had a highly successful debut in that short September stint he received. Sure, his 2023 did not start off so well, and it’s understandable that the front office decided to send him down then, but considering how the offense has performed in the months since and the tear that Peraza has personally gone on down in Triple-A it’s incredible to think that Oswaldo Cabrera has gotten far more opportunities than he has.

It’s highly reminiscent of how Estevan Florial’s season has gone, and his case is perhaps more confusing than Peraza’s has been. At the very least you could make a solid argument that keeping Peraza down to hold his trade value up made sense so long as the team was buying ... but then they didn’t really buy, and his name wasn’t the first called to join the roster after the deadline. There’s a whole list of problems with the team, and while Peraza may not be a guaranteed solution for them all he could at least feasibly be a solution for some of them. At the very least, he’s playing every day so his development hasn’t gotten messed up, but that’s a small consolation when the pressure is growing each day to turn things around.

NYCKING asks: One word to describe New York Yankees going forward in the next five years?