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Yankees Mailbag: Making mega deals, offseason pace, and Cashman’s ranting

Look no further than the GM’s poorly-planned comments for the topic at hand this week.

New York Yankees GM Brian Cashman Photo by J. Conrad Williams, Jr./Newsday RM via Getty Images

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 bi-weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com.

MSP Giant asks: Like many I am hoping for two substantial FA signings or a substantial trade along with one substantial FA. Substantial = expensive. Say Soto and Yamamoto. Or Bellinger and Yamamoto. Don’t get hung up on names. BUT ... likely? Knowing Hal?

I won’t say likely, but the Yankees do have their name in the hat of multiple free agents as it stands. They’re certainly gunning to get at least one of the big names that have been floated, but the almighty budget probably doesn’t have it in them to grab multiple major splashes.

Looking more externally, it’s also just going to be difficult to compete with the amount of contending teams that are in need of an upgrade to their rosters. The Yankees seem to have the right connections if reports are to be believed in the Juan Soto sweepstakes, so at least the odds are decent that they’ll land someone of note, but it may be tweaks at best around their one move.

The idiot that said, “Harper is coming” asks: When will we see the first big offseason move? Unless I’m mistaken, I thought there’s usually at least some movement before Thanksgiving, but nothing has really happened yet.

I’ve been wondering what the pace of this offseason will look like — will it be fast-paced like the past few offseasons or more drawn out like in 2018-19. The Winter Meetings are always typically the date for seeing whether we’re going to get major action or not, but a decent amount of rumor mill spinning in the weeks preceding it would be a good sign. We haven’t gotten much in that regard, and it makes sense if the landscape is dictated by one superstar, and there’s no mistake that this one is. Shohei Ohtani’s free agency is likely to hold up plenty of other plans, and though many assumed the Dodgers would just be natural favorites entering the sweepstakes, it appears that plenty of other teams have their phone at the ready waiting for Ohtani’s agent to pick up.

This can be frustrating if you’re a fan of a team that isn’t in the race, and as far as we’re aware the Yankees aren’t in those waters. The one bright side I could offer is I don’t see the trade market suffering as badly so things could develop at a moment’s notice with Soto, but the free agents simply have to play the waiting game.

SEYanksAndCards88 asks: Do you think Brian Cashman’s public temper tantrum at last week’s GM meetings was him justifying running back the same team next season, even though the fans saw how the 2023 season ended? And do you also think that he is feeling some heat?

I struggle to understand what Cashman is doing any time he steps up to the mic at this point, because no matter what he says, it comes with some level of damage. Hal Steinbrenner has already gone on the record about this past season being a complete failure and something they won’t stand for, and while I don’t take his comments as a whole as calling for rapid change it’s clear that the results can’t be repeated, so why risk running it back? Sure, there was a lot of bad luck involved, but there was also a lot of predictable regression. Steinbrenner isn’t opening up the wallet for a wholesale change, but it’s clear that the status quo won’t suffice either.

Cashman’s position with the team is still a solid one, so I don’t view these tirades as indicative of his job security. Rather, I see it as lashing out at the change in public perception — the fanbase has turned heavily against him, and while he always had some detractors he was generally viewed as one of the best GMs in the game for years. There’s an ego that can form from having that connotation to your name, and Cashman certainly carries an ego with him. It’s visible in how he conducts trade negotiations — obviously every GM wants to win out on their side, but he wants the world to know he won the trade the moment it gets made. The terms are always only what he’s comfortable with. Now that the past few years of trading hasn’t gone in his favor and the fanbase has reacted to that, he’s gotten increasingly defensive over it.

Will this have any tangible effect on how the offseason plays out? Perhaps, but not from the agents of players either already playing for or potentially coming to New York. I don’t think Giancarlo Stanton particularly liked what Cashman had to say about him, and I don’t think the agent whose clientele also includes Yoshinobu Yamamoto did either, but it’s just noise at the end of the day. Business prevails in the industry, and if the offer from New York is the right one then they’ll take it. The soundbites and the smarmy attitude will affect fans far more than it will players, but it is indicative of where Cashman’s mind is at as he’s surveying the field. If his eyes get blinded by pride, then the road to a potential deal may just be left unfinished.