Predicting the 2025-26 Yankees offseason: outside acquisitions

This is part two of the story that I posted on the subreddit last week.

Had to cut for space, but I also think that Ryan Helsley on a 1 year/$15 million pillow contract with a 2027 player option that vests at 30 appearances at the same rate with a $3 million buyout would be an interesting alternative in lieu of one of the options in the story.

In regard to Volpe and the shortstop situation, I'm of the belief that the front office will let it ride one more season, at least until the deadline, before making a big change. The market is quite top heavy. Bichette is limited defensively. Kim would be an interesting option, but I'm not sure it's an upgrade worth upwards of $15 million dollars. I think Caballero working his way into a timeshare is more likely than any outside alternative.

Please let me know what you think and what you would change!

12 comments

  2. I’m hearing the Dodgers are all in on Bichette. The Yankees are making a big mistake not going for him. His defense is good enough and his offensive abilities makes him worth the upgrade. We need better offense this year.

  3. Why does like every offseason fantasy draft just omit Williams or write him off without much thought

    I could 100% see them bringing him back

  4. I am getting so sick of hearing the Caballero should play short garbage.

    Let’s make sure we understand a few things. Shortstop is Caballero’s worst defensive position he is 2025 Volpe bad defensively at short.

    He is a differently terrible hitter to Volpe 84 OPS+ to Volpe’s 82 OPS+ Volpe has power and some speed Caballero will take a walk and some speed both suck at making contact and their SB% are almost the same 77 vs 79

    Caballero is a very valuable BENCH player capable of covering multiple positions 2B, 3B, SS, LF, RF but if he is playing one position every day you need an upgrade.

  6. One thing is for sure. Volpe needs to ride the bench a lot this season, giving Caballero more chances to play. Caballero is just better, at the plate and in the field. It’s really not that tough a thing for management to figure out.

  7. Feel like we get linked with Brendan Donovan every offseason yet the Cardinals never seem to want to move him. I’d like to see him in a Ben Zobrist like Super Utility role where he doesn’t have one defined everyday position but instead moves around between LF, 2B, 3B, and SS throughout the year.

  8. Pretty unlikely they move McMahon to the bench. He’s played only 3B for years and makes too much money to be a bench piece. Bench players, because there’s only a few, have to be able to play multiple positions. We’re stuck with him unless we trade him and eat some of his salary. Also, the Yankees don’t see Dominguez as a CF.

  9. Donovan’s best season was his rookie year. And he didn’t even play 3B last season. There has to be better options.

  10. Realistically the Yankees aren’t spending that kind of money on relievers. Why would they get Suarez AND Fairbanks when they already have Bednar and Doval, plus Bird as the Blake project? They’ll sign some fixit arms and maybe a more reliable middle leverage reliever than Leiter.

    I also don’t think the Yanks are trading Jones. If they were, they’d have done that years ago when he was at his most valuable (or during his superhot run last season). I think if he rocks it in the spring, he plays his way onto the team as 4th OF, otherwise they stash him back at AAA, hope he figures out the K issue and bring him up if there’s an injury.

    I think they do something at starter but am inclined to think they wait to see if Imai is posted. He’d be a higher upside arm than Woodruff and would allow them to trade extra arms (Gil or Schmidt?) for deadline help where needed. And the Yankees showed they’re open to making big bets on quality Japanese players with Yamamoto. Unlikely, but my hope is actually that they sign Imai and Okamoto somehow (Okamoto can play 3B, 1B and LF well and is a righty bat with contact skills). Would prefer that over Donovan.

  11. Great job as always! Thanks for this.

    I think the Helsley and Woodruff contracts are a little pricy, but love the idea of Donovan.

    I have a total payroll of $343M before McMahon gets traded. I don’t see Steinbrenner going that high. I see him sticking at the $320M area.

    Take out Helsely and Woodruff and trade McMahon (to put Donovan at 3B) and you are at about $305M. Which gives you about $15M for pitching and other depth.

    You need to include the $33 million dollars in benefits and retained contracts (DJ). I don’t think that that was included in your $314M number.

    Love the content though!

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