My (Sober) Yankees Offseason Master Plan

By E.J. Fagan

November 15, 2025

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NOTE: The following comes from EJ Fagan's substack page and is shared with permission.

Please check out EJ's substack page for more great articles.

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If I were Brian Cashman, here is what I would do this offseason. A few rules:

• I have to stay close to the $304 million luxury tax threshold. I can go over by a few million but not much more.

• I can only trade for candidates on the MLB Trade Rumors trade candidate list.

• I have to pay free agents the contracts predicted by MLB Trade Rumors.

  
  

For the purposes of today, I’m going to assume that Trent Grisham does not take the qualifying offer. I’ll revise if it does.

Let’s start with clearing some money off the board. I’m going to non-tender:

• Mark Leiter Jr.

• Jake Cousins

• Ian Hamilton

• Scott Effross

  
  

With their salaries off the board, Fangraphs estimates the Yankees payroll at right around $257 million. I have ~$50 million to spend.

This post is going to be my very sober version of a plan. Every move here is very plausible. In a future post, I’ll go a little crazy.

Step 1: Sign Cody Bellinger

This one makes too much sense for everyone. Bellinger had an excellent season with the Yankees. He fills a need as a long-term left fielder and occasional center fielder. He’s a lefty hitter, but has reverse platoon splits. He’s one of the better contact hitters in baseball.

All of that said, I think that Bellinger is a tad bit overrated.

Bellinger overcomes his relatively low bat speed and exit velocity with a combination of lots of good contact and a straight pull swing. He’s a short porcher.

MLB Trade Rumors estimates his contract at $28 million over five years. That eats up a lot of our budget, but Bellinger is worth it. We’re down to about $20 million.

Step 2: Trade for Joe Ryan

The Yankees need a starting pitcher. My initial plan was to do what I thought the Yankees were going to do: piece together a rotation with a fill in or two until Cole and Rodon return.

But Brian Cashman said in a press conference that starting pitching is a priority for them and rumor has them interested in Lucas Giolito. Maybe the Yankees are going to follow the Dodgers and load up a rotation with more than five guys knowing that someone will probably be injured.

And in truth, it’s real hard to sign a free agent starting pitcher worth his salt for less than $15 million. We’re working on a tight budget here, so trading for a cheaper pick makes more sense.

Why Joe Ryan? Ryan is under team control for two more seasons and set to earn around $5.6 million in arbitration. He’s a solid mid-rotation starter, but not the kind of guy who will require the Yankees to empty out their farm system:

Ryan would compete with Carlos Rodon and Cam Schlittler for playoff starts, but comfortably edges out Will Warren and Luis Gil.

Running with the Twins Ownership Are Super Cheap Theory, I am going to offer some young, cost controlled arms in return:

• Yankees Get: Joe Ryan

• Twins Get: Luis Gil, Kyle Carr, Bryce Cunningham

  
  

I’m giving up Gil (I considered Warren as well), which may put the Yankees in a tough spot in the early season. But Ryan is a step up from Gil in terms of reliability.

There might be a version of the trade where Ryan Jeffers comes to the Yankees in exchange for JC Escarra, but that doesn’t fit into my budget now. $15 million left.

Trade for JoJo Romero

The Yankees need another lefty in the bullpen. I struggled to find a decent candidate. I was hoping for more of a power lefty, but JoJo Ramirez will do.

Like Tim Hill, he’s more of a weak ground ball / soft contact guy. He’s held lefties to a mid-.500 OPS at points throughout his career. Righties by no means hammered him, but consistently posted an OPS in the .700s. His 2025 breakout was mostly a product of finally figuring out righties. Your guess is as good as mine as to how long that lasts.

Romero is due about $4.4 million in arbitration and a free agent after the season. He won’t cost too much to acquire, assuming the Cardinals are shopping him. Something like:

• Yankees get: JoJo Romero

• Cardinals get: Cade Smith and Henry Lalane

  
  

$11 million left. Time to fill out the roster.

Yankees Resign Ryan Yarbrough, Amed Rosario and Austin Slater

These are pretty boring moves, but I think they are important. Ryan Yarbrough did a fine job as a fill in starter and longman last year. The Yankees are going to need someone to man the 5th starter spot for a month or so who can do something else once the starters return. Yarbrough will keep you in games.

And then we fill out the bench. The Yankees were way too vulnerable to left handed pitching last year. They need some lefty-mashing right handed bats off the bench to keep teams honest. That was the logic at the trade deadline when they acquired Rosario and Slater, and the logic is still sound.

Rosario is a career .800 OPS hitter against lefties (.667 against righties). Slater is a career .787 OPS against righties (.640 against righties). Rosario can fake it at 3rd, 2nd and right field. while Slater can play all three outfield spots. They are perfect bench platoon players. Hopefully Boone can use platoons to keep guys fresh the way he used his outfield surplus last year.

They would join lefties Oswaldo Cabrera and JC Escarra to form a pretty balanced and versatile bench. Cabrera or Rosario might have to go when Volpe returns, but that’s a problem for another day.

Bottom Line: A Tweaked But Improved Roster

At first glance, you might be underwhelmed. I’m returning mostly the same roster from the 2025 season. Grisham is being subbed out for more Jasson Dominguez at bats and centerfield defense. Devin Williams is being subbed out for JoJo Romero. Joe Ryan is a big upgrade over the combination of Gil, Stroman and Carassco from last year. They probably have a little more juice to squeeze out of guys like Dominguez, Volpe, Wells and Warren to make up for any regression from veterans.

But I don’t think that the Yankees are by any means treading water here. They have a little bit of a addition by subtraction with Luke Weaver and Devin Williams leaving the bullpen. The roster got a lot better in the second half with the improved bench and promotion of Cam Schlittler. And of course, Gerrit Cole is on his way back.

All of this for a team with an expected 97 win record in 2025. I think that the Yankees would go into the 2025 season as the favorite in the American League, depending on what the Blue Jays and Red Sox do.