Five Questions That the Yankees Have to Answer This Offseason

By EJ Fagan

November 1, 2026

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The following post comes from EJ Fagan's Substack, Baseball Is Life. It is shared with permission.

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Welcome to the offseason! Since the Yankees were eliminated from the playoffs, we had our second child! I’ve been holding back on posting to take care of the new kid, but I’m back and ready to write.

I’m going to avoid writing about labor issues until the lockout begins. There will be plenty of time with nothing else to talk about. For now, let’s focus on baseball.

The Milwaukee Brewers have won the World Series! Congratulations to them and their fans. Now it’s time for the Yankees to get to work. The team has a lot of questions to answer. Here are the five big ones in no particular order.

Who Plays Third Base?

Ryan McMahon was awful last year.

If McMahon were a Gold Glove third baseman, maybe you could tolerate a strikeout-heavy .297 xWOBA and .636 OPS. But he took a massive step back on defense as well last season. From April onward, McMahon looked old and broken at third base. The Yankees need to eat his contract and find an upgrade.

Unfortunately, the third base market is pretty thin. McMahon is actually the #2 trade candidate at the position on MLBTR’s top 40 list. The free agent market is similarly thin at third (and everywhere else). The team is going to have to get creative.

The biggest name available is Japanese Triple Crown winner Teruaki Sato. There’s a ton to like about Sato. He’s probably the best hitter in the world not playing in the majors leagues. He’ll be 28 years old next year. But he’s also another strikeout prone lefty hitter.

I’ve heard mixed reviews on his defense. Some scouting reports say he’s unplayable there. But he also won the NPB Gold Glove at the position. He looks more athletic to my eye than Murakami.

I’m planning a post on creative solutions at third base. Some names that I think the Yankees could pry loose: Nolan Arenado, Matt Shaw, Pedro Ramirez, Josh Jung, Isaac Paredes, Maikel Garcia. But it sure would be nice to solve the problem with money given the questions below.

Who Plays Second Base?

The Yankees will be not be offering Jazz Chisholm a qualifying offer. I doubt that they bring him back in any capacity. Someone else will have to play the position.

Anthony Volpe is the incumbent right now. I thought he looked strong on defense at the position. His weak arm caused him to rush at shortstop, but it plays well enough at second. His range and reads are strong.

Can his hitting play up at an easier position? Probably not, but strong defense can make up for it. I think his late season performance was strong enough that they’ll tender Volpe a contract

Still, I think the Yankees would prefer an upgrade. The available options are a little bit better. My favorite is Xavier Edwards on the Marlins.

Edwards is just flawed enough to be available. He’s a high contact noodle bat who gets on base mostly by taking a lot of walks and putting the ball in play. He’s fast but not lightning quick. He’ll be 27 with lots of team control left.

Some other names that will fill out a post one day: CJ Abrams, Zach Neto, Ezequiel Duran, Michael Massey. The Yankees can definitely get one of these trades done if they want to, although the degree to which they do will be determined by the answer to the next question.

Will the Yankees Trade from Starting Pitching?

The Yankee farm system is in rebuilding mode. The best Yankees trade chips are going to be major league players. And while they have a few interesting hitters to trade, the obvious surplus is in starting pitching.

The team enters the offseason with six bonafide major league starters: Gerrit Cole, Carlos Rodon, Max Fried, Cam Schlittler, Will Warren and Ryan Weathers. They also have Clark Schmidt, Elmer Rodriguez and Carlos LaGrange waiting in the wings, Brandon Beck and an emergency starter and a proven ability to develop more pitching.

But will they be comfortable trading away one of their major leaguers? Things can go south real quick on starting pitching. But I think too much caution here is unwarranted. It’s just as risky to go into the season relying on Ryan McMahon and Anthony Volpe at key positions.

A lot of teams need starters. The Cubs have to rebuild pretty much their entire rotation. The Athletics are building an interesting core of hitters on top of a garbage fire of a pitching staff. The Nationals, Giants, Marlins, Padres, Royals and Braves could all use starters.

Pretty much every major trade proposal that we talk about this season is going to involve sending a starter or two elsewhere. But will the Yankees do it?

How Do You Rebuild the Bullpen?

The Yankee bullpen was both thin and excellent in 2026. But David Bednar and Paul Blackburn are free agents. What happens next?

Both seem likely to come back. Bednar probably gets and accepts a qualifying offer.

Blackburn gets a smaller deal but a little more money. Don’t mess with success.

After that, the team has to get creative. There aren’t a ton of big free agents available. While I’d love Adrian Morejon, he’s probably going to be super expensive.

I think we’ll probably see a permanent Carlos LaGrange bullpen conversion this offseason. They played with fire by converting him midseason and almost got burned by a major shoulder injury. Let the man throw 103 for one inning at a time.

Clark Schmidt is another likely conversion. I suspect that they’ll tell Schmidt to prepare to starter in case of injuries, but he’ll likely enter Spring Training as the 6th or 7th starter on the roster.

One trade candidate that I’ve heard people speculate on is Juan Morillo, who is coming off a banger year for the Diamondbacks.

The speculated trade? Luis Garcia Jr, since Arizona badly needs a first baseman. Which leads us to our last question:

Where Does Garcia Jr. Play?

Garcia Jr. can hit. After the trade but before his wrist injury on September, Garcia hit .285/.317/.482 for the Yankees. He’s got a bit of a different look than other Yankee lefties, with a bad ball contact oriented approach.

But defense is more complicated. He looked pretty strong at 1st base, with more range than a typical defender but lacking some of the fundamentals of a professional 1B. He has a longer history at 2nd, but was pretty awful there.

Do the Yankees try to solve their problems at 2nd or 3rd base with Garcia? I kind of hate it. Their attempts to play guys out of position have not worked out well recently.

To me, the Garcia question is ultimately a Giancarlo Stanton question. Without Stanton, the Yankees have a strong 1b/DH/RF combination of Rice, Garcia, Ramos and Judge. Ramos and Garcia effectively form a platoon, with Rice and Judge taking the DH slot. But that all breaks down with Stanton, with both Garcia and Ramos lacking a place to play.

I could see Garcia Jr. getting traded. He’s an intriguing bat. Someone might want to add some thump their lineup. Even without Stanton, the Yankees might want to add some flexibility to the DH slot. Garcia for Juan Morillo? I don’t think I do it, but I sure do think about it. Garcia for Nolan Arenado? Cleveland, Seattle, Miami and Pittsburgh all want to content but got no production out of 1st last year.

But I hope they hold on to Garcia Jr. I’m kind of excited to see him in a lineup next to Judge, Rice and Bellinger. And he pairs well with Heliot Ramos as two must-platoon players.