Yankees questions for 2025 season after World Series loss

It might not feel like it right now, but — even considering the amusingly absurd championship-or-bust expectations that Yankees fans have for their team — this season was a success.

They won 94 games and the AL East title. They got a soon-to-be MVP season from their star slugger. They went to the World Series. It had been 15 years since they last did that, after all. While winning the World Series is obviously the ultimate goal for the Yankees (and really any team), if you can’t take at least a bit of joy from making it there, well, maybe happiness is just going to prove elusive for you.

But that said: Now that the Yankees have fallen short … they better go out and win one next year. It’s going to be a fascinating offseason as they try to take the next step forward. And what will that entail?

Here are five pressing questions for the Yankees this winter. Remember, these are the Yankees: They better figure it all out … or else.

1) Can they outbid everyone for Juan Soto?
If you needed any proof of just how important Soto is to this team, you got it in this postseason: He was pretty much the only guy who was consistent the whole way through. Of course, Soto would be incredibly important for any team in baseball. That’s why everyone’s going to want him so badly. Soto’s free agency is obviously the biggest story of the Yankees’ offseason, and really, of the offseason in general. He will have suitors everywhere, from San Francisco to Los Angeles to Queens to maybe even his old team in Washington, D.C. The Mets, in particular, are likely to be aggressive; you can almost see Steve Cohen salivating. But as we saw this year, the Yankees may need Soto more than any of those other teams. Can they really let him get away? If they do … are they really the Yankees we’ve always known?

2) Will Aaron Boone be back? If so, for how long?
It feels like Boone has been under fire since he became the manager of the Yankees, which sounds stressful until you remember that he’s the manager of the Yankees: That’s just part of the job description. The Yankees do have a club option on him for 2025, and that they haven’t extended him (either before this season or during it) is a sign of how he was managing for his job this year. You’d think getting the Yankees to the World Series would be enough to bring him back, right? Well, maybe, though there will be Yankees fans who will be holding that decision to bring in Nestor Cortes in Game 1 against him for a long time. Is he the guy moving forward? Will they just pick up that option? Will they extend him? Will they make a change entirely? It will be absolutely fascinating to see what decision is made here.

3) Is it time to move Judge out of center?
Aaron Judge has been an adequate center fielder in his career, but his defense tends to erode as the season goes along, as you might expect: He is a huge man in his 30s, after all. But in many ways, he has sort of had to play center field because of the Yankees’ roster construction: There just hasn’t been anyone else to put out there. But it’s probably time. Judge has a tendency to wear down late in the year, and there’s nothing more important to this team than his bat. There are questions about whether Jasson Domínguez will be able to hold onto center field long term, but in the short term, it might make sense to put him out there and let Judge take left field … or if Soto doesn’t sign, maybe even right. Judge had a good run out there in center field. But if he’s going to stay healthy through 2031 when his contract ends, getting him back to a corner spot is the logical way to do it.

4) How do they deepen and diversify this lineup?
The biggest issue with the Yankees this year was how reliant they were on Judge and Soto. That’s a reason they need to bring back Soto. But that’s also a reason they need to lengthen that lineup in the offseason. There are some obvious spots to target, particularly in the infield. What’s most important, though, is that the Yankees find some guys you can move around, so one injury doesn’t wreck them, so they have some options other than just trotting the same lineup out there and hoping everyone stays healthy. You saw how much the Dodgers were helped by having someone like Tommy Edman in the postseason, a smart ballplayer who can play anywhere. The Yankees may need to find themselves a Tommy Edman.

5) Do they get themselves a closer?
Luke Weaver was excellent for the Yankees down the stretch and in the postseason, but you have to admit: There were several moments when you thought to yourself, “wait … the Yankees closer is Luke Weaver?” The spirit of Mariano Rivera will forever float above this franchise, and with Clay Holmes hitting free agency after a rough year, you wonder if the Yankees will get aggressive to bring in an established, lockdown closer they can build the rest of the bullpen around. The Cardinals may be putting Ryan Helsley on the market. “Hells Bells,” his bullpen entrance song, would sound pretty great coming out of those Yankee Stadium speakers, wouldn’t it? Even if Weaver is the closer moving forward, though, bringing in another high-leverage option to replace Holmes is a must.