Yankees Inbox: Which New York team is closer to winning a trophy?

October 30th, 2025

While the Blue Jays and Dodgers continue to battle in an entertaining World Series, the Yankees have already flipped their calendars to 2026. That makes this a good opportunity to open up the Yankees Inbox. (Questions edited for clarity.)

CC Sabathia said he thinks the Mets are closer to winning a World Series than the Yankees. Thoughts? – James B., via Instagram
Yes, Sabathia did say this on a recent episode of Boardroom’s Network with Rich Kleiman.

"The Mets are going to be super motivated next year because they didn't make the playoffs,” Sabathia said. “It's going to be tough for the Yankees to get by after what they just went through and even last year, going to the World Series. The deeper you get into the playoffs, the harder it is to reset and get ready for the next year. The Mets still have a lot to prove with a great roster and a lot of talent."

Part of Sabathia’s take was that the Mets have a strong foundation with Juan Soto, Francisco Lindor and Brandon Nimmo, plus a trio of young pitchers: Jonah Tong, Nolan McLean and Brandon Sproat. I’m good with all of that – New York baseball should be entertaining for years to come. As recently as July, people were talking about the possibility of a Subway Series.

So just a few months later, are the Mets closer to a title than the Yankees? I hate to disagree with a first-ballot Hall of Famer – but I’m going to do it here.

The Mets spent $342 million on payroll and sat out all of October, proving financial might doesn’t buy guarantees. The Yankees were defending American League champs and won 94 games in a season in which Gerrit Cole didn’t throw a pitch, Aaron Judge had to deal with a right elbow injury and much of the pitching staff was a mess that needed to be fixed on the fly.

I get that no one is raising a flag for a Wild Card, but the Yankees were engineered to get back to October and take a swing at a championship. As manager Aaron Boone put it, they got “outexecuted and outplayed” by a Toronto team that had their number all year. As for the young pitching, Cam Schlittler’s early returns give a reason for fans to be encouraged, with more arms potentially on the way.

The Yankees are still built to win now – and they’d better be, because Judge’s title window won’t stay open forever. But whether we're talking about 1986 or 2009, I think we can all agree on this: It has been too long since the most recent parade.

Is there any question about Judge in right field? Could we see him at first base? – Tony A., via e-mail
Boone said at his end-of-season press conference that he expects Judge to be the Yankees’ right fielder, shooting down any suggestion of a position switch.

Judge, as you know, is recovering from the right flexor strain he sustained in July that impacted his throwing late in the season. It looked better, if not 100%, in October. The current plan is for a full offseason of rehab and strengthening, with surgery not recommended.

Have the Yankees addressed who is going to be at third base on Opening Day? – Rick A., via e-mail
It seems a safe bet that they’ll go into the season with Ryan McMahon at third base. McMahon’s defense was a vast improvement over what they had at the hot corner previously, and even though his bat didn’t play up to expectations (.641 OPS in 54 games), he delivered a few clutch moments. McMahon is earning $32 million through 2027, which likely precludes a serious run at a free agent like Alex Bregman.

What was the logic behind the coaching changes? – Justin T., via e-mail
The Yankees did not offer 2026 contracts to first base/infield coach Travis Chapman and bullpen coach Mike Harkey. Both were on expiring deals; general manager Brian Cashman said the team wanted to “open up and evaluate opportunities in the marketplace.” Harkey was the last in-uniform link to the team’s most recent World Series championship, but the Yankees were interested in bringing back Desi Druschel after a one-year stint with the Mets..

Additionally, assistant hitting coach Pat Roessler might move to another organizational role, with Jake Hirst promoted to the big league staff in his place. Hirst had received big league offers elsewhere, according to Cashman, who said the organization wanted to keep him. The Yankees also exercised 2026 options on pitching coach Matt Blake and catching coordinator Tanner Swanson.

What are the plans at shortstop? Will José Caballero get a look? – Andrew K., via Instagram
The Yankees do prefer Caballero in a super-utility role, their ideal 10th man, which gives them more flexibility in using him defensively or as a stolen base threat off the bench. However, with Anthony Volpe out for at least the first month of the 2026 season, it probably will give Caballero a real opportunity for playing time.

The Yankees are likely to bring in an experienced shortstop or two as non-roster invitees in Spring Training, but it’s difficult to see them committing to anyone on a significant contract (like, for example, Bo Bichette) when they are publicly stating that Volpe remains their shortstop of the present and future.

“He’s 24 years old,” Boone said of Volpe. “The reality is, he’s a really talented player that works his butt off, that has tremendous makeup and toughness. He’s a great person in our room. I’m going to bet on that.”