Yankees Could Face Big Time Shortstop Question

The New York Yankees are at a shortstop crossroads this offseason. Anthony Volpe, their 2025 Opening Day shortstop, is recovering from shoulder surgery after a dismal season, and their backup options are ready to go.

The Yankees' front office obviously loves Volpe, whose background as a New Yorker and Yankee fan make him a fantastic success story -- if he's successful. So far, he has fallen short, and there may be better folks for the job. But will the Yankees let them do it?

The New York Post's Greg Joyce listed the shortstop debacle among the Yankees top questions this offseason, pointing to comments from Yankees manager Aaron Boone that the Yankees intend to get Volpe right back out there once he is healthy again. Will that change if his replacement can outperform him?

"But what happens if José Caballero crushes it in April as the Yankees’ fill-in starting shortstop?" Joyce posited. "At this time last year, no one expected Grisham to be the kind of impact player he was, an example that Cashman brought up while cracking the door slightly more open for Caballero to give the Yankees a difficult decision once Volpe is back."

Volpe's Issues in 2025

Sep 30, 2025; Bronx, New York, USA; New York Yankees shortstop Anthony Volpe (11) can't handle a ground ball by Boston Red Sox shortstop Trevor Story (not pictured) during the fifth inning of game one of the Wildcard round of the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

Volpe finished the regular season with the second-most fielding errors in the MLB, and while he did suffer from a severe shoulder injury (right there through the summer, based on the timeline provided), he had not been strong offensively for some time, and he had fallen off defensively before the injury.

Caballero, a trade deadline acquisition who notably joined the Yankees from the Tampa Bay Rays in the middle of a Yankees/Rays game, is the most likely to take over at the position. Caballero and Volpe are both quick and boast elite baserunning value, but Caballero gets on base more often, and he's the far superior defender. After a season where the Yankees were often defined (often, by Volpe) by their shoddy infield defense, they might have the opportunity to break that mold with Caballero.

Offseason Discussion of Volpe

Sep 18, 2025; Baltimore, Maryland, USA; New York Yankees shortstop Jose Caballero (72) throws to first for an out during the eighth inning against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | Daniel Kucin Jr.-Imagn Images

Yankees legend Alex Rodriguez recently commented that Volpe's speed, his greatest asset, is of little use when it comes to impacting winning because of his poor offensive skills -- which A-Rod suggested is indicative of the Yankees' generally flawed approach to offense. The lack of focus on contact has long been a problem for the team, rife with sluggers, and Volpe looks increasingly out of place as they (hopefully) work to mend that approach.

It seems from an outside perspective, however, that the Yankees -- particularly Boone -- still see Volpe as an elite player. Their insistence on playing him through what was clearly a debilitating injury may remain a mystery forever, but the organization clearly loves him. Caballero's performance at shortstop in the spring will serve as a forecast for the summer, when the Yankees will likely have some tough choices to make.

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