New York — The New York Yankees face a decision that could reshape their postseason roster. Anthony Volpe, once seen as the long-term answer at shortstop, now finds his October role under serious threat.
Yankees insider makes bold playoff prediction
Joel Sherman of the New York Post delivered a prediction that jolted Yankees Nation. The veteran writer believes Jose Caballero will replace Volpe as the starting shortstop in the playoffs.
“I’m gonna make a prediction: I say Jose Caballero is their shortstop in the playoffs,” Sherman said during the “Pinstripe Post” podcast with Ryan Sampson.
Sherman’s words carry weight. His ties inside the organization are deep, and his statement suggests the front office may already be weighing alternatives to their struggling third-year player.
Numbers paint troubling picture for Volpe
Volpe’s 2025 campaign has been a sharp fall from expectations. The once-touted prospect has hit just .207/.269/.396. Those numbers are disappointing for any major league regular, but the defensive side raises even greater alarm.
Baseball Savant reports Volpe has recorded -8 Outs Above Average, ranking in the fourth percentile among shortstops. That is a stunning drop from his Gold Glove rookie season in 2023, when he posted 13 OAA, and his strong 2024 follow-up.
The collapse from elite defender to liability has left Yankees officials and fans stunned. Defense was supposed to be his strength, even while his bat developed.
Trade deadline acquisition emerges as viable alternative
José Caballero came to New York from Tampa Bay at the trade deadline. At first, he was viewed as depth rather than a potential playoff starter.
Yet his play has earned notice. In 26 games with the Yankees, Caballero has slashed .233/.346/.419 in 53 plate appearances. In the field, he has delivered two Outs Above Average at shortstop in limited chances.
Sherman acknowledged Caballero’s modest track record. His career OPS sits at .647 across 1,091 plate appearances. Even so, Sherman argued that level of production still looks like an upgrade over Volpe’s current output.
“I know if Caballero plays more, we’ll see things we don’t like,” Sherman said. “We’ve already seen him get thrown out of two games you can’t get thrown out of. But in the short-term, when the ball is hit to him at shortstop, you’re not holding your breath.”
Well-connected insider delivers harsh assessment
The debate intensified when longtime Yankees insider Bill Madden publicly called for Volpe to be benched. Madden’s voice carries influence. His relationship with the Steinbrenner family stretches back decades.
On social media, Madden blasted what he labeled “stubborn support” for Volpe inside the front office. He warned that such loyalty could derail the team’s championship push.
“Brian Cashman has done a really good job addressing the issues with the Yankee lineup with his no pain trades for Chisholm McMahon Caballero but it’s all going to be for naught if continues this self-defeating stubborn support for Volpe who is a liability and has to be benched,” Madden wrote.
Organizational divide creates internal tension
Madden’s remarks point to division within the Yankees. His comments suggest some decision-makers are ready to move on while others hold firm in their belief in Volpe.
The timing also raised eyebrows. With his access to ownership, Madden’s words may signal rising frustration at the highest levels.
Fans have voiced their displeasure as well. Boos often greet Volpe’s at-bats, adding pressure to an already volatile situation.
Playoff implications loom large
The Yankees cannot afford weak links in October. Every roster spot matters in the chase for their first World Series title since 2009.
Volpe’s struggles create an opening for opponents to exploit. His 19 home runs and 70 RBIs have not masked his overall decline. His .661 OPS over his first two seasons already marked below-average production for a shortstop. Now even that floor has dropped.
Sherman’s forecast of Caballero starting in October suggests the organization may already be leaning toward change. The Yankees appear poised to prioritize playoff wins over long-term development.
Decision point approaches rapidly
As the season winds down, the Yankees face a critical choice. Volpe’s performance makes his benching look less like a possibility and more like an eventuality.
For the player, losing his postseason role would be a dramatic setback in what was supposed to be his rise as the franchise’s anchor at shortstop. For the Yankees, the move would be a blunt statement that winning takes priority above all else.
The next few weeks will reveal whether the Yankees act on the voices of their insiders and the frustration of their fans—or stick with a struggling player at the heart of their infield.
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