Aug 1, 2025; Miami, Florida, USA; New York Yankees pinch runner Jose Caballero (72) celebrates after scoring against the Miami Marlins during the ninth inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images Sam Navarro-Imagn Images

Yankees New Shortstop Causes Mayhem at Fenway

Originally posted on New York Yankees on SI
By Joseph Randazzo | Last updated Sep 13, 2025 10:00 AM ET

José Caballero stood across from the New York Yankees dugout, hours before the conclusion of the Major League Baseball trade deadline. At some point, somebody within the Tampa Bay Rays organization must have tapped him and pointed to the other side, most likely saying, "Hey, you're going over there."

Seeing what he's been able to produce now, that Caballero trade seems like a steal, and even though Everson Pereira has an above-average power tool and adequate glove, sending only him and the vaunted "player to be named later" feels like shortchanging a rival. Especially knowing that Caballero is under team control until 2029.

Since putting on those pinstripes, Caballero is hitting .264/.365/.434, with twelve stolen bases. With him is also an elite glove that can play any position at a high level. According to Outs Above Average, Caballero has a 2 OAA in right field, a 2 OAA at third base, and a 5 OAA at shortstop. Shortstop, his most valued position, also happens to be the place on the infield where these Yankees need him most, while Anthony Volpe deals with a nagging shoulder injury.

In the pivotal first game against the Boston Red Sox at Fenway Park, all of Caballero's tools were on display. In the top of the 7th, Caballero hit into a ground rule double, which nearly missed being a home run and sliced toward the Pesky Pole. It had an eerie similarity to Tony Clark's ground rule double during the 2004 ALCS, which, had it stayed in play, would have surely sealed another World Series berth for the New York Yankees.

José Caballero haciendo su trabajo con los Yankees
pic.twitter.com/WQvzDCLwmi
— (@leoaguilar_29) September 13, 2025

During that game, those old Fenway ghosts from decades prior did not work against the Yankees. Caballero's legs made sure of that. He then stole third base. Moving on contact, Caballero jetted home when Ryan McMahon hit a sharp groundball which almost left the infield were it not for a diving stop. Caballero was almost thrown out at the plate, but Carlos Narváez, having to work faster than usual to tag out the speedy baserunner, bobbled the ball. Caballero scored, and Ryan McMahon made his way to second.

After the game, according to Gary Phillips of the Daily News, the word manager Aaron Boone used to describe Caballero was "havoc." It's a fitting description for the way his new shortstop moved around the infield in that seventh inning.

"He wreaks havoc on the bases. He's a little daring and makes you hold your breath sometimes, but he's got a real good feel. He's a really confident player."