
Image of Jose Caballero after hitting his second home run of the game against the Rays on August 19th, 2025. Credit: Yankees on X
TAMPA, FLA — On trade deadline day, the focus for most Yankees fans was on how much bullpen help the team would acquire, but Brian Cashman made on under the radar move. When Jose Caballero crossed dugouts in the middle of the game on deadline day to join his new team, I did not imagine the impact that Caballero would have on the Yankees.
“I’ve yelled at him when he was an opponent…” Boone said on Sunday. “I couldn’t stand him playing against him and now he’s turning into one of my favorite players.”
It is easy to see why Caballero would be a pest to the opponent. Caballero has the ability to turn a walk into a triple and score on a wild pitch. Caballero is one of those players who’s tenacity and speed makes things happen, and we saw that all weekend in St. Louis where the pressure he put on the opposing team paid dividends for the Yankees, turning into wins.
Jose Caballero SPEED SPEED SPEED
— #Talkin' Yanks (#@TalkinYanks)
9:09 PM • Aug 17, 2025
“I’m trying to make them hate me,” Caballero said speaking about his opponents. “I don’t want them to like me.”
Caballero is the kind of scrappy player that was common in a different era of Baseball and frankly, is refreshing to have on the team. If the Yankees are going to do something special this season — like win the world series — role players like Jose Caballero are essential to their success because they make things happen.
Caballero’s teammates have also liked what he has brought to the team in his short tenure with the Yankees so far. “I told him I hated playing against him because you can see his speed…” Paul Goldschmidt said following his return to St. Louis on Sunday. “He’s made a difference… he can play shortstop and play outfield. He’s a really valuable asset for us and can do it in so many different ways.”
The fact that Caballero can play multiple different defensive positions also provides Aaron Boone with different options to work him in the lineup each game. Caballero’s defensive versatility is even more important with the injury to Oswaldo Cabrera, likely ending his season.
Jose Caballero is also super fun to watch because he is always involved in something. The past four Yankee wins, Caballero has done something in the game that directly correlated to the win, which is super important. I can already see Caballero stealing an important base in the postseason that leads to a big win. And the best part, Caballero is under team control until 2029, so he is under control for a long time.