NEW YORK —Jose Caballero was standing near the batting cage in the visiting dugout at Yankee Stadium when he felt a tap on his shoulder. Within minutes, the Panamanian infielder was hugging his Tampa Bay Rays teammates goodbye, packing his gear, and walking across the field to join the home team.
It was July 31, 2025. The trade deadline was ticking. And the Yankees had just pulled off one of the most surreal acquisitions in recent memory, acquiring a player from the opposing dugout during a game between the two clubs.
“Everything happened so quickly,” Caballero said. “You have to pick up and move over, switch teams. And now you’ve got to give your best and hopefully bring a championship to this city.”
Seven months later, Caballero is the Yankees’ Opening Day shortstop.
From Las Tablas to the JUCO World Series
Caballero grew up in Las Tablas, the capital of Panama’s Los Santos province. He played soccer, volleyball, basketball and baseball as a kid before focusing on the diamond. No Division I program came calling, so he attended Chipola College in Marianna, Florida.
He made the most of it. In 2017, Caballero led Chipola to the JUCO World Series championship and was named the tournament’s Most Valuable Player after driving in 16 runs and hitting five home runs. The Arizona Diamondbacks selected him in the seventh round of the 2017 draft with the 202nd overall pick.
Caballero spent years in the minors before the Diamondbacks traded him to the Seattle Mariners organization. He debuted with Seattle in April 2023 at age 26. After that season, the Mariners traded him to Tampa Bay, where Caballero found his footing.
How the Yankees landed him in the strangest trade of the deadline
The scene at Yankee Stadium on deadline day was unlike anything most fans had seen. A two-hour, 45-minute rain delay had already paused the Yankees’ game against the Rays. When play resumed, Caballero entered the game at second base for Tampa Bay. Shortly after, Rays manager Kevin Cash informed him of the trade.
Cameras captured Caballero exchanging emotional hugs with Brandon Lowe and Taylor Walls in the visiting dugout. He then walked through the stadium to the Yankees clubhouse. The Yankees sent outfielder Everson Pereira and minor league outfielder Marshall Toole to Tampa Bay in return.
“I’ve said it for many, many years now,” Rays manager Kevin Cash said. “Cabby does a lot to help you win baseball games, whether it’s defensively or on the bases, coming up with the big hit here and there.”
Yankees manager Aaron Boone had been watching the scene unfold from the home dugout.
“I saw him hugging people,” Boone said. “I knew we were definitely in the picture, so I figured maybe that was the case.”
What Caballero did after joining the Yankees
The debut was rough. In his first Yankees game at Miami, Caballero made an error as a late defensive replacement that helped the Marlins walk off. After that, everything changed.
In 40 games with the Yankees, Caballero hit .266/.372/.456 with three home runs, 15 stolen bases and a 134 wRC+, by far the best offensive stretch of his career. He played shortstop, second base, third base, right field and left field. He reached base in 19 of his 23 starts.
The signature moment came on Sept. 23 against the White Sox. With the Yankees needing a win to clinch a playoff spot, Caballero singled home Aaron Judge in the ninth inning for a walk-off victory. It was the first Yankees walk-off hit to clinch a postseason berth since Jorge Posada in 2002.
Caballero led all of MLB with 49 stolen bases in 2025, his second straight season leading the American League in steals after swiping 44 in 2024. His speed on the basepaths, converting 49 of 60 attempts, gave the Yankees a dimension they had lacked all season.
The 2026 role and what the Yankees expect
The Yankees signed Caballero to a one-year, $2 million contract to avoid arbitration in January. With Anthony Volpe recovering from offseason shoulder surgery for a partially torn labrum, Caballero projects as the everyday shortstop to open the 2026 season.
He represented Panama in the 2026 World Baseball Classic before returning to Yankees camp, slashing .267/.421/.533 with a homer and two steals for his national team. He also worked at Driveline Baseball over the winter to increase his bat speed, setting a goal of reaching double-digit home runs for the first time in his career.
Caballero is not a star. He is a 29-year-old utility player with a career .228 batting average who has carved out a role through elite speed, positional versatility and a competitive edge that teammates and opponents alike have noticed. When asked after the mid-game trade who his favorite player was growing up, Caballero had a one-word answer that landed perfectly in his new clubhouse: Jeter.
How do you see Caballero?
