Jose Caballero’s Two Blunders Flip Yankees Lead Into Rays Stunner
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Home News Jose Caballero

Jose Caballero’s bad hop sinks Yankees, ugly error sparks Rays’ shock rally

Esteban Quiñones by Esteban Quiñones
May 23, 2026 at 6:27 am EDT
in Jose Caballero, Anthony Volpe, Gerrit Cole, Jazz Chisholm Jr., News, Tim Hill
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Yankees' Jose Caballero committed an error and caught stealing bases in 4-2 loss in New York, May 22, 2026.
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NEW YORK — Jose Caballero waited 10 days to get back on the field. It took one bad hop in the eighth inning to undo the Yankees and hand the Rays the night.

The Yankees led 1-0 and looked set to finally beat Tampa Bay. Then a routine grounder skipped off Caballero’s glove. What followed turned a tidy pitcher’s duel into another gut-wrenching 4-2 defeat.

Caballero had returned from the injured list hours earlier with high hopes. He had even collected two hits. But the night will be remembered for the plays he did not make, not the ones he did.

Caballero’s return scrambles the shortstop picture

Caballero came back Friday after missing the minimum 10 days. He had fractured his right middle finger and landed on the injured list. He slid right back in at shortstop and batted seventh against the Rays.

His return created a fresh puzzle for the Yankees infield. Anthony Volpe had made eight starts at shortstop in his absence. Now manager Aaron Boone has two players for one spot.

Boone said Volpe will start working out at second base on days he does not play short. He made clear both men will stay in the Yankees mix. He stopped short of naming an everyday starter at the position.

Pressed on who his shortstop is going forward, Boone kept his options open. “We’ll see,” Boone said. He noted that Caballero’s versatility now matters again with Volpe back on the roster.

He framed the logjam as a good problem for the Yankees to have.

“Both guys are going to play,” Boone said. “It’s a good situation to be in because we have two players that we feel like can play vital roles in us winning games.”

The numbers help explain the choice. Caballero entered Friday hitting .259 with four homers, 13 RBIs and 13 steals across 41 games. Volpe was batting just .217 since his May 13 season debut, with seven walks.

One bad hop opens the floodgates in the eighth

Yankees' Jose Caballero committed an error in the eight inning in 4-2 loss in New York, May 22, 2026.

The game turned on a single play in the top of the eighth. Tim Hill came on with the Yankees clinging to a 1-0 lead. The first batter changed everything.

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Speedster Chandler Simpson chopped a grounder toward short to start the inning. The ball took a short hop, glanced off Caballero’s glove and rolled away for an error. The leadoff man reached, and the rally was born.

Junior Caminero singled up the middle to put runners on the corners. Jonathan Aranda then ripped a 106.5 mph double to tie the game. It drove in his AL-leading 38th run of the season.

The Yankees intentionally walked Yandy Diaz to load the bases. Up came Richie Palacios, and the bounces stayed unkind for the Yankees. He chopped a ball that ticked off Hill’s glove, then skipped just over a leaping Caballero into center.

That two-run single put Tampa Bay ahead for good. Ryan Vilade added a sacrifice fly off Camilo Doval to make it 4-1. Hill was charged with four runs, three earned, and never recorded an out.

Caballero owned the miscue that started it all afterward.

“It’s a line-drive short hop and kind of skipped on me,” Caballero said. “But I’ve got to make a play on it. No excuses.”

Jose Caballero error pic.twitter.com/mPHgfDa4EK

— Talkin' Yanks (@TalkinYanks) May 23, 2026

Boone did not let his shortstop off the hook either. He said Simpson hit the ball sharply, but the play was still makeable. He felt Caballero gave ground instead of charging for a cleaner hop.

“It’s a play he’s got to make,” Boone said. “He just didn’t make the play.”

A caught steal and a key out compound the damage

Yankees' Jose Caballero caught stealing bases in 4-2 loss in New York, May 22, 2026.

The error was the loudest mistake, but not the only one. Caballero was also caught stealing earlier in the night. The Yankees needed every baserunner against the Rays, baseball’s best team.

His glove cost the Yankees again in the bottom of the eighth. New York had clawed back within 4-2 and put the tying run in scoring position. Caballero came up with a chance to keep it going.

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Cody Bellinger doubled with one out to start the threat. Jazz Chisholm Jr. then tripled to right-center to drive him in. That brought the deficit to two and the crowd back to life.

Caballero grounded out to strand Chisholm at third base. The rally fizzled, and the Yankees never got closer. A 2-for-4 night at the plate could not erase the damage in the field.

Jose Caballero picks up his second hit of the night but then he's out after review on this stolen base attempt pic.twitter.com/b8i1kLCaNr

— Talkin' Yanks (@TalkinYanks) May 23, 2026

Wasted chances and Cole’s gem lost in the loss

Caballero’s return spoiled the comeback gem of Gerrit Cole. The ace tossed six scoreless innings in his first start since the 2024 World Series. He allowed two hits and walked three before exiting after 72 pitches.

The loss dropped the Yankees a season-high 5½ games back in the American League East. Tampa Bay improved to 34-15 and moved to a perfect 4-0 against the Yankees. The Rays have now won five straight.

Boone summed up the maddening pattern against this rival.

“It kind of hasn’t bounced our way against them,” Boone said of the Rays. “But we’ve got to find a way to beat that club.”

But Caballero’s overenthusiasm doomed them. Had the Yankees delayed his return, the result would have been different!

What do you think? Is Caballero the only villain?

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Tags: AL Eastanthony volpegerrit coleJazz Chisholm Jr.Jose CaballeroNew York YankeesTampa Bay Raystim hillYankees errorYankees shortstop
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Esteban Quiñones

Esteban Quiñones

Esteban Quinones is a proud graduate of the S.I. Newhouse School of Public Communications at Syracuse University. Growing up just blocks away from Yankee Stadium in Upper Manhattan, Esteban developed a deep love for the New York Yankees, a passion that has been a constant throughout his life. Whether it's cheering for the Yankees or crafting strategic communications, Esteban brings dedication and enthusiasm to producing content around all things Yankees.

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