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TORONTO, ONTARIO - OCTOBER 05: Brian Cashman, Senior Vice President and General Manager of the New York Yankees, looks on before game two of the American League Division Series against the Toronto Blue Jays at Rogers Centre on October 05, 2025 in Toronto, Ontario. (Photo by Mark Blinch/Getty Images)

Shortstop remains a gaping hole on the Yankees’ roster given Anthony Volpe’s ongoing struggles. In 76 at-bats since coming off the injured list, Volpe is hitting just .237 with a .662 OPS.

With the MLB trade deadline a little more than six weeks away, the Yankees are widely expected to upgrade the position in hopes of solidifying themselves for a run at the World Series. As such, ESPN insider Jeff Passan has connected them to one of the potential top targets on the board: Astros shortstop Jeremy Pena.

“Replenishing a bad farm system with few players close to the big leagues takes a move like trading Pena, and the only question at this point is whether it will be before Aug. 3 or before the Dec. 1 lockout,” Passan writes.

Yankees’ Struggles Continue at Shortstop

Volpe’s June slump and defensive miscues have only intensified calls for the Yankees general manager Brian Cashman to upgrade at shortstop. The 25-year-old has seven hits in 33 at-bats, including only one for extra bases.

For the season, Volpe has one home run and 11 RBI.

Veterans Jose Caballero (7 HR, .734 OPS) and Max Schuemann (.222 AVG., .787 OPS) have also seen time at shortstop this season for the Bronx Bombers.

Despite the club’s struggles at the position, the Yankees have been one of baseball’s hottest teams. Winners of eight of their last 10 games, the Yankees are an AL-best 44-27. They also lead the majors in homers (106) and rank fourth in runs scored (370).

Pena Could be Pricey for Yankees

With the Astros (34-41) continuing to sputter, Passan speculates that Pena could be on the block. But the 28-year-old still has one year remaining on his current deal, meaning he won’t come cheap.

After missing almost five weeks with a hamstring strain, Pena is hitting .273 with three homers, 13 RBI and five stolen bases.

“Replenishing a bad farm system with few players close to the big leagues takes a move like trading Pena, and the only question at this point is whether it will be before Aug. 3 or before the Dec. 1 lockout,” Passan writes. “No longer are the Astros in the position they were when they held onto George Springer, Carlos Correa and Alex Bregman all the way to free agency. This is a Kyle Tucker situation — only now the Astros aren’t good, either, which could precipitate moving their shortstop before the deadline.”