The Bronx Bomber's Ticking Clock: Is Volpe's Pinstriped Dream Turning into a Pumpkin?
Published on: September 9, 2025
The crisp autumn air is rolling into the Bronx, carrying with it the scent of playoff baseball and the weight of expectations. For the New York Yankees, the annual pilgrimage towards a 28th World Series title is underway, but this year, a familiar face might be watching from the dugout. Anthony Volpe, the young shortstop who burst onto the scene like a supernova in last year’s Fall Classic, is teetering on the precipice of postseason irrelevance. And if veteran baseball scribe Joel Sherman’s crystal ball is anything to go by, Volpe’s pinstriped dream could be turning into a pumpkin.
Last October, Volpe was the toast of the town. His bat crackled with the energy of a thousand subway cars, culminating in a grand slam that echoed through the canyons of New York City during Game 4 of the World Series against the Dodgers. He was the fresh face, the symbol of a new generation of Yankee greatness. Fast forward a year, and the narrative has taken a decidedly sour turn.
Volpe's 2025 campaign has been a symphony of strikeouts, miscues, and general baseball malaise. His slash line of .207/.269/.396, punctuated by 19 home runs and 70 RBIs, paints a picture of inconsistency. While the long balls offer glimpses of the raw power that tantalized fans last year, they are overshadowed by a batting average that sits stubbornly below the Mendoza Line and an on-base percentage that would make a leadoff hitter blush. And then there are the errors. Volpe leads all American League shortstops in throwing the ball away, adding a layer of defensive liability to his offensive struggles.
Manager Aaron Boone and General Manager Brian Cashman have publicly maintained their faith in the young shortstop, preaching patience and development. But the whispers in the dugout, the hushed conversations in the front office, tell a different story. The pressure cooker of October baseball demands results, not potential. And with a slick-fielding Jose Caballero waiting in the wings, the Yankees' patience might be wearing thinner than a worn-out catcher’s mitt.
Sherman, speaking on the "Pinstripe Post" podcast, didn't mince words. "Caballero has played three or four games at shortstop, and when you watch him you’re like ‘oh right, that’s the natural movements of a shortstop. That’s the easy arm," he observed. "Watching Anthony Volpe is like watching the Tasmanian devil play shortstop. It’s hectic. He’s not a comfortable player right now.”
Sherman’s analysis cuts to the heart of the matter. While Volpe’s physical tools are undeniable, his game lacks the fluidity and grace of a seasoned shortstop. He appears rushed, almost frantic, in his movements, a stark contrast to Caballero's smooth, effortless style.
The Yankees have a history of making tough decisions when the stakes are highest. Sherman points to Gary Sanchez and Isiah Kiner-Falefa as recent examples of players who were given the benefit of the doubt during the regular season, only to be benched or relegated to diminished roles come playoff time. "In 2020, they played seven playoff games, and Kyle Higashioka started five," Sherman noted, highlighting the Yankees' willingness to prioritize performance over sentimentality. He then recalled Kiner-Falefa’s 2022 season, stating, "they got to the playoffs, and he didn’t start every game.” The message is clear: past performance and organizational loyalty are no guarantee of a starting spot in October.
Caballero, acquired from the Tampa Bay Rays at the trade deadline, is primarily known for his blazing speed. He currently leads the majors in stolen bases, a skillset that could be a valuable asset in the pressure-packed environment of playoff baseball. However, his offensive production raises concerns. While he boasts a respectable .765 OPS this season, his career OPS sits at a pedestrian .647.
"Is he a great offensive player? He is not,” Sherman conceded. “But this version of him is so much better than Volpe and especially what Volpe used to do well, which is steal some bases, is no longer part of his thing.” The implication is that even with his offensive limitations, Caballero offers a more well-rounded package than the struggling Volpe, particularly considering the latter’s diminished base-stealing prowess.
Sherman also highlighted Caballero’s recent disciplinary issues, including two ejections – one for arguing a play at second base and another for disputing balls and strikes. “You’re a part-time player, you’re starting today for a very specific reason,” Sherman argued. “Lefty on the mound probably, we’re going to start you here and then move you to right field because we don’t want Stanton or Judge in right field today, and you’ve allowed yourself to get thrown out of two games.” These incidents, while seemingly minor, suggest a lack of maturity and composure, traits that are not conducive to playoff success.
The fact that Caballero has been traded twice before even reaching arbitration eligibility raises further questions. “Here’s a guy who isn’t even arbitration eligible until this off-season, and he’s been traded twice, and he’s very talented,” Sherman observed. “Why have two organizations given up on him? You start to see a little bit with those two ejections.” The implication is that there might be underlying issues with Caballero's attitude or work ethic that have led to his nomadic journey through the league.
As the Yankees prepare for their postseason push, the shortstop position remains a question mark. Will Volpe rediscover the magic that made him a postseason hero just a year ago? Or will Caballero seize the opportunity and solidify his place in the starting lineup? Only time will tell. But one thing is certain: the ticking clock of October baseball waits for no one, and the Yankees will need to make a difficult decision, one that could determine their fate in the quest for championship number 28.
Last October, Volpe was the toast of the town. His bat crackled with the energy of a thousand subway cars, culminating in a grand slam that echoed through the canyons of New York City during Game 4 of the World Series against the Dodgers. He was the fresh face, the symbol of a new generation of Yankee greatness. Fast forward a year, and the narrative has taken a decidedly sour turn.
Volpe's 2025 campaign has been a symphony of strikeouts, miscues, and general baseball malaise. His slash line of .207/.269/.396, punctuated by 19 home runs and 70 RBIs, paints a picture of inconsistency. While the long balls offer glimpses of the raw power that tantalized fans last year, they are overshadowed by a batting average that sits stubbornly below the Mendoza Line and an on-base percentage that would make a leadoff hitter blush. And then there are the errors. Volpe leads all American League shortstops in throwing the ball away, adding a layer of defensive liability to his offensive struggles.
Manager Aaron Boone and General Manager Brian Cashman have publicly maintained their faith in the young shortstop, preaching patience and development. But the whispers in the dugout, the hushed conversations in the front office, tell a different story. The pressure cooker of October baseball demands results, not potential. And with a slick-fielding Jose Caballero waiting in the wings, the Yankees' patience might be wearing thinner than a worn-out catcher’s mitt.
Sherman, speaking on the "Pinstripe Post" podcast, didn't mince words. "Caballero has played three or four games at shortstop, and when you watch him you’re like ‘oh right, that’s the natural movements of a shortstop. That’s the easy arm," he observed. "Watching Anthony Volpe is like watching the Tasmanian devil play shortstop. It’s hectic. He’s not a comfortable player right now.”
Sherman’s analysis cuts to the heart of the matter. While Volpe’s physical tools are undeniable, his game lacks the fluidity and grace of a seasoned shortstop. He appears rushed, almost frantic, in his movements, a stark contrast to Caballero's smooth, effortless style.
The Yankees have a history of making tough decisions when the stakes are highest. Sherman points to Gary Sanchez and Isiah Kiner-Falefa as recent examples of players who were given the benefit of the doubt during the regular season, only to be benched or relegated to diminished roles come playoff time. "In 2020, they played seven playoff games, and Kyle Higashioka started five," Sherman noted, highlighting the Yankees' willingness to prioritize performance over sentimentality. He then recalled Kiner-Falefa’s 2022 season, stating, "they got to the playoffs, and he didn’t start every game.” The message is clear: past performance and organizational loyalty are no guarantee of a starting spot in October.
Caballero, acquired from the Tampa Bay Rays at the trade deadline, is primarily known for his blazing speed. He currently leads the majors in stolen bases, a skillset that could be a valuable asset in the pressure-packed environment of playoff baseball. However, his offensive production raises concerns. While he boasts a respectable .765 OPS this season, his career OPS sits at a pedestrian .647.
"Is he a great offensive player? He is not,” Sherman conceded. “But this version of him is so much better than Volpe and especially what Volpe used to do well, which is steal some bases, is no longer part of his thing.” The implication is that even with his offensive limitations, Caballero offers a more well-rounded package than the struggling Volpe, particularly considering the latter’s diminished base-stealing prowess.
Sherman also highlighted Caballero’s recent disciplinary issues, including two ejections – one for arguing a play at second base and another for disputing balls and strikes. “You’re a part-time player, you’re starting today for a very specific reason,” Sherman argued. “Lefty on the mound probably, we’re going to start you here and then move you to right field because we don’t want Stanton or Judge in right field today, and you’ve allowed yourself to get thrown out of two games.” These incidents, while seemingly minor, suggest a lack of maturity and composure, traits that are not conducive to playoff success.
The fact that Caballero has been traded twice before even reaching arbitration eligibility raises further questions. “Here’s a guy who isn’t even arbitration eligible until this off-season, and he’s been traded twice, and he’s very talented,” Sherman observed. “Why have two organizations given up on him? You start to see a little bit with those two ejections.” The implication is that there might be underlying issues with Caballero's attitude or work ethic that have led to his nomadic journey through the league.
As the Yankees prepare for their postseason push, the shortstop position remains a question mark. Will Volpe rediscover the magic that made him a postseason hero just a year ago? Or will Caballero seize the opportunity and solidify his place in the starting lineup? Only time will tell. But one thing is certain: the ticking clock of October baseball waits for no one, and the Yankees will need to make a difficult decision, one that could determine their fate in the quest for championship number 28.
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