The New York Yankees’ march toward October has hit an unexpected roadblock at arguably the most crucial position on the diamond. With an 83-67 record securing their playoff berth, the Bronx Bombers now confront a glaring vulnerability that threatens to derail their championship aspirations: The deteriorating performance of shortstop Anthony Volpe.

Volpe’s shoulder injury has become the elephant in the Yankees’ clubhouse, with the young shortstop battling through a partially torn labrum that has systematically dismantled his effectiveness. The numbers tell a sobering story of decline. After posting a respectable .233/.326/.442 through May 3, Volpe has catered to .197/.248/.378 over 108 games since, culminating in an overall .206/.268/.393 line that falls far short of championship standards.

The former Gold Glove winner’s defensive reliability has crumbled alongside his offensive production, as Volpe now leads the American League with 19 errors. His defensive metrics have plummeted to the second percentile league-wide with -9 Outs Above Average, transforming what was once a strength into a liability. The Athletic’s Jennings highlighted how this shortstop dilemma feels more fraught than the Yankees’ other concerns, including bullpen adjustments and keeping Aaron Judge healthy.

José Caballero has seized five consecutive starts, batting 6-for-18 with a .980 OPS while delivering steady defense, though Jennings noted the utility player lacks Volpe’s offensive upside and organizational significance. Yet, following Volpe’s injury disclosure, his five-game absence has allowed Caballero to showcase impressive abilities with dynamic baserunning that leads baseball in stolen bases. This emergence raises legitimate questions about the Yankees’ postseason plans. Just look at Caballero (.233/.332/.345) and Volpe’s slash line contrast.

Manager Aaron Boone acknowledged the situation before Monday’s game, stating that Caballero “is playing great” and emphasizing that “we’re at that time of year where it’s all hands on deck.” Boone diplomatically noted that “everyone’s going to play an important role. You never know on a given day who has the most important role. But I expect them both to play an important role for us down the stretch.” Though the timing forces management to weigh loyalty against October baseball’s demand for peak execution.

However, the Yankees’ playoff concerns extend beyond just the shortstop position.

Grisham’s September collapse compounds Yankees’ playoff pressure

The shortstop uncertainty represents just one piece of a larger puzzle threatening the New York Yankees‘ championship ambitions. While management grapples with Volpe’s situation, another everyday player has created additional headaches with his alarming decline.

Trent Grisham wasn’t supposed to become this crucial to the Yankees’ 2025 plans, yet the 28-year-old outfielder has transformed from a depth acquisition into an everyday starter. His career-best campaign features 30 home runs and a respectable .236/.347/.458 slash line across 132 games, supported by 64 RBIs and a solid 127 wRC+ that demonstrates above-average offensive production.

However, those season-long numbers hide a devastating September nosedive that threatens to sabotage everything. Grisham has managed just a .183 average with a .321 on-base percentage over the past month, with his last 15 games producing an even more troubling .143/.265/.286 line. His deteriorating contact rates and plummeting barrel percentage have transformed the leadoff experiment into a liability.

Now, the Yankees trail Toronto by five games while maintaining just a one-game advantage over Boston, making every at-bat crucial. Grisham’s struggles at the top of the order have turned him from a table-setter into a rally-killer, creating another urgent decision for a franchise that cannot afford extended slumps during its championship window.