4 Yankees With the Most on the Line in Final Stretch of Regular Season

The New York Yankees are aiming to make their deepest playoff run yet.

Although the Bronx Bombers will almost certainly enter the postseason as a wild card and without Aaron Judge, they still have plenty of talent to stack up against the best teams in baseball. That said, the Yankees need a collective effort for any chance of a pennant or World Series title, especially without their best player.

A few players have extra motivation to shine as the games matter most. The Yankees will see some key contributors hit free agency after the season, and even those with team control could be playing for their long-term futures in the Bronx.

Depending on whether they thrive or struggle in October, these players could be playing their last games in pinstripes or solidifying their role with the club.

Here are four Yankees who have the most to play for.

Anthony Volpe

If anything, Volpe is already playing with his Yankee future at stake. A victim of overwhelming expectations from both the organization and the fanbase in his first three seasons, Volpe's Triple-A reset has served him well upon his return to the majors, both offensively and defensively.

But a strong postseason would fully bring Volpe back into everyone's good graces. The 25-year-old thrived during New York's playoff run in 2024, slashing .286/.407/.408 in 14 games and hitting a grand slam in Game 4 of the World Series. He also drew 10 walks, struck out 13 times, and went 5-for-5 on stolen base attempts. In contrast, Volpe went just 5-for-26 at the plate in the 2025 postseason, but one of those hits was a home run.

Even with his increased defensive versatility, the sticking point with Volpe is whether he can rediscover the offensive potential that made him a top prospect. And if he puts it all together during October, or at least produces as he did in 2024, then the Yankees will be far more inclined to give him a defined role moving forward.

Jazz Chisholm Jr.

When Chisholm Jr. returns from the injured list in the coming days, he could very well be playing his final games in a Yankee uniform. It's impossible to deny that his 2026 season has been a massive disappointment, especially since Chisholm is slated to become a free agent this winter.

However, a great postseason could change everything. Chisholm struggled in both the 2024 and 2025 playoff runs, but still had a handful of clutch moments on the bases and even hit a big home run in Game 3 of last year's ALDS.

This season, Chisholm has also shown a knack for delivering in high-leverage situations, hitting .342 with a .579 slugging percentage in 42 plate appearances.

Chisholm's combination of speed, power, and defense is tantalizing even with a down 2026 season. So if that game-changing talent is on display during October, the Yankees could remain a suitor for the 28-year-old when he hits the open market.

Trent Grisham

This is an interesting situation because Grisham will almost certainly be playing his last games with the Yankees. His regression both offensively and defensively, and the emergence of Spencer Jones, should already convince the Bronx Bombers to move on from the veteran outfielder after the season.

Yet Grisham has still shown flashes of his 2025 form, which would have earned him a solid free agent contract had he not accepted the Yankees' qualifying offer last winter. Also, Grisham's propensity for coming through in clutch scenarios with big home runs carried over to this season, hitting .282 with a .564 slugging percentage in 44 high-leverage plate appearances. Last year, he had an absurd 1.259 OPS and seven homers in high-leverage situations, yet his xwOBA (.426) is the same as this year in those scenarios.

Grisham is also looking to redeem himself after a miserable 2025 postseason, in which he hit just .138 (4-for-29). If he does that, then perhaps more teams will be interested in signing him this winter, even if the Yankees won't be part of those sweepstakes.

David Bednar

Lastly, Bednar is another upcoming free agent, but compared to Chisholm and Grisham, he's enjoyed a great season as the Yankees' closer.

Yet the postseason is a whole different animal. The good news is that Bednar looked strong in his very first taste of playoff action last year. In five games and six innings, he allowed only one run on three hits and a walk while striking out nine, picking up a pair of saves in the process.

There will never be another Mariano Rivera, but after witnessing numerous playoff meltdowns from Aroldis Chapman and other relievers, Bednar's dominance last October was a breath of fresh air. Another great postseason would further endear Bednar to the organization and fans, and perhaps land him a nice payday to stay in the Bronx.

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