The Yankees are heading into the stretch run with more than October positioning on the line. With a postseason berth likely to come as a wild card and Aaron Judge absent, the pressure shifts even more toward the players who can shape both this run and their own futures in pinstripes.
A handful of Yankees are carrying extra weight as the regular season winds down. Some are set to hit free agency after the year. Others still have team control, but their long-term place in the Bronx could hinge on what happens when the games matter most.
Anthony Volpe may already be living that reality. His first three seasons brought plenty of noise and plenty of expectation, and after a Triple-A reset, he has come back looking sharper on both sides of the ball. The real question remains the same one that has followed him: can he deliver enough offensively to match the belief the Yankees once had in him?
October would go a long way toward answering that. Volpe was excellent during New York’s 2024 playoff run, hitting .286/.407/.408 in 14 games and launching 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 the 2025 postseason, though, he went 5-for-26, even if one of those hits left the yard.
If he can put together something closer to that 2024 run, his role in the organization looks a lot more secure.
Jazz Chisholm Jr. is in a different spot, but the stakes are just as real. When he returns from the injured list in the coming days, he could be taking the field for the last time in a Yankees uniform. His 2026 season has fallen well short of expectations, and he is slated to become a free agent this winter.
Still, Chisholm has shown enough to keep the door open. He has had his moments in the postseason before, including a big home run in Game 3 of last year’s ALDS, even if his overall playoff track record in 2024 and 2025 was uneven.
This season, he has also produced in the biggest spots, batting .342 with a .579 slugging percentage in 42 plate appearances in high-leverage situations. The mix of speed, power and defense is still there, and if it shows up in October, the Yankees could decide they want him back.
Trent Grisham is another player who looks likely to be moving on after the season. His offensive and defensive regression, along with the rise of Spencer Jones, makes his future in New York look bleak. Even so, Grisham has flashed the kind of clutch power that can change how teams view a player in free agency.
That was true in 2025, when he would have been in line for a strong market if he had not taken the Yankees’ qualifying offer last winter. It has shown up again this year in high-leverage spots, where he has hit .282 with a .564 slugging percentage in 44 plate appearances.
Last season, he was even louder in those moments, posting a 1.259 OPS and seven home runs, while his xwOBA of .426 in those situations matched this year’s mark. He’ll also be trying to erase the memory of a rough 2025 postseason, when he hit .138, going 4-for-29.
Then there is Devin Bednar, the one player in this group who has mostly done his job. He is also headed toward free agency, but unlike Chisholm and Grisham, he has already delivered a strong season as the Yankees’ closer. October, though, is where reputations get tested.
Bednar handled his first playoff experience last year with ease. In five games and six innings, he gave up one run on three hits and a walk while striking out nine and collecting two saves.
After so many postseason letdowns from Aroldis Chapman and other relievers, that kind of work stood out. Another strong run now would only strengthen Bednar’s case to stay in the Bronx, and maybe set him up for a payday that keeps him there.
In Other News...
Clarke Schmidt Just Hit A Brutal Moment In Yankees October Plans
Clarke Schmidts return to the Yankees was already set up as a relief-driven finish after the club activated him on Sept. 16 following his recovery from a second Tommy John surgery. For a team trying to map out October, having Schmidt available at all gave Aaron Boone another experienced arm to work with, even if the initial plan was for him to fit into the bullpen rather than back into the rotation.
That path hit a snag on Sept. 24, when Schmidt felt cramping in his right biceps during warmups and was unable to pitch in the game. The encouraging part for the Yankees is that tests showed no structural damage, but the moment still adds another layer of uncertainty to a postseason pitching picture that already has Gerrit Cole, Cam Schlittler, and Max Fried lined up as starters, with Schmidt among the relief options alongside Carlos Rodn and Will Warren. [Read more 🡒]
Yankees Would Be Taking On More Than Rafael Devers Bat
ESPNs Buster Olney floated Rafael Devers as a possible fit for the Yankees, a notion that immediately carries more baggage than a simple bat-for-lineup conversation. Devers has long been one of the most productive hitters in the division, but his history with the Red Sox has also included positional disputes that shaped how he was viewed in Boston and continue to color any discussion about where he might land next.
For the Yankees, the question is not whether the offense would get a boost, but whether that upgrade would come with the kind of clubhouse fit and willingness to adapt the organization would need. Any serious pursuit would have to account for more than the numbers at the plate, because adding a player of Devers profile would mean bringing in a far bigger story than his bat alone. [Read more 🡒]
Yankees Suddenly Have A Playoff Infield Decision Fans Will Debate
Jazz Chisholm Jr.s return from a thumb injury has already pushed the Yankees into a familiar late-season puzzle, and this one is about the infield alignment. Former manager Joe Girardi floated the idea that Chisholm could slide to third base because of his previous experience there, a suggestion that fits with the clubs recent lineup shuffling and the way Aaron Boone has used Jose Caballero and Ryan McMahon as he sorts out the best look.
Boone was more measured when asked about the possibility of moving Anthony Volpe to third, which only adds to the debate over how the Yankees should arrange the left side of the infield if Chisholm is ready to play. Chisholms track record at third gives the concept some real footing, and his offense still matters to a team trying to position itself for October, but the next move could say plenty about how Boone values defense, flexibility and roles in a crowded playoff picture. [Read more 🡒]