5 Biggest Questions Facing the Yankees After Their 2026 Season

1 – Will Aaron Boone and Brian Cashman return?

Boone is entering the last year of his contract and Cashman was on the last year of a contract. There is no indication they are not returning to the Yankees though many fans are hoping for a change in the dugout. Cashman has constantly defended Boone so if the Yankees actually change managers, it is because Hal Steinbrenner wanted a switch, but it does not seem likely he wants to pay Boone for not managing and pay another skipper.

2 – What is the condition of Aaron Judge’s calf, and will it contribute to declining production?

The Yankees described Judge’s calf as “moderate” strain shortly before the playoffs and it was enough to keep slugger from playing. Judge had not even progressed to running in his recovery before the Yankees were unceremoniously eliminated by the Rays in the ALDS and even if he could have played there’s no telling how compromised he would have been from facing major league pitching in only 66 games due to a fractured rib. The rib injury likely impacted Judge going from a batting champion to a .241 hitter and increased his strikeout rate to 29.8%. Judge is entering his age-35 season and besides being told to play outfield more conservatively, he likely will need more designated hitter appearances.

3 – What will the Yankees do about Giancarlo Stanton?

Stanton is beloved in the Yankee clubhouse, and fans appreciate his postseason performances, especially in 2024. At the same time, he cannot be counted on to stay healthy after striking out in two postseason at-bats that were his first game action since injuring his calf April 24. Stanton stayed healthy in debut season in 2018 but since them has injured his hamstring, quadriceps, ankle and Achilles along with his elbows. Stanton’s contract is winding down with a $25 million salary for 2027 and a $10 million buyout of his $25 million club option for 2028. He turns 37 next month and it is plausible to think the Yankees release him to free up the DH spot for Judge and others.

4 – Can Ben Rice transform into a reliable first baseman?

Offensively, Ben Rice was a star for the Yankees, who always cited his high exit velocity and bad luck in 2025. He was fourth in baseball with 41 homers, third in OPS but most of his production was as a designated hitter. Rice only played 56 games at first base and while he only made four errors and posted a .991 field percentage, advanced metrics such as minus-7 outs above average motivated the Yankees to keep him off the field in the final months and creates questions about if Rice is simply a hitter in the mold of Kyle Schwarber, who played 10 games in the field last season.

5 – Who’s on second and third?

By the end of the postseason, it seemed apparent Jazz Chisholm’s time with the Yankees were nearing its end and he will not re-signed in free agency after a disappointing season that saw him strike out a career-high 157 times. The question is can the Yankees trust what they saw in the final month from Anthony Volpe in his switch from shortstop when he was demoted and lost the job to rookie George Lombard Jr.

At third, Ryan McMahon is entering the final year of his contract, and his glove was a disappointment at times, especially in Game 2 of the ALDS. McMahon made nine errors and his fielding percentage dropped to .960 along with his outs average plummeting from plus-7 to zero in 2026. McMahon is not much of a hitter, and it seems to have gotten worse since being acquired from the Rockies as he has a .211 average in 178 games. It is possible the Yankees try to trade him, but more likely they see if his defense can return to normal and his bat can improve in a contract year.