With the offseason about to open, the Yankees are already facing one of their first big calls, and it could shape how much flexibility they have left to remake the roster.
Because there are no club or player options to sort through, the only mandatory decisions waiting in that early November window are whether to tender qualifying offers to David Bednar and Jazz Chisholm Jr. Bednar looks like the easy one. After what he did in the Bronx, he appears headed for a qualifying offer, and his market value may be pushing toward the $23 million attached to it.
Chisholm is the harder debate, but the case against keeping him on that number is pretty straightforward: the Yankees need room to act elsewhere, and a guaranteed one-year commitment could narrow those options fast. Even in a down 2026, he still produced 3.5 fWAR, with most of that value coming from defense and baserunning. He also showed enough upside early in his Yankees stint to make the idea tempting.
Still, the safer play may be to move on.
The Yankees already lived through a version of this last offseason with Trent Grisham. Coming off a huge 2025, when he looked like an All-Star-caliber player after years as more of a fourth outfielder, Grisham received a $22 million qualifying offer from the Yankees and accepted it. Plenty of people expected him to take the long-term security, but instead he bet on himself and on another strong season setting up a larger deal in 2027.
That bet crashed into reality. Grisham dealt with multiple hamstring issues, and his bat and glove both slipped badly. He never got close to the level that made the qualifying offer make sense in the first place.
From a process standpoint, the Yankees weren’t wrong to make that offer. The front office had developed a high-contact 29-year-old hitter who seemed to fit cleanly at the top of the lineup.
The problem was what came next. Once Grisham was on the books, a huge chunk of the offseason budget was tied up early, and the Yankees used most of their money bringing him back and keeping Cody Bellinger at higher rates.
That’s the warning here. Chisholm’s upside is real, and the possibility of losing a player who can be a dynamic 30/30 threat and one of the sport’s best all-around second basemen would hurt. He was still arguably one of the American League’s best at the position despite his struggles, even with how rough 2026 was for players like Ernie Clement after he led the Junior Circuit in All-Star voting.
But the Yankees have also been pushed by ownership to overhaul the offense, and that’s not going to happen if they lock up most of their offseason budget with Chisholm and Bednar. The draft compensation attached to a qualifying offer doesn’t really change the calculation either; as a luxury tax team, the return is only a fourth-round pick.
The Yankees can live with losing Chisholm if he rebounds somewhere else. What they can’t afford is paying $23 million for a rebound that never comes and then running out of money before they address the bigger holes they already know are there.
In Other News...
Trent Grisham's Yankees Future Suddenly Looks Far Less Certain
Trent Grisham had positioned himself as a useful piece for the Yankees after his offensive contributions in 2025, but the conversation around him has shifted as the 2026 season has worn on. His defense has slipped, and a hamstring injury only added to the uncertainty, giving the front office another reminder that his profile is no longer quite as straightforward as it looked a year ago.
With other players emerging around him, Grisham's role in New York suddenly feels less secure than it did before. There has already been speculation that clubs such as the Astros could keep an eye on his situation, and while nothing official has happened, the Yankees now have a decision to make about how much they value what he brings versus the alternatives beginning to crowd the picture. [Read more 🡒]
Yankees Face A Bigger Catcher Decision Than Fans Expected
Austin Wells spent much of the first half of the 2026 season fighting through a stretch that included time on the injured list with cervical headaches, and it made the catcher picture look far less settled than the Yankees probably hoped. Even so, his work behind the plate stayed steady throughout the year, giving the club at least one reliable element in a position where defense can matter as much as anything else.
The more interesting part now is what comes next. Wells' stronger second half and playoff showing gave the Yankees a reason to believe in the version of him they saw down the stretch, but the front office is still weighing a broader offseason plan at catcher, with free agents and trade options in the mix. In other words, this is no longer just about whether Wells can handle the job, but whether the Yankees are comfortable betting on that improvement as the foundation of the position. [Read more 🡒]
Yankees May Have A Ryan McMahon Decision They Can't Ignore
Ryan McMahon has given the Yankees the kind of steadiness they wanted at third base, at least on the defensive side, but the bat has not matched the glove. With the front office already weighing its next move, the question is no longer whether third base matters, but whether New York can keep living with the current balance of run prevention and run production at the position.
Alec Bohm has surfaced as a possible answer, and his appeal is obvious for a team looking for more offense from the right side of the plate. The catch is just as obvious: Bohms defensive metrics have trended down, which leaves the Yankees staring at the same old trade-off, whether to stick with McMahon, shrink his role, or chase a different fit altogether. [Read more 🡒]