With the World Series having kicked off in Milwaukee, the clock is ticking on the start of the MLB offseason. The minute it ends, all 30 teams are able to go to work on building towards 2027.

In those first few days, the Yankees will have exclusive negotiating rights with their free agents for five days and will be able to make decisions on whether they want to bring them back or not.

With no club or player options to sort out, the only mandatory decisions that the team has to make by the time the five-day period ends in early November are whether to tender the qualifying offer to David Bednar and Jazz Chisholm Jr.

Bednar seems likely to get one after his strong body of work in the Bronx, and his market value is likely stretching toward the $23 million that the qualifying offer is worth, but what about Chisholm? He was more than worth that number to start his Yankees career, and even in a down 2026, posted 3.5 fWAR off almost exclusively defense and baserunning value.

Despite his upside and floor, the Yankees should learn from their past and just cut ties with their second baseman instead of making a guaranteed money commitment that could hinder the rest of their offseason.

Why Trent Grisham's qualifying offer failure might doom Jazz Chisholm's bid for one

Last season around this time, the Yankees faced a similar decision with a player on the opposite end of the spectrum, Trent Grisham, someone who broke out in a big way in 2025 after years of being a typical fourth outfielder and suddenly was hitting the market off an All-Star-caliber season.

The Yankees extended Grisham a $22 million qualifying offer, which he accepted to the moderate surprise of the baseball world. Many believed that he would opt for long-term security off a contract year, but he accepted an opportunity to maximize his money now and set up a bigger payday in 2027 if he had another strong season.

That, of course, didn't happen. Grisham battled multiple hamstring ailments and slumped both with the glove and with his bat, not coming close to replicating what made him worth the qualifying offer in the first place.

The process of extending the offer to Grisham was not a bad process from management, who oversaw the development of a high-contact 29-year-old bat who seemingly fit like a glove atop the batting order, but injuries can always throw a curveball.

The bigger worry with Grisham wasn't the collapse risk, but rather how it tied up a lot of the Yankees' money early in the offseason. Management believed the 2025 team was worth running back, so the team spent a vast majority of their offseason budget retaining Grisham and Cody Bellinger at higher rates.

Fast forward to this offseason, where giving Chisholm a one-year prove-it deal doesn't seem like the worst in the world, but when you think about the team's limited budget to make the clear additions they need to make after Hal Steinbrenner aired out the offense's struggles, it doesn't seem like the smart move.

Despite his upside, it's best for Yankees to part ways with Chisholm

The other side of a qualifying offer is draft compensation, but as a luxury tax team, it's only a fourth-round pick. It's hardly a hedge to make.

Chisholm has all the ability in the world to get back to the dynamic 30/30 talent he was in 2025 as one of the best all-around second basemen in the sport. Hell, you can make the argument that Chisholm was one of the American League's best at the position even with his struggles. Just look at how awful Ernie Clement was after leading the Junior Circuit in All-Star voting!

It would certainly sting if the Yankees let Chisholm go elsewhere and he put his 2026 in the past, but the team can't afford to have him on the books for $23 million next year and have him not rebound. The onus has been put on the front office by ownership to overhaul the offense, and that's not possible if the team ties up most of their offseason budget in Chisholm and Bednar.