As the World Series unfolds in Milwaukee, the New York Yankees face an early offseason choice that one writer says could define their winter.
Michael Zeno of Yankees On SI argues the club must avoid repeating last year’s qualifying offer to Trent Grisham by declining to extend one to second baseman Jazz Chisholm Jr.
The decision is among the few mandatory ones the Yankees must make by early November, when exclusive negotiating rights with free agents expire. Closer David Bednar is viewed as a likely recipient after a strong season in the Bronx, with his market approaching the $23.15 million qualifying-offer value.
Chisholm presents a different calculation. He posted a 3.5 fWAR in 2026 despite a down offensive year, drawing most of that value from defense and baserunning while batting .231 with 19 home runs and 41 stolen bases.
Zeno contends the Yankees should learn from Grisham’s experience and cut ties rather than lock in guaranteed money that could constrain other moves.
Grisham accepted a $22.025 million qualifying offer last winter after a breakout 2025 campaign that included 34 home runs and an .811 OPS. Many expected him to seek multiyear security, but he took the one-year deal.
The result was a regression. Grisham battled multiple hamstring issues, hit .211/.308/.395 with 18 home runs in 121 games, and posted only 0.7 fWAR amid defensive decline.
Zeno notes that the process of offering Grisham was reasonable given his high-contact approach and fit atop the order, yet injuries disrupted the plan. More critically, the commitment consumed early offseason resources as the Yankees also retained Cody Bellinger at a higher rate while believing the prior roster merited a return.
That approach left limited flexibility. Owner Hal Steinbrenner has since placed the onus on the front office to overhaul an offense he called “detrimental” after the Yankees finished 93-68, second in the AL East behind the Rays, and were swept in the ALDS while scoring just five runs in three games.
Steinbrenner emphasized inconsistency in run production throughout the year and said the organization would examine the offensive side from top to bottom. The Yankees scored 739 runs, down from 849 the previous season, with batting average dropping to .235.
Giving Chisholm a one-year prove-it deal at roughly $23 million might appear viable on paper, given his upside as a potential 30-30 talent who ranked among the American League’s better second basemen even in a down year. Zeno argues it would be unwise amid budget constraints and the clear need for offensive additions.
Draft compensation offers little offset. As a luxury-tax payer, the Yankees would receive only a fourth-round pick if Chisholm rejected the offer and signed elsewhere — “hardly a hedge,” in Zeno’s assessment.
The risk of Chisholm rebounding elsewhere would sting, Zeno acknowledges, but the team cannot afford another season in which substantial money is tied to a player who fails to rebound while ownership demands an offensive overhaul.
Bednar remains the clearer qualifying-offer candidate. Extending one to Chisholm, however, risks repeating the early-budget commitment that limited options after Grisham’s acceptance and subsequent underperformance.
With the five-day exclusive window approaching once the World Series ends, the Yankees must weigh Chisholm’s defensive and baserunning floor against the broader need to address an offense Steinbrenner has singled out for scrutiny.
Zeno’s caution centers on avoiding guaranteed money for a borderline case when flexibility is required to build toward 2027. The Grisham precedent, he writes, serves as a cautionary tale about how early commitments can hinder the rest of the offseason.
