The Yankees are facing a pivotal decision with Trent Grisham, a star who has quietly become a valuable contributor and a lingering concern in their lineup. While he has shown flashes of power and consistency at the plate, the looming offseason has put his future under Aaron Boone and the Yankees under the spotlight. 

Grisham arrived in the Yankees as part of the blockbuster Juan Soto trade, yet for much of the season, he has been identified as the “forgotten man.” Despite that perception, the star’s performance has been hard to ignore. On pace for 30 home runs and slotted as the leadoff hitter, he has provided clutch moments with grand slams and timely home runs. However, Grisham’s inconsistency in the outfield — sometimes appearing to loaf on fly balls with high catch probability — has left fans and analysts split on whether Grisham is worth keeping beyond this season.

The Yankees now face the tough question of whether to extend him a qualifying offer at the end of the season. That decision could hinge on multiple moving stars — the future of Cody Bellinger, the rise of top prospect Spencer Jones and the willingness to bet on Grisham’s health. With the qualifying offer projected around $22 million, it is a gamble that could reshape the team’s outfield for 2025 and beyond.

Joel Sherman of the New York Post Sports summed it up candidly: “To me, it’s like, if you know you’re keeping Bellinger, you don’t have to keep Grisham.” Sherman’s point highlights the balancing act the Yankees face. If Bellinger is locked in as the long-period answer, Grisham becomes expendable. However, if uncertainty lingers, Grisham could be the fallback option, albeit one with risks tied to his track record and durability. Sherman also raised the vital question of whether this season is a true breakout or just a “walk year mirage” which could regress once a deal is secured.

The financial side intricates matters further. If the Yankees issue the qualifying offer, Trent Grisham could accept it, effectively locking the star in at a one-year, $22 million deal. For the team, such a figure is steep for a star with limited consistency; however, for Grisham, it could be safer than testing a free-agent market that could only ensure a mid-tier multi-year deal, perhaps three years in the $40–45 million range. As Sherman said, Grisham is 28 and plays a position of high demand; however, questions related to his durability and defensive focus weigh largely. The Yankees need to now decide if Grisham’s bat is enough to justify the risk — or if it is time to let him walk.

However, while his on-field production is undeniable, the larger storyline now shifts off the field, where his deal situation looms large.

Deal decisions loom as Bellinger’s value skyrockets

With a .279/.332/.501 slash line and a proven capability to deliver in clutch moments, Cody Bellinger has quickly evolved from an elite offseason addition to an indispensable Yankee. The star’s versatility in the field and power at the plate make Bellinger more than just a midseason spark — he looks like a cornerstone piece. That is why Bellinger’s powerful opt-out has become a pressing concern for the management.

If he continues to produce at this level, the Yankees could have no choice but to invest heavily in his future. Free agency could draw interest from multiple big-market teams, specifically, given his pedigree as a former MVP and Comeback Player of the Year. The decision will not just shape Bellinger’s career path — it could determine whether the team’s surprising turnaround is a short-period surge or the beginning of a new era of dominance in the Yankees.

The Yankees’ resurgence has been fueled by Cody Bellinger’s resurgence at the plate and his Player of the Week honor only enhances his rising value. As the Yankees eye October, the management faces a pivotal decision—lock up their star slugger or risk losing the heartbeat of their turnaround.