The New York Yankees' 2025 season concluded short of expectations, ending their World Series hopes prematurely in the American League Division Series. As the franchise pivots to an essential offseason aimed at bolstering their roster, a key component of their recent success is set to test the free-agent market. That player is Trent Grisham, and his projected contract has stunned many observers, highlighting one of the most remarkable and risky stock rises in recent MLB memory.
Bleacher Report’s Joel Reuter recently projected that Grisham, a seven-year veteran, will command a massive deal worth $72 million over four years. This valuation is extraordinary considering where Grisham stood just one season prior—a performance so underwhelming that he was, by all accounts, considered a non-tender candidate. His journey from a potential roster casualty to a player poised to earn a nine-figure contract is a testament to the life-changing power of one stellar season.
The $72 Million Resurgence: An Outlier Campaign
Grisham’s 2025 contract stock is built almost entirely upon a single, dramatic outlier season. Before 2024, his profile was defined by inconsistency and disappointing offensive production. Over the previous three seasons (spanning 1,288 plate appearances), Grisham struggled mightily, hitting a cumulative .191 with an 84 OPS+, numbers typically associated with a bench player, not a high-profile free agent. As Reuter noted, "Teams won't simply forget the fact that he hit .191 with an 84 OPS+... over the previous three seasons."

However, his performance in 2024 provided the ultimate counter-narrative: a massive turnaround culminating in a 34-homer season. He showcased a power-hitting dimension previously unseen, transforming himself into an offensive force who did perhaps "more to boost his stock than perhaps any player in the 2025-26 free-agent class." This sudden surge—the transition from liability to slugger—is precisely what has created such a volatile and intriguing market.
The Risk-Reward Calculus for Suitors
The team that ultimately signs Trent Grisham for four years and up to $72 million will be making one of the riskiest, yet potentially most rewarding, investments of the winter. They are essentially betting that his 2024 breakout is his new baseline, rather than an isolated peak.
The risk is substantial. Is the signing team paying for the power output of an elite year, or are they committing to the player who spent three years struggling to stay above the Mendoza Line? Historically, players who experience such a drastic, late-career spike carry a high probability of regression. If Grisham reverts even partially to his prior form, the contract could quickly become a major financial liability.

However, the reward is equally compelling. At his best, Grisham provides elite power and a veteran presence who has shown he can handle the pressure of playing in the demanding New York market. The projected $18 million average annual value (AAV) is significant for a veteran but is far less than the contracts reserved for the truly elite sluggers, making him a tantalizing option for teams seeking powerful offense without breaking the bank for a top-tier superstar. Insiders suggest that a more likely final deal will land in the $50 million to $70 million range, over three or four years, reflecting the market's cautious optimism tempered by his track record.
The Yankees' Critical Offseason Decisions
For the New York Yankees, Grisham’s departure would be a microcosm of their broader offseason restructuring. While the Yankees are primarily focused on the potential retention of Cody Bellinger—a far more established, high-end free agent—the club must decide if they are willing to compete for Grisham's services at his new price point.
Given the Yankees’ immediate need to fill outfield and offensive gaps, re-signing Grisham offers continuity and minimizes the need for an expensive trade. However, the Yankees are expected to attract a host of other suitors, and team management must weigh the value of Grisham's 2024 performance against the significant financial risk. If they allow him to walk, they lose a proven piece of their lineup and free up the resources to pursue other targets, perhaps adding multiple solid players rather than gambling on a single, high-variance contract. Grisham’s free agency, therefore, becomes a crucial secondary domino that will indicate the Yankees' overall strategy: aggressive retention or a pivot toward external talent acquisition. The outcome of the sweepstakes for this newly-minted DH/outfielder will be one of the most closely watched narratives of the offseason.
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