The New York Yankees are no strangers to massive contracts or the long-term risks that come with them. When Bleacher Report set out to identify MLB deals that could turn into financial headaches by 2028 and beyond, the Yankees landed squarely in the conversation—not because of present failure, but because of future uncertainty.
Bleacher Report’s exercise wasn’t about luxury-tax math or payroll optics. It focused strictly on cash owed, including deferred money, starting in 2028. In that lens, two Yankees contracts stood out as deals that could test the franchise’s flexibility in the second half of the decade, even if both players remain productive in the short term.
Aaron Judge’s Contract Is About Age, Not Decline—Yet
Aaron Judge appearing on a list like this almost feels contradictory. Judge is still the face of the franchise, a perennial MVP candidate, and one of the few hitters in baseball who can change a game with a single swing. Over the last three seasons, his production has remained elite despite a significant toe injury in 2023.
The concern Bleacher Report raises has little to do with current performance. It’s about time. Judge will be entering his age-36 season in 2028 with four years and roughly $160 million remaining on his nine-year, $360 million deal. Historically, very few players—especially power hitters with Judge’s physical profile—maintain elite production into their late 30s.
There are exceptions. David Ortiz and Nelson Cruz aged gracefully, and Judge’s discipline and strength give him a chance to do the same. But even a modest $40 million decline per year carries consequences. Reduced availability, more frequent maintenance days, or a shift toward designated hitter usage could all limit roster flexibility. The Yankees didn’t sign Judge expecting pain in the early years; the risk has always lived in the back end, and that window is now clearly visible.
Max Fried’s Deal Could Strain Future Rotation Planning
While Judge’s contract is a bet on a superstar aging well, Max Fried represents a different kind of gamble. The Yankees signed Fried to an eight-year deal with the expectation that his prime seasons would stabilize the rotation immediately. By most measures, his first year in pinstripes delivered on that promise, highlighted by a sub-3.00 ERA and a noticeable uptick in fastball velocity.
Bleacher Report’s concern centers on the years that follow. Fried will turn 34 in 2028 and will still owe $29 million annually through 2032. That alone wouldn’t be alarming if not for his medical history. Forearm strains in consecutive seasons before joining the Yankees raised flags, and while he has avoided major injury, some underlying trends are worth monitoring. His curveball and changeup—once dominant offerings—have become incrementally less effective, even if they remain above league average.
The timing is what makes the contract potentially tricky. Gerrit Cole and Carlos Rodón are no longer under contract after 2028, meaning Fried could be asked to anchor the rotation well into his mid-30s. If his stuff declines or durability becomes an issue, the Yankees could find themselves paying ace money without ace-level certainty.
Neither contract is a mistake in isolation. Together, they illustrate how quickly long-term commitments can narrow options. Bleacher Report isn’t predicting failure—it’s warning that the Yankees’ margin for error is shrinking as the calendar turns toward 2028.
Yankees Face Growing Questions About Two Major Long-Term Deals