The New York Yankees are not going to sign Alex Bregman—it’s simply not in the cards. However, if they were to tap into even a hint of creativity based on their own tendencies, they absolutely could make it happen! So, let’s entertain a slightly alternate reality for a moment.
For the 2025 season, the Yankees are clearly determined to stay under the Cohen Tax threshold, set at $301 million. According to Spotrac, they’re roughly $20 million shy of that mark. In theory, this makes someone like Bregman, who is expected to command over $20 million annually, out of reach unless the Yankees free up more salary. Even then, the front office likely wants some financial flexibility to maneuver at the trade deadline without being constrained by their spending.
That said, Bregman’s reported contract demands align perfectly with the Yankees’ usual approach. Recent rumors indicate the All-Star slugger is still seeking a six- or seven-year deal, even after all this time. Doesn’t this present an ideal opportunity for the Yankees to do what they love most? Whenever possible, the Yankees extend contracts over more years to minimize the impact of the Competitive Balance Tax (CBT) over time.
In this hypothetical scenario, a seven-year deal for Bregman might seem excessive, but is it really? The Yankees have handed out lengthy contracts before—eight years to Max Fried, six years to DJ LeMahieu, seven years to Aaron Hicks, and they even took on Giancarlo Stanton’s massive 13-year deal. So, while it might appear over the top, it’s not entirely out of character for the Yankees.
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