The New York Yankees find themselves on the brink of elimination as they prepare for Game 3 of the American League Division Series. This precarious position is not just about the immediate outcome; it also marks the unofficial beginning of the Hot Stove season for general manager Brian Cashman, who is already eyeing potential offseason acquisitions.

One name prominently linked to the Yankees’ offseason plans is Alex Bregman, the talented third baseman for the Boston Red Sox. Bregman has opted out of his contract, positioning himself for a second consecutive offseason in free agency. Last winter, he made a bold move by signing a three-year, $120 million deal with the Red Sox, which included opt-out clauses, demonstrating his confidence in his abilities.

In the 2023 season, Bregman showcased his worth by posting a .273 batting average, complemented by 18 home runs and 62 RBIs over 114 games. His performance has solidified his status as a three-time All-Star, making him a sought-after player in the upcoming market.

The financial implications of signing Bregman are significant. His contract demands could exceed the Yankees’ previous investments, with estimates suggesting an average annual salary around $40 million. Although that figure comes with deferrals, it places him among the elite players in Major League Baseball. As he enters his age-32 season in 2026, Bregman will likely seek a deal that extends well beyond the 2027 season.

An American League executive weighed in on the situation, expressing skepticism about Bregman maintaining such a high annual average value in the long term. However, the same source indicated that the total guarantee for Bregman could be comfortably over $80 million.

The Yankees’ willingness to invest heavily in Bregman remains uncertain, especially considering their recent commitments to other star players, including outfielder Aaron Judge and pitchers Max Fried and Carlos Rodon. These past expenditures raise questions about the team’s budgetary flexibility and their strategy moving forward.

As the Yankees navigate their postseason challenges, the looming possibility of acquiring Bregman could alter the franchise’s trajectory. How Cashman addresses this critical offseason remains to be seen, but the stakes are high, and the pressure to enhance the roster is palpable.