Yankees Face Huge Price Tag for Red Sox Star

The New York Yankees face elimination from the postseason in Game 3 of the American League Division Series, which means Hot Stove season could be around the corner for general manager Brian Cashman.

Among the many players being connected to the Yankees on the open market is Boston Red Sox third baseman Alex Bregman.

He is opting out of his contract and will spend his second consecutive offseason in free agency. Bregman bet on himself last winter, taking a three-year, $120 million contract with opt outs from the Red Sox.

So how much will it take to sign the three-time All-Star, who hit .273 with 18 home runs and 62 RBIs in 114 games for Boston?

"Bregman’s annual average salary of $40 million, even with the deferrals, puts him in elite company, though he’ll be entering his age-32 season in 2026, giving him incentive to find a deal that takes him past ‘27," MLB.com's Mark Feinsand reports.

“I struggle to see him sustaining that level of AAV [annual average value],” an American League executive said to Feinsand. “But the total guarantee should be well north of $80 million.”

It would be interesting to see if the Yankees are willing to commit that much to Bregman after handing out huge deals in past seasons to outfielder Aaron Judge and left-handers Max Fried and Carlos Rodon.

Keep in mind the Yankees spent much of the 2025 regular season trying to find a solution at third base after losing Oswaldo Cabrera in May to a broken ankle.

New York traded for Colorado Rockies third baseman Ryan McMahon before the July 31 deadline. He helped stabilize the position defensively but hit just .208 in 54 games.

Bregman drew praise in Boston for his clubhouse presence with the Red Sox having several young prospects, including stud outfielder Roman Anthony, in need of mentoring.

Boston Red Sox third baseman Alex Bregman — Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third base Alex Bregman (2) hits an RBI double during the ninth inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

But Bregman missed seven weeks with a quad injury and is clearly on the downside of his career.

“I think he thinks there is unfinished business there,” an AL executive said to Feinsand. “They could restructure something longer-term.”

“He probably tests the whole market unless Boston pays a premium,” another AL executive said to Feinsand after predicting a front-loaded five-year contract for the third baseman.

“I think a lot of it depends on how much he has enjoyed his time in Boston,” a National League executive said, per Feinsand. “Assuming the change in scenery was something he took to, I could see him opening up again to see what the bidding might bring this time around.”

Among the other clubs potentially competing with the Yankees for Bregman are the Detroit Tigers, Seattle Mariners Chicago Cubs and Los Angeles Dodgers.

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