Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third base Alex Bregman (2) hits a single during the first 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

Should Yankees Sign AL East Rival?

Originally posted on New York Yankees on SI
By Michael Rosenstein | Last updated Oct 15, 2025 11:00 AM ET

So you're saying there's a chance? The New York Yankees received some big news Tuesday when the New York Post's Jon Heyman reported Boston Red Sox third baseman Alex Bregman will be opting out of his contract and hitting the free-agent market.

The Yankees spent the 2025 campaign searching for stability at third base afterlosing Oswaldo Cabrera in May to a season-ending broken ankle.

Yankees general manager Brian Cashman stabilized the hot corner before the MLB trade deadline by acquiring Ryan McMahon from the Colorado Rockies.

McMahon flashed some leather at third base, but struggled in the batter's box, hitting .208 in 54 games with the Yankees. According to Spotrac, the 30-year-old is under contract for two more season at $16 million apiece.

Instant Upgrade for Yankees

Certainly signing Bregman would be an instant upgrade. He's a three-time All-Star with a Gold Glove and Silver Slugger Award on his resume.

But here's the rub: Bregman is opting out of his three-year, $120 million contract with the Red Sox because he thinks he can get more on the open market. So what is he looking for? Five years and $200 million?

Certainly the Yankees have shown the ability to drop big nine-figure contracts on free agents, doing so with both Max Fried (eight years, $218 million) and Carlos Rodon (six years, $162 million). And don't forget the nine-year, $324 million deal the Yankees gave Gerrit Cole. Or the nine-year, $360 million deal Aaron Judge signed to stay in the Bronx.

Maybe It Doesn't Make Sense, Though

Given the amount of money already committed to the team's core, perhaps dropping a ton of cash in Bregman's lap doesn't make the most sense.

Also keep in mind Bregman's age: 31. A long-term contract for a slugger on the down side of his career might not make sense. After all, he missed a almost two months of the 2025 season with a right quad strain.

And there are the optics. Bregman won a pair of World Series titles with the Houston Astros, including 2017 when the team beat the Yankees in the American League Championship Series. MLB later punished the Astros for the illegal sign-stealing scam they used on their way to winning their first title.

Brad Penner-Imagn Images

Sure, Bregman received glowing reviews for his clubhouse presence in Boston. And yes, he would be a defensive stalwart at third who also brings some thunder to the lineup.

But the Yankees have more pressing needs, especially in the outfield as Cody Bellinger and Trent Grisham hit the open market. McMahon and a healthy Cabrera are more than capable of holding things down at third base, especially if the Yankees want to make a run at Chicago Cubs outfielder Kyle Tucker, who's the best bat on the free-agent market.

Don't forget the Yankees also have some big free agency decisions to make with their bullpen as well, with Luke Weaver and Devin Williams possibly leaving the Bronx.

As for what Bregman's market could look like, Heyman reports the Red Sox "still seem like a logical fit." He also listed the Detroit Tigers, Toronto Blue Jays, Seattle Mariners and Kansas City Royals as potential suitors.

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