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One of the outstanding questions about the Yankees approach to free agency that has emerged in recent days, especially as the team missed out on Juan Soto and, subsequently, a trade for the Astros’ Kyle Tucker, is whether GM Brian Cashman’s disdain for all things Houston–dating back to the team’s sign-stealing scandal of 2017–would prevent him from pursuing star third baseman Alex Bregman.

Bregman remains in free agency, even as the Astros appear more likely to move on from him following the move to trade away Tucker, who landed with the Cubs.

Cashman has made no bones about the fact that he feels that the Yankees might have won a World Series in 2017 if not for the Astros’ cheating. While Bregman was not specifically a culprit in that scandal, he was one of the faces of that team. Cashman would have to swallow hard to sign Bregman.

Alex Bregman Is in Play

On Friday, in somewhat frank terms, Cashman indicated that he would be willing to do just that. He was  whether he would be willing to sign Bregman despite what he represents for the Yankees.

“My job is to find a way to make us as quality as we can year in and year out,” Cashman said. “So we’re going to vet every opportunity out there. First and foremost, find out if that can match. He’s been a thorn in our side for years along with a lot of other peoples’ side. He’s now into free agency. I’m sure he’s got a whole boatload of choices. Really good players like him make a lot of money.

“I have had a conversation or two with Scott Boras, with a lot of his clients, including Alex Bregman. I certainly respect the player and his ability and how much winning he’s been a part of, but that’s about as far as I will say at this point.”

Yankees & Red Sox in Bidding War?

Certainly, the Yankees could use Bregman, who and batted .260 this season. He’s a two-time All-Star who has spent his entire nine-year career in Houston, but after a relatively down season, he could be ready for a change of scenery.

After the season, Bregman seemed to indicate he was done with the Astros. “Thank you Houston,” Bregman wrote on Twitter/X.

Bregman won’t be cheap, but the Yankees have needs in the infield. His projected contract at Spotrac–is not out of the Yankees’ range, and with the team’s trade for reliever Devin Williams, which sent out top  to Milwaukee, the likelihood has increased that New York will move Jazz Chisholm to second base and sign a third baseman.

While Bregman’s options are dwindling, he does remain in the middle of a potential bidding war between the Yankees and their archrival, the Red Sox.

Sean Deveney is a veteran sports reporter covering the NBA, NFL and MLB for Heavy.com. He has written for Heavy since 2019 and has more than two decades of experience covering the NBA, including 17 years as the lead NBA reporter for the Sporting News. Deveney is the author of 7 nonfiction books, including “Fun City,” “Before Wrigley became Wrigley,” and “Facing Michael Jordan.” More about Sean Deveney