The New York Yankees are inching closer to their first World Series appearance since 2009. But that doesn’t mean preparations for the 2025 roster aren’t also happening while the Bombers play in the ALCS. Could third baseman Alex Bregman be a fit for New York in free agency this winter?

While the Yankees might need someone new to play third base, Bleacher Report’s Joel Reuter named them as the “worst landing spot” for the right-handed slugger.

“Can you imagine? The bad blood between the Astros and Yankees stemming from the sign-stealing scandal could make the idea of signing Bregman a non-starter,” he said. “However, it’s interesting to consider how he might be received by the fanbase, and the Yankees do have a clear need at third base.”

Bregman has spent the last nine seasons with the Houston Astros. He’s been selected to two All-Star Games while winning one Silver Slugger Award and two World Series titles. The third baseman finished a five-year, $100 million extension in 2024.

Spotrac is pegging Bregman’s market value at four years and $119 million. However, fellow third baseman Matt Chapman getting a $151 million extension with the San Francisco Giants will likely be the starting point in negotiations for agent Scott Boras. Bleacher Report’s Zachary D. Rymer predicted on August 1 that Bregman would land a seven-year, $210 million contract.

Alex Bregman Is a Fit for the Yankees on Paper

Based on the Yankees’ anticipated 2025 roster construction, they might need a third baseman. Bregman would seemingly be a natural fit.

“Assuming they let Gleyber Torres walk in free agency, Jazz Chisholm Jr. can slide back to his natural position at second base, leaving a hole at third base that should not be filled by DJ LeMahieu again,” Reuter said.

Torres made $14.2 million in 2024 and will hit free agency this winter. He’s previously stated a desire to stay in the Bronx. However, it’s unknown how motivated general manager Brian Cashman is to retain the infielder. However, acquiring Jazz Chisholm Jr. at the trade deadline gives the Yankees options.

Chisholm has been mostly playing third base since landing in New York. But he spent his first three big-league seasons primarily playing second base for the Miami Marlins. His defensive versatility gives the Yankees flexibility to pursue different kinds of players to fill out the infield.

Bregman rebounded from a tough start to his 2024 campaign to hit .260/.315/.453 with 26 home runs, 75 RBI and 79 runs scored in 634 plate appearances. He mostly plays every day and has plenty of postseason experience.

But then again, how current players feel about the Astros’ sign-stealing scandal is unknown. Aaron Judge commented on it in February 2020 and said Houston’s 2017 World Series title holds no value because they cheated.

Will the Astros Let Alex Bregman Leave via Free Agency?

On the flip side of his article, Reuter picked the Astros as Bregman’s best landing spot this winter.

“The Astros do need to consider how they want to distribute available funds with Kyle Tucker and Framber Valdez both headed for free agency after the 2025 season, but if they are still committed to winning with the current core, keeping Bregman is a must,” he said.

Second baseman Jose Altuve has also started lobbying for his longtime teammate to return on a new contract. “We’re not going to be the same organization without him,” Altuve said on October 2 via ESPN’s Alden Gonzalez. “In my mind, there’s not a chance this is the last one [game together].”

Gonzalez also noted that before the Astros were eliminated in the Wild Card Series, Houston general manager Dana Brown sounded optimistic about re-signing Bregman. “I think it’ll work out,” he said. “When you get down to it, I think he [Bregman] wants to stay here. I think we want him to stay here. And it’s just a matter of coming up with some type of an agreement.”