Alex Bregman spent the season with the Boston Red Sox and is now likely heading toward free agency this winter. The Red Sox will certainly miss his presence at third base if he decides to walk, as he’s fully expected to opt out of his current contract.

“Alex Bregman plans to opt out of his contract with the Boston Red Sox, a source told ESPN on Tuesday night, confirming a New York Post report. The move was expected and doesn’t rule out the veteran third baseman returning to Boston, but for now, he will be part of the free agent class for a second straight offseason,” ESPN wrote.

Bregman is expected to command a strong contract at this point in his career — perhaps the last major deal he’ll sign.

“Both Alex Speier of The Boston Globe and Tyler Milliken of WEEI suggested Matt Chapman’s contract as a comparison to what Bregman could get. The third baseman signed a bridge deal with the San Francisco Giants in 2024, posted a rebound season, then signed a six-year, $151 million extension,” BoSox Injection’s Katie Manganelli wrote.

This winter, Bregman will have the opportunity to sign anywhere in the league. The Athletic’s Jim Bowden believes a fitting destination could be the New York Yankees.

“Bregman was a leader in the Boston clubhouse by example and words, mentoring many of the Red Sox young future stars. He will be sought-after in free agency as the industry views him as a winning player who can contribute on both sides of the ball and perform on the biggest stage in the biggest moments. He’ll likely seek a long-term contract instead of settling for a shorter-term deal like he did last year,” Bowden wrote.

Adding Bregman to the Yankees would certainly create lineup complications, particularly with Ryan McMahon already holding down third base. Bregman would likely need to use his defensive flexibility and shift to left field.

Signing him would make for an intriguing offseason in New York — one full of questions about fit, positioning, and long-term direction.