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The Boston Red Sox made a huge splash in free agency last offseason when they signed superstar infielder Alex Bregman to a massive three-year, $120 million deal. But the Red Sox gave Bregman an opt-out clause in this deal, which allowed him to opt out of his contract after one season in Boston. Now that the star is back in free agency, the Red Sox are going to need to win the sweepstakes again in order to keep their World Series window open as wide as it was this year. But it’s going to be a tough task. Spotrac recently projected Bregman would sign a four-year, $110 million deal in free agency this winter, but other outlets project him to sign for even more. NEW YORK, NEW YORK – OCTOBER 02: Alex Bregman #2 of the Boston Red Sox attempts to field a ground ball during the second inning against the New York Yankees in game three of the American League Wild Card Series at Yankee Stadium on October 02, 2025 in the Bronx borough of New York City. (Photo by Al Bello/Getty Images) The Red Sox are bound to have some aggressive competition in the Bregman sweepstakes. He could fit with the Philadelphia Phillies. Philadelphia could lose Kyle Schwarber in free agency, which would allow the team to be more flexible with the designated hitter slot in the lineup. The Detroit Tigers could also make sense as a fit for Bregman in a final attempt to win the World Series with Tarik Skubal on the roster. But it could be tough for Detroit to find the money to sign Bregman while also seemingly attempting to sign Skubal to an extension. More MLB: Kyle Tucker’s Massive 10-Year, $401M Contract Projection May Limit Suitors
