When the MLB Winter Meetings began in Orlando on Monday, almost everyone was expecting a big move by the Boston Red Sox. By the time everything came to an end on Wednesday, the Red Sox were shut out.
One of the two players they were hoping to land was Kyle Schwarber. However, he re-signed with the Philadelphia Phillies. The other player they were linked to was Pete Alonso of the New York Mets. Not only did Boston not get him, but he signed with the Baltimore Orioles in the American League East.
After news broke of Alonso signing with the Orioles, Red Sox chief baseball officer Craig Breslow had a blunt response, according to Tim Healey of the Boston Globe. “Got to figure out how to get him out.” Instead of him peppering the Green Monster at Fenway Park for 81 games, Boston will need to figure out how to pitch to him. Not what Breslow had in mind entering the Winter Meetings.
The Red Sox will head back to Boston and figure out how they’re going to pivot without adding a major bat. Third baseman Alex Bregman remains a free agent. Bob Nightengale of USA Today gave a promising update on Boston’s former corner infielder and a potential return to Boston.
Red Sox Predicted to Re-Sign Alex Bregman in Free Agency
With the Winter Meetings done, Nightengale wrote an article about 10 questions that still hang over the offseason. As far as Bregman goes, Nightengale predicted a landing spot for Bregman, and it would be what the Red Sox need.
“A year ago, the Boston Red Sox, Detroit Tigers, and Chicago Cubs were in hot pursuit of Bregman. He signed a three-year, $120 million deal with the Red Sox, but opted out after the first season, leaving $80 million on the table,” wrote Nightengale. “Now, one year later, the Red Sox and Tigers are still interested, with the Cubs saying they’re perfectly comfortable with rookie third baseman Matt Shaw.
“Prediction: Bregman returns to Boston, but won’t get anywhere near the $40 million annual salary he left behind.”
If he doesn’t get the $40 million he left behind by opting out of his contract with Boston, then that would be devastating for Bregman and agent Scott Boras. You would have to think that if he does return to the Red Sox, he gets at least that. Ryan Finklestein of Just Baseball predicted Bregman would get $155 million from Boston.
Red Sox Put in Difficult Spot By Losing Out on Pete Alonso
Alonso was built to hit at Fenway Park. He would have done some major damage with the Green Monster. Now, Breslow needs to pivot quickly from Alonso and find his next big bat. Bregman will turn 32 years old in March before Opening Day. Options are quickly becoming less and less available in free agency.
“We saw what he was able to bring on the field, in the clubhouse last year. He’s still out there, and he’s a guy that could fit our roster particularly well,” said Breslow.
Bregman missed 48 games for the Red Sox in 2025 with injuries. He slashed .273/.360/.462 with 18 home runs and 62 RBIs. He had an OPS of .821.
Not many expected Boston to leave Orlando without a big bat, but here they are. Bregman returning would be the best-case scenario right now for the Red Sox. If it doesn’t happen, then things are really uncomfortable in Boston for Breslow.
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