Insider Gives Hope For Red Sox-Alex Bregman Sweepstakes

The 2025 Major League Baseball Winter Meetings will begin in just about three weeks.

Players can sign and get traded at any point now, but the Winter Meetings are typically the powder keg that really brings the offseason to another level. For the Boston Red Sox, that's important specifically when it comes to Alex Bregman.

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There's going to be buzz and rumors left and right until the day he signs on the dotted line with a team. Bregman signed with the Red Sox ahead of the 2025 season in February. There's no way to know if he will wait that long to sign this year, but this is a sweepstakes that isn't likely to end imminently.

What's next for Alex Bregman?

Oct 2, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) is forced out by New York Yankees shortstop Anthony Volpe (11) at second base in the ninth inning during game three of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

On the bright side, though, MLB.com insider Mark Feinsand suggested that Boston may be more open to giving Bregman a long-term extension this offseason after signing him to a three-year deal last offseason.

"Red Sox: Alex Bregman, 3B," Feinsand said. "Bregman’s first year in Boston went well despite injuries limiting him to 114 games, as he posted an .821 OPS with 18 homers. The Red Sox were only willing to give the third baseman a three-year deal last offseason, but now that he’s been in the clubhouse for a year, his value on and off the field could make Boston more comfortable with giving Bregman a longer contract."

If the Red Sox are going to find a way to keep Bregman, that's likely what it's going to take. He opted out after signing a three-year, $120 million deal with Boston. He's due for a long-term deal now.

Analysts and insiders have projected potential contracts for Bregman left and right all offseason so far. For example, The Athletic's Tim Britton projected that Bregman will end up getting a six-year, $171 million deal.

Spotrac is projecting a much lower market value at just over $110 million across four years.

If the Red Sox want him back, they are going to have to give him a much-deserved long-term deal. Feinsand's suggestion is something to hold onto, at least.

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