Aug 22, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) prior to the game against the New York Yankees at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images Gregory Fisher-Imagn Images

3 Huge Red Sox Offseason Predictions - Including Bold Trades

Originally posted on Boston Red Sox on SI
By Zach Pressnell | Last updated Oct 9, 2025 5:00 PM ET

The Boston Red Sox had some high expectations coming into this season. They were one of the more active teams in the offseason last winter, so they were right to have high expectations. Boston added Garrett Crochet and Alex Bregman, among others, and both pickups performed like All-MLB talents.

But this offseason could be even better for Boston. The team is coming off a crushing loss to the New York Yankees to end the season, so it's safe to assume the front office is upset and prepared to make big moves to assure this kind of loss doesn't happen again.

Here are three huge predictions for the Red Sox's offseason:

Prediction: Red Sox sign Alex Bregman for $150-plus million

Bregman is going to be the top name to follow in Boston this winter. He signed to a three-year, $120 million deal last winter, but the opt out in his contract gives him the opportunity to enter free agency again this offseason.

If Bregman opts out, he's likely looking for a deal worth over $150 million, which the Red Sox could and should give him.

Boston needs to do everything in its power to re-sign Bregman, even if it means giving up close to $200 million in the deal.

Prediction: Red Sox add a frontline starting pitcher (Joe Ryan OR Dylan Cease)

The Red Sox were missing a solid No. 2 pitcher all season and it came back to haunt them down the stretch.

They're likely going to be active in the pitching market this winter and two names come to mind: Minnesota Twins righty Joe Ryan and San Diego Padres free agent Dylan Cease.

The Red Sox will likely go after these pitchers very aggressively. Landing one would take their pitching staff to the next level, even if it costs a lot of money or prospect capital.

Prediction: Red Sox trade Jarren Duran to a contender

Red Sox outfielder Jarren Duran was at the center of a lot of trade buzz this season and it'll likely continue into the offseason.

Boston has four or five high quality outfielders, so trading Duran wouldn't crush them, especially if a team like the San Diego Padres is willing to give up a haul to land him.

This offseason, the Red Sox will be able to test Duran's value on the market and land a solid return in a big trade. Don't be surprised if Duran has played his final game with the Red Sox.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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