3 Way-Too-Early Red Sox Offseason Predictions, Including Alex Bregman's Decision

If all goes according to plan, it will be an uneventful last few weeks of the regular season for the Boston Red Sox.

With the lineup struggling since Roman Anthony's injury and the starting rotation wearing down, the Red Sox just need to maintain a grip on their postseason spot. But while their focus is on these last three weeks and the playoffs, we can start thinking about some of the huge questions Boston will face this winter.

Is Alex Bregman coming back? Can Boston prevent some of these question marks in the rotation from popping up again? And who else besides Bregman might be on the way out?

Red Sox finally pull off Joe Ryan trade

Boston's near miss in trying to trade for Minnesota Twins All-Star Joe Ryan (or not that near, to hear some tell it) was the cause of much consternation at the July 31 deadline. But trades are easier to pull off in the offseason, and Boston should still be equally motivated to find another ace.

Maybe Payton Tolle won't be on the table this time, but between top prospects like Franklin Arias and Jhostynxon Garcia and the possible inclusion of a big-league outfielder like Jarren Duran or Wilyer Abreu, the Red Sox should have enough firepower to get a deal across the finish line.

Someone totally unexpected gets dealt

Aug 3, 2025; Boston, Massachusetts, USA; Boston Red Sox second baseman Romy Gonzalez (23) throws to first for an out during the sixth inning against the Houston Astros at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

We're on our toes for a Duran trade this offseason, and top prospects are always on the table. But the Red Sox have shown a penchant of late to make aggressive trades, even beyond the Rafael Devers deal, and that could easily lead to another surprise deal.

Maybe some team believes Romy González can be an everyday player and offers the Red Sox value they can't ignore. Maybe they move on from a former top prospect like Kristian Campbell or Marcelo Mayer. Without a firm guess, this is just a bet on Craig Breslow going chaos mode.

Alex Bregman returns on 5-year contract

This is the big-ticket item for the Red Sox. Some panicked last week when ESPN's Jeff Passan reported that Bregman is expected to opt out of the rest of his three-year deal, but that was always the most likely scenario. Now is the time for the front office to put up or shut up.

Bregman is essential to this Red Sox team, both in the lineup and as a clubhouse leader. For five years, $185 million, Breslow manages to keep him in town.

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