Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox third baseman Alex Bregman against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images Mark J. Rebilas-Imagn Images

Predicting 3 Final Red Sox Offseason Moves Amid Alex Bregman Uncertainty

Originally posted on Boston Red Sox on SI
By Jackson Roberts | Last updated Jan 4, 2026 8:44 PM ET

As offseason activity ramps back up across Major League Baseball (knock on wood), the Boston Red Sox undeniably still have needs.

Alex Bregman is still a free agent, and if the Red Sox don't re-sign him, there will be hell to pay with the fan base. There are also still members of the 2025 Red Sox floating around the market, and Boston could have another trade to make.

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With the holiday season over and the sprint to spring training officially kicking off, let's predict how the remainder of this very important Red Sox offseason will play out.

Alex Bregman returns on 5-year contract

The Toronto Blue Jays signing Kazuma Okamoto presumably took one suitor out of the picture, which means Bregman's market is down to the Red Sox, Arizona Diamondbacks, and Chicago Cubs (if we consider the Detroit Tigers a distant fourth).

Boston's hesitancy to add extra years to Bregman's deal could either be a sign that they're trying to get the best possible deal, or that they're just not willing to keep him into his late 30s. This is a bet on the former, because the Red Sox have to know that a championship team takes risks on some of their contracts winding up as sunk costs.

Lucas Giolito winds up back in the Windy City

Giolito told Rob Bradford on "Baseball Isn't Boring" last week that his free agency market has been "crickets" to this point, which unfortunately seems to be the case for all pitchers not named Dylan Cease. But eventually, some team will wind up giving the veteran a chance to prove he can repeat his very productive 2025 campaign.

The Cubs, especially if they miss out on Bregman, should have money to spend on something besides relief pitching. And Giolito's comfort with Chicago, where he spent the first 6 1/2 years of his career playing across town, would undoubtedly be a selling point if the Cubs came calling.

Jarren Duran isn't traded, after all

Early in the offseason, it seemed like there was about an 80% chance the Red Sox would trade one of their outfielders. As things stand on Jan. 4, it now feels like those odds have dipped to maybe 45%.

Duran sticking around would virtually eliminate the need for Masataka Yoshida, and that's before factoring in the return of Triston Casas as well. But the Red Sox believe a surplus is not necessarily a bad thing, and it seems they aren't finding the deals for Duran they'd hoped for.

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

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