Sep 10, 2025; West Sacramento, California, USA; Boston Red Sox third baseman Alex Bregman (2) is congratulated by teammates after scoring a run against the Athletics during the third inning at Sutter Health Park. Mandatory Credit: Dennis Lee-Imagn Images Dennis Lee-Imagn Images

Top 3 Alex Bregman Free Agency Fits: Way Too Early Edition

Originally posted on Fastball on SI | By Zach Pressnell | Last updated Sep 19, 2025 9:18 AM ET

The Alex Bregman sweepstakes were one of the bigger storylines of last offseason. As we head into another offseason in a month or two, Bregman has the ability to opt out of his contract and head back to free agency.

Considering how well he's playing, this seems like the most likely option. The Boston Red Sox won the Bregman sweepstakes a year ago, and they'll likely battle some steep competition to win it again this winter.

Who are the top three free agency fits for Bregman?

Philadelphia Phillies

The Philadelphia Phillies are seemingly always in the market to add talent. They seemed to have some interest in Bregman last winter, but with Kyle Schwarber headed to free agency, their interest in the star third baseman could increase.

Alec Bohm is a question mark in the lineup most of the time, which opens a hole for Bregman in the City of Brotherly Love. Bohm could also move to the outfield or first base, depending on the day and situation, to fill a hole for the Phillies.

Detroit Tigers

The Detroit Tigers have the obvious connection between Bregman and his former manager, AJ Hinch. The Tigers have reportedly been interested in Bregman every step of the way, but they fell short in free agency, and Boston didn't seem to want to trade him, for good reason. With the opportunity to land him on the open market likely to emerge again, the Tigers could be doubly aggressive in pursuing the star infielder. He's the veteran leader and talented bat that Detroit desperately needs.

Boston Red Sox

The fit for the Red Sox is obvious. Bregman seems to love Boston, and the fans definitely seem to love him. The match has been perfect, and the two parties could top it off with a World Series title this October. Boston has shown a willingness to spend the money for stars. Considering how well Bregman has played with the Red Sox, the front office might feel a bit more inclined to give him the money, contract length, and incentives that he wants in order to keep him on the roster for the next few years.

More MLB: 3 Players Blue Jays Should Pursue This Winter To Bolster Roster: Too Early Edition

This article first appeared on Fastball on SI and was syndicated with permission.

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