Inside The Red Sox

Red Sox Favored In Crucial $120 Million Free Agency Sweepstakes

The Red Sox need to prioritize re-signing Alex Bregman this winter...
Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third base Alex Bregman (2) hits a single during the first inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images
Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third base Alex Bregman (2) hits a single during the first inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

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The Boston Red Sox had a great season, but they came up short of the ultimate prize. Injuries crippled the team down the stretch. The front office didn't add enough starting pitching to keep up with the top contenders, either.

After falling short to theeir rivals, the New York Yankees, the Red Sox will have some big decisions to make in the offseason. The biggest decision and storyline revolves around star infielder Alex Bregman.

Bregman has an opt out clause in his contract and he's expected to use it and enter free agency again this winter.

Bleacher Report's Tim Kelly recently listed the Red Sox as the favorites in the free agency sweepstakes for Bregman. Bregman's decision could make or break the immediate future of the Red Sox

Alex Bregman sweepstakes will determine Red Sox's future

Boston Red Sox infielder Alex Bregma
Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third base Alex Bregman (2) hits an RBI double during the ninth inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

"While there will certainly be other suitors, Bregman remaining in Boston for the foreseeable future is still the scenario that makes the most sense, by far," Kelly wrote. "Yes, at times it feels like the Red Sox have too much young position talent for their own good, but keeping that makes the veteran presence of Bregman that much more important.

"They also burned the bridge with Rafael Devers, so there's not a good internal option to replace Bregman at third base in 2026. Alex Cora wanted to reunite with Bregman last offseason, so much so that the Red Sox gave up draft-pick compensation to sign him. With Devers gone and no ability to give Bregman a QO, the Red Sox should be the most motivated player in the sweepstakes for Bregman."

The Red Sox should be willing to offer Bregman practically whatever length and value he wants on his next deal. He was a crucial piece of the puzzle for the team this year. His value to the team goes beyond the field, as he's the leader for the slew of young infielders within the team's system.

The Red Sox will have some tough competition in the Bregman sweepstakes, but money shouldn't be the issue. Boston fell in love with their star infielder and he seemed to love the team, fanbase, and city right back.

Now, the front office will need to give him the money he feels he's worth.

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