Inside The Red Sox

Red Sox Named 'Perfect Fit' For Free Agent Who Should Sign Soon

When will Sox fans get to stop waiting?
Jackson Roberts|
Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox manager Alex Cora against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images
Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox manager Alex Cora against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images | Mark J. Rebilas-Imagn Images

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Boston Red Sox

Boston Red Sox fans are waiting on pins and needles waiting to find out where Alex Bregman is going.

Though nothing is guaranteed, it seems as though Bregman's decision is likely to come soon, based in part on the posting window for Japanese corner infielder Kazuma Okamoto, which closes on Jan. 2. Bregman has been linked to the Red Sox, Toronto Blue Jays, Arizona Diamondbacks, and Chicago Cubs, all of whom could theoretically pivot to Okamoto if they miss out.

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Having the Bregman sweepstakes resolved soon would be a plus for Red Sox fans, but only if he chose to return. What should everyone's confidence level be?

Shouldn't Red Sox be Bregman's permanent home?

It's only one small part of the puzzle, but for what it's worth, people outside the Red Sox circle seem to agree that Bregman returning is the most likely scenario and/or the best fit.

On Thursday, Andrew Simon of MLB.com designated "perfect fits" for several star free agents, and despite challenges from all the teams listed above, he chose the Red Sox for Bregman.

"Why not go with the guy who you already know is a fit, establishing himself as a clubhouse leader upon arriving last season?" Simon wrote. "Bregman’s overall numbers were strong, and the Red Sox got a look at the best version of him when he hit .299/.385/.553 before sustaining a right quad injury in late May.

"By keeping Bregman at the hot corner, Boston could also keep Marcelo Mayer at second, sharpening its defense up the middle."

Bregman had a 3.5-WAR, .821 OPS season with the Red Sox on the diamond, but what made him the perfect fit was his work in the dugout and clubhouse. Boston's young core shouldn't have to continue adjusting to the big leagues without Bregman there to mentor them.

Still, money talks the loudest, and we've yet to learn whether the Red Sox will shell out the kind of money other teams will offer (or already have offered). Within the next week or so, we could finally have our answer.

More MLB: Red Sox Fans Get Christmas Day Alex Bregman Free Agency Update

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org

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