MLB.com Says This Team is a “Proven Fit” for Alex Bregman

On Christmas Eve, MLB.com’s Andrew Simon released a piece called “Finding perfect fits for top 14 remaining free agents.”

And, as we all know, this means one-time Red Sox third baseman Alex Bregman was going to be among the names listed.

Here’s what Simon said about the two-time World Series champion, describing him as a “proven fit” for Boston:

“Red Sox chief baseball officer Craig Breslow made it clear that even after acquiring first baseman Willson Contreras on Monday, the Sox are looking for another significant lineup piece. That almost certainly means an infielder, which could be another free agent, such as [Bo] Bichette, or a trade acquisition, perhaps someone like Arizona’s Ketel Marte or St. Louis’ Brendon Donovan. But why not go with the guy who you already know is a fit, establishing himself as a clubhouse leader upon arriving last season? 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 is going to be expensive. A deal north of $150 million feels inevitable, and that’s the kind of number that forces real conversations inside a front office to be had - especially with Fenway Sports Group’s frugal edict in place.

But fit isn’t about finding the cheapest answer. It’s about identifying the one place where the cost actually makes sense. For the Red Sox, Bregman checks that box because he already solved problems they’ve spent years trying to patch over during his one season with the team.

Before a quad injury cut his season short in late May, Bregman stabilized everything. Third base stopped being a revolving door. The infield started looking intentional instead of improvised. And if Marcelo Mayer is going to slot in at second base along with Contreras at first, this infield has a chance to be special in 2026.

That’s why the contract projection matters, but it isn’t disqualifying.

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Paying Bregman means paying for some version of certainty - positional clarity, defensive alignment clubhouse leadership, and a lineup that doesn’t need nightly justification. The alternatives might be cheaper, but they come with more questions, and this roster already has enough of those.

And then there’s the money you don’t see on the payroll sheet.

Bregman’s influence in the clubhouse showed up fast and often in 2025. Young players listened. Preparation followed. When guys like Mayer and Roman Anthony talk about him like he was a coach, they’re describing a presence that doesn’t come discounted.

If Boston lets him walk, they’re not just reallocating dollars, they’re gambling that leadership and structure will magically replace themselves.

That’s why Simon’s “proven fit” line lands.

Even with the price tag, Bregman makes sense in Boston.

The Red Sox don’t need another idea. They need to commit to the one that already worked.

I’ve said it once, and I’ll say it again:

Don’t. Screw. This. Up.

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Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.