Red Sox Insider Spells Out Reasons Alex Bregman Return Isn't Assured

This one won't feel safe until it's official

Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) takes batting practice before game one of the Wildcard round of the 2025 MLB playoffs against the New York Yankees at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

Alex Bregman's free agency is in full swing already, and it's only going to get more nerve-wracking from this point forward.

For the most part, the prevailing emotion among Boston Red Sox fans seems to be wanting Bregman to return, and for good reason. He gave Boston a productive season on the diamond, but arguably more importantly, he set the foundations for a winning clubhouse culture.

We're still in the information-gathering phase, and so far, we haven't heard many concrete reports of teams being aggressive or passive on the Bregman front. But one insider's reasons for doubting a new deal for Bregman have a lot of wisdom to them.

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Why Red Sox are at such high risk of Bregman walking

On Sunday, MLB.com Red Sox beat reporter Ian Browne gave the case for and against Bregman returning to Boston, and the strongest argument at the moment as to why Boston might not secure the partnership is essentially that they didn't offer what he was looking for last offseason.

"Last season, the Sox offered the three-year contract with opt-outs after the first two years. If the club doesn’t change its stance, that will likely prevent Bregman from committing to Boston on a short-term deal with a high average annual value. Otherwise, why did he opt out in the first place?" Browne wrote.

"(Bregman's) priority will be to find a team that should be a sustainable winner (the Red Sox seem to fit that mold) while also being willing to offer him five years or more (unclear if Boston will do that). Why might the Red Sox face more competition for Bregman’s services than they did a year ago? It is simple. He no longer has a qualifying attached to him."

Browne wasn't asked to make a prediction either way, and he gave some solid reasons as to why Bregman might want to return (not the least of which was the fact that other teams could easily be just as hesitant to give out long-term deals).

But we know the Detroit Tigers were willing to offer six years and $171.5 million last offseason. This offseason, Detroit has to worry about Tarik Skubal's free agency in a year's time, but if they throw the same offer out there (or if any other team does), don't be shocked to see Bregman take it.

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