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Red Sox Receive Big News in Alex Bregman Re-Signing Talks

Alex Bregman, Boston Red Sox
Boston Red Sox third baseman Alex Bregman fields his position against the Detroit Tigers at Comerica Park, May 14, 2025.

The Boston Red Sox have seen limited progress in discussions aimed at bringing back third baseman Alex Bregman, as the team assures supporters that conversations with his representatives continue.

Yet, recent developments in the free-agent landscape could shift the balance in Boston’s favor against agent Scott Boras, known for his tough negotiating style.

FanSided contributor Mark Powell suggests that Boras and Bregman must accept the reality that demand for the infielder simply has not materialized as expected, making a massive contract unlikely.

Typically, Scott Boras prefers to extend negotiations deep into the offseason before recommending that his players commit to agreements. In many years, this approach proves effective once more.

However, the current environment for free agents remains unusually restrained. The more time passes under these conditions, the greater the risk that numerous Boras-represented players, Bregman among them, end up accepting shorter commitments and returning to the market sooner than planned.

This offseason represents Bregman’s best opportunity for a substantial, extended pact. Accepting another brief arrangement would push his next free-agency period into his mid-30s, diminishing his earning potential regardless of performance.

“As always, Scott Boras likes to wait until late in the winter before advising his clients to sign on the dotted line. Under normal circumstances, he’d be wise to do so again. But this market isn’t most markets, and the climate is ice cold. The longer Boras waits this time around, the more likely it is that several clients of his – including Alex Bregman – are forced to sign short-term deals and test free agency again in the near future…This is Bregman’s final shot at securing the long-term deal of his dreams. If he signed another short-term contract, he’ll reach free agency again in his mid-30’s, which will significantly hurt his value no matter what statistics he puts up. Coming off a 3.5 bWAR season in just 114 games, Bregman ought to cash in whenever the offer comes,” Powell wrote.

During the previous campaign, Bregman posted a batting line of .273/.360/.462/.821, including 28 doubles, 18 homers, and 62 runs batted in across 114 contests. These figures fall short of justifying expectations around a five-year pact worth $170 million.

Should the subdued market persist, Boston might gain the upper hand. Bregman thrived in the city and appears inclined to remain there.

A proposal from the Red Sox spanning three or four years, potentially including additional options, could prove sufficient to retain him in the organization’s colors.

It remains to be seen whether team leadership recognizes this opening and moves quickly to present a formal proposal to Bregman’s side.

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