What if Alex Bregman is too expensive for the Red Sox?

It's amazing how one year can change everything.

Last year, the teams that talked to Alex Bregman, who was free as a bird, didn't want to give him a long-term contract. Many clubs felt he was asking for too many years.

In fact, I often said that if he were to sign long-term, he might be (apart from Juan Soto, who signed a contract in another stratosphere) the guy whose contract would age the least.

But in the end, he signed a short-term deal in Boston, where he was excellent. He even pushed Rafael Devers – despite himself – out of town.

Right now, every Red Sox fan wants to see the Red Sox take a portion of the money that was earmarked for Devers to make Bregman, a player who should be out of contract this winter, a long-term member of the Red Sox.

Because yes, he's expected to become a free agent in a few weeks.

Bregman a near certainty to opt out of Red Sox deal, per source; what will his market look like? https://t.co/7j0Wds8LlW

– Mark Feinsand (@Feinsand) October 4, 2025

But behind these negotiating levers in favor of Scott Boras (Bregman's agent), the fact remains that right now, the Red Sox may have the same doubts as last winter regarding a long-term contract with the veteran, who was significant in 2025.

According to Chris Cotillo, who covers the Red Sox, we shouldn't necessarily be surprised to see the Red Sox being more cautious than we might think in the matter… and therefore not giving Bregman as much as he hopes.

More of a take than a report here FWIW

– Chris Cotillo (@ChrisCotillo) October 3, 2025

In other words? Don't think his return to the city is just a formality.

It's true that Bregman could age badly, as we thought a year ago. His many weeks on the injured list in 2025 are an excellent reminder of this.

Even though he's been excellent on the pitch and incredible for the club's culture, especially the way he's surrounded the club's youngsters, fans have to worry: will he go elsewhere?

I imagine people in Detroit must be dreaming just as much about Bregman (who has a connection to A.J. Hinch) as they did last winter.

In the end, I think the Red Sox will understand the player's importance to the organization's youth and will find a way to keep him in town for several years. No matter what the price.

And if that doesn't happen, the owner will be called cheap… and Rafael Devers' fans will say he was traded for nothing.

This content was created with the help of AI.