New Alex Bregman Report Raises Red Sox Red Flags

The holidays are behind us and now it's time to get back to work for the Boston Red Sox and specifically add a bat before the market thins out even more.

This is, of course, in reference to third baseman Alex Bregman. Boston was fortunate to have Bregman in 2025. He was a leader for the club and helped to balance the lineup with right-handed pop. This isn't something the fanbase doesn't know, though. Bregman has been the talk of the offseason and if someone followed the organization in 2025, they know what the three-time All-Star brought to the table.

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On Monday, Evan Petzold of the Detroit Free Press did a dive in the Bregman sweepstakes. While discussing the Detroit Tigers and how they can swoop in if Bregman doesn't get an offer he likes elsewhere. The Red Sox, Chicago Cubs, Arizona Diamondbacks, and Toronto Blue Jays remain the four teams most connected to him. But Petzold noted that two of the four (Red Sox and Cubs) haven't been willing to make a long-term commitment to him at this time.

The Red Sox need to get aggressive

"In the 2025-26 offseason, the Red Sox, Cubs, Toronto Blue Jays and Arizona Diamondbacks are the four teams in the mix for Bregman after he opted out of his Red Sox contract, with the Tigers having lukewarm interest and taking a wait-and-see approach," Petzold wrote. "Although Bregman is determined to sign a long-term contract, two of the four teams – the Red Sox and Cubs – haven't shown a willingness to make that type of commitment, so if the Blue Jays and Diamondbacks bow out, the Tigers could re-emerge as the only team willing to sign Bregman for at least five years. Bregman projects to command six years, $170 million."

If you're a Red Sox fan, this isn't likely what you want to see -- and shouldn't be the case in general. Boston has been open and candid about wanting to add bats that move the needle this offseason. It did a good job acquiring Willson Contreras, but there clearly has been something with the organization and signing players in free agency to long-term deals in their 30s.

Pete Alonso, a significant bat who was on the market and met with Boston, signed a five-year, $155 million deal with the Baltimore Orioles. The Red Sox lost the bidding to one of their biggest rivals and reports surfaced from Tim Healey of the Boston Globe that Boston's offer to Alonso was for "fewer years and significantly less money."

Now, could things change in a minute and Boston meet Bregman's asking price? Absolutely. But -- especially after trading Rafael Devers -- this idea of not meeting asking prices has been a tough look. It could all end up being a negotiation tactic, but if the smaller market Diamondbacks are willing to go with a longer deal than Boston, then does the club really want the infielder?

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