Alex Bregman Update Is Nightmare Fuel For Red Sox

The Boston Red Sox’s biggest need is obvious: another thumper in the middle of the order. Alex Bregman remains the most obvious fit to fill the hole. That has been the case all offseason and even during the season before Bregman even opted out of his deal in the first place.

If the question of whether Bregman will be back simply is just about money, Boston realistically should be able to get him back. The Red Sox have done well in the trade market, but this is a team that hasn’t signed a free agent to a big league deal yet. Sure, the club has taken on money in the trades for guys like Sonny Gray and Willson Contreras, but not in the long term. Gray is signed for the 2026 season with a mutual option for 2027. Contreras is signed for two seasons with a club option for a third.

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There is long-term flexibility with the organization, but MLB.com’s Mark Feinsand dropped an update on the sweepstakes fans won’t love. Feinsand noted that the Toronto Blue Jays and Arizona Diamondbacks appear to be the two most aggressive teams in the market right now for the third baseman.

Not the best update

"Bregman’s market has seemingly included as many as a half-dozen teams, though none have been aggressive enough to give him the long-term deal he’s been seeking," Feinsand wrote. "The Blue Jays, Diamondbacks, Cubs, Red Sox and Tigers have been connected to him throughout the offseason.

"Detroit made a strong bid to sign Bregman last winter, before he inked a three-year, $120 million deal (half of which was deferred) with the Red Sox, a contract he opted out of after the 2025 season. The Tigers’ offer last offseason was for six years and $171.5 million with some deferred money, though Detroit doesn’t appear to be in the same range this winter. Sources believe the Blue Jays and Diamondbacks may be the two most aggressive clubs in the hunt for Bregman, though a Red Sox reunion remains a possibility."

Arguably, this shouldn’t be the case. Boston seemingly is one slugger away from really contending and Bregman not only would bring that bat, but also is someone with World Series experience under his belt. He was a leader for the organization in 2025 and the club has been candid about its pursuit of a big bat. If the Red Sox aren’t going to be as aggressive as the Blue Jays or smaller-market Diamondbacks, then who is Boston considering?

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