Why Red Sox Lost Alex Bregman Sweepstakes To Cubs

The Boston Red Sox unsurprisingly were heavily linked to All-Star third baseman Alex Bregman all offseason.

He was everything the club could've hoped for in 2025, but the two sides didn't get an extension done during the season, which opened the door to free agency. Boston consistently expressed optimism in the Bregman market. Back in September, Red Sox president and CEO Sam Kennedy spoke fondly of Bregman and made a point down the stretch to make it clear that Boston wanted Bregman and he seemingly wanted the club too.

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"That will all take care of itself," Kennedy said in September. He wants to be here. We want him to be here. I'll leave it at that. He's such an important part of this season and what we're doing. All focus right now are on these next 15 games."

It didn't work out, though. Nothing got done in the season and then Bregman opted out of his deal with the organization and entered free agency. ESPN's Jeff Passan reported that the third baseman and the Cubs agreed to terms on a $175 million deal over five years.

Another free agency miss

That's a pretty large deal. After the news broke on Saturday night, Chris Cotillo of MassLive.com reported that Boston was willing to go to five years on a deal for Bregman, but was outbid.

"Red Sox are said to have been willing to go to five years for Bregman. They were outbid by the Cubs at that $175M mark," Cotillo wrote.

Despite objectively good moves this offseason -- like adding Sonny Gray, Willson Contreras, and Johan Oviedo -- it's hard to sugarcoat the Bregman sweepstakes for the club. Boston is the only team that hasn't signed a player to a big league deal this winter. They have added money via the trades, but they also traded Rafael Devers -- and his massive contract -- to the San Francisco Giants after all the drama that was brought on by adding Bregman.

So, now, the Red Sox have been outbid for their reported "priority" in Bregman, as well as Pete Alonso, who they were heavily linked to. Boston has been outbid by the Baltimore Orioles and Cubs for the two big-time sluggers. Not a great look.

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