Red Sox Face ‘Sleeping Giant’ Threat In Alex Bregman Sweepstakes

The Boston Red Sox need to get moving as fast as possible...

Sep 10, 2025; West Sacramento, California, USA; Boston Red Sox third baseman Alex Bregman (2) is congratulated by teammates after scoring a run against the Athletics during the third inning at Sutter Health Park. Mandatory Credit: Dennis Lee-Imagn Images | Dennis Lee-Imagn Images

The Alex Bregman sweepstakes has lived to see another day.

He remains among the group of big-name free agents waiting out the market, along with Kyle Tucker, Bo Bichette, and Cody Bellinger, among others. For the Boston Red Sox, Bregman would obviously be the best bet of the group. There are only so many ways to say this. Bregman has been available all offseason after a great year with the organization in 2025.

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If you're a Red Sox fan, one team to worry about is the Chicago Cubs. Earlier in December, FanSided's Robert Murray reported that Bregman held a Zoom meeting with Chicago. On Monday, he followed up and called the Cubs a "sleeping giant" in the sweepstakes for Bregman.

The Red Sox need to act

"The sleeping giant: Chicago Cubs," Murray wrote. "It’s pretty clear in looking at the Cubs’ offseason that their priority was to shore up the bullpen, and they’ve absolutely done that. But they have to do more — a lot more. It’s pretty clear that Kyle Tucker will not return to Chicago, and if that’s the case, they need a star player to replace him. And Bregman is a great candidate to do so. But will the Cubs splurge to sign Bregman? I’m skeptical. It’s not typically their M.O."

For the Red Sox, it would be better move sooner, rather than later. The Cubs made a splash last offseason to bring Tucker to town. As of this moment, a Tucker return to Chicago doesn't seem very likely. But Tucker is still available in free agency so nothing can be completely ruled out. The second Tucker ultimately does land elsewhere, then the floodgates are completely open.

Bregman is there in free agency and Boston knows the first partnership worked in 2025. The MLB offseason is full of negotiations. Right now the Red Sox may even have the leverage, but there comes a time when you have to get something done if you really want a player. Arguably, Bregman's market is going to get more difficult, not less. It's time to move before a team, like the Cubs, opts to strike.

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