Will Red Sox Regret Not Paying Alex Bregman?

Jan 12, 2026

The American League is always a tough division to win, and the Boston Red Sox haven't won it since 2018. The division looks loaded again in 2026, but the Red Sox took a big hit over the weekend.

Boston still desperately wanted to re-sign third baseman Alex Bregman, who played with them in 2025 but opted out of his three-year, $120 million deal. He wanted a long-term contract, and the Red Sox apparently offered him five years and $165 million.

The Cubs one-upped them and offered the same length but $10 million more, a $175 million deal. According to reports, he's taking it. Here's our Roundtable Sports national story about it.

The Chicago Cubs didn't get much out of rookie Matt Shaw at third base last year, and they only scored a total of seven runs in their four playoff losses a year ago. They made a big move to fix that over the weekend, agreeing to a five-year, $175 million deal with Alex Bregman, according to reports.

roundtable.ioCubs Reportedly Set to Sign All-Star 3B Alex Bregman to 5-Year DealThe Chicago Cubs didn't get much out of rookie Matt Shaw at third base last year, and they only scored a total of seven runs in their four playoff losses a year ago. They made a big move to fix that over the weekend, agreeing to a five-year, $175 million deal with Alex Bregman, according to reports.

I think the Red Sox are really going to regret this. They have a lot of young talent on this team, but Bregman's power — especially at Fenway Park — would be a factor.

The Toronto Blue Jays nearly won the World Series last year, and were the best team in the AL East. The New York Yankees weren't far behind, and the Baltimore Orioles have added a lot of pieces so far, too.

Without Bregman, can the Sox really contend? I don't think so.