Cubs' Alex Bregman Already Giving Red Sox Cause for Free Agency Regret

The production on the field was only half the reason the Boston Red Sox loved having Alex Bregman last season.

Bregman's reputation as one of the sport's best mentors has steadily grown over the past year. He was crucial to the Red Sox's development of the rookie position players on the roster, Roman Anthony in particular, and even put in time to help the pitching staff.

When Bregman signed with the Chicago Cubs last month, the Red Sox had to know they weren't just losing a Gold Glove-caliber third baseman. They lost the unquestioned leader of their clubhouse, as well as a de facto extra member of the coaching staff.

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New piece from The Athletic shows all the reasons Bregman will be missed

Alex Bregman, Michael Busch — Feb 11, 2026; Mesa, AZ, USA; Chicago Cubs Alex Bregman (3) and Michael Busch (29) get ready to hit during spring training camp at Sloan Park. Mandatory Credit: Rick Scuteri-Imagn Images | Rick Scuteri-Imagn Images

Two days into Cubs spring training, Ken Rosenthal of The Athletic released a feature on Bregman's short time with the Cubs thus far. The amount of work he's already done to help further Chicago's goals of winning a title this year is somewhat staggering.

For one, All-Star center fielder Pete Crow-Armstrong seems convinced that Bregman has already found some key teaching points to help him lower his swing rate and boost his walk rate, which could make him one of the very best players in the sport.

“He’s excited to see my OBP go up and my swing rate go down,” Crow-Armstrong said, per Rosenthal. “It’s everything that everybody else probably wants to see. But the way he talks about it is really cool.

“It’s a nerdy approach to hitting, but it’s never overcomplicated.”

There's no accident behind the fact that Bregman has never missed the playoffs in his major league career. He's 9-for-9, and with a Chicago team that made it to the division series last year, his odds of making it double digits seem to be high.

Starting pitcher Jameson Taillon may have put it best. When Bregman asked him why the Cubs didn't win the division last season, per Rosenthal, the veteran simply said it was because “We didn’t have you.”

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