Alex Bregman has come storming back and now it's worth wondering if Red Sox kept him

Boston Red Sox fans were outraged when the club let Alex Bregman leave after the 2025 season to sign with the Chicago Cubs in free agency. Eventually, Caleb Durbin settled in and grew into one of the Sox's best hitters, making the pain Bregman loss go away.

But Bregman is well on his way to making Boston regret letting him walk (again). The third baseman got off to an underwhelming start this season to the tune of a .241/.336/.359 slash line with nine home runs over 94 games before the All-Star break. He's since come roaring back to his status as one of the best infielders in the game — he's batting .300/.365/.622 in the second half (as of September 4) while maintaining his elite defense.

In the last few weeks, Bregman's post-All-Star heater has reached another level. He's become home run-happy and the long balls come in groups. Bregman logged three multi-homer games in August: he hit three bombs on August 12 against the Washington Nationals, he had a two home run game against the Seattle Mariners on August 21, and he closed out the month red-hot with another three homer game against the Milwaukee Brewers.

Alex Bregman's second-half offensive surge with Cubs re-starts conversation about Red Sox missing out

Bregman's sudden power surge would've looked great in Boston. All but four of his 24 home runs have left the yard over left field this season and his ability to pull the ball in the air would've put the Green Monster to good use, as he did in 2025.

This isn't to say that Durbin hasn't been extremely valuable, because he was one of the main spark plugs behind the Sox's insane July and August run. Durbin is batting .250/.327/.384 with 22 doubles, a triple, a 12 home runs, 62 RBI and 17 stolen bases through 134 games. But Bregman has twice the home runs Durbin does all while playing half his games at Wrigley Field, which he doesn't suit as well as he did Fenway Park.

Bregman and the Cubs will visit the Red Sox for the final series of the year and his return to Fenway should be interesting, especially if he maintains his hot streak. Despite his status as a leader and fan favorite on the 2025 squad, Red Sox fans may not receive Bregman well because he opted out of two years of a lucrative deal with Boston. If he has another multi-homer game while in Boston, the sting of his departure might return.

Since June, Durbin has been everything the Red Sox have needed him to be. But Bregman's torrid stretch during Chicago's playoff push will still have fans wondering what could've been.

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