Red Sox’s Biggest Mistake This Season Wasn’t Alex Bregman

May 12, 2026; Atlanta, Georgia, USA; Chicago Cubs third baseman Alex Bregman (3) celebrates after a home run against the Atlanta Braves in the fourth inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images Brett Davis-Imagn Images

Red Sox’s Biggest Mistake This Season Wasn’t Alex Bregman

Originally posted on Boston Red Sox on SI
By Patrick McAvoy | Last updated May 14, 2026 11:00 AM ET

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Before the 2026 Major League Baseball season kicked off, the biggest story around the organization was the loss of Alex Bregman.

Losing Bregman dominated headlines, the radio shows and certainly television talk shows not only just in Boston, but all across the baseball world. Boston took a lot of heat for its decision to let Bregman walk, and it was warranted. The Red Sox made it clear that Bregman was their priority publicly, but didn't step up to the plate in contract negotiations and get a deal over the finish line.

Now, Bregman is a member of the Chicago Cubs. So far this season, Bregman hasn't been as good over in Chicago as he was last year in Boston. He's slashing .246/.335/.359 with four homers, 14 RBIs, 22 walks and five doubles in 42 games played. He's been solid, but not spectacular. But even then, he would be a significant upgrade over what the Red Sox have had offensively over at the hot corner.

Unfortunately, letting Bregman walk doesn't look like Boston's biggest miss of the offseason. That would be the club's trade with the Milwaukee Brewers centered around Caleb Durbin and Kyle Harrison. Durbin has shown signs of progress but he is slashing .165/.245/.241 after 40 games played. He is playing Gold Glove Award-level defense, but he's giving the team almost nothing offensively right now. But that's not even the biggest reason why this deal looks like the biggest miss of the offseason for Boston. That would be the performance of Kyle Harrison over with the Brewers.

The Red Sox Trade Isn't Aging Well

Harrison, the gem of the Red Sox's deal with the San Francisco Giants last year to cut ties with Rafael Devers, has a 2.41 ERA in seven starts across 33 2/3 innings of work. That one stings. Boston traded Devers after a lot of self-inflicted drama last season. He isn't having a great season, but still would be better than what Boston has offensively, for the most part. Getting rid of Devers' contract was a positive, though. But the Red Sox never really gave Harrison an extended chance.

Boston went out this past offseason and added pitching left and right rather than seeing what it had in Harrison. For example, the Red Sox acquired Johan Oviedo from the Pittsburgh Pirates. Why not simply see what Harrison could've done instead?

It's a tough look that the Red Sox have traded starters to the Brewers in back-to-back years only for them to go off and look like stars in Milwaukee. Last year, it was Quinn Priester. This year, it's Harrison. After he was the centerpiece of the Devers deal, this one looks way worse.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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