Red Sox Criticized for Letting Alex Bregman Walk to Cubs

Early season struggles have Boston regretting offseason decision to not re-sign the All-Star third baseman.

Apr. 14, 2026 at 6:03am

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A cubist, geometric painting depicting a fragmented baseball game or match, with sharp, overlapping planes of red, white, and navy blue representing the dynamic action on the field.The Red Sox's decision to let star third baseman Alex Bregman leave in free agency has created a gaping hole in their lineup that has contributed to their early-season struggles.Boston Today

The Boston Red Sox have faced early-season struggles, sitting at 6-9 and in fourth place in the American League East. One of the key decisions the team made in the offseason that is now being criticized is allowing All-Star third baseman Alex Bregman to sign with the Chicago Cubs as a free agent.

Why it matters

Bregman was a key part of the Red Sox lineup and a team leader. His departure has left a hole in Boston's offense that the team is struggling to fill, potentially costing them a playoff spot in the competitive AL East.

The details

The Red Sox have had an uneven start to the 2026 season, going 5-5 in their last 10 games. While they've had some impressive series wins, their overall 6-9 record has them in fourth place in the division. Analyst Jim Bowden of The Athletic believes the Red Sox made a mistake in letting Bregman leave, saying they 'really miss' the third baseman and need to improve at that position to free up another player for a super-utility role.

  • The Red Sox allowed Bregman to sign with the Cubs as a free agent during the offseason.

The players

Alex Bregman

An All-Star third baseman who signed with the Chicago Cubs in free agency after playing for the Red Sox.

Caleb Durbin

A Red Sox player who could potentially fill a super-utility role if the team improves at third base.

Jim Bowden

An analyst for The Athletic who criticized the Red Sox for letting Bregman leave in free agency.

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What they’re saying

“The Red Sox need another bat and a team leader. They really miss third baseman Alex Bregman, who signed with the Cubs in the offseason, and they really needed to pivot to Bo Bichette before he signed with the Mets.”

— Jim Bowden, Analyst

The takeaway

The Red Sox's early-season struggles have highlighted the mistake they made in letting Alex Bregman, a key offensive contributor and team leader, leave in free agency. The team is now facing the consequences of that decision and may need to make a move to fill the hole at third base if they want to compete for a playoff spot in the tough AL East.