Alex Bregman's swing has always thrived at Fenway Park. This was obvious when Bregman was a member of the Houston Astros visiting Fenway, and it was reiterated when Bregman played for Boston last season.
Wrigley Field hasn't been as kind to Bregman. He's regressed in a Chicago Cubs uniform in 2026. With his numbers dropping below his career norms, Bregman has been trying to work himself out of the doldrums with his new team. He's even posted some of his workouts to TikTok, and a recent video went viral for a hilarious reason.
Bregman posted a video of himself working out in the cage with the HitTrax program, which simulates different MLB ballparks (sort of like how indoor golfing simulates courses on a screen).
What's funny about Bregman's vid is that he chose Fenway Park for the HitTrax simulation, a detail that fans ran with, suggesting that Bregman is pining for the dimensions of Fenway, which catered to his swing and allowed for more attainable production at the plate for the three-time All-Star.
Alex Bregman posted a Fenway Park-simulated batting cage workout to TikTok
Bregman really picked Fenway Park on HitTrax https://t.co/IMMUQD0Ebu
— The WARmonger (@TheWARmonger_) June 20, 2026
Bregman would still be a Red Sox if Craig Breslow had operated with competence last winter
If Bregman is indeed missing Fenway, he must be doubly annoyed with how Red Sox chief baseball officer Craig Breslow and the rest of Boston's front office handled Bregman's free agency process over the winter.
Through pettiness, entitlement, and a general lack of awareness, Breslow and Co. botched the re-signing of Bregman by haughtily assuming they had the best offer on the table when they absolutely did not. It was another sad chapter in the Breslow Era, and plenty more have followed since then.
Bregman's not exactly missing out on a winning experience by not playing for the 2026 Red Sox
It appears that both the Red Sox and Bregman were better off with each other than without each other. As Breggy struggles to look like himself in Chicago, the Red Sox are experiencing their worst season in over 60 years.
Bregman's talented understudy, Roman Anthony, has been a complete non-factor in 2026 while nursing a hand injury. Marcelo Mayer, another of Bregman's pupils, has also been mediocre this year. Both young players would definitely benefit from having Bregman still around.
It's clear that Bregman enjoyed and fed off the mentor role that he naturally embodied in Boston, too. There's less of a need for it in Chicago, outside of Pete Crow-Armstrong.
Bregman and the Red Sox were a really nice marriage ruined by Boston's pathetic front office. Now, all Bregman can do is look back fondly on his time at Fenway while simulating those memories in the cage.
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