Inside The Red Sox

Alex Bregman Wastes No Time Rubbing Salt In Red Sox Fans' Wounds

The pain won't end...
Jackson Roberts|
Aug 27, 2025; Baltimore, Maryland, USA; Boston Red Sox third baseman Alex Bregman (2) gestures on the field before the game between the Baltimore Orioles and the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images
Aug 27, 2025; Baltimore, Maryland, USA; Boston Red Sox third baseman Alex Bregman (2) gestures on the field before the game between the Baltimore Orioles and the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images | James A. Pittman-Imagn Images

In this story:

Boston Red SoxChicago Cubs

Alex Bregman is in Chicago, presumably to make his deal official with his new ballclub, the Chicago Cubs.

The last few days have been full of anguish for Boston Red Sox fans, who saw Bregman choose a five-year, $175 million deal with the Cubs over a five-year, $165 million offer from Boston that inexplicably did not include a no-trade clause.

But while the Red Sox have just begun scrambling to find a Plan B, Bregman has been able to kick his feet up and enjoy the final month of his offseason.

If you like our content, choose Sports Illustrated as a preferred source on Google.

Bregman dons first Chicago jersey at Blackhawks game

On Monday night, Bregman attended a Chicago Blackhawks hockey game at United Center, introducing himself to his fan base and receiving a hearty ovation when shown on the Jumbotron during a stoppage in the action.

Bregman wasn't able to spur a young Blackhawks team to a victory over the defending Western Conference champion Edmonton Oilers, who downed Chicago 4-1. That was about the only thing that's gone wrong for Chicago sports fans this week.

With Bregman and Edward Cabrera both joining the team in the span of a week, the Cubs have had the kind of decisive, aggressive offseason every Red Sox fan was hoping their team would have.

It's just unbelievable, from Red Sox fans' perspective, that Bregman was only in town for 11 months. The Red Sox enraged Rafael Devers in large part by acquiring Bregman and installing him at third base without warning, only to not make the biggest offer for Bregman when it came time.

On Tuesday, it seems likely Bregman will swap out his Blackhawks jersey for a Cubs one at a press conference. It's only been 335 days since Bregman put on a Red Sox cap and excitedly told Boston media how much he was looking forward to helping a Boston team with a lot of promise take its next steps.

Truly, what a spectacular display of asset mismanagement.

More MLB: Red Sox's Alex Bregman Tactics Look Worse As New Evidence Emerges

Published
Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org

Home/Boston Red Sox News