Inside The Red Sox

Major Blue Jays-Alex Bregman Update Should Force Red Sox To Act

Time to stop messing around...
Aug 12, 2025; Houston, Texas, USA; Boston Red Sox third baseman Alex Bregman (2) hits a home run during the sixth inning against the Houston Astros at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images
Aug 12, 2025; Houston, Texas, USA; Boston Red Sox third baseman Alex Bregman (2) hits a home run during the sixth inning against the Houston Astros at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images | Troy Taormina-Imagn Images

Maybe it's a classic Scott Boras leverage play, but in light of the latest update on Alex Bregman's free agency, the Boston Red Sox need to wise up.

After a long week of hearing about the Arizona Diamondbacks pursuing Bregman, the Toronto Blue Jays entered the conversation on Friday, but only indirectly, ESPN's Jeff Passan said he believed the Blue Jays remained in the picture for Bregman, which was enough to set off alarm bells.

Now, thanks to a Saturday report from Ken Rosenthal of The Athletic, we know about direct contact between the Blue Jays and Bregman's camp.

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

Contact between Bregman, Blue Jays has to bother Boston

According to Rosenthal, the Blue Jays and Boras have spoken recently about the prospect of three-time All-Star heading to Toronto.

"Team officials have been in recent contact with Bregman’s agent, Scott Boras, according to sources briefed on the conversations," Rosenthal wrote. "Ideally, the Jays want to add a left-handed hitter, but either the right-handed Bregman or Bichette would fit their defensive alignment better than Tucker or Cody Bellinger, both of whom bat left."

The vast majority of Red Sox fans would consider this offseason a disaster if Bregman signed anywhere but Boston, especially now that Kyle Schwarber and Pete Alonso, the true power hitters, are off the board. But imagine if he signed with a division rival? The same division rival that won the American League pennant this year?

Candidly, the Red Sox need to wake up and smell the coffee. Every other team in baseball besides thet Colorado Rockies has signed a major league free agent. They haven't, and they've slow-played Bregman to the point that Boras is clearly doing everything he can to drum up the All-Star's market.

It shouldn't matter if the Red Sox save a few million bucks, or even get off the hook for Bregman for one less year in his mid-thirties. The Red Sox need him back, and Toronto, even if he's not the first choice, won't nickel and dime a marquee free agent.

More MLB: Red Sox, Cardinals Trade Speculation Gets Boost from Boston Insider


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