Cubs Rumors: Alex Bregman chatter returns after new trade deadline twist

Alex Bregman defined the end of the Chicago Cubs' offseason last winter, as despite the front office identifying Bregman as the final piece to the puzzle that was their 2025 roster construction, the Cubs' offer to the All-Star third baseman fell well short of the ones submitted by the Boston Red Sox and Detroit Tigers.

Bregman landed with the Red Sox on a three-year deal worth $120MM, but the contract includes player options after the 2025 and 2026 seasons. That is important context for Bregman and the Red Sox with the trade deadline approaching.

In the aftermath of trading Rafael Devers, the expectation has been that the Red Sox wanted to sign Bregman to an extension. Of course, Bregman is represented by Scott Boras, and an in-season extension is a task that is often easier said than done.

During a recent trade deadline mailbag for The Athletic, Jim Bowden was asked about the idea of Bregman signing an extension with the Red Sox, and his response opened the door for a potential trade.

"The Red Sox would like to extend Bregman before the trade deadline, but it won’t be easy with Scott Boras as his agent. And, I’m hearing, in my conversations throughout the league, if he’s not extended, they could end up trading him to Seattle, Detroit or Milwaukee."

Alex Bregman pipe dream isn’t dead after all

Bowden didn't mention the Cubs, but considering Matt Shaw's regression and the past interest in the veteran third baseman, chances are Jed Hoyer will come calling if Bregman is made available ahead of the trade deadline.

Given his contract situation, Bregman would still check the box for the Cubs that they believed he could last February, but leave the door open for Matt Shaw to resume third base duties for the team in 2026.

However, there is context needed when talking about the Red Sox trading Bregman. Especially in the aftermath of trading Rafael Devers last month. Short of the Red Sox falling out of contention, the idea of Boston trading Bregman would be a move that only furthers the divide between the fanbase and organization. As of this week, the Red Sox remain one of the top contenders for an American League Wild-Card spot

Bregman was named to the American League All-Star game, but has been sidelined since the end of May with a quad injury. Still, Bregman has 11 home runs on the season with a 156 wRC+. Bregman is expected to return around the All-Star break, meaning he should be healthy before the deadline passes. Given that Eugenio Suarez is the Cubs' only other realistic option for a third base upgrade, Bregman's situation is something they will monitor.

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