Red Sox Made Fatal Mistake in Alex Bregman Negotiations: Report

"If Alex Bregman wanted to be here, ultimately he'd be here."

Those were Boston Red Sox CEO Sam Kennedy's comments over the weekend, when asked about why Bregman, the three-time All-Star third baseman, had skipped town for the Chicago Cubs. Kennedy dodged a question about the Red Sox's unwillingness to give Bregman a no-trade clause, and effectively dumped the blame for the relationship ending after one year on the player.

Bregman recently had his chance to respond, and as most Red Sox fans who saw how he conducted himself in Boston might have predicted, he took the high road. However, a concurring report also revealed yet another reason the Red Sox have no reason to be shocked that Bregman departed.

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Red Sox thought Bregman's side was bluffing, per report

Boston Red Sox third baseman Alex Bregman fields his position against the Detroit Tigers at Comerica Park, May 14, 2025. | Junfu Han / USA TODAY NETWORK via Imagn Images

In a conversation with USA Today's Bob Nightengale that was published on Friday, Bregman suggested that the lack of a no-trade clause wasn't the sole reason he ultimately decided to leave.

“It was more than just that," Bregman told Nightengale.

And had the Red Sox simply matched the Cubs' offer, complete with no-trade clause, would he have returned? In other words, was Sam Kennedy wrong?

“I just really don’t want to get into it,’’ Bregman told Nightengale. “It’s not worth it."

Bregman went on to say that he loved his time in Boston, specifically shouting out manager Alex Cora.

However, in the same Nightengale report, the insider alleged that the Red Sox believed themselves to be in a bidding war against themselves, and that they essentially were blindsided by the Cubs having the highest offer on the table.

"While Bregman declined to provide details of the talks, a person with direct knowledge of the negotiations believes that the Red Sox were convinced Bregman and agent Scott Boras were bluffing. The Red Sox were confident they had the highest bid, and thought they’d bidding against themselves," Nightengale wrote. "So, basically, it was (a) take-it-or-leave-it offer."

There will be years ahead to dissect the whole Bregman saga and how it worked out for the Red Sox on the field. But one thing that's hard to dispute at this point, especially if we assume Nightengale's report to be true, is that they failed to put their best foot forward if they truly wanted him back.