Alex Bregman Extension? Insider Makes Alarming Red Sox Prediction

Is it going to be too big an ask?

May 10, 2025; Kansas City, Missouri, USA; Boston Red Sox third baseman Alex Bregman (2) throws to first base in the first inning against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Peter Aiken-Imagn Images / Peter Aiken-Imagn Images

Every major transaction the Boston Red Sox have made in the last year has come as something of a surprise in the moment.

Few foresaw the Garrett Crochet trade, especially in the early days of the winter meetings before it happened. Even fewer foresaw the Alex Bregman signing, because it consistently sounded like the Red Sox wouldn't match his price tag.

Now, Bregman is the sole savior of the Red Sox lineup, because Boston made a trade no one foresaw by sending Rafael Devers to the San Francisco Giants. And Bregman not only remains on the injured list, but he remains uncommitted to Boston beyond this season.

Extending Bregman needs to be a top priority for the Red Sox the rest of the way in 2025. It's something both Bregman and agent Scott Boras have professed their openness to getting done. But one insider has a somewhat ominous inclination about what will need to happen.

On Thursday, Jon Heyman of the New York Post predicted that for Boston to re-sign Bregman, principal owner John Henry will need to demand that chief baseball officer Craig Breslow and the front office pay whatever it takes to keep the third baseman in house.

"Bregman surely won’t exercise his option to stay ($80M, two years) but he’s open to extension in Boston, which fits him. Talks haven’t begun yet but there’s pressure to lock up Bregman after trading Devers to make room for him at 3B," Heyman wrote.

"Unlike the Tigers, who offered Bregman $171.5M over six years, Boston wouldn’t go long in winter. To get this done, the guess here is owner John Henry might need to override his front office... The belief here is they’d have to offer the $184M Bregman countered to Detroit (or maybe even $200M) to get it done."

Bregman, 31, had a .938 OPS and 2.9 bWAR in the 51 games he played before his quad injury. The Chicago Cubs and Detroit Tigers could be all over him again if he makes it to the open market, and there's even been some suggestion that he could be traded by the end of the month if the Red Sox slide down the standings.

Frugality is an awful look for a big-market team, and it's a look the Red Sox have worn far too often in years past. If they can't get a Bregman extension done after freeing up over $250 million in the Devers trade, the fan base will never let them hear the end of it.