Alex Bregman was everything the Boston Red Sox hoped he would be, yet signing him hasn’t gone according to plan whatsoever.

Bregman, the 31-year-old two-time World Series champion, has never missed the postseason in his eight full seasons. That could be on the verge of changing, though, as he’s on the injured list with a quad strain and the 30-34 Red Sox have gone 4-8 in his absence.

Bregman took a three-year, $120 million deal with the Red Sox over a longer, more lucrative deal with the Detroit Tigers partly because it would allow him to opt out and hit free agency again if the year went well. And assuming he comes back reasonably soon and continues his hitting from early in the season, he’ll be opting out indeed.

Because they could lose him for nothing in a few months time, Red Sox insider Sean McAdam of MassLive discussed the possibility that Boston could trade Bregman in a Friday column.

“If things continue to go sideways and the Red Sox think that Bregman is going to opt-out anyway, they could move him at the deadline and then try to re-sign him over the winter — albeit to a longer pact than last time,” McAdam wrote.

“Imagine the amount of interest at the deadline from the Chicago Cubs and Detroit Tigers — two teams that unsuccessfully pursued Bregman last offseason – since both are expected to be very much in playoff contention.”

But McAdam also provided some hope about the Red Sox looking to extend Bregman, though they’d have to pay a fortune to prevent him from allowing the other 29 teams to bid on his services.

“Given Bregman’s impact both on and off the field, it’s entirely feasible that the Sox could approach him in the coming weeks with a longer extension and remove the chance of moving him next month,” McAdam wrote.

“If not, Bregman’s trade value will by sky high if the Sox are forced to sell.”

Seeing Bregman walk out the door just five months into his tenure would be a gut punch. But those punches have become something of a daily routine for Red Sox fans in 2025.

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