Not much reporting had come out about Alex Bregman in recent weeks. While other major Scott Boras clients Kyle Schwarber and Pete Alonso signed mega contracts during the Winter Meetings, the rumor mill stayed relatively quiet about the former Red Sox third baseman.
That was until Dec. 16, when baseball insider Bob Nightengale revealed that the Arizona Diamondbacks were checking in on Bregman. That came on the same day that Red Sox media personality Jared Carrabis, who is friends with the three-time All-Star, said he wasn't feeling great about a Bregman-Red Sox reunion. Carrabis even went as far as to comment on Nightengale's X post, saying the Diamondbacks are "more than kicking the tires" on signing Bregman.
As all of this was unfolding, MassLive's Chris Cotillo said Boston is more needy for a Bregman deal than before Alonso and Schwarber came off the board. He did add that neediness doesn't equate to any likelihood of a deal, though.
The Arizona Diamondbacks have become a surprise entrant in the Alex Bregman sweepstakes and are ‘kicking the tires’ on the possibility. The Dbacks would certainly have the financial flexibility if they move 2B Ketel Marte and could move 3B Jordan Lawlar to 2B
— Bob Nightengale (@BNightengale) December 16, 2025
This is now concerning for any Red Sox fan who had hoped for a reunion between Bregman and the Sox. Before all the reporting about the Diamondbacks, the only other teams connected to the 31-year-old were the Cubs and Tigers. Now, there seems to be added pressure to get a Bregman deal across the line. There has been no official reporting on contract numbers (as of writing this), though Carrabis' sentiment seems to point to an offer that Bregman's camp must like.
A Bregman-Diamondbacks link is also confusing. In recent weeks, the Red Sox had been rumored to be in trade talks with Arizona around Ketel Marte. MLB insider Ken Rosenthal reported that Ketel Marte would need to be traded before any deal with Bregman can be made. The Red Sox aren't the only team linked to Marte, though, as reports suggest the Rays, Mariners, and Blue Jays are among the teams interested in acquiring his services.
In 2010, the Red Sox signed a 31-year-old Adrian Beltre to a one-year pillow contract. The third baseman had one of the best seasons of his career, and instead of re-signing him, Boston allowed him to leave in free agency a year later. That sounds all too familiar to current events with Bregman. Same age, same position, and a pillow-type contract.
The Red Sox would end up regretting the move because Beltre finished a Hall-of-Fame career in Texas. Let's hope they don't make the same mistake twice.