Where MLB Insider Puts Alex Bregman Among Upcoming Top Free Agents

The Boston Red Sox once again made headlines over the weekend when they signed All-Star closer Aroldis Chapman to a $13.3 million contract extension for the 2026 season. The deal, which also includes a mutual option for 2027, was formally announced during a press conference Saturday.

Currently in the midst of a career year at age 37, extending Chapman instead of letting him hit free agency was an easy decision amid a season in which he’s produced 28 saves and 1.00 ERA across 59 appearances.

With Chapman back in the fold for next season, agreeing to terms with third baseman Alex Bregman on an updated contract extension is likely among Red Sox chief baseball officer Craig Breslow’s next orders of business. But with Bregman likely to opt out of the three-year $130 million deal he signed in February, retaining the three-time All-Star figures to be a more complicated process.

During a recent appearance on MLB Network, New York Post insider Jon Heyman named Bregman as the second most coveted free agent position player available this offseason after Kyle Tucker. While Heyman believes Bregman will have no shortage of potential suitors, he thinks his offensive numbers at Fenway Park will factor into a decision to remain with Boston.

“I think he fits Boston perfectly with that ballpark,” said Heyman. “A young team, and he’s a great leader. He makes incredible sense. I mean, obviously, he was out for a while with an injury, but he still has 16 home runs and an 848 OPS.”

There were a handful of teams interested in signing him last offseason before he reached an agreement with the Red Sox during spring training. Heyman believes two of those teams could once again be in the mix should he test the free agent market this winter.

“The teams that were interested in him previously were the Tigers and Cubs beyond the Red Sox,” said Heyman. “Now (Matt) Shaw is doing better at third base. I’m not sure about the Cubs, but the Tigers are certainly a team looking for a third baseman where he could be a fit. It does look like Boston is the best fit.”