The first opt out in Alex Bregman's three-year, $120 million contract with the Boston Red Sox fast approaches, and despite saying he would be open to negotiating a contract extension with the team, there are growing suspicions that he'll take to the open market this offseason.
The Red Sox are paying Bregman quite handsomely on his current deal, which has $40 million average annual value, and he may be hard-pressed to find such a deal elsewhere, especially since he spent two months on the injured list this year. But plenty of big-market teams will be in the market for third basemen this winter. In his August 15 piece for The Athletic, MLB insider Jim Bowden named Bregman the third-most desirable free agent in this year's class, and tabbed the Phillies, Yankees, Tigers, Dodgers, Mariners and Mets as potential suitors (subscription required).
Bregman going to the Yankees or Dodgers would be a particularly crushing blow for the Red Sox. LA has become something of an easy second home for recent former Red Sox players, and it seems to be capable of fleecing Boston in trades and somehow, free agency, at every opportunity. And the Yankees are, well, the Yankees.
It took the Red Sox until players reported to Fort Myers for spring training to sign Bregman in 2025, and their only real competition was the Tigers, who offered a significantly lower AAV. If Boston tries to be stingy with Bregman — which it has been known to do with elite free agents in the last half-decade or so — the Phillies, Yankees, Dodgers or Mets could be ready with an offer he can't refuse.
MLB insider Jim Bowden names Yankees, Dodgers among best fits for Red Sox's Alex Bregman if he opts out
Unfortunately, the Red Sox axed all their leverage in potential Bregman contract negotiations in June when they traded Rafael Devers to the Giants. Boston doesn't have a third baseman to fall back on if Bregman walks, and he knows exactly how much loose change the front office has after San Francisco ate the entirety of Devers' $250 million contract.
Bregman's openness to sign an extension with the Red Sox could mean he'll want to stick around without testing the water. He's embraced the city with Wally the Green Monster gear, a recent partnership with Sam Adams, and he's said he and his family love Boston on a few occasions. But the Red Sox and their fans would be wrong to bank on such a move.
The Red Sox absolutely must extend Bregman since he's such a good fit for Fenway Park, they have no other options at third base and the team has fully embraced him as the leader. If he signs elsewhere in free agency, especially with the Yankees or Dodgers, it'd be a gut punch that would take Boston a few seasons to recover from.