Last offseason, the Boston Red Sox pulled off one of the biggest moves of the winter by signing Alex Bregman away from the Houston Astros.
To lure the two-time World Series champion to Fenway Park, Boston had to hand him a short-term contract loaded with an opt-out clause — a gamble that paid off for the infielder this year.
Bregman delivered in his lone season wearing a Red Sox uniform. He posted a strong .821 OPS, earned his third career All-Star nod, and ranked among Boston’s most reliable performers. True to form, he exercised that opt-out after the season, thrusting himself back into the open market at age 31 and in the prime of his career.
The expectation around the league is that Bregman is finally about to secure the massive, long-term contract that eluded him last winter.
Zach Mentz of Cleveland.com recently forecasted a six-year, $174 million pact for the star third baseman.
“Bregman hits free agency again after signing a shorter, opt-out contract with the Red Sox last winter,” Mentz wrote. “After posting an .821 OPS and earning his third career All-Star selection with Boston this season, Bregman is likely to finally cash in on a long-term deal. The Chicago Cubs and Detroit Tigers are rumored to be among interested suitors.”
Several big-market clubs are expected to drive the bidding.
The Chicago Cubs and Detroit Tigers, both of whom pursued Bregman a year ago, still have glaring needs at the hot corner and the financial flexibility to address them. The New York Mets, stung by a frustrating 2025 campaign, are under pressure to make a headline-grabbing addition that can push them back into postseason contention. Meanwhile, the Philadelphia Phillies could enter the mix if they lose pending free agents such as Kyle Schwarber or Ranger Suárez and need an impact bat to replace departing production.
Yet many insiders still view the Red Sox as the frontrunners. Boston knows exactly what Bregman brings to the lineup and the clubhouse, and ownership has shown a willingness to spend big to keep him in the fold for the remainder of his prime years.
With a weak crop of free-agent third basemen behind him, Bregman holds significant leverage. Whichever team wins this winter’s sweepstakes will not only fill a premium position but likely lock down a proven winner for the second half of his career.
