No one in the Greater Boston area is thrilled about losing Alex Bregman. Brought in as the apparent long-term successor to Rafael Devers—and ironically the player whose arrival kicked off the entire Devers drama in the first place—Bregman appeared in 114 games for the Red Sox, earned $40 million, and then hit free agency. The Cubs promptly handed him a $175 million contract, part of a six-year deal worth $215 million total.
Boston Red Sox end of season press conference.
You can’t fault Bregman for taking the money and running. After the messy departures of Mookie Betts and Rafael Devers, asking for a no-trade clause was entirely reasonable for a star of his caliber. The Red Sox refused to include one; the Cubs happily obliged. Bregman chose security and a bigger paycheck.
It’s an ugly conclusion to a poorly handled situation, but these things happen in sports. There’s little point in dwelling when viable third-base alternatives like Eugenio Suárez and Isaac Paredes remain available on the market.
Unfortunately, Red Sox president and CEO Sam Kennedy seems determined to keep the wound open.
According to The Athletic’s Jen McCaffrey, Kennedy is enthusiastically backing a proposal for a dedicated free-agent signing period—an idea MLB Commissioner Rob Manfred has floated ahead of the 2026 CBA negotiations. Kennedy claims it would “boost fan interest,” but it would also restrict players’ ability to let the market develop and maximize their earnings.
For the only team this offseason that has yet to sign a single major-league free agent to a guaranteed contract, it’s an awful look to be publicly campaigning for rules that would tilt the financial scales even further toward ownership.
Yes, Boston has added payroll through trades, acquiring Sonny Gray, Willson Contreras, and Johan Oviedo. But Gray and Contreras came with significant salaries attached from St. Louis, none of the three is under contract past 2027, and the Red Sox offset much of that spending by offloading more than $250 million in future obligations when they traded Devers to the Giants in June.
Like a hard salary cap, a free-agent signing deadline is almost certainly a non-starter for the MLBPA. The union might concede ground on other issues to avoid a prolonged lockout, but proposals this blatantly anti-player rarely make it into a ratified agreement.
Yet after getting outbid and outmaneuvered on Bregman, the Red Sox front office appears eager to change the rules anyway—a move that feels less like good faith negotiation and more like sour grapes, further eroding whatever trust remains between the organization and its frustrated fanbase.
