Boston – Like a bomb going off in the middle of the offseason — sources close to the matter say the Red Sox are planning to offer Bregman a contract worth around $300 million to stay with the team long-term. If realized, it would be one of the biggest contracts in MLB history for a key player.
Bregman, 31, only signed a three-year, $120 million contract with the Red Sox in early 2025, with the option to opt out each year.
But new information shows that the two sides are negotiating an extension — a longer term, higher value, possibly up to six years or more to create stability.
“Boston doesn’t want to have Bregman for a year or two and then lose him,” a source said. “They want him to be a mainstay for years to come.” With the amount of money being negotiated, it’s clear the Red Sox are betting big on their star player.
However, not everything is going smoothly. Bregman is said to be open to the free market if he can’t get a suitable contract.
A recent article even suggested that the Red Sox “already have a replacement in place” — Marcelo Mayer — in case he leaves.
On the other hand, the source said that to reach the “near $300 million” mark, Bregman’s performance, health, and leadership role will be scrutinized more than ever. He has been injured and has been infrequently available, which gives the team a lot of leverage in negotiations.
After a relatively quiet offseason, Boston clearly wants to send a message: they don’t just want to “get in,” they want to “fight” at the top. The move to a “big” contract for a key player reflects a desire to build a long-term competitive roster.
Bregman—a two-time All-Star, with World Series experience and the ability to play multiple positions—is a big unknown: if he stays healthy and consistent, he could be the key. But if he doesn’t—the investment becomes a liability.
What makes this news even more shocking is the “$300 million” figure—a rare figure for a position like third base, not to mention Bregman’s age, 31. If true, the contract could be for five or six years at an average of about $50 million per year—far above current contracts for similar positions.
“They want this to be a statement: ‘Boston is back,’” a source said. But there’s also a caveat: “If it fails—it’s not just money lost, it’s the entire payroll structure and roster.”
This isn’t just about Boston and Bregman — it’s about MLB as a whole: When a team is willing to spend hundreds of millions on a position, is the risk too great? Can long-term stability be bought with money?
If the deal is signed, it will be a “seismic” move in the free agent market next season and could change the spending norm. If not — Boston will have to pivot quickly, find cheaper, more flexible options.
Boston is preparing to make a big bet on Alex Bregman — $300 million, multiple years, a pivotal role. But the investment also puts the team in a “no win, no lose” position with fans. All eyes now turn to Bregman — will he sign or will he go? And what will Boston do if he waits too long?
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