Red Sox insider's plan for Alex Bregman contract extension just might work

The Alex Bregman question is one burning a hole in Boston Red Sox fans’ heads. Through almost the entirety of the 2025 season Bregman’s astounding play on the field and presence in the clubhouse has been transformative, but clouded by one big question: What happens when he opts out?

Bregman came to Boston over other suitors like Detroit because it “felt like it was a place I could prove the caliber a player that I believe I am.”  In doing so, he took less money and a shorter timeline but gained opt outs after each season in Fenway. An all-star selection in 2025 (his first since 2019) and slashing .279/.361/.474 and owning an OPS+ of 129, he’s firmly lived up to the hype surrounding his signing, even with a two month mid-season absence.

Worry over Bregman walking this winter is a constant point of emotional turmoil for fans, but Red Sox insider Peter Abraham has floated a possible extension solution that could keep him wearing those green and highlighter yellow City Connect uniforms long into the future. Abraham suggests a big signing bonus ahead of 2026’s CBA negotiations, and keeping the $40 million owed to him for each of the next two seasons in his current arrangement intact. Then, adding two additional years at $35 million apiece. That would be a new, $150 million, four-year deal at minimum, with an AAV of $37.5 million. Can it work: Sure! Here’s why.

The Boston Globe's format for a potential Red Sox/Alex Bregman contract extension just might work

Virtually all voices agree, Bregman isn’t going to remain a member of the Boston Red Sox in 2026 unless he gets a new contract. Marcelo Mayer delivered quality coverage at the hot corner while Bregman recovered on the IL, but his plate presence wasn’t nearly as dynamic as his flow while fielding balls. Mayer has also unfortunately shown an injury bug throughout his time as a pro, and that came back into the picture to close out 2025. Mayer could be a stopgap solution while Trevor Story delivers leadership and game-time grit through his two (or three, depending on moves this offseason) remaining contract years at short. But that’s not a particularly confidence-inducing replacement for Bregman’s magnetic company.

Numerous organizations around the league will be looking for a stud to fill their third base vacancy. This will make the market harder to navigate and compound the importance of resigning Bregman, no matter the cost. Boston.com’s Chad Finn wrote in July that “He’s exactly what the Red Sox need now,” guiding the early-career trajectory of superstars-in-the-making Roman Anthony and Mayer. “He was born to play in Boston,” Finn concludes.

The thing about ball players is that they make decisions for a complex host of reasons. Bregman is a two-time World Series winner. He earned his first Gold Glove last season, and was a Silver Slugger in 2019. His 43 bWAR through 10 seasons is approaching Hall of Fame territory. Bregman isn’t a player that looks to peter out now that he’s crossed the 30 threshold, but his time in the game is absolutely a diminishing asset. Bregman wants to get paid, but the way he approaches the game and his talk suggest that he’s looking for a winning culture to call home, and one that might add another title to his resume. It’s well documented that both the player and his family have loved Boston, and a partnership with Sam Adams helps sell that reality further.

Bregman turned down additional guaranteed money last winter, and with plenty of possible suitors knocking on his door, the decision to play for a team poised to remain a contender and siding with a bigger payday might just tip in the same direction. Detroit will likely be interested again, but the team’s pitching has been too spotty and with Javier Baez lingering around third base (and elsewhere) while costing Detroit valuable cash, that fit might be less ideal for the Tigers than it seems.

Abraham also highlights the Mets, Phillies, Yankees, and Rangers as teams in serious need of a third base upgrade, but each one has other serious roster concerns. More importantly, he’s already the highest paid third baseman in baseball this year (and T-4th among all players with Aaron Judge), so negotiations will certainly revolve around time rather than dollars.

As a leader among an exciting young bunch of players who are largely contracted for lengthy tenures already, Bregman fits ideally in Boston for many reasons, and it seems that he knows it. If the Sox make a deep playoff run this year, Bregman will almost certainly be amped to stick with the core developing around him. Even if Boston doesn’t live up to these goals, it’s still a place he can round out a Hall of Fame career calling home. In New York, Philly, or elsewhere, he’d become a cog in a machine rather than the shimmering face of success while getting paid enormous money either way.