The Boston Red Sox are still spending like a big-market team - but the results suggest they’re not operating like one. Around the league, there’s no doubt about Boston’s financial muscle.
The real concern? What they’re doing with it.
As we settle into February, the picture is becoming clearer - and it’s not pretty. Two cornerstone players are gone.
The roster looks thinner. And the criticism isn’t about payroll size - it’s about front office choices that have left fans and analysts scratching their heads.
The frustration boiled over on February 3, when MLB analyst Alanna Rizzo voiced what many around the game have been thinking for months: the Red Sox don’t have a money problem - they have a decision-making problem. “Let’s wait around because we think people want to play for the Red Sox,” Rizzo said, calling out a strategy that feels more reactive than proactive. Her comments echoed what insiders like Jared Carrabis and Tony Massarotti have been saying for some time - that Boston’s front office has misread the market and mismanaged its own assets.
At the heart of the criticism is the Bregman-Devers situation, which has now come to define the team’s recent missteps. The Red Sox made a splash in early 2025 by signing Alex Bregman, one of the premier third basemen in the league.
But the move immediately created friction. Rafael Devers - the face of the franchise and a fan favorite - was asked to move off third base.
He resisted. Tensions escalated.
And by June, Devers was dealt to the San Francisco Giants in what many around the league viewed as a salary dump of over $250 million.
That trade alone would’ve raised eyebrows. But the real gut punch came in November, when Bregman opted out of his deal.
Just two months later, he signed a five-year, $175 million contract with the Chicago Cubs. The difference in offers?
Not much on the surface - same five-year term, just $10 million more in total value. But the structure of the deal told a different story.
Chicago didn’t just offer more money. They offered clarity.
A full no-trade clause. A cleaner contract with fewer deferrals and less financial maneuvering.
Boston, on the other hand, stuck to its usual playbook - heavy deferrals and a firm no-trade stance, even for a franchise-caliber player. It was a gamble, and it backfired.
Bregman walked.
Insiders didn’t hold back. Carrabis called the situation a front-office failure.
Massarotti questioned how the Red Sox could let a clubhouse leader slip away over what amounted to a marginal financial difference. The consensus?
Boston overplayed its hand - and lost both of them.
This isn’t about one bad contract or one tough negotiation. It’s about a pattern that’s starting to define the Red Sox in the post-Devers era.
They’re still spending like a contender, but the decisions behind the spending are raising real questions. The Bregman-Devers saga didn’t just cost Boston two elite players - it exposed a deeper issue with the team’s roster-building philosophy.
For a franchise with the resources to compete with anyone, the margin for error should be higher. But in this case, the Red Sox created their own mess - and now they’re left cleaning it up without the star power they once had.