The Boston Red Sox are still spending like a big-market team. That much isn’t in question.
But around the league, the conversation isn’t about whether Boston is willing to write the checks-it’s about what happens after those checks are signed. The issue isn’t the wallet.
It’s the blueprint. Or, more accurately, the lack of one.
We’re now into February, and the picture is clear: two cornerstone players are gone, the roster feels thinner, and the frustration is no longer just coming from fans. It’s coming from inside the baseball world itself. Executives, insiders, and analysts are all asking the same question: What exactly is the Red Sox’s plan?
The tipping point came on February 3, when MLB analyst Alanna Rizzo didn’t hold back. Her comments echoed what voices like Jared Carrabis and Tony Massarotti have been saying for months.
“The Red Sox don’t have a money problem. They have a decision-making problem,” Rizzo said.
“Let’s wait around because we think people want to play for the Red Sox.” That quote hit hard, because it cuts to the heart of what’s gone wrong in Boston.
Let’s rewind to the start of this saga. In early 2025, the Red Sox made a splash by signing Alex Bregman, a move that should’ve been a defining moment.
Instead, it set off a chain reaction that unraveled their roster. The team immediately asked Rafael Devers-arguably the face of the franchise-to move off third base to make room for Bregman.
Devers pushed back, tensions escalated, and by June, he was shipped to the San Francisco Giants in a deal that looked, to many around the league, like a $250 million salary dump.
That trade alone raised eyebrows. But what happened next turned confusion into outright criticism.
Bregman, the player Boston had chosen over Devers, opted out of his deal just months later and signed a five-year, $175 million contract with the Chicago Cubs on January 10, 2026. On paper, the difference between Boston’s offer and Chicago’s wasn’t massive-same length, just a $10 million gap in total value. But the details told a different story.
Chicago’s offer was cleaner. No financial gymnastics.
Full no-trade clause. A structure that showed commitment and clarity.
Boston’s counter? It came with heavy deferrals and stuck to the team’s long-standing no-trade policy-even for a franchise-level player like Bregman.
That stance didn’t sit well. Not with Bregman.
Not with agents. And not with league insiders.
Carrabis called it a front office blunder. Massarotti questioned how a team could lose a clubhouse leader over a relatively slim financial margin.
And around the league, the consensus is growing: the Red Sox misread the room, overplayed their hand, and ended up empty.
This isn’t about one bad contract or a single offseason misstep. It’s about a pattern of decisions that seem disconnected from the realities of today’s game.
Boston still has the resources to compete with anyone. But if the decision-making doesn’t match the spending, the results won’t either.
Right now, the Red Sox aren’t losing because they can’t pay. They’re losing because they can’t seem to get out of their own way.