The Red Sox are entering 2026 with a renewed sense of urgency - and a fair share of questions. After snapping a playoff drought that stretched back to 2021, there’s cautious optimism around this group. But with two cornerstone bats now gone and a retooled roster stepping into the spotlight, Boston’s path forward is anything but simple.
New Faces, New Direction
There’s no denying the talent infusion Boston brought in over the winter. Veteran arms like Ranger Suárez and Sonny Gray add depth and experience to the rotation, while Willson Contreras brings a steadying presence behind the plate.
And then there’s Roman Anthony, the rising outfield prospect who could be poised for a breakout year. If his development continues on track, he might just be the spark this lineup needs.
But talent alone won’t erase the turbulence that defined last season - particularly the saga surrounding Rafael Devers and Alex Bregman, two All-Stars who were supposed to anchor the Red Sox lineup for years to come.
The Devers Departure: A Rift That Couldn’t Be Mended
It’s still jarring to think about how quickly things unraveled. Just a year ago, Devers and Bregman looked like a formidable one-two punch in the heart of Boston’s order. Fast forward a few months, and both are gone - Devers traded midseason to San Francisco, and Bregman walking in free agency to the Cubs.
Team president and CEO Sam Kennedy didn’t shy away from the missteps when speaking to reporters in Fort Myers. Reflecting on the Devers situation, Kennedy admitted the team could have handled things differently.
“Would we have done things differently leading into it? Absolutely,” Kennedy said.
“You question yourself: Where did we make mistakes? What could we have done better?”
It’s clear that Devers’ frustration over the Bregman signing - which effectively bumped him off third base - created a rift. He initially agreed to shift to DH, but when Triston Casas went down with a season-ending injury, Devers declined to move to first. That refusal, coupled with a deteriorating relationship behind the scenes, led to the front office pulling the trigger on a trade that few saw coming.
“You can always do better in communication,” Kennedy added. “And that’s two ways. Two-way communication.”
Bregman’s One-and-Done in Boston
In theory, Bregman was supposed to be the long-term answer at third. He brought leadership, a steady glove, and his usual All-Star-level production. But his stint in Boston lasted just one season before he inked a five-year, $175 million deal with the Cubs.
Why didn’t the Red Sox lock him up? According to league sources, one sticking point was a full no-trade clause - something Bregman reportedly prioritized in free agency.
Kennedy was asked directly whether Boston has a policy against including those clauses in big contracts.
“If Alex Bregman wanted to be here,” Kennedy said, “ultimately he’d be here.”
Pressed further, Kennedy kept things vague: “It’s theoretical. It’s hard to know.
There’s many different parts of a contract negotiation. We did not come to an agreement.
So obviously he’s a Chicago Cub and wish him well until the end of the year.”
Commitment to Winning Still in Place
With Devers’ massive 10-year, $313.5 million deal off the books and Bregman gone, it’s fair to ask where the Red Sox go from here. But Kennedy was quick to push back on the idea that ownership has lost its competitive edge.
“There’s only one [criticism] that, for me, is hurtful, and that’s that we might not care or have the passion for winning,” he said. “That one, I just know it to be untrue.
That one gets frustrating. There’s one way to address that, however: Win.”
And while the roster has changed, the financial commitment hasn’t exactly disappeared. According to Spotrac, the Red Sox are projected to carry a luxury tax payroll of $256.1 million - the seventh-highest in baseball.
“You can go do the math and know where we are,” Kennedy said. “I think it just shows that John [Henry] and Linda [Henry] and Tom [Werner] and Mike Gordon in ownership are continuing to put the resources necessary into the Boston Red Sox to be successful. Now, we’ve got to go out and do it.”
Looking Ahead
The pieces are there. Maybe not the same ones that fans expected to see a year ago, but enough to stay competitive in a loaded American League.
The pitching staff has more bite. The farm system is producing.
And the front office, for all the turbulence, still believes in the direction they’re headed.
But make no mistake - the pressure is on. After a chaotic 2025 that saw two franchise players walk out the door, 2026 has to be a year of clarity.
A year where the Red Sox show they’re not just spending, but building something sustainable. The only way to silence the doubt?
Win.