What Sam Kennedy said about Bregman, Devers, and ‘hurtful’ narrative about Red Sox

Expectations are high for the 2026 Red Sox, with the team fresh off of making their first playoff appearance since 2021 last October.

Boston might be bolstered by continued development of Roman Anthony and offseason pickups like Ranger Suarez, Sonny Gray, and Willson Contreras. 

But, questions remain over the state of Boston’s lineup — especially just a year removed from the Red Sox boasting two impact bats in Rafael Devers and Alex Bregman in the heart of their order.

Things unraveled in just a few months, with Boston trading away Devers in June before Bregman — Devers’ replacement at third base — opted to sign with the Chicago Cubs in free agency last month.

Speaking to reporters at Fort Myers on Sunday, Red Sox team president and CEO Sam Kennedy acknowledged that the team could have handled things differently last season when it came to managing a disgruntled Devers before it led to a shocking midseason trade.

“Would we have done things differently leading into it? Absolutely,” Kennedy told reporters of the Devers’ saga. “You question yourself: Where did we make mistakes? What could we have done better? But at the end of the day, we were faced with a decision that was a hard one, and we made it and are really proud of everybody who worked together on that. Time will tell. We’ll see how the results are.”

Devers — initially irate over the Red Sox’s decision to sign Bregman and bump him off third base — eventually relented and moved to DH before refusing to shift over to first base following Triston Casas’ season-ending injury. 

By the time Boston shipped Devers to San Francisco, the slugger’s relationship with the Red Sox was seemingly fractured for good. 

“You can always do better in communication,” Kennedy said. “And that’s two ways. Two-way communication.”

Despite Devers’ exit, the Red Sox ideally had a solution at third base moving forward in Bregman, who earned another All-Star nod in Boston and quickly asserted himself as a veteran leader in the Red Sox’ clubhouse.

But, Bregman’s tenure in Boston only lasted for one season. He eventually signed a five-year, $175 million contract with the Cubs. 

League sources told Tim Healey of The Boston Globe that a full no-trade clause stood as a “major variable” for Bregman in terms of what he was seeking in free agency this offseason. 

As such, Kennedy was asked if the Red Sox have an organizational policy against handing out no-trade clauses on hefty contracts.

“If Alex Bregman wanted to be here,” Kennedy said, “ultimately he’d be here.”

“We try not to talk about organizational policies and the finer points of negotiations because it just doesn’t serve you well if you do that,” he added. 

Kennedy was then asked if Bregman had specifically requested a no-trade clause as part of any contract negotiations with Boston before ultimately signing with Chicago.

“It’s theoretical,” Kennedy replied. “It’s hard to know. 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.”

Despite losing Bregman in free agency and removing Devers’ 10-year, $313.5 million contract off their books, Kennedy pushed back against the assertion that Red Sox ownership has lost the desire to compete after winning four World Series titles since 2004.

“There’s only one that, for me, is hurtful, and that’s that we might not care or have the passion for winning,” Kennedy said. “That one, I just know it to be untrue. That one gets frustrating. There’s one way to address that, however: Win.”

According to Spotrac, the 2026 Red Sox are projected to have a luxury tax payroll of $256.1 million, the seventh-highest payroll in MLB. 

“You can go do the math and know where we are,” Kennedy said of Boston’s payroll commitments. “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.”

 

Conor Ryan is a staff writer covering the Bruins, Celtics, Patriots, and Red Sox for Boston.com, a role he has held since 2023.