The Red Sox front office stepped in front of the mics at Spring Training this week, and while the sun was shining in Fort Myers, the tone around a few offseason storylines was anything but warm.
Team president/CEO Sam Kennedy and chairman Tom Werner addressed several key topics, but the spotlight naturally fell on two high-profile departures that continue to stir conversation in Boston: Alex Bregman’s exit to Chicago and the Rafael Devers trade that shook the fanbase last summer.
Bregman to the Cubs: A Deal That Didn’t Get Done
Alex Bregman’s decision to sign a five-year, $175 million deal with the Cubs left many Red Sox fans scratching their heads. Boston reportedly made a competitive offer-five years, $165 million-with both deals heavy on deferred money. But the sticking point, it seems, wasn’t just dollars and cents.
Reports suggested Bregman wanted a full no-trade clause, something Chicago was willing to include. Boston, on the other hand, reportedly wasn’t.
That raised speculation about an internal policy against such clauses-something Werner flatly denied, saying, “We don’t” have a policy against no-trade protection. Kennedy was more cautious, avoiding a direct answer but adding, “If Alex Bregman wanted to be here, ultimately he’d be here.”
It’s a revealing comment. The implication is that Boston believed it made a fair offer, and if Bregman truly wanted to stay, he would have.
Werner added that geography may have played a role, noting Bregman’s preference to be in Arizona for Spring Training, closer to his family. “I have enormous respect for Alex,” Werner said.
“But it wasn’t meant to be and we moved on.”
That may be true from a front office perspective, but for fans, it’s not so easy to move on from a player who brought leadership and production to a team that clawed its way back into the postseason. Before a quad injury slowed him down, Bregman was a stabilizing force at third base and in the clubhouse. His exit leaves a void-and questions.
The Devers Fallout: Regret and Frustration
The Bregman signing last offseason had ripple effects, none larger than what it meant for Rafael Devers. Once the face of the franchise, Devers was nudged out of his third base role, shifted to DH, and then asked to learn first base after Tristan Casas went down with a season-ending knee injury.
That didn’t sit well with Devers, and the tension eventually led to his trade to the Giants last June. Kennedy admitted the situation could’ve been handled better.
“Would we have done things differently leading into it? Absolutely,” he said, pointing to a breakdown in communication.
Werner’s comments, however, were more pointed-and likely to reignite debate. While he called Devers “a wonderful person,” he didn’t hide his disappointment.
“It was a discouraging episode,” he said. “Just pick up a glove.”
That blunt assessment underscores how strained the relationship had become. Devers’ reluctance to switch positions was clearly a breaking point for the front office. Whether it was a matter of pride, discomfort with the switch, or a deeper frustration with how things were handled, the end result was a trade that still stings for many in Boston.
A New-Look Roster and Renewed Optimism
Despite the drama, the Red Sox brass is focused on what’s ahead-and they believe this roster is built to compete. Boston was active on the trade front this winter, bringing in Willson Contreras, Sonny Gray, Johan Oviedo, and Caleb Durbin. The biggest splash came in free agency, with the signing of lefty Ranger Suárez to a five-year, $130 million deal.
Kennedy called it “a successful offseason… long, arduous, lots of scenario planning, but excited that we improved the club in many ways.” Werner echoed that optimism, highlighting defensive upgrades and a pitching staff he believes “is elite.”
And they’re not done yet. Werner made it clear the team has financial flexibility to make in-season moves, saying, “We actually have the powder to execute some more moves during the season.”
The Financial Picture
After finishing the 2025 season with a payroll around $208.9 million and a luxury tax figure of $246.5 million, the Red Sox are currently projected for a slightly lower payroll ($195.5 million) but a higher tax number ($263.7 million). That puts them just under the second tier of the luxury tax threshold ($264 million), setting up a scenario where Boston could dip into that next tier if the team is in contention and looking to add at the deadline.
It would mark the first time since 2019 the Red Sox hit that level of tax penalization, a sign that ownership is willing to spend-at least when the roster looks ready to make a run.
Final Word
So where does that leave the Red Sox heading into 2026? They’ve lost two cornerstone players in Bregman and Devers within a year, and while the reasons behind those exits are complex, the front office is standing by its decisions. The focus now shifts to a revamped roster that’s got talent, depth, and a pitching staff with serious upside.
But in Boston, results are the only currency that matters. The moves made this winter-and the ones that weren’t-will be judged by what happens between the lines. And for a fanbase still processing the loss of two big names, winning might be the only thing that quiets the noise.