Inside The Red Sox's Credibility Crisis
The franchise is defined by mixed signals, shifting priorities — and what some inside call “toxic positivity.”
On Saturday, the Boston Red Sox fired manager Alex Cora.
Shortly after the news broke, the team released a statement from owner John Henry.
“Alex Cora led this organization to one of the greatest seasons in Red Sox history in 2018, and for that, and the many years that followed, he will always have our deepest gratitude,” Henry said. “He has had a lasting impact on this team and on this city. He has led on and off the field in so many important ways. These decisions are never easy, but this one is especially difficult given what Alex has meant to the Red Sox since the day he arrived.”
Henry has spoken publicly about this franchise only rarely since February 17, 2020, when he last addressed the media in a press conference following the trade of Mookie Betts. Cora’s firing was framed as accountability – a team underperforming, a decision made. But inside and around the organization, it landed as something more complicated: a clear action taken within a structure that has in the last decade struggled to define who, exactly, is responsible for the direction of the team.
In an organization where authority has become diffuse, accountability does not disappear. It concentrates. And as April 2026 came to a close, that accountability landed on Cora.
But the firing did not happen in isolation. It was the latest turn in a year of rapid, disorientating change — one that has left the organization looking fundamentally different from the version of itself it presented as recently as the end of the 2025 season.
A year ago, the team was selling something close to stability. They had a manager widely respected inside the clubhouse. A veteran core anchored by sluggers Rafael Devers and Alex Bregman. A front office speaking confidently about a window of contention. A fan base that, while frustrated, could still see a path forward.
Much of that stability is now gone.
Last summer, the Red Sox traded star third baseman Rafael Devers in a cost-cutting move that saved Boston roughly $254 million but returned no cornerstone pieces, with Jose Bello the only part of the return still in the organization. At the 2025 trade deadline, after weeks of leaks and public signals suggesting action was coming, the team stood pat. Their season ended in a wild-card loss to the Yankees. In the aftermath, chief baseball officer Craig Breslow insisted the Red Sox were in their “contention window,” later promising an offseason that would be “aggressive and decisive.”
That’s not how the winter played out. Despite finally promoting their long-awaited homegrown core — Roman Anthony, Marcelo Mayer and Kristian Campbell — in the lead-up to the 2026 season, the Red Sox again stopped short of exercising their big-market financial advantages. They were loosely connected to nearly every major free agent but rarely were the team setting the market. They passed on the top hitter available. They allowed Bregman — the symbol of their supposed pivot — to walk.
The roster has been reshaped around a younger core that has struggled to produce in the early part of the 2026 season. Twenty-seven games into the 2026 season, the Red Sox sit at 10-17, last in the American League East. The firing of Cora, hitting coach Peter Fatse, third base coach Kyle Hudson and bench coach Ramón Vazquez was the kind of decisive action the organization had long promised its fans, and rarely delivered. Whether it addresses what ails the Red Sox is a different question entirely — and the answer requires understanding how the organization arrived here.
Around the league, several general managers describe the Red Sox as a franchise embroiled in an identity crisis. They carry the expectations of a big-market team — ticket prices, media scrutiny, historical weight — while behaving like a risk-averse small-market team. The result is a club that neither maximizes its financial advantages nor fully commits to restraint, judging by the $130 million invested in pitcher Ranger Suarez and the total of $7 million spent on free-agent additions Isiah Kiner-Falefa and Danny Coulombe. Spending is reserved for moments when projections suggest overwhelming odds, not merely a competitive window. And as long as Fenway fills, jerseys sell and hope flickers each spring, the model holds. Winning the World Series becomes a nice surprise rather than the goal.
For years now, Red Sox leadership has asked fans to be patient. To trust the plan. To believe better days are coming … just not quite yet.
The problem now is not patience. It’s credibility.
“There’s been a growing sense of frustration,” Kennedy told me in an interview before 2026 Opening Day. “Understandably.”
But to understand how the Red Sox arrived here, you have to go back even further. The decisions that produced this moment were made years ago, long before a single game was played in 2026.
Fans are no longer sure what kind of team they’re supposed to be watching. The messaging no longer matches the behavior. And the question — from fans, from agents, from people inside the organization — is no longer just what’s the plan?
It’s why should anyone still believe in it?
It was supposed to be a turning point.
In February 2025, after the Red Sox signed Alex Bregman to a three-year, $120 million contract, Linda Pizzuti Henry posted a photo of her husband, Red Sox principal owner John Henry, smoking a cigar. It was the image of a triumphant Henry, satisfied after years of fan unrest and cautious spending that the Red Sox had finally made a splash, capping off an impressive offseason in which the team also added ace Garrett Crochet via trade with the Chicago White Sox. Team officials talked about entering a window of contention. The front office started using words like “aggressive” again. The message was clear: Boston was back.
One year later, that image — and the team itself — looks quite different.
Bregman is no longer a member of the Red Sox, having opted out of his contract after the 2025 season and signed with the Chicago Cubs for five years and $175 million. And while the front office successfully fortified the rotation with veteran stability in Sonny Gray and Ranger Suarez, and replaced Bregman with Rookie-of-the-Year finalist Caleb Durbin, the moves this winter failed to satisfy much of the Red Sox fan base, which expected more money to be spent on a team that made the playoffs. As of Opening Day, the Red Sox ranked 12th in payroll in Major League Baseball, behind teams like the Houston Astros, San Diego Padres and Detroit Tigers.
Bregman loved playing for the Red Sox. He loved the history, the high expectations and playing for the same franchise as his childhood hero, Dustin Pedroia. He still cherishes his relationship with Red Sox manager Alex Cora, who served as a mentor for him during his early days with the Houston Astros. By the end of his only season in Boston, Bregman had unofficially become the team captain, an extra coach and a mentor to young stars such as Roman Anthony. Bregman made it no secret that he wanted to play for the Red Sox for the rest of his career.
“I expected to love playing here, and I have definitely loved playing here,” Bregman told MassLive in June. “It’s a great place to play baseball. Being able to play for this organization is awesome.”
Bregman’s fondness for the Red Sox shaped how the organization handled negotiations. According to sources familiar with the talks, Bregman pushed late in the regular season for an extension, signaling both openness and urgency. The Red Sox didn’t try to close. When the offseason began, they made an offer that Bregman’s agent Scott Boras indicated fell short of the market and he held his ground. When Bregman’s camp said there was interest elsewhere, team officials dismissed it as a negotiating tactic. It wasn’t until Bregman made clear that he was prepared to sign with another club that Boston moved, countering with five years and $165 million, heavily deferred and refusing a no-trade clause.
To Bregman, the issue was never just the money. It was trust. The Red Sox have shown a willingness to trade any player, regardless of stature, and their unwillingness to offer a no-trade clause reinforced the idea that commitment flowed only one way. What the organization framed as discipline — holding firm on the team’s boundaries for player contracts — Bregman experienced as indifference. A take-it-or-leave-it posture toward a player asking not for special treatment but for certainty. According to a source close to Bregman, the Red Sox’s decision to trade Devers fueled his insistence on a no-trade clause, which the Cubs ultimately offered.
When team president Sam Kennedy was asked about the team’s refusal to grant Bregman a no-trade clause, rather than defending a specific organizational boundary, he deflected the blame onto the player. “If Alex Bregman wanted to be here, ultimately, he’d be here,” Kennedy said.
Handling superstars has always been one of the clearest tests of big-market conviction, and in the early Henry days, the Red Sox passed it. Manny Ramirez tested the organization’s authority constantly, pulling himself from lineups, claiming injuries that mysteriously healed, confronting management and even once shoving team traveling secretary Jack McCormick during a fight over tickets. Yet Ramirez was treated as an asset to be managed, not a problem to be avoided. David Ortiz, too, had space to challenge the organization in the press and the clubhouse. The Red Sox may not have been appeasing their stars, but they had a relationship with them.
Boston’s most recent superstar stress test arrived with Rafael Devers. It began quietly. Early in 2025, the Red Sox privately assured Devers that he would remain the club’s third baseman, then signed Bregman weeks later. Publicly, leadership insisted there was no conflict, framing Bregman as a second baseman.
Inside the clubhouse, the burden shifted. Devers, after being told his job was secure, was soon portrayed implicitly and explicitly as unwilling to “take one for the team.”
In March, Breslow and Cora met with Devers in hopes of resetting the relationship. They asked him to make way for Bregman at third base and become designated hitter. Devers initially declined but agreed to become DH.
When first baseman Triston Casas suffered a season-ending injury in early May, the Red Sox asked Devers to cover first, which he had never played before. He declined. The sequence strained trust on both sides. Devers didn’t demand a trade, but he signaled his openness to one. Not long after, he was sent to San Francisco for Kyle Harrison, Jordan Hicks, Jose Bello and James Tibbs III, three of whom are no longer in the Red Sox organization.
The Red Sox lost a generational star in Devers. But what mattered more was what the Devers trade revealed: an organization unable to articulate a coherent plan, internally or externally. With no single voice owning the decision, confusion spread beyond the clubhouse to agents, rival executives and the fan base. And that lack of clarity didn’t disappear when Devers was shipped to San Francisco.
The lack of a coherent plan created a vacuum in messaging to the fan base, where uncertainty had to be explained somehow. And because Red Sox ownership no longer speaks regularly to the public, they attempted to fix their messaging through leaks to the media.
John Henry used to talk. Maybe not often, and rarely with warmth, but when the Red Sox made a big decision — or landed in a big mess — the team’s principal owner would step forward and explain it.
That began to change in 2016. At spring training that year, after the club’s third last-place finish in four seasons, Henry stood in front of a small group of reporters and did something uncharacteristic: he admitted fault.
“We have perhaps overly relied on numbers,” he said. “Too much a reliance on past performance and trying to project future performance.”
In any context, that comment would have made headlines. Coming from one of sabermetrics’ earliest champions, it stunned people inside the organization. Those in baseball operations recall the moment as jarring — not because the criticism was unwarranted but because it was public.
When the news conference ended, Henry returned to the team’s executive suite in Fort Myers, Florida. “I put my foot in my mouth again,” he told a room of executives, according to a source who was present. “I need to stop doing press conferences.”
It wasn’t a joke. People inside the organization point to that day as the moment Henry began to retreat from taking accountability in public. Over the next several years, Henry’s visibility steadily diminished. News conferences became rare. Public statements were tightly managed. And when Henry did speak, the posture had shifted. This was no longer the owner who once walked unannounced into the Felger and Massarotti radio studio to confront criticism head-on. Instead, the team largely stopped explaining its decisions.
Leaks from the front office increasingly replaced Henry’s lack of public communication. The pattern eroded trust among team employees. Rumors and secondhand explanations took over accountability for decisions, according to three sources who spoke on the matter.
Many inside the organization point to the handling of Mookie Betts as a key example. After the 2018 championship, the Red Sox faced a familiar big-market dilemma: whether to retain a generational, homegrown star after an aggressive spending cycle. Internally, then-president of baseball operations Dave Dombrowski was unequivocal about keeping Betts. According to multiple people with direct knowledge of the conversations, Dombrowski believed Betts needed to be signed to a long-term deal at market value. It’s the cost of doing business in Boston.
Henry disagreed. Having recently committed significant money to core members of the title team, including Chris Sale and Nathan Eovaldi, he increasingly viewed long-term contracts as liabilities rather than investments. That philosophical divide marked the beginning of the end of Dombrowski’s tenure and reshaped how the organization spoke about its choices.
As internal resistance to a Betts extension grew, a different story began to circulate publicly: Betts didn’t want to be in Boston. The narrative first surfaced in off-the-record conversations — that Betts preferred to play closer to his hometown of Nashville or wasn’t fully committed to the market. Betts and his inner circle were confused by this narrative. He was direct with those around the team: he wanted to stay in the only place he had known in the majors, and he wanted to be paid at market value. There was no request for special treatment or lifestyle concessions, only a refusal to accept a hometown discount.
The distinction mattered. But with ownership unwilling to say “this is the price we won’t pay,” the implication lingered that Betts’ expectations were unreasonable, even emotional. By the time he was traded to the Los Angeles Dodgers, the ground had softened. The decision landed to many fans not as a clear-eyed choice but as the collapse of the relationship between the Red Sox and Betts. According to people inside the organization, the lesson was simple. When leadership won’t own its self-imposed limits, they buy time, diffuse blame and reframe decisions to deflect responsibility.
What began with Betts became a pattern. When decisions were difficult, communication became indirect. When the choice to prioritize financial flexibility over franchise stars proved unpopular to many fans, ambiguity shielded the front office from public backlash. Responsibility diffused outward through selective leaks rather than clear declarations of intent. This insulated ownership while forcing baseball operations, players or circumstance to absorb the blame. By the time Devers became the next star to test the system, the infrastructure was already in place. It emerged not in one moment but in a series of smaller contradictions — in public messaging, in leaks and in how the organization explained itself.
In December 2023, chairman Tom Werner declared the team would go “full-throttle” in free agency. Just weeks later, Kennedy walked that back, saying payroll would “probably be lower” than the year before. Last summer, there were repeated leaks suggesting the Red Sox were “close” on a trade for Minnesota Twins starter Joe Ryan. But Twins front-office sources say the teams were never close. Some describe this type of leaking as a form of triage, less about closing deals than slowing panic and buying time. It’s like patching leaks during a rising flood, doing just enough to keep the water from spilling over, even as pressure continues to build.
As Henry retreated from the public, someone had to speak for the organization. In the 2016 season, Sam Kennedy emerged as the Red Sox’s primary public voice, not because he controlled baseball decisions but because he was trusted to lower the temperature around them.
Promoted to team president that year, Kennedy became the organization’s highest-ranking public-facing figure, polished, accessible and relentlessly optimistic. Inside the offices of Fenway Park, he is widely respected as a capable business and political operator — someone comfortable in front of microphones, trusted by ownership and adept at managing relationships with sponsors, politicians and local power brokers. But Kennedy’s role cannot be understood without understanding what happened to the organization’s incentives.
In 2012, the Dodgers were purchased by a group that included private equity executive Mark Walter of Guggenheim Partners. What followed was a sustained commitment to winning — record payrolls, aggressive acquisition, a farm system developed alongside spending rather than instead of it. The Dodgers have been to the World Series five times since. They won it in 2020, 2024 and 2025.
When the Red Sox fired Dombrowski in 2019, I was reporting on the team for ESPN. Sources in the front office explicitly said they wanted to recreate the Dodgers model in Boston. The implication was clear: a data-driven, well-funded franchise that had figured out how to marry analytics with sustained financial commitment. The Red Sox wanted to be that.
What they became was something different.
After the 2019 rule change allowing private equity investment in MLB franchises, Fenway Sports Group sold minority stakes to Arctos Sports Partners and RedBird Capital. Neither firm took operational control. But control was never the point. When outside investors enter an organization, the questions that get asked start to change. Not always visibly. Not always immediately. But the metrics that matter — valuation growth, margin stability, risk management — begin to compete with the metrics that fans care about.
The Dodgers, backed by Guggenheim, took a longer view. Championship investment as brand building. It’s why they’ve spent so much money on players like two-way superstar Shohei Ohtani, outfielder Kyle Tucker and World Series MVP Yoshinobu Yamamoto. Sustained payroll as asset appreciation strategy. Winning as the mechanism for franchise value growth.
The Red Sox took a different lesson from the same moment. Flexibility over commitment. Risk management over star retention. The worst outcome not a lost championship, but a bad contract on the books.
That philosophy didn’t announce itself. It arrived gradually, embedded in the logic of individual decisions that each seemed defensible in isolation. It looked like Dave Dombrowski being fired after winning a championship. It looked like Mookie Betts being traded — and a quiet narrative circulating that he hadn’t really wanted to stay. It looked like Rafael Devers being promised security and then pressured into a corner. It looked like Alex Bregman being told, in effect, that the organization’s financial models mattered more than his desire to stay.
What changed wasn’t the team’s ambition. It was what the organization was willing to risk to fulfill it. I went deep on this topic recently in a video with More Perfect Union.
When I asked Kennedy if private equity had any influence on the team, he said, “Zero impact on operations. Zero.”
Kennedy is not — and has never claimed to be — a baseball executive. He did not come up through scouting, player development or roster construction; he began his career on the sales side as an account executive and worked his way up. He rose through the organization's business side — from vice president of sales and corporate partnerships to chief marketing officer to chief operating officer — building Fenway Sports Management along the way into a global sports marketing agency. His ascent was entirely commercial. He has never worked in scouting, player development or baseball operations.
Inside the organization, there has long been recognition that Kennedy lacks a deep understanding of baseball operations. His approach has occasionally raised eyebrows, surprising some with his questions about on-field strategy or moments of celebration in the executive suite that seem disconnected from what’s happening on the field.
He has filled that knowledge gap with his trademark optimism. In news conferences and private meetings alike, he emphasizes belief, patience and progress. He is affable, durable under criticism and rarely defensive.
And unlike his predecessor, Larry Lucchino, he has largely stayed out of baseball operations altogether. Lucchino was famously opinionated, but his confidence was rooted in fluency. He would relay what his plumber said about team construction to former general manager Theo Epstein — not because the plumber’s opinion mattered, but because Lucchino understood the fan’s emotional relationship to roster decisions well enough to translate it into baseball terms. And he understood what a team like the Red Sox is in Boston: a public trust with a private balance sheet. When the Red Sox zigged, he could tell the city why — and own it.
Kennedy, when presented with those characterizations, acknowledged the distinction. “I’ve never been a general manager,” he said. “That’s not my role.”
But several current and former employees describe it as a form of “toxic positivity,” a refusal to publicly acknowledge budget constraints, internal friction or structural confusion. One former staffer likened it to “being told the building isn’t on fire while you’re standing in the smoke.”
When presented with that characterization, Kennedy did not dispute it. “If the accusation is that I’m a positive, or even overly positive, person, guilty as charged,” he said. “I’ll take that as a compliment. It’s been said that people are not inclined to follow pessimism, so I do try to lead with a positive approach and attitude.”
To that end, Kennedy often sets expectations while lacking control over whether they can be met. He speaks confidently about windows, aggressiveness and alignment without owning the constraints imposed by Henry. When those expectations collapse, the responsibility doesn’t land on ownership. It lands on baseball operations.
Kennedy pushed back on that dynamic: “I personally, I specifically deserve criticism. The job of a CEO is not a popularity contest.”
That dynamic has defined chief baseball officer Craig Breslow’s tenure.
Kennedy played a central role in hiring both former chief baseball officer Chaim Bloom and Breslow, emphasizing communication and shared vision in both cases. But Breslow’s early tenure was marked by breakdowns, most visibly in the handling of Devers. Since that trade, multiple people inside the organization say Breslow has become more direct internally and more transparent publicly. But those changes have also exposed the bind within which he operates. Kennedy’s relentless optimism sets expectations that Breslow often cannot meet due to the budgetary and structural constraints he has been given.
Several executives and agents describe Breslow as tethered to the organization’s internal models and, at times, inflexible. In their view, the Red Sox don’t just negotiate cautiously; they negotiate as if deviating from projections is a failure, even when the moment calls for risk. Rival evaluators say the club behaves like an organization waiting for the data to remove all doubt — and in a sport built on varying degrees of uncertainty, that moment never comes.
This reputation is registering with players as well. A veteran member of the 2025 team described the club’s approach as “arrogant,” arguing that the front office’s model-driven posture turns information into ironclad dogma. The handling of Bregman was a failure not just to read the market but also an ideological one, with the organization treating free agency like a transaction to be optimized, rather than a relationship to be managed. “It’s ‘Moneyball’ computer beep-boop nonsense,” the veteran player said.
Inside the Red Sox, several people point to a larger structural issue. The team is run very differently than Fenway Sports Group’s other flagship property, Liverpool. There, longtime executive Michael Gordon serves as a true bridge between ownership and sporting operations, enforcing budget discipline while empowering soccer leadership to act decisively. In Boston, no such intermediary exists. Major baseball decisions routinely bypass Kennedy and flow directly to John Henry.
When asked why questions of trust and coherence have persisted across different front office regimes, Kennedy declined to engage. “Not gonna respond to that one,” he said. Breslow and Cora did not respond to a request for comment.
The result has been persistent ambiguity. Baseball operations have cycled through competing philosophies — prospect-hoarding, free-agent splurging, strict adherence to internal models — layered atop one another.
Multiple executives and former Red Sox employees described the organization as a high-pressure environment with diminishing internal support, particularly over the last five years. Current front office staffers noted the job listings posted by the Washington Nationals, now led by former Red Sox assistant general manager Paul Toboni. Washington’s job posting this winter emphasized joy, humility, integrity and competitiveness – values that read less like corporate boilerplate than a corrective to the environment Toboni experienced in Boston, according to people familiar with his thinking.
Longtime executives believe this reflects Henry’s approach. They describe a recurring cycle of moments of deep pessimism about the sport’s future followed by sharp, reactive course corrections. After the 2008 financial crisis, Henry worried privately that fan spending and media economics might never fully rebound, prompting restraint, according to a former Red Sox senior executive. Then came the overcorrection: In the winter of 2010-11, the team committed more than $300 million to Adrian Gonzalez and Carl Crawford. When that gamble failed, the lesson Henry appeared to take from it was not moderation but caution.
The cycle has repeated in different forms ever since. The team let Jon Lester walk, unwilling to meet his price and commit significant money to a pitcher into his mid-30s, only to pivot two years later and commit more than $200 million to David Price. While exercising restraint on pitching, the impulse resurfaced again with the signings of Hanley Ramirez and Pablo Sandoval. Both ended with the players designated for assignment, a failure that still lingers and contributes to the current aversion to long-term risk.
And with Cora fired, there are no more buffers. The organization is Breslow’s now. What happens next will tell us whether anything has actually changed — or whether the same forces that produced this moment will simply produce the next one.
Through it all, there’s no single voice empowered to reconcile those swings into a clear direction or explain when they fail. Executives and agents around the league describe the Red Sox post-Lucchino as “incoherent,” a franchise unsure whether it’s trying to win now or merely protect itself from regret.
Around the league and inside the organization, there’s a quiet belief that this posture seems unlikely to change. Henry last spoke to the media publicly on Feb. 17, 2020, following the trade of Betts. He did not respond to a request for an interview.
That silence broke during the offseason – not to address the Devers trade, the Bregman departure or the questions that have consumed his fan base for years. Henry posted a single word on social media – “Historic” – to mock Boston Globe columnist Dan Shaughnessy who had issued a correction about NESN’s broadcasting practices. When asked about Henry’s return to social media, Kennedy responded on MassLive’s Fenway Rundown podcast, “I saw that and I obviously had to smile. … The choice to not engage day to day with members of the media is a choice that has served John well because it’s just something he leaves to others.”
Several people familiar with ownership’s thinking point to one moment as proof of what actually moves Henry: the backlash to the European Super League. When Fenway Sports Group helped spearhead the breakaway soccer competition in 2021, the reaction was immediate and overwhelming. Fans protested outside stadiums. Politicians weighed in. Sponsors expressed concern. Within 48 hours, the project collapsed, and Henry issued a public apology. Inside the Red Sox, that episode is cited less as a moral awakening than as a structural lesson. The backlash worked not because fans were angry — they often are — but because it threatened the business, the brand and the long-term value of the asset.
By contrast, several people in the Red Sox organization believe the team’s current model is designed to absorb dissatisfaction without forcing a reckoning. The intention is to build a team competitive enough to inspire hope, cautious enough to limit risk, profitable enough to stay insulated. The organization has learned how to manage the temperature without choosing a direction, signaling ambition without absorbing the risks that real commitment requires. And because no one is empowered to speak plainly about money, urgency or limits, fans are left decoding mixed signals.
The fan base hasn’t stopped loving the Red Sox. It just no longer knows who in the organization, if anyone, is telling them the truth.
Really well reported article. The private equity approach the Sox have adopted is miserable. It also makes clear how important a strong counter weight like Luchino or dombrowski is FSG’s nonsense. Kennedy comes off as nothing more than a corporate hack.
Perfect Sunday reading Joon!
I can’t tell if I want owners of teams to be the evil villains no matter what, or wish that they were as passionate as fans and would do insane things with money to deliver wins at all costs.