How Liverpool and Red Sox owner John Henry won it all
Roula Khalaf, Editor of the FT, selects her favourite stories in this weekly newsletter.
Within 10 minutes of meeting John Henry for the first time, alarm bells started ringing. We’d exchanged pleasantries and were sitting alone in his suite at Fenway Park, home of the Red Sox baseball team he owns, on a colourless November afternoon in Boston. Settled into our plush leather chairs overlooking home plate, we were enveloped by walls displaying a gallery of rich memories: trophy celebrations for the Sox and the English Premier League football club Liverpool, also owned by Henry’s Fenway Sports Group (FSG); a joyous snap at a World Series parade with his wife Linda and Boston icon David “Big Papi” Ortiz; Henry’s two youngest children grinning along the first-base line, just yards away.
That’s when we were interrupted by a deafening crash directly above. The fire alarm began to pulse urgently, and an automated woman’s voice spoke over the intercom: “This is an emergency. Please locate the nearest exit and vacate the premises immediately.” I had come to Fenway for an off-the-record meeting with Henry, to learn about how he manages a crisis. Now I was watching him up close. “Let’s go this way,” he said, gathering his small leather backpack and leading me down the hall to a concrete stairwell. His movements, like his speech, are languid but deliberate. At 74 he has the manner of someone who’s had command of the room for many decades. Dressed in a black hooded jumper, stonewashed jeans, and scuffed rubber trainers, Henry appeared so casual it was hard to believe I was being escorted to safety by the owner of the Major League Baseball stadium we were trying to escape.
After descending several flights of stairs, we reached the street, where a stream of Fenway front-office staffers were filing out. “Which one of you guys did this?” Henry said with the hint of a grin. We learnt the ruckus had been a false alarm.
There was, however, another rescue mission unfolding. Upstairs in the front office, a group of executives had ignored the alarm and were scrambling to complete a term sheet for Henry’s newest project, a proposed $3bn investment in professional golf. That placid sport, known for stuffy tradition, had recently been in tumult over its future and Henry sensed an opportunity.
It was just another of the obsessions that have fuelled him personally and enriched him professionally. Since acquiring the Sox in 2002 and Liverpool in 2010, FSG has become the modern blueprint for a transatlantic sports empire, buying troubled institutions and restoring them.
Henry’s company has ended World Series curses and Premier League droughts, bringing back the good times to fans who had forgotten what victory felt like. It has also frequently enraged and frustrated those fans.
Sports ownership has changed radically in the past few years. Professional owners like Henry have amassed portfolios in top-flight US and English sports leagues, pooling teams into multi-club conglomerates. As the sticker price for elite teams skyrocketed, the number of individuals able to afford them shrank precipitously.
Appetite from sovereign wealth funds, particularly from the Middle East, and from institutional investors has only forced prices upwards. FSG has driven this change and mastered the corresponding power shifts more effectively than any other sports owner today.
A commodities billionaire by profession, Henry’s stature in the global sports industry is matched only by his reluctance to speak about it. He agreed to spend some time with me in person on the condition he not be quoted directly, instead answering questions by email. After the evacuation at Fenway Park, I followed him back upstairs and watched as one of the best-known but least-understood owners in modern sports got back to work hammering out the terms of his next reinvention bid.
“Why do rich men and rich women want to own baseball teams?” The question was put to Henry by Charlie Rose on his US public broadcast show in 2004, not long after the Red Sox had won their first World Series in 86 years. On a victory lap for the historic feat, Henry was happy to go on the record. “That’s a good question,” he said, calmly scratching the space above his left ear as he pondered his answer. Dressed impeccably in a charcoal suit with a crisp mustard tie, his close-cropped hair more pepper than salt, Henry spoke with the serenity of someone who had nothing to prove. “I think that probably different people have different answers. As for myself, if you’re a huge sports fan and you can afford it, why wouldn’t you?”
His answer seemed simplistic but Henry was correct in saying that sports-owning billionaires are not all cast in the same mould. There are the flashier, more public-facing owners who delight in hosting fans in their suites and answering questions on social media, like New York Mets owner and hedge fund manager Steve Cohen. There are recluses such as the Manchester United-owning Glazer family, whose rare utterances about their teams and rumoured intergenerational dynamics are parsed for signs by supporters. And there are the old-guard dynasties, like New York’s Mara family, which has passed down its stake in the Giants football team since the inception of the NFL in the 1920s.
Henry’s philosophy — “Well, why not?” — was on full display again last June. He was in New York to attend a routine meeting of baseball owners. FSG’s to-do list was daunting. His football club Liverpool appeared to be running out of steam, after several years going toe-to-toe with a Manchester City team owned by Abu Dhabi royal Sheikh Mansour. FSG’s recently acquired ice hockey team, the Pittsburgh Penguins, had just missed out on the Stanley Cup playoffs. The baseball billionaires had plenty to discuss too, including plans by the owners of the Oakland Athletics to relocate the team 500 miles from Oakland.
But Henry had something different on his mind. Just a week beforehand, the commissioner of golf’s US-based PGA Tour and the governor of the Saudi Public Investment Fund (PIF) had announced a plan to merge, live on CNBC. The markets-focused cable channel regularly reports surprising M&A moves, but this was a shocker. Ever since the Saudis had bankrolled the breakaway LIV Golf competition, luring top players with the promise of vast riches, the Tour had been at war with the PIF. The about-face that proposed to bring the rivals together was an even more stunning development.
Henry couldn’t understand how it had come to this. Why was golf, the most well-heeled of elite sports, so desperate for financial salvation that it would merge with its ideological and marketplace opposite? Seated in a midtown skyscraper with a half-dozen of his fellow billionaires — all men, all American — at the MLB meeting, he saw a group of like-minded titans. Couldn’t they come up with an alternative plan for the PGA Tour, he wondered. Henry started asking around the room: would you put up some funds to invest in golf? How about you?
To others present for the meeting, golf was the last thing they thought Henry would be interested in. “He has a lot of hobbies, but that’s not one of them,” recalled Sam Kennedy, chief executive of FSG and one of Henry’s closest associates for more than two decades. But Henry wasn’t making a passion play. He had seen a problem and was in a roomful of people with the means to fix it.
Previously unreported, the MLB owners’ meeting became the unofficial launch pad of the Strategic Sports Group, a consortium of American businessmen whose portfolios include all manner of global sports. Their objective would become transforming the PGA Tour from a non-profit that organised tournaments into a global sporting and entertainment juggernaut.
The Mets’ Cohen became a co-lead, as did Arthur Blank, founder of the Home Depot retail chain, owner of the Atlanta Falcons NFL team and Major League Soccer’s Atlanta United. Blank had never met Henry before that summer, but the Red Sox owner’s reputation preceded him. “He reminds me of those old EF Hutton commercials,” Blank told me, referencing 1980s TV adverts in which crowded rooms of people fell silent at the mere mention of the New York brokerage. “When EF Hutton talks, people listen,” went the tagline.
As Blank recalled, Henry’s pitch went like this: the world of golf was in “turmoil”, and would he have any interest in joining an optional financial lifeline to the PGA Tour, either instead of or in addition to the PIF merger? The Tour and the PIF had signed a memorandum of understanding to negotiate the details of a proposed joint commercial entity for the game of golf. It didn’t, to the other owners’ knowledge, have any provisions for an open market process. Meaning that Henry was, in fact, pitching a rogue operation. Nevertheless, Blank said he was in. “We saw it as doing the right thing, as leading American businessmen.” Thus began six months of delicate negotiations between the wealthiest leaders in sport and the various warring factions of golf’s once-genteel brotherhood.
During our various in-person discussions, Henry had a tendency to answer my questions with a simple “yes” or “no”, even when I made relatively benign inquiries about his hobbies. At one point, his wife Linda, the CEO of another institution owned by Henry, the Boston Globe, gently prodded him to open up a bit more. (He conceded that he enjoys collecting cigars.) Close friends and colleagues confirmed that Henry is not particularly given to loquaciousness.
Many of them found this to be a strength. “Ownership comes in every different flavour of ice cream you can imagine,” said Blank. “But I do think the owners . . . the ones that are listened to the most are the ones who listen the most.” A few people I spoke to found his elusiveness to be a demerit. “That’s part of John Henry’s problem these days. He’s been in town for 22 years, and he’s still a stranger,” said John Harrington, chair of the Boston-based Yawkey Foundation and former custodian of the Yawkey Trust, from which Henry bought the Red Sox. “If you ask around town now, you’re gonna find most people don’t have a good fix on him . . . I think he doesn’t mind that.”
Born in 1949 to Midwestern farmers, Henry loved baseball from an early age. His childhood hero was the St Louis Cardinals slugger Stan “the Man” Musial. He also spent hours playing records by the Beatles, Jimi Hendrix and Pink Floyd. In his twenties, he dabbled in the study of philosophy but never received a college degree, instead pursuing rock ’n’ roll fame in a band he started called Elysian Fields.
When Henry’s father died in the mid 1970s, he left his son a trove of soyabean crops. Using knowledge of farming trends and his penchant for statistics, he began to dabble in commodities trading. Early on in his new career, Henry found that a hunch he had about the direction of soyabean prices had been wrong and that he’d only been saved from a severe loss because he’d never actually executed the trade. That near miss sparked his obsession with divorcing human emotion from market moves.
For the better part of 1979, Henry devoted himself to studying historical crop prices and developing a dependent model for trading on them. He adopted a strategy known as “trend following”, a deceptively simple theory in which one buys when prices trend upward and sells when prices trend down, usually at a pre-determined interval, such as X number of days after a 30-day high. Henry wasn’t its first disciple, but he adopted it at a uniquely opportune moment in history: the dawn of the computer age. He invested heavily in servers and data, and John W Henry & Company launched as a managed futures fund in 1981.
Peter Borish, a Wall Street legend best known as the second-in-command to hedge-fund titan Paul Tudor Jones, was a contemporary of Henry’s in the 80s. Both men became tremendously wealthy around the same time and thrived during the crash of 1987, in part because of their sober calculations ahead of time. He agreed to meet me for coffee one afternoon in Brooklyn. When I asked Borish how a Beatlemaniac college dropout became so successful, he told me I was not the first to have asked the question. “John is kind of like Tom Hanks in — what’s the movie with the box of chocolates?” Forrest Gump, I told him. “Yes. He’s like him. He’s a good guy and a total savant. It probably angers some people, you know, to think, ‘What makes this guy so special?’” The answer, he said, is that Henry has a strong sense of self and the ability to ride out both high and low tides.
Nearly everyone I spoke with described Henry as unflappable. “He’s been so successful investing in sports I think it’s fair to say it’s not luck,” said Jonathan Nelson, co-founder of Dynasty Equity, which took a stake in Liverpool last year. “You need conviction.”
When I asked Henry about this — specifically, whether he agreed with the assessment that he is preternaturally self-confident — he demurred. “I’ve always doubted everything and especially my own thinking,” he wrote to me in an email this spring. “You have to take risks in order to do things of significance, but there is far too much self confidence everywhere these days. You have to concentrate on what can go wrong over the long term, not the short term. You have to question yourself and others.”
One inspiration has been the Indian philosopher Jiddu Krishnamurti. “[He] caused me to question everything and begin to pay attention to ‘what is’ rather than what should be or could be,” Henry wrote. “That really helped me as I developed market strategies. It’s best to pay more attention to a market than to what you think about the market.”
The brief history of Henry’s start in sports goes like this: in 1991, he bought some minority shares in the New York Yankees. He befriended and learnt the ropes from the team’s owner at the time, George Steinbrenner. In 1999, Henry bought his first team, the Florida Marlins, a relatively new Major League Baseball club which had recently won its first World Series trophy.
He got a fast lesson in the challenges of ownership, including sunk costs and stadium economics, and wondered if he should sell. Around the same time, in 2001, the Yawkey family trust, which had owned the Red Sox for nearly 70 years, was forced to sell. The team hadn’t won a championship since it traded away slugger Babe Ruth in 1920, which fans referred to as the Curse of the Bambino. Yet it was still seen as one of baseball’s blue-chip franchises. Despite his frustrations with the Marlins, Henry agreed to join two other interested parties — The Cosby Show producer Tom Werner and lawyer Larry Lucchino — in bidding on the Sox on one condition: he would take the control ownership role. The sale was approved in early 2002 for a then record sum of $700mn.
To counter their arch-rivals, Steinbrenner’s freewheeling Yankees, the new owners began deploying a more analytics-focused management style. The chief architect of the new Sox approach was a 28-year-old Yale graduate, Theo Epstein, brought in to be the team’s general manager. The club traded away fan favourites and acquired unheralded talents like third baseman Bill Mueller, who in his seven-year MLB career had never hit more than 10 home runs in a season when the Red Sox signed him as a free agent. This was the era of Moneyball, of optimising performance with a deep well of research on every player’s trending averages for strikes, balls, walks and home runs. It was a philosophy that appealed to Henry as a trend-following quant.
In 2004, the Red Sox became the first and only team in baseball history to rebound from a 0-3 deficit to win a championship series, thanks in part to a heroic hit by Mueller. In the subsequent World Series, they trounced Henry’s childhood team, the Cardinals, in four straight games. Curse broken. Fanbase fulfilled. The normally publicity-shy Henry lapped up the singular glory that comes from owning a winning team.
That winter Sam Kennedy was kicking back with the Red Sox chief operating officer Mike Dee when Henry dropped by. “John was needling us, like, ‘You guys better think about what’s on for next year, or you might be short-timers’,” recalls Kennedy. That was “a hallmark of [Henry’s] personality.” A challenge and a directive wrapped up in a playful jest.
Henry hadn’t come into team ownership seeking to build a transatlantic empire, but that conversation with Kennedy marked its start. Henry describes his career as “one thing leading to another”. His wife calls them “quests”. He prefers “steps”. But he saw that success in one field could generate lessons for others. Henry established New England Sports Ventures before he bought the Sox in 2002. After buying Liverpool in 2010, needing a less regional-sounding company, NESV was renamed Fenway Sports Group. With Liverpool, Henry set about finding the value in another famous name that had fallen on hard times. As in Boston, where he had raised Sox revenue by renovating Fenway Park, he added 10,000 seats and around $50mn each year to Liverpool’s coffers.
As FSG grew and diversified, the perception that it is made up of businesspeople first and sports fans second has gained traction. Henry disputes this. Having spent “a lot of time” with fellow sports owners over the past couple of decades, he says “most of them feel responsible to their communities to bring championships.” And during Henry’s tenure, the Red Sox have won four World Series, the most of any baseball team this century. Liverpool also ended its dry spell of 30 years without a league title. Yet fans always want more, and Henry knows the numbers are stacked against him. “Because fans expect championships almost annually,” he wrote to me, “they easily become frustrated and are not going to buy into what the odds actually are: one in 20 or one in 30.”
When the 2023 MLB season officially concluded on November 1, executives across the league began readying themselves for baseball’s free agency period. The star attraction was the Japanese superstar Shohei Ohtani, often called the second coming of Ruth. Ohtani was destined to earn a record contract. The only questions were: how much? And with which team? The Red Sox would certainly have had time to prepare a move. Their season had ended early when they finished bottom of their division. The day after the World Series concluded, the team introduced its new top baseball executive, Craig Breslow. FSG chair Tom Werner acknowledged fan disappointment and promised the organisation would go “full throttle in every possible way”.
Henry was in the thick of negotiations for golf, his latest quest. The Strategic Sports Group he’d co-founded, known as SSG, was facing competition. Investment bank Allen and Company was evaluating interest in the Tour from several outside investors. Another bank, Raine Group, which ran the auction of Premier League club Chelsea after its Russian owner Roman Abramovich was sanctioned by the British government, was advising a group of PGA Tour players. A few of these athletes held considerable power: they sat on the Tour’s policy board, giving them a position to vote on any proposed outside investment. The leader of that group is the most famous golfer in history, Tiger Woods.
On the morning of November 9, Woods invited the prospective investors to his oceanside offices in Jupiter, Florida. According to people who were present, Woods was joined by fellow players Rory McIlroy and Patrick Cantlay, as well as the Raine Group’s Colin Neville, along with various staff. Several other players tuned in via Zoom. The SSG delegation consisted of Henry, his wife Linda, FSG executives Werner and Kennedy, Arthur Blank and Andy Cohen of Steve Cohen’s Private Ventures, among others.
Packed into the office, over a spread of coffee and fruit trays, the group’s conversation bounced back and forth between competing interests and parties. SSG wanted to hear out the players’ concerns and present itself as a collection of accomplished stewards with a track record in virtually every other professional sport on both sides of the Atlantic. The players wanted to establish an equity programme to give as many Tour players as possible a financial stake in the new enterprise. Several of the PGA stars present were rumoured to have passed up offers worth hundreds of millions of dollars to join LIV, staying loyal to the Tour only to be blocked out of the PGA-PIF merger talks. This time, they weren’t going to miss out.
Despite his reputation, Henry was anything but reticent that morning. “John probably repeated 10 times, ‘We want to be aligned with the players’,” one person who was present told me. It left a good impression with the golfers, and SSG went back to their offices to polish the finer points of their proposal.
All the while, the baseball world was rife with speculation about Ohtani’s future. The pitcher’s decision was so eagerly anticipated that some 4,000 people live-tracked a private jet departing from Anaheim, California, near his home, to Canada, erroneously believing he was about to sign with the Toronto Blue Jays. But on December 9, Ohtani announced he had inked a 10-year deal worth $700mn with the Los Angeles Dodgers. It was the richest known contract in modern professional sports. The free-spending Dodgers, owned by a consortium of financial engineers from the money management firm Guggenheim Partners, swiftly followed up by signing another coveted Japanese star, Yoshinobu Yamamoto.
The Red Sox had yet to pick up a pen. The problem wasn’t specifically missing out on Ohtani or Yamamoto but what fans were beginning to perceive as a downward trend. The club had finished last in the American League East for three of the previous four seasons. At the same time, the average cost of attendance at Fenway Park for a group of four had become the most expensive in baseball, at nearly $400.
It didn’t help that within hours of Ohtani announcing his move, the PGA voted to advance negotiations with SSG. Fans started to ask whether Henry’s play for golf was coming at the expense of his baseball team.
In over two decades of ownership, Henry and his co-owners had refurbished Fenway Park, won four rings and invested $120mn in charitable works in greater New England. But to fans the team appeared unwilling to keep pace on MLB player contracts, one of the key predictors of sporting success. In every one of the Henry-era World Series wins, the Red Sox payroll had ranked between first and third highest overall in MLB.
“We used to be on the same level as the Dodgers and Yankees, and now we aren’t because of how [Henry] managed the team this decade. This is not a take or opinion,” the media executive Bill Simmons told me. Simmons has built an empire of his own on Boston sports takes and opinions. He defined the voice of the modern American sportswriter with the launch of his blog, The Boston Sports Guy, during the first dotcom boom, before starting his present site, The Ringer.
Few individuals are more closely associated with Boston sports fandom than Simmons, so I asked him to explain how fellow Sox supporters are feeling about Henry. “He ran the first competent ownership group that the Red Sox ever had. They spent real money, revitalised Fenway Park, and genuinely seemed to give a shit. And 2018 was the best Red Sox team ever. All of that was incredible,” Simmons wrote to me. But in the past several years, “we watched him in real time shifting his focus. And the Red Sox suffered horribly for it.”
Henry disputed the idea there was a risk attached in stretching his attention span across so many complex businesses. “There would be a risk,” he wrote, “if FSG was not so deep and strong in personnel.” He also took issue with the obsession over his and Werner’s remarks about “expensive” ballplayers and going “full throttle”. The latter had “overshadowed every other word, paragraph and interview of the winter because it reaches so deeply into the false belief that many fans and media have that you should mortgage the future each year for the present.” Creating a sustainable future for the Red Sox was, he argued, more important than any given year’s payroll. “You have to base acquisitions and dispositions on the future, not the past,” he said. “That is unpopular generally.”
But the inescapable fact for FSG is that the owners of other clubs have been spending a lot more. Boston committed $54.9mn on free agent contracts during the 2023-24 winter transfer window, ranking 12th out of 30 MLB teams and nowhere near the $1.1bn spent by the Dodgers. On social media and in local Boston sports columns, most tended to agree with Simmons.
Billionaires getting together to disrupt the established order doesn’t always have a happy ending. In April 2021, Henry was among a group of European football club owners forced into a humbling climbdown after announcing the European Super League, which guaranteed places for an elite group of clubs.
Within 48 hours of its announcement, the plan had unravelled totally amid mass public protests from fans, politicians and players. In the aftermath, Henry, dressed in a casual check shirt and unthreatening gilet, sat alone for a videotaped apology to Liverpool fans. “In this endeavour, I have let you down,” he said. “It’s something I won’t forget and shows the power the fans have today and will rightly continue to have.”
Henry’s “Well, why not?” approach had run smack into an implacable answer: tradition. The English Premier League is the most popular in the world, watched on TV in more than 200 countries. The riches it generates have attracted not just private owners from the US and China but state investment from Abu Dhabi and Saudi Arabia. But he and the other owners behind the would-be Super League had hugely overestimated the extent to which the fans would tolerate change.
Liverpool is more than a football club to many of its supporters. For years, it was the most successful team in England. But by 2010, the club was at risk of falling into administration until Henry’s ownership resuscitated it. His lieutenant and FSG co-owner Mike Gordon was seconded to the northwest of England. The choice of the inspirational German head coach, Jürgen Klopp, was a masterstroke. But there had been mis-steps, such as the failed attempt to trademark the word “Liverpool”. (Rejected for the obvious reason.)
Initially, Henry left unanswered all of my questions about Liverpool, including what lessons he had learnt from the debacle. Despite his apology and the ferocity of the backlash, most people believe a European Super League is an idea that will happen one day. But Werner, the FSG chair, is clearly not out of other ambitious ideas. “I’m determined one day to have a Premier League game be played in New York City,” he told me. “I even have the sort of crazy idea that there would be a day where we play one game in Tokyo, one game a few hours later in Los Angeles, one game a few hours later in Rio, one game a few hours later in Riyadh and make it sort of a day where football, where the Premier League, is celebrated.”
He acknowledged the idea had at least one significant knot: local fans of clubs who wouldn’t be able to support their teams at their home stadium. “Let’s figure out a way to offer them very cheap travel [and] accommodations so that if Liverpool is playing Nottingham Forest, we will support fans coming to New York and make this an attractive thing for the fans as well.”
Werner said it wasn’t that FSG’s executives thought they were smarter than anyone else in exploring such ideas. “It’s a very competitive business,” he said. “I think 20 years ago there was a lot more low-hanging fruit, where a Theo Epstein could find success in an avenue that other people weren’t looking at. But sports is now big business, right? Teams even in the NBA are going for $4bn. I don’t think we have any secret sauce, is what I’m trying to say.”
Henry eventually responded to my pressing on Liverpool. He made it clear that Werner’s plans for a New York game were “not something that I advocate or am particularly interested in”. FSG’s more immediate task had been handling Klopp’s January announcement that he would step down at the end of the season after almost a decade in charge. In May, a day after Klopp’s emotional farewell, Dutch coach Arne Slot was confirmed as his successor.
Will he be Henry’s final head coach at Liverpool? In late 2022 it was revealed that FSG was exploring a sale of the club. While Henry officially called it off three months later, the process resulted in a minority investment by the emerging sport-focused private equity firm, Dynasty, valuing Liverpool at more than $5bn. Still, fans sensed ambivalence.
Henry paid tribute to Klopp’s “simply magical” tenure at the club over emails. “The force of his personality and emotions lifted all of us who support the club to a level I’ve not seen before anywhere,” he wrote to me. I decided to ask him point-blank: would you ever sell the Red Sox, Liverpool or the Penguins? Henry wrote: “My wife and I live and work in Boston. We are committed to the city, the region. So the Sox are not going to come up for sale. We generally don’t sell assets.”
It was unusually overcast for mid-February in Florida when I pulled up to JetBlue Park, also known as Fenway South, for spring training. John Henry, Linda, Werner, Kennedy and the new baseball operations chief Breslow were set to meet with the entire squad for the first time. I greeted Henry briefly in the hall of the training facility, where he apologised for falling behind on some of our correspondence. I mentioned the $3bn SSG investment, which the players on the PGA Tour Policy board had just voted to approve, creating a new commercial entity for the sport. Henry’s eyes lit up. He looked delighted to be asked about what he described as a fascinating new project, but the bustle of the official start of the Red Sox season cut us short.
We were ushered past the locker rooms and weight rooms to an unremarkable food hall, where cafeteria tables had been pushed out of the way to make room for dozens of black plastic chairs. Third baseman Rafael Devers sat there along with the newly acquired starting pitcher Lucas Giolito and roughly a hundred other position players, bullpen stalwarts, coaches, trainers and front office staff. Henry and the other executives perched on bar stools against one wall, with general manager Alex Cora acting as master of ceremonies.
Some players were still in workout gear, while others kicked around in their plastic slides. The only giveaway this wasn’t a meeting of a summer camp was the crew of cameramen and boom operators, hoisting a boom microphone over Cora’s head. They were filming what was expected to be a season-long Netflix documentary about the efforts of the nine-time World Series champions to find redemption after their disastrous 2023.
Speaking in his rounded Puerto Rican accent, Cora was sanguine about the low expectations for the team, which had been compounded by the free-agency saga. He asked the players to toss out criticisms they’d read in the media so he could offer a counterpoint. Then Cora concluded, “Let’s be the best fucking version of the fucking Red Sox.” Werner, Kennedy and Breslow each offered brief remarks and paid tribute to essential personnel. Henry stayed in his seat throughout, clapping at intervals and gazing placidly over the crowd.
After the meeting, players dispersed, while Henry and the executives huddled for several minutes, before heading out to the practice fields. I followed them outside, where a small bunch of baseball beat writers, identified by their credential lanyards, were waiting. Henry declined their interview requests, gliding towards a group of fans gathered some 50 metres away to watch throwing practice. He looked pleased to sign baseballs and patiently answered their questions.
Werner was standing nearby and I took the opportunity to ask him if everything has a price. “In life, I guess, everything has a price,” he said. “But John and I are both quite wealthy so, for us it’s the joy of owning . . . ” he interrupted himself to gesture at the Sox players in front of us drilling pitches, preparing for a year in which a successful season could be defined as anything above last place. “How great would it be if this team defied expectations, you know? That’s what drives us,” said Werner. He told me that in just a few minutes, he and Henry had a lunch meeting with the PGA Tour’s European counterpart. There was still plenty to work on with all of golf’s stakeholders.
During one of our exchanges, Henry reflected that he’s watched the sports industry evolve from “mom and pop operations” to “tough, competitive businesses”. Whether the professional team owners of the 21st century are responsible for that trajectory or merely responding to it, he didn’t say. But he may be among the last of a generation of kingmakers in sport, wealthy enough to buy in on his own, savvy enough to chart the course from community institution to conglomerate.
He has faced calls to sell each of his clubs. Where he struggles is when to push back. “I don’t think people in my position can win publicly — your words are often used against you — so the less I say I generally think the better,” he told me. This is not always a recipe for keeping fans happy, which is also part of Henry’s job. Happiness, though, isn’t something that can be researched, funded and reaped. Henry expects to get flak and supporters of his clubs are likely to keep dishing it. Neither side may ever be satisfied. But he has structured his entire professional life by approaching the market as it is, not how people think it should be. If everything in Henry-land follows a coherent logic, the formula belongs only to him.
Sara Germano is the FT’s US sports business correspondent
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