Inside the mind of John W. Henry, Liverpool's 'semi-detached' owner

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It was a protest at a potential 13 per cent rise in ticket prices over the next three years, depending on inflation, but Henry was not on Merseyside to see it. At the same time that protest was taking place, around 3,000 miles away in Boston, Henry and his executives at the Red Sox, the other crown jewel in the Fenway Sports Group (FSG) sporting empire, were deciding to fire the team’s manager, Alex Cora, along with five coaches. Later that day, Henry, the franchise’s chief baseball officer, Craig Breslow, and CEO Sam Kennedy flew on Henry’s private plane to give Cora and his staff the bad news. But at a press conference the following morning, it was Breslow and Kennedy who confirmed the news to the media. According to The Athletic’s reporting, Henry was present when players were told, but said nothing. Henry has not entertained the baseball media at any press conference since 2020, when the Red Sox made the controversial move to trade the team’s most exciting player, Mookie Betts. It has left fans annoyed, and calling for him to sell up. On Tuesday, The Athletic invited Henry, who tends to conduct interviews with journalists by email, to answer questions about the running of Liverpool and the Red Sox, but he did not engage directly. Liverpool were also invited for comment. Six separate points were later put to the owner. A representative from FSG responded to one of them about ticket prices and their hopes that inflation will follow a predicted line of 7.3 per cent over the next three years rather than 13. The message is unlikely to reassure protestors who feel that the price path threatens to eradicate future discussion about the issue. With Henry’s uneasy silence being felt on both sides of the Atlantic, questions fill the void. Does he really take this criticism to heart? How truly engaged is he with the two biggest sports franchises in his FSG portfolio? And what is his long-term vision? The Athletic spoke to those who have dealt with Henry regularly in recent years to glean their impressions of the man, what motivates him and how he reacts under fire. It is coming up to a year since Henry last watched a Liverpool game in the flesh. That occasion was another game against Palace at Anfield — although this one, more memorably, marked the 2024-25 Premier League title party. Henry is 76, so regular transatlantic flights are perhaps more challenging. But throughout FSG’s 16-year tenure, the pattern has largely stayed the same, with Henry only visiting Anfield once or twice a season. Via Zoom, he was at the first meeting with Liverpool supporters when new ticket prices were discussed late last year but none of the leading FSG figures were present at three later summits about increases. Requests from fans to speak directly with the owners in more detail have not been granted since. There was a reason fans chose that picture of Henry with his fingers in his ears to display on Saturday — his lack of engagement means chief executive officer Billy Hogan effectively acts as his representative on earth, a conduit between the levels of management below him and the tier of ownership above. It was Hogan who had been tasked with explaining to fans why ticket prices were rising, in an email sent in April to season-ticket holders and members. And it was he who was left shifting awkwardly in Anfield’s executive seating when a cry of “You greedy b*******, enough is enough” went up in the 13th minute on Saturday. Hogan has left a generally good impression on supporters who have worked with him in the past due to his responsiveness. Senior executives elsewhere in football have formed the view that FSG rate him extremely highly, but it is also very clear he is there to do a job for them. Though he is viewed as intelligent and well-mannered, he always seems very much on duty and comfortable in the corporate world. Few can imagine him diving into a deep conversation about football. Yet much of Liverpool’s commercial growth since his arrival in 2012 can be attributed to him, having signed off on partnerships that have created stronger finances for the football department to operate in. This was part of his reasoning to fans in that thorny email last month. “We have a responsibility to run the club sustainably, and to do so with an ambitious vision: to compete for all major trophies, to win trophies, and to keep winning trophies,” he wrote. “That requires strength on the pitch, and it also requires that we compete in every way possible off the pitch…” The challenge of running Liverpool has been harder than Henry imagined. Privately, he has confessed to associates his deep frustrations about the possible impact of allegedly inflated sponsorships elsewhere because it undermines other clubs in their pursuit of true valuations, making them more competitive. Manchester City, the club which has denied Liverpool success more than any other in recent years, have 115 charges hanging over them, with more than 100 for allegedly breaching financial rules, all of which they deny. Publicly, at least, this is something Henry has never discussed, even carefully, but it would probably improve his standing with Liverpool supporters if he did. FSG operate in a real economic world. Ultimately, though, Liverpool stands to gain just £1.2million ($1.6m) from their new ticketing structure. Is the hassle really worth it? It would seem that Henry thinks so, although he has not always felt that way. In 2016, Henry backtracked on proposals laid out by Liverpool’s former CEO Ian Ayre to raise some ticket prices to £77, a move that would have made the club less than £25,000 but prompted a huge backlash due to wider concerns about the direction of pricing. Much has changed since, however. A Champions League and two Premier League titles have helped take Forbes’ most recent estimations of Liverpool’s value to $5.4billion (£4bn), the fourth-highest in the world. Perhaps he has realised no one can afford to take on the challenge of running it — it is over three years since he ruled out a full sale of Liverpool — and now is the time to maximise revenues, regardless of the impact or backlash. Executives from other clubs have heard less about Henry over the last few years. Some have seen that as his interest in Liverpool retreating. Others believe he was so burned over the criticism he received for Liverpool’s involvement in the European Super League (where he ended up apologising to fans, as well as Hogan, for announcing the club’s commitment to the failed competition to staff) that he has stopped getting involved in the politics of football. Henry’s bigger passion project had been Project Big Picture, another grand plan that never got off the ground before the botched Super League launch. This proposed a 25 per cent redistribution deal with the English Football League on the condition that parachute payments would be scrapped, the number of teams in the Premier League would be cut and a club’s voting rights in the top flight would be shaped by the length of their membership. To Henry, this would have been for the greater good of English football, but the reaction was again one of anger and Henry was annoyed that the idea was killed off. The Super League was a rebound and throughout that period in 2021, he was hurt by how people viewed him. He tends not to show much emotion — and those who have spent a reasonable amount of time in his company have rarely seen him angry — and communication can be sporadic. He can call at apparently random times, often not committing to pleasantries, before picking up the same conversation six months later, as if it was yesterday. If he is not interested in an idea being discussed, he can completely ignore contact. Tony Evans, the former football editor at UK newspaper The Times and now the host of The Athletic’s Walk On podcast, met Henry for dinner on a number of occasions in London at The Wolseley restaurant in the first half of the FSG era at Liverpool. He remembers having to lean in close to hear what he was saying because he spoke so quietly. According to Evans, Henry was very honest about his own failings and, in those early years at Liverpool, he knew FSG was making mistakes. Henry would speak regularly about his wretched experience owning the Florida Marlins, of which he was regularly reminded whenever he visited his home in the state. But he also spoke proudly about ending the Curse of the Bambino by winning the World Series with the Red Sox in 2004. He had never been a “jock” at school and not only was this the first time he felt a bit like a player, but it was also the first time he felt the love of a place. At Liverpool, they did not know how to get it right until the appointment of Jurgen Klopp as manager in October 2015, but Henry was never going to be as popular on Merseyside as he was at one point in Boston — the city he calls home — because, ultimately, he does not have any other connection to the area. Evans describes Henry as “semi-detached” and formed the impression that, for long periods, he did not really think about what was happening at Liverpool. Then, when mistakes were made, he tended to react quickly. On one such occasion, according to Evans, the Hillsborough Independent Panel wanted to put flyers on seats at Anfield, asking for people to come forward to give evidence. Someone at the club pushed back on the idea because of litter. Within a few hours of Evans telling Henry by email that it was an outrageous position, he had overturned the decision. “When he’s engaged, things happen,” Evans says. “When he’s not, the club drifts.” Kennedy defended Henry on Thursday, acknowledging on Boston radio station WEEI that “he’s very selective in terms of how he engages with the media. But that should not ever be confused with a lack of involvement or care”. There are leading figures in football who admire what Henry and FSG have done with Liverpool. One points out that when FSG took over in 2010, Liverpool were trailing Manchester United, Chelsea and Arsenal on and off the field, while City’s threat to that order was clear and has since been proven to be real. Despite a bad season for Liverpool, it would generally be accepted they are ahead of three of their old rivals now on all sorts of levels, having won more trophies during a decade when FSG has also settled the Anfield stadium question through huge redevelopment and built a new training ground. Can Henry keep it going?  He used to ask trusted contacts connected to Liverpool how he was doing but the answer depended, he was reminded, on why he bought the club and what he was aiming for. The simple answer was that Liverpool was very cheap and, even then, he nearly walked away from the deal, having waited in a London law firm’s office for nearly four hours while the previous owners unsuccessfully attempted to try to sack the board before they could sell up. Even when the former stand-in chairman, Martin Broughton, rushed out and told Henry that he had got himself a football club, he was reluctant to commit. He did not have a passion for Liverpool FC or for football, but it was at a price that any decent opportunist could not miss. That commercial instinct has remained intact but the last week has reminded him, once again, that to their supporters, the value of Liverpool and the Red Sox cannot simply be measured on a spreadsheet. Spot the pattern. Connect the terms Find the hidden link between sports terms