A few days after Manchester City were found guilty of cheating, a former Premier League chairman tried to explain just how difficult it has become to maintain order in English football.
After pausing to consider his answer, he offered Daily Mail Sport a memorable summary: “It can be a bit like managing a creche.”
The comment was put to an executive at one of the Premier League’s current 20 clubs. He amended the analogy slightly: “It’s more like a difficult high school now – the kids have grown up and in some cases become delinquent.”
Both men were joking, but their remarks captured a serious truth: few roles in sport carry the same level of complexity as the one held by Richard Masters.
Since becoming Premier League chief executive in December 2019, Masters has navigated a global pandemic, Project Big Picture proposals led by Manchester United and Liverpool, the rebel Super League plans, the rapid expansion of foreign and state ownership and, above all, Manchester City’s era-defining legal battle.
As one former colleague and close friend put it: “Taking those areas as a whole, it’s a f****** tough hand to be dealt.”
Premier League chief executive Richard Masters’ tenure will ultimately be defined by the outcome of the organisation’s legal case against Manchester City
Masters would strongly reject any suggestion of a campaign against Manchester City, stressing that guilt was established by an independent commission and that his role is to enforce rules approved by the clubs
Daily Mail Sport has spoken to 12 people who know Masters or have worked closely with him in an effort to understand the most senior figure representing football’s establishment.
Most agree on three key points. First, Masters bears little resemblance to his long-serving predecessor, the charismatic Richard Scudamore, an accomplished political operator who was adept at charming – or pressuring – clubs during an era of relentless financial expansion. Second, the environment in which Masters operates is vastly different. Third, he would firmly reject the idea that he is pursuing Manchester City, insisting that an independent commission reached its verdict and that his basic responsibility is to administer rules the clubs themselves agreed to follow.
There is, however, a significant point to consider. The willingness to spend an estimated £100million on legal resources in the City case has challenged the long-standing claim that football’s legal system is tilted towards its biggest clubs. English football has never faced a dispute of comparable importance or financial scale.
Whether or not Masters believes the battle has been unfairly attached to his own identity, its eventual outcome will define his tenure. It could also determine a much broader question: the credibility of the Premier League over the past 20 years.
That is a remarkable distance from Masters’ arrival, which came in highly unusual circumstances. He was initially only the fourth choice to succeed Scudamore after an 18-month recruitment process descended into chaos. Susanna Dinnage was announced as the new chief executive but later declined the role, while Tim Davie, now the BBC director general, also rejected the position. David Pemsel then accepted the job but resigned before taking up the post following allegations concerning his private life. That series of events ultimately created the opening for Masters.
A sales and marketing specialist who had spent lengthy periods at the England and Wales Cricket Board, the EFL and the Premier League, Masters was viewed as an accidental appointment – a perception that did little to help him as he entered football’s fiercely political world.
“Richard wouldn’t have been human if there wasn’t a little bit of imposter syndrome in the initial months in the job,” said one former colleague familiar with the workings of Premier League stakeholder meetings. Another source recalled that some attendees – usually two representatives from each club alongside around a dozen Premier League staff – believed Scudamore’s successor was not equipped for the role.
Much of that judgment stemmed from comparisons between two very different personalities. One Premier League executive said Scudamore would regularly make phone calls well beyond midnight to bring all 20 clubs behind major decisions during his two decades in charge. “A chief whip in another life,” the source said.
Masters is regarded as fundamentally different from predecessor Richard Scudamore, an influential political operator who could charm or pressure clubs during a period of sustained financial growth
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More corporate and less naturally charismatic, Masters has gradually seen his approach recognised as a strength as football has demanded a new form of diplomacy
Scudamore’s reputation was that of a chief executive who rarely entered a vote without a strong sense of how it would finish. A former staff member described him, with some affection, as “didactic” and “controlling”. Yet his greatest achievement was widely considered to be his ability to “keep the peace” among 20 clubs with competing interests. Many believed that was more impressive than presiding over the Premier League’s steady growth in television income.
Masters, an Aston Villa supporter who turned 60 in June, is more corporate, more methodical and considerably less flamboyant. Initially, those qualities were seen as disadvantages. But after seven years in which football’s landscape has demanded a different brand of diplomacy, many within the Premier League have come to regard his measured approach as a valuable asset.
‘There are still one or two in the room that are not convinced by him,’ said a prominent source at a Premier League club.
There is no denying that Masters has had questionable moments – his reference to Everton and Nottingham Forest as ‘small clubs’ during their Profitability and Sustainability Rules skirmishes in 2024 was easy fodder for some of those who have detected two-tier justice in how the Premier League apply its rules.
A bigger matter was the takeover of Newcastle United by Saudi Arabia’s Public Investment Fund. The Premier League claimed they have ‘legally binding assurances’ that the Saudi state would not control Newcastle, which has long struggled with the smell test for one fact above others – the Saudi crown prince Mohammed bin Salman is also the chair of the Public Investment Fund.
Some will see such decisions as flawed and acts of willing delusion; another would say that football’s world has changed beyond recognition and there are not enough tiny violins to play notes of sympathy for those trying to control it. Masters’ record within it is not without blemishes, especially in the balancing between financial regulation and the stifling of ambition. But there is an acknowledgement that he has overseen a uniquely challenging time, starting with Covid just months after taking office and extending to the City debacle.
‘There was a perception that the Masters regime was worse than the Scudamore regime but that has softened quite a bit,’ said an executive at a Premier League club.
‘Scudamore had great abilities to do certain things. He was a master politician and a superb negotiator. He was a brilliant anticipator of problems and would get ahead of them. If Richard Masters could do anything better, it might be for him and Alison (Brittain, the Premier League chair) to get ahead of the problems quicker. They aren’t as skilled politically, don’t have the same nous, but he is very strong at working through a problem.
The takeover of Newcastle United by Saudi Arabia’s Public Investment Fund has been among the key challenges faced by Masters during his time as Premier League chief executive
‘The stuff Masters has had to contend with is more extreme than his predecessors. He has done a very decent job of it in very, very choppy water. Covid was a huge thing to deal with – almost overnight, the revenue streams were being stopped and he was the man on a Zoom call having to answer 40 faces on a screen about when football could resume.’
A different source cites the threat of a Super League as the biggest crisis and City merely the messiest. ‘It helps that he is a very calm guy,’ said a club source. ‘Whatever people think of how the Premier League works under him, he is a decent man with decent values and he is mostly applying the rules we as clubs have voted for.
‘I have never seen him lose his temper in the meetings and there have been times when the criticism has been personal.
‘He can be blamed for anything and everything. If there is a bad refereeing decision, he will get a call. If the economy in Singapore affects revenue, he will get blame. But again, he is very calm in the way he works through the role, very good at compartmentalising an issue, and I think he has done a solid job on balance.’
In a room of Premier League clubs, ‘solid’ and ‘decent’ can pass for a compliment.
Those meetings, of which there are around five per year, can be feisty. Some can spend hours arguing about the seemingly trivial. According to a source, one recent debate saw multiple changes to the draft of a rule about which side of the dugouts should be used for substitutes warming up mid-match.
Perhaps unsurprisingly, the meetings around the Covid protocols or the Super League breakaway are understood to have been the most heated. Discussions around Manchester City have not reached those levels. Presumably, too much popcorn was being consumed in the creche to kick up a fuss.