Premier League’s Richard Masters risks reputation, £100m vs Man City

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 comparison: “It can be a bit like managing a creche.”

The remark was put to an executive at one of the 20 clubs currently in the top flight. He refined 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 comments captured a serious truth: few jobs in sport carry the same level of complexity as the one held by Premier League chief executive Richard Masters.

Since taking charge in December 2019, Masters has faced a global pandemic, Project Big Picture’s manoeuvrings involving Manchester United and Liverpool, the breakaway ambitions of the European Super League, a surge in foreign and state-backed 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.”

Daily Mail Sport has spoken to a dozen people who know Masters or have worked alongside him, seeking a clearer picture of the Premier League’s most senior establishment figure.

Most readily agree on three points. First, Masters is entirely different from his long-serving predecessor, the charismatic Richard Scudamore, an accomplished political operator who was more comfortable charming or pressuring the room during an era of relentless financial expansion. Second, the environment in which Masters operates has changed beyond recognition. Third, Masters would firmly reject the idea that he has pursued a crusade against Manchester City. He would point out that guilt was established by an independent commission and that, in the simplest terms, his responsibility is to enforce rules approved by the clubs themselves.

Even so, one point stands out: the decision to commit an estimated £100million in legal resources to the case against City has challenged the long-standing accusation that football’s judicial system favours its biggest clubs. English football has never witnessed a confrontation of comparable scale.

Whether or not Masters believes the dispute has been unfairly personalised, its outcome will define his tenure. It will also shape a much broader question: how much trust can be placed in the integrity of the Premier League over the past 20 years?

That is a remarkable distance from the circumstances of Masters’ appointment. He was only the fourth-choice candidate to succeed Scudamore after an 18-month recruitment process descended into confusion. Susanna Dinnage was announced as the successor but later declined the role, while Tim Davie, now the BBC director general, also rejected the position. Then David Pemsel was appointed, only to resign before taking up the job amid allegations concerning his private life. That chain of events ultimately created the opening for Masters.

A sales and marketing specialist with lengthy spells at the England and Wales Cricket Board, the EFL and the Premier League, Masters’ image as an accidental appointment did little to strengthen his position in football’s intensely 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 a former colleague familiar with the dynamics of Premier League stakeholder meetings. Another source said some people attending those gatherings – usually two representatives from each club alongside around a dozen Premier League staff – questioned whether Scudamore’s successor was equal to the task.

Much of that doubt stemmed from comparisons between two very different personalities. One Premier League executive recalled Scudamore regularly making phone calls well beyond midnight in an effort to unite the 20 clubs behind major decisions during his two decades in charge. “A chief whip in another life,” the source said.

Scudamore was portrayed as a chief executive who rarely entered a vote without first having a strong sense of the likely result. A former staff member described him, with some affection, as “didactic” and “controlling”. His greatest achievement, many believe, was his ability to “keep the peace” between 20 clubs with competing interests. By that measure, it was more impressive than presiding over the Premier League’s sustained growth in television income.

Masters, an Aston Villa supporter who turned 60 in June, is more corporate, more methodical and considerably less charismatic. Initially, those qualities were regarded as shortcomings. But after seven years in which the football landscape has demanded a different type of leadership, his cautious, process-led approach has gradually come to be viewed within Premier League circles as a strength.

‘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 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.