A couple of days after Manchester City were found guilty of cheating, the former chairman of a Premier League club attempted to describe the challenge of imposing law and order on British football.He had a little think and then offered this soundbite to Daily Mail Sport: ‘It can be a bit like managing a creche.’That view was then relayed to an executive at one of the current 20 clubs comprising our top-flight. He made a slight update to the assessment: ‘It’s more like a difficult high school now – the kids have grown up and in some cases become delinquent.’They were both joking around a serious point, but played to the common sentiment that few jobs in sport exist with the same complications as those faced by Richard Masters.Since his appointment as CEO of the Premier League in December 2019, Masters has been confronted with a global pandemic, the Project Big Picture manoeuvrings from Manchester United and Liverpool, the mutinous intentions behind a Super League, an acceleration in foreign and state ownership and, of course, the era-defining trial of Manchester City.To cite one of Masters’ former colleagues and a close friend: ‘Taking those areas as a whole, it’s a f****** tough hand to be dealt.’ Premier League chief executive Richard Masters’ reign will be defined by the eventual outcome to their legal case against Manchester City Masters would strongly reject any notion of a crusade against Man City, highlighting that guilt was reached by an independent commission and that his job is to administer rules set by clubsDaily Mail Sport has consulted a dozen sources who know Masters and have worked around him to better understand the highest-ranking individual on the side of the establishment.Most are quick to agree on three details. One: Masters is nothing like his long-time predecessor, the charismatic Richard Scudamore, an arch-politician who found it easier to charm or coerce the room during a reign of constant financial growth. Two: The landscapes in which they worked have changed dramatically. Three: Masters would strongly reject any notion of a crusade against Manchester City, highlighting that guilt was reached by an independent commission and that his job, in the most reductionist terms, is to administer rules the clubs themselves had voted to play by.But, on the latter, there is an observation worth making – the appetite to commit an estimated £100million in legal resources to the City battle has challenged the perennial accusation of judicial bias in favour of the big clubs. British football has never known a confrontation of such stakes.Irrespective of whether Masters finds the personalisation of this fight inaccurate, his reign will be defined by its eventual outcome, as will a somewhat bigger issue – the integrity of the past two decades of the Premier League.It is a far cry from Masters’ arrival in the role, which occurred in highly unusual circumstances, because he was only fourth choice to replace Scudamore. A shambolic recruitment process that stretched 18 months had seen Susanna Dinnage named as successor, but she declined after her appointment had been announced and the current BBC director general Tim Davie also turned it down. Completing a chaotic hat-trick, David Pemsel was given the job but resigned before starting because of allegations about his private life. All of which opened a sliding door to Masters.As a sales and marketing man, with long stints at the England and Wales Cricket Board, the EFL and the Premier League, his perception as an accidental candidate didn’t help in the hornet’s nest of football politics.’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 well acquainted with the machinations of a Premier League stakeholder meeting. Another source adds that there were individuals in those meetings, typically attended by two representatives per club and a further dozen Premier League staff, who felt Scudamore’s replacement wasn’t up to it.Much of that derives from comparisons between very different men. One Premier League executive describes Scudamore as routinely making phone calls beyond midnight to corral the 20 clubs on big issues across his 20-year reign. ‘A chief whip in another life’, said the source. Masters is viewed as being nothing like his predecessor Richard Scudamore, an arch-politician who found it easier to charm or coerce the room during a reign of constant financial growth Masters is more corporate in style and less charismatic in nature, but his approach has slowly been viewed as a strength as football landscape has required a different kind of diplomacyThe depiction is of a CEO in Scudamore who never knowingly entered a vote without being reasonably sure of the outcome. ‘Didactic’ and ‘controlling’ were words used with some affection by a former staffer, with Scudamore’s sharpest achievement rated as his ability to ‘keep the peace’ between 20 separate entities with conflicting agendas. By consensus, that was a more impressive feat than overseeing the consistent rise in television revenues.Masters, an Aston Villa fan who turned 60 in June, is more corporate in style, more process-driven, far less charismatic in nature. For a time, that was interpreted as worse. But within Premier League circles it has slowly been viewed as a strength after a seven-year period in which the football landscape has required a different kind of diplomacy.’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.