From Playboy pin-up to prohibitionist: the man taking on British gambling

Rupert Hawksley Rupert Hawksley
 Harvey Rothman
issue 26 September 2026

The August 2004 cover of Playboy features a topless Eva Herzigova (‘The supermodel is supernaked’) and promises a piece about ‘America’s 10 sexiest bartenders’. If that isn’t enough to excite you, another article is puffed, no less conspicuously: ‘Weird new casino games (and the men who invent them)’.

Turn to page 73 and a bald, bespectacled man, with ‘prominent ears on a frank, slightly frowning face’, stares out at you. This, we learn, is the ‘Bill Gates of card game inventors’ and his name is Derek Webb. The Englishman made his money at the poker tables in Derby: ‘I could play three times a week with a £50 buy-in and make £8,000 a night.’ From 1979 to 1994, Webb split his time between the East Midlands and Las Vegas. After losing $50,000 on a single hand, Webb realised there must be an easier way to become the richest man in the casino. He began inventing games. ‘You can become a multimillionaire,’ he tells Playboy, ‘that’s the attraction.’

Webb later sold the rights to his first game – three card poker – for $25 million. The feature concludes with Webb enthusing about his next invention: a machine that, as Playboy explains, can ‘take the elements of a table game and put them inside a slot machine’.

Fast forward two decades and Webb, now in his seventies, has swapped poker for policy – and the gambling industry, where he made his fortune, is firmly in his crosshairs. In 2012, Webb founded the Campaign for Fairer Gambling and successfully lobbied for the maximum stake on fixed odds betting terminals (FOBTs) to be reduced from £100 to £2. He donated £1.3 million to the Labour party between 2023-24 and funds the Social Market Foundation (SMF), a thinktank which has played a fundamental role in shaping government policy on gambling, as well as advocacy groups Clean Up Gambling and the Coalition to End Gambling Ads.

It’s an extraordinary pivot for a man whose inventions, Playboy notes, are ‘designed, as all casino games must be, so that the longer a gambler plays, the more he or she is likely to lose’. What exactly prompted this poacher to turn gamekeeper is unclear. Webb dismisses as ‘evil’ the suggestion he is acting on behalf of casinos, which benefit when gamblers desert high-street bookmakers. In 2024, he told the Guardian he is simply ‘motivated to try to change the gambling regulatory system’, adding, ‘it would be a dereliction of duty if they [the Treasury] don’t do something, but that’s not up to me.’

Yet all the right people appear to be listening to Webb. One of Andy Burnham’s first announcements was a ‘crackdown’ on betting shops, the latest salvo in a sustained attack on the gambling industry. Punitive tax rises in last year’s Budget, followed by the phased introduction of financial risk assessments (FRAs) for punters, have hit the industry hard. When bookmakers warned last year that raising remote gaming duty (RGD) – tax paid on online casino betting – from 21 per cent to 40 per cent would lead to shop closures, job losses and a boom in the black market, they were accused of crying wolf.

Yet here we are. Last week, Entain, parent company of Ladbrokes and Coral, announced 400 job cuts. This follows news that Betfred and Paddy Power will close a combined 232 shops. Step back and the numbers are even starker. In March 2014, there were 9,111 book-makers in the UK; there are now fewer than 6,000. As one gambling expert puts it: ‘[This is] a policy justified by proliferation, aimed at a sector in retreat.’

A misunderstanding, or misuse, of data seems to be a recurring theme. In recent years, the Gambling Commission, which advises the government, released the results of the Gambling Survey for Great Britain (GSGB) and the Young People and Gambling survey. One number jumps out: 5.3 per cent of children had been prompted into unplanned gambling by an advert or promotion. Look more closely and this claim disintegrates: 61 per cent of those claiming to have been prompted to gamble also reported… not having gambled. Moreover, the most common forms of ‘gambling’ among young people are arcade games, such as the claw machine, or betting with friends and family.

Gordon Brown is dismissing racing as collateral damage in his crusade against the gambling industry

The Gambling Commission has been alerted to flaws in this survey, yet it is still being used to influence policy. Last week, a House of Lords Liaison Committee published a report recommending a ‘comprehensive’ ban on gambling advertising, despite hearing evidence that the GSGB ‘cannot be considered to be a reliable source of statistics on the licensed market’. Stephen Foster, who worked at the Gambling Commission for 15 years before retiring in 2022, is withering. ‘The public health approach to gambling is simply a fig leaf for those that feel gambling is morally wrong,’ he wrote recently.

The prohibitionists won’t stop. There are already loud calls for further tax rises on bookmakers at the Budget. In August, Gordon Brown told the Today programme that an increase in machine games duty (MGD) could raise ‘up to £500 million’ for the Treasury. ‘In the immediate future I think Andy Burnham, I know him well, will want to do something along the lines I am suggesting,’ Brown explained. Which, in a roundabout way, brings us back to Derek Webb. Last year, the All-Party Parliamentary Group on Gambling Reform received, from a firm called Dentons Global Advisors, between £16,501 and £18,000. Documents show this was actually paid by Webb. And it is perhaps interesting to note that a head of public affairs at Dentons Global Advisors is Katherine Morgan, who served as private secretary in Gordon Brown’s Treasury.

The consequences of this war on gambling are far-reaching. Horse racing, the second most-attended sport in the country, depends on bookmakers for media rights payments and the levy, where a percentage of every bet is returned to the sport. Each round of shop closures further erodes this sum of money. The sport of kings is being suffocated by left-wing thinktanks and Labour politicians determined to tell working-class people how they should spend their money.

So when Brown calls for an increase in machine games duty, he is essentially dismissing racing as collateral damage in his crusade. ‘I’m not asking anyone to feel sorry for bookmakers,’ Betfred boss Fred Done wrote in the Sunday Times last weekend. ‘But I am asking the government to open their eyes. You can’t squeeze any more out of this industry. Every penny more of tax will kill investment, kill jobs, and kill horse racing.’

These are hard truths. But for the anti-gambling lobby so generously funded by Derek Webb, whose cold rationale made him millions at the poker table and earned him a profile in Playboy, it seems ideology now trumps reason.

Comments