In Richard Desmond’s hands, simple objects become terrifying. There’s the receptionist’s bell that he uses to interrupt executives in board meetings, or the cups of tea that occasionally fly over underlings.

For me, the terror begins when he picks up the wine list. This is Coq d’Argent, a rooftop restaurant overlooking the Bank of England. The prices look like cricket scores — and Desmond is on the hunt for an innings victory.

Illustration by James Ferguson of Richard Desmond
© James Ferguson

“We’ll have that one,” he says, before I can intervene. As the sommelier skips away, the sum of £580 lingers on my retina.

So this, I think, is how it feels to be screwed by Richard Desmond. It took less than 10 minutes.

At least I am not the first. If the media mogul goes down in history for anything, it will be screwing — and not just because of his investments in adult TV, which include the world’s most honestly titled channel, Filth.

There was the time when he devised a contractual clause so advantageous that the distributors of his magazines nearly went bankrupt. A judge eventually stepped in; but Desmond nonetheless walked away with £17m.

Last summer, after employees at his Express newspaper titles went a seventh consecutive year without pay rises, the National Union of Journalists described Desmond as “Britain’s greediest billionaire”. “Worst human being on earth,” opined a Sony executive extravagantly and without any explanation, when mulling a possible bid for his broadcaster Channel 5.

But Desmond usually finds a way to answer his detractors. He sold Channel 5 for £463m last year — more than four times the amount he paid for it in 2010. Overlooked for a peerage by the Conservative party, he reinvented himself as the biggest donor to Nigel Farage’s UK Independence party.

Arranging this lunch has taken a year, a period in which Desmond has fallen out with two of his closest communications advisers. He usually comes to Coq d’Argent with his bankers. “You always get a nice table, you can smoke if you want to outside,” he explains. “Of course I don’t smoke because I’m a winner.”

This catches me by surprise; last I heard, cigars were a key part of Desmond’s media-mogul shtick. “The worst thing about giving up smoking is that I’ve put on 16 fucking pounds,” he says. “There was one day that I couldn’t do up any pair of trousers.”

I lower my gaze, and silently agree that the pinstripes on his blue suit do look unnaturally stretched. Desmond, 63, asks how old I am. Thirty-two, I say. “Eight years. Then you’re fucked.”

The menu features a few dozen French dishes, typed in the kind of dull font that is better suited to reading mortgage terms and conditions. “What’s the fish today?” asks Desmond, who used to be pescatarian, and still rarely eats meat. He settles for the waiter’s recommendations — a tuna steak, medium-rare, with a tomato salad to start.

I choose from the vegetarian options — a goat’s cheese-based starter, followed by a goat’s cheese-stuffed main. Desmond orders sides of beans and spinach, presumably for us both.

He turns to me, with the question I had hoped to answer after a glass of wine. “So tell me — what did you think of the book?”

The Real Deal, published this month, is Desmond’s autobiography — the story of how a miserable Jewish kid from north London became a billionaire, and clambered on to the ramparts of the British establishment in the process.

In it, Desmond claims to have started selling advertising at the age of five, as an interpreter for his father Cyril, who had suddenly gone deaf. At 13, he was working in the cloakroom of the Manor House pub, where he quickly realised that if he put two coats on a single hanger he could pocket an extra sixpence. By his early twenties, he had set up his first magazines — International Musician and Recording World, and Home Organist. Then, in 1983, he snapped up the licence to publish Penthouse in the UK, establishing him as one of the country’s porn kings.

Desmond’s trick — be it with celebrity magazines, newspapers or telephone sex lines — has been to copy the market leader and to compete with it ruthlessly. In 1993, seeing the leading celebrity magazine Hello! was full of obscure European royalty — “Prince Schnorbitz of Bratislavia” is how he describes it at lunch — Desmond launched OK!, a rival which focused on British soap stars.

That, and a tight control over costs. By his own account in the book, Desmond once turned down a prostitute because he calculated her fee was the equivalent to the profit on a page-and-a-half of advertising.

“Did it come across that we weren’t in it for the money — but for the craic, for the stirring it up?” he asks. This is how Desmond wants to be seen, and his disarming, jovial persona generally backs it up. But, even at a quiet table overlooking a wisteria-clad patio, his menace is sometimes barely concealed.

His business career? “There’s always some cunt trying to stop me.” The death of Hello!’s owner, Eduardo Sánchez Junco, in 2010, with whom Desmond fought a lengthy court battle over photographs of Michael Douglas and Catherine Zeta-Jones’s wedding? “I take full responsibility for that,” he smiles. A decision by ad agency Omnicom to stop buying spots on Channel 5 the day after he sold it? “I’d have knee-capped them. I’d have gone after the clients directly.”

The food arrives swiftly, along with the wine, a 1983 Bordeaux from the Château Palmer estate. “This is our last bottle,” the sommelier says, in an act of financial mercy. “Oh, I bet you tell that to all the boys,” Desmond replies.

The sommelier is worried that the wine has only just emerged from the cooler, and will still be about 11°C. Might this be grounds for a discount, I wonder hopefully? He assures us that it should be fine within five minutes. “The nose is absolutely fantastic,” he adds.

Desmond picks up his wine glass, and asks if I have any children. No, I reply. “To your children,” he toasts, undeterred.

We move on to politics. Desmond, who in the Daily Express and Daily Star owns two tabloids with combined sales of 1m copies a day, tells me he feels snubbed by the Prime Minister David Cameron.

“Rude,” says Desmond, who claims Cameron once trod on his foot at a party in a rush to approach that bigger media fish Rupert Murdoch. “He’s very lightweight. But he’d be very good running this restaurant, wouldn’t he?”

Desmond fancifully attributes their poor relationship to an encounter years earlier, when Cameron was a PR man whose boss wanted to turn OK! into a TV show. He also blames class: “The non-posh people like me are jealous of the posh people because they have the confidence.”

Despite donating £1.3m to Ukip so far, Desmond is not sure he agrees with its main policy, leaving the European Union. “I don’t know. I don’t think anyone knows,” he says. “But we need a referendum.”

The main courses arrive, and Desmond greets them with his second favourite f-word. “Fantastic. They do look after you here, don’t they?”

I carve into a courgette tart. Desmond heaps English mustard to the left of his tuna. The cuff of his right sleeve rubs into the pesto. The wine is delicious, especially now that I have stopped seeing the reflection of the FT expenses department in my glass.

For decades, Desmond has strived for more. Is he ready to rest yet, I wonder?

In 2012 he married his second wife, Joy Canfield, a former British Airways manager, whom he met in an airport lounge. The two have a four-year-old daughter, and a son, born in January. Robert, Desmond’s son from his first marriage, is also expecting a child. “I’ll be a grandfather and a father in the same year,” Desmond says. “The two boys will be in the same class.”

Why not loosen up, I suggest — starting with a few pay rises for his staff? “There are two types of people: people who think they’re rich and people who think they’re poor,” he explains. He puts himself in the latter category. “All you need is a bad move here, a bad move there, and you’re out.”

His father’s fate — after losing his hearing at the age of 45, he ran up gambling debts — serves as a lesson. “Prime of your fucking life, and the phone doesn’t go. And if the phone went, you couldn’t hear it. So then you do more gambling, more gambling, more gambling.”

Is it paradoxical that Desmond himself now promotes gambling, via his lossmaking Health Lottery? “You can only lose a pound,” he says, referring to the price of a ticket.

Desmond was in his late twenties when his father died. “The more I talk, the more I feel like my father,” he says at one point. Did he like him, I ask? “Did I like him?” he repeats. A long pause. “I didn’t know him.”

In his book, Desmond, a liberal Jew, suggests that he finds it easier to do business with fellow Jews. “Everyone’s having a go at you, so you’ve got to be the fighter,” he says, explaining the camaraderie. “This weekend the Hasidic rabbi will come round with a cheesecake because it’s Shavuot or one of the festivals. It’s nice,” he says. “I mean, I’m not going to eat the cake.” With restraint in mind, we skip dessert, but order espressos.

From outside, it is hard to see where Desmond goes next. His newspapers are past their prime, specialising in dubious headlines such as “Why watching TV gives you diabetes”. “BuzzFeeds, SchmuzzFeeds — at the end of the day, you trust the Daily Express,” he argues.

The internet is not his game. He once met with some Google managers to discuss putting OK! online. “They’re all very smooth, they’re all like out of Thunderbirds, and they’ve all got these fantastic sweaters — don’t know where they get them,” he says.

“By the time you have the fourth meeting, the whole deal’s completely fucking changed. They are the biggest gangsters in the world and they get away with it. One thing I’ve got to say about the European Union is that they are giving them a good kicking.

“I was always slow to adopt the internet, because I knew what would happen,” he says, adding: “It’s interesting how vinyl’s coming back, isn’t it?”

So what does happen next? Desmond has to turn round the Health Lottery — which lost £28m last year, but is a key advertiser for the Express. Since it was established in 2011, it has generated £65m for good causes. He owns property from a former print site on the Thames that he intends to develop. He also holds stakes in an online estate agents, Tepilo, and Lulu, an app for “girls to review guys”.

At one point, while I am trying to make the most of the wine, Desmond suggests that there may be no more big deals. “I’m in spend-down. I’ve got a billion in cash,” he says. “You can’t leave people a billion pounds, can you?” His elder son won’t receive more than £100m, he says.

But when I ask whether the Health Lottery will be his last big project, he doubles back. “I wouldn’t have thought so. Life’s not like that. You bumble through. You’ve got to keep your brain.”

One motivator is his enmity with Camelot, the Canadian-owned company that runs the UK’s National Lottery. “That’s why I’ve got to keep going — so that I can bid for the National Lottery.”

This would give Desmond a public profile that he mostly lacks. He says he was approached to present the UK version of The Apprentice, a show now hosted by his former friend Lord Sugar. “I wanted to be Rupert Murdoch, not Simon Cowell,” he shrugs. (Which is lucky because, according to one person involved in The Apprentice, he was “never close to being a contender”.)

Associates think he is desperate to become a member of the House of Lords. Our espressos drained, I ask if he would accept a Ukip peerage. “I don’t think so. I’m an outsider. I’m like Branson,” he says.

Really? He could be Lord Desmond of Manor House, I say, nodding to the pub where he used to take coats. A mental switch flicks.

“Oh, that is good. I like that, Henry, I like that. That is good, that is good. Oh, that is good. Oh, I like that. Oh, that’s funny. I like that. Oh, that’s funny. Lord Desmond of Manor House, I like that. Cos then there’s a reason, isn’t there — there’s a story. It’s not just another Jew who’s made a few bob and wants to be poncey. That’s, ‘Fuck you!’ ”

I drink the last of my wine, a final jolt of blackcurrant and smoke. Desmond still has half a glass left, but appears to have lost interest. His phone rings, and he listens to his ringtone, a tune by the 1960s US soul duo Sam & Dave, while drumming his fingers on the table.

“Lord Desmond of Manor House,” he says idly, returning to the conversation, before launching into a confusing story about his friend Roger Daltrey, the singer of the Who. “Pete Townshend liked that story,” he says, disappointed by my reaction. He gets up and goes to the loo while I pay the bill.

The restaurant has emptied. We take the lift down together, to where his driver has been waiting. “Remember — this is the start, so don’t, don’t… ” he tells me. At least it’s more subtle than the time he told a hedge fund manager, “I’m the worst enemy you’ll ever have.”

That afternoon Desmond calls three times to clarify various points. Asking about liking his father was a “very very good fucking question”, he says, without elaborating much on his answer.

I take the opportunity to ask what he thought of the wine. “Fucking nice,” crackles the reply. “I asked my wife this morning, ‘Shall I order my usual wine?’ And she said, ‘Yes, you’re a billionaire. If you just order a glass of house red, people will think — what’s wrong with him?’”

Henry Mance is the FT’s media correspondent

Illustration by James Ferguson

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