Churchill may have cheated with society’s wildest woman

Winston Churchill was in one of those ‘black dog’ depressing periods in his life, the ‘wilderness years’, as he called them, when he was frustrated, nothing was going right and there seemed no outlet for all that potential for greatness he felt inside him.

He was out of Parliament following the rout of the Tories in the 1929 general election and broke, having lost a fortune in the Wall Street Crash that same year. He threw himself into a heady social life. He drank and gambled and holidayed abroad as the guest of his chum, the wealthy newspaper magnate Lord Beaverbrook.

At Beaverbrook’s villa in France in the spring of 1930, he was introduced to the sassy Doris Delevingne, a society temptress who happens to be the great-aunt of supermodel Cara Delevingne.

Winston Churchill wearing a top hat, long coat and using a walking stick, travelling to Westminster Abbey with his wife Clementine in 1930

He painted her then, if rumour is to be believed, bedded her — though, given her track record, it was more likely she who did the bedding. According to much-repeated gossip, he slept with the voluptuous and highly skilled Doris at the Ritz in Paris where, after their fling, he apparently told her: ‘Doris, you could make a corpse come’.

Another of her countless lovers claimed her phenomenal success with men was down to a sexual trick known as ‘Cleopatra’s grip’.

It’s not easy to think of Churchill — the soon-to-be hero of World War II, his greatness captured in the film Darkest Hour, now winning Baftas and probably Oscars — as a bad boy in this way.

Certainly he was a passionate man when it came to politics. But in matters of sex, he was pretty much a non-starter, always seen as a steadfast, one-woman man loyal to the formidable Clemmie, and not interested in romance. His biographer, the politician Roy Jenkins, calls him ‘probably the least dangerously sexed major politician on either side of the Atlantic since Pitt the Younger’.

So did he really stray in those dog days between the world wars? A book by biographer Lyndsy Spence hints very strongly that he did and a Channel 4 documentary next month called Churchill’s Secret Affair pursues the same theme.

So far, the evidence is slim, resting on the fact that, to his wife’s frustration, he did not dispel the salacious gossip about him and, on the contrary, seemed to revel in it, perhaps enjoying the boost it gave his ego.

But if he really did succumb, the one person who could have proved irresistible, even to him, was the self-indulgent diva described by a cousin as ‘the most arrogant, temperamental, foul-mouthed and ecstatically beautiful woman in London’.

Doris Delevingne was a courtesan in the tradition of Lady Hamilton and Nell Gwyn, who beguiled and entrapped wealthy men and lived on the riches they, in their infatuation, bestowed on her. (Doris, too, set her cap at a king — Edward VIII — only to find her way blocked by the similarly ambitious and sexually inventive Wallis Simpson.)

She was a haberdasher’s daughter, born into a respectable lower-middle-class home in Streatham, South London, a far cry from the Mayfair haunts that would be a magnet for her in her drive to escape her roots and advance in the world.

She began by selling second-hand evening dresses to actresses and chorus girls and was then swept into their demi-mondaine world of nightclubs and rich, footloose men on the lookout for fun.

Doris Castlerosse, nee Doris Delevingne, posing for a portrait ni 1936, but did society's most beautiful woman count Winston Churchill as a lover?

Doris Castlerosse, nee Doris Delevingne, posing for a portrait ni 1936, but did society’s most beautiful woman count Winston Churchill as a lover?

She was taken up by the actress Gertrude Lawrence whose infatuated lover — Household Cavalry officer Philip Astley (his country home was Chequers no less, before it became the country residence of prime ministers) — paid for the Park Lane flat the two women shared as well as the Rolls-Royce and chauffeur that drove them round London.

This was the style she adored and would spend the rest of her life trying, largely successfully, to maintain as she cruised the high society of millionaires, aristocrats and celebrities in search of lovers and suckers.

They flocked to her, drawn by her outrageous, loud-mouthed personality, knowing blue eyes and long legs, flaunted by her daringly high hemlines. She was rewarded with money, Cartier jewels, Schiaparelli dresses and silk stockings from Paris that she wore once then discarded. Her bad-girl reputation went before her and made her even more alluring. A bitchy female acquaintance suggested she write a book called Around The World In 80 Beds.

She fell for a tall, handsome polo-playing American playboy, carpet heir Laddie Sanford. He set her up, then dumped her (for Earl Mountbatten’s wife) and broke her heart.

Her avaricious eyes then fell on Valentine Browne, or Viscount Castlerosse as he was entitled to call himself, the balding son of an Anglo-Irish earl and so fat he couldn’t bend over to tie his own shoelaces.

Despite his physical shortcomings, he was as promiscuous as Doris and had women falling at his feet. It was from this position one of his lovers, performing a sex act on him, looked up and caught him reading the Evening Standard. She ditched him.

A gargantuan and a glutton, he was also every bit as much a kept man as Doris was a kept woman. He got massively into debt and was bailed out by Beaverbrook, who touted him around as his travelling companion and court jester and gave him a job as a gossip columnist (writing in bed, propped up by pillows).

Castlerosse and Doris became inextricably bound up in each other, in a relationship (and eventually a marriage) that was to become a daily hell of public rows, brawling and shouting matches. Once, after Beaverbrook spotted bruises on Doris’s arm, he warned Castlerosse about his conduct, only for Castlerosse to roll up his trousers and show him her teeth-marks on his calf.

Churchill met Doris Delevingne, a society temptress, in the spring of 1930, she also happens to be the great-aunt of supermodel Cara Delevingne (pictured)

Churchill met Doris Delevingne, a society temptress, in the spring of 1930, she also happens to be the great-aunt of supermodel Cara Delevingne (pictured)

What the attraction was no one —not even the two individuals concerned — could say, but it was deep, lasting and terrifying.

Nor did it bring the financial rewards she expected. When they married in 1928, his shocked parents cut him off without a penny. So Doris, now a viscountess with coronets stitched on her Crepe de Chine pillowcases, continued to ply her trade in adultery and intrigue.

He spent money he did not have trying to keep her. She flaunted in his face the diamonds some new besotted lover had given her. They couldn’t be in the same house and took separate suites at Claridge’s, continuing their marital warfare in the hotel’s grand corridors.

That was the state of play in their marriage when she supposedly seduced Winston Churchill in 1930. Two years later, it seems, having had the father, she also had the son. Randolph Churchill was just 21 when she took up with him.

Their affair was discovered by the maitre d’ of the Cavalry Club, who opened the door to an anteroom and was ‘confronted by a pair of long, gorgeous legs waving happily in the air’. Doris, whose face he could not see but whose legs were unmistakable, let out a gasp. When the ‘man between the legs looked up’, the maitre d’ saw it was Randolph Churchill. ‘Get out!’ Randolph yelled.

Soon, the secret affair was common knowledge among London society, and an alarmed Winston intervened and told his son to behave — perhaps, suggests author Lyndsy Spence in her book The Mistress Of Mayfair — ‘thinking it bad form to go where he himself had once trodden’.

But Randolph, an overweight wastrel, persisted and even taunted Castlerosse that he was bedding his wife. He phoned Castlerosse and said: ‘Guess where I am?’ before telling him he was in bed with Doris. He even had the gall to make it a reverse-charge phone call.

A nasty feud developed. When they confronted each other at the Kit-Cat Club, Castlerosse threatened to hit his rival. ‘Don’t do that,’ replied Randolph. ‘I’m not your wife.’

At the San Carlo restaurant, the writer Evelyn Waugh recorded how Castlerosse hurled a vase at Randolph but he ducked and it knocked out Lady Birkenhead, whose husband had been on a wartime expedition to Yugoslavia with Randolph.

It was all too embarrassing. Eventually, parental pressure from Winston prevailed. Doris and Randolph parted, she moving on with barely a backward glance to the next affair.

Winston Churchill was recently brought back to world attention following the release of the Darkest Hour film, which sees Gary Oldman play the former Prime Minister

Winston Churchill was recently brought back to world attention following the release of the Darkest Hour film, which sees Gary Oldman play the former Prime Minister

She did, though, continue to correspond with Winston, and when they met up again at a villa party in the South of France (along with Clemmie) he painted her again, a full-length portrait in the shorts she always wore to flaunt her legs.

Throughout all this, the state of the Castlerosse marriage carried on, but rockier than ever. Castlerosse filed a petition for divorce, withdrew it, then re-instated it.

She continued in her wild ways. When introduced to a new man, she would ask if they had already slept together because she’d been in so many beds she couldn’t always remember.

Such was her confidence in her seductive powers that she drew the photographer Cecil Beaton into her bed, even though she knew he was, in his own words, ‘terribly homosexualist’. She believed she could ‘cure’ him.

She failed, though fellow revellers listened outside their bedroom door and heard the effete Beaton squeal: ‘Oh goody, goody, goody.’ Meanwhile, divorce proceedings dragged on but eventually, in 1938, the marriage was formally ended.

By that time, Doris had found a new benefactor to bed — wealthy American woman Margot Hoffman. She didn’t mind being in a lesbian relationship. As her biographer puts it: ‘She had no scruples when it came to sex. She used it as a means of survival.’ Margot bought a palace in Venice to entertain their friends and they had liveried gondoliers to glide them along the Grand Canal.

But it was a dream that was about to shatter. When war broke out in 1939, Doris was in an enemy country, Italy. She fled to New York with Margot. But the two proved incompatible, however, as with so many of Doris’s dalliances.

They parted, and she was now on her own for the first time in her life and having to fend for herself. She was scared.

She wrote to Castlerosse, who suggested that perhaps they should get back together again, if only she could get back to England — not easy in wartime.

And here came the final twist in the Churchill connection.

She had been writing to him over the years, seeking his advice, offering help with his difficult children, trying to stay connected. There is not much evidence that he responded. Almost certainly he found her an embarrassment, not suitable for a man of his political ambition and high standing.

It didn’t help that she had been a close friend of the fascist Oswald Mosley, and at Blackshirt rallies sat at the front with his wife Diana, one of the notorious Mitford girls.

Churchill had no truck with that. Doris had also deserted England at a time of war — a bad mark against her. But there she was in America and appealing for his help.

What’s more, she had in her possession that portrait he had painted of her. If she went public with it, it could be an embarrassment he did not need at a sensitive time in relations with Washington. ‘Winston and the courtesan’ was not a headline he wanted to see.

Doris’s account, which may well be an invention, is that on a trip to America in 1942, Churchill invited her to a private party at his Washington hotel and insisted that she return home. One fact is indisputable. Someone pulled strings to get her on a Clipper plane to Britain.

Such priority places were rare. Had Churchill quietly made sure she was whisked home and no longer able to cause him trouble? It’s certainly possible.

But home proved not to be as welcoming as she hoped. Castlerosse was there to greet her but was not about to remarry her, having a new wife in mind. Doris was on her own and penniless.

She tried to pawn her diamonds but the police came calling. Such a transaction was forbidden in wartime. She could see no future, certainly not one that fitted with her image of herself.

She was 42, her looks were failing, her allure had dimmed. She swallowed an overdose of barbiturates and never regained consciousness.

And her dalliance with Churchill? However close it was, she took the secret to her grave.