Lady Castlerosse: The Courtesan Who Seduced Churchill and Shamed British High Society

Lady Castlerosse: The Courtesan Who Seduced Churchill and Shamed British High Society

Doris DeVine, born Jessie Doris DeVine in 1900 above a haberdasher’s shop in Streatham, South London, spent her life engineering a transformation that would make her one of the most scandalous figures of the British upper class. From a modest childhood, she climbed into the beds of millionaires, the drawing rooms of aristocrats, and eventually into a disastrous marriage with an English lord, a union marked by public brawls, mutual violence, and relentless gossip. Her father was a haberdasher who sold French trimmings to London’s aspiring classes, and through frugality, he moved the family to a more respectable home in Beckenham. Her parents believed in hard work and quiet dignity, but Doris wanted more.

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She was clever, musical, and ambitious at a time when British women were expected to retreat into domesticity after the First World War, giving up jobs and dreams so returning soldiers could reclaim their place. Doris chose work instead of marriage, opening a secondhand dress shop in London. There she met Gertrude Lawrence, a red-haired showgirl who taught her a survival rule she would live by: never ask questions, never confirm the truth. Gertie took a job dancing at Murray’s cabaret and was set up in a Park Lane flat by Captain Philip Ashley, a war hero.

Gertie invited Doris to move in, placing her steps away from the homes of dukes and the clubs where a rising politician named Winston Churchill socialized. At the Grafton Galleries in Mayfair, Doris worked as a hostess, wearing black or white opera gloves that became her signature. London began calling her “the girl with the gloves. ” The club was raided and shut down in 1923, but Doris had already learned the skills she needed.

She began an affair with Steven “Laddie” Sanford, an American polo heir to a $40 million fortune. He installed her in a fashionable address with a Rolls-Royce, a driver, and a lady’s maid. She was lavished with Cartier bracelets and handmade Italian shoes, wearing Parisian silk stockings once before discarding them. The relationship ended when Sanford left her for Edwina Mountbatten, an heiress and granddaughter of a close friend of King Edward VII.

When the money stopped, Doris pawned her jewels and kept up appearances. She was the woman left behind, and she hardened. The first time Lord Castlerosse saw Doris, she walked into the St. James nightclub and he forgot the horse race he had lost, the drink in front of him, and the crowd around him.

He was born Valentine Edward Charles Browne in 1891, heir to the Earl of Kenmare. His mother, Lady Kenmare, from the Baring banking dynasty, never forgave her son for arriving short, stout, and with dark features she resented. He was mocked at school and ignored by his father. He was wounded in the First World War when a German bullet struck his arm, leaving him permanently maimed, and he returned home addicted to heroin given to him during treatment.

After the war, Castlerosse failed at finance and turned to writing. Lord Beaverbrook gave him a column in the Sunday Express called “The Londoner’s Log,” where he mocked dukes, dined with dancers, and named names. Readers adored him, but behind the wit was a lonely man who craved affection and trusted no one. Their first meeting was brief.

He called her exhilarating. Days later, her photograph appeared in his column. She found him refreshing at first, describing him as a little boy with a warm heart, but his attention became suffocating. He sent paintings, furs, and jewels he could not afford.

When she warned him to stop, he told her he was not just in love, he was obsessed. What followed was a volatile relationship. They argued publicly and violently. On one occasion, bruised and furious, Doris showed Lord Beaverbrook the marks on her arm and threatened to go to the police.

Castlerosse, summoned and furious, lifted his trouser leg to show where she had bitten him. They swore they would not see each other again, but they could not stay away. In 1928, they married in secret at Hammersmith Register Office. His mother was furious and threatened to cut off the family trust.

His uncle did cut him off. Within 24 hours of the wedding, the marriage collapsed into quarrels about money. Doris ordered coronets stitched onto her pillowcases and embossed on her luggage, while Castlerosse feared his mother’s disapproval. Their fights escalated into public scenes of violence.

She bit him. He slapped her. They rolled across restaurant floors in full view of London society. Six weeks into the marriage, Doris moved out, but she refused to surrender the title.

She had her bruises photographed by her lawyer. They reconciled, separated, and reconciled again. Doris continued affairs with other men, including Randolph Churchill, who taunted Castlerosse by telling him he was in bed with his wife. Castlerosse beat one suspected lover with a blackthorn cane and brawled with Randolph Churchill in Venice.

The marriage became a public spectacle staged in restaurants and printed in the gossip columns. Castlerosse hired detectives. Doris staged affairs. By 1933, they formalized their separation, but they kept circling each other.

Castlerosse collapsed from overeating and overweight, and when Doris sent a telegram asking him to come to Biarritz, he went. By 1936, Doris had become close to Margot Flick Hoffman, a wealthy American heiress. The press called them companions, and society whispered that Margot was in love with Doris. Margot paid the bills and promised a new life in America.

In December 1937, the divorce decree was granted. Doris, in Venice with champagne in hand, posed for photographers, triumphant. The years that followed brought silence and exile. The invitations stopped.

Doris attended fascist rallies not for ideology but out of loyalty to her friend Diana Guinness. She sailed for America with Margot in the spring of 1939, remaking herself in Palm Beach and Palm Springs as a friend of Winston Churchill and an intimate of the Duke of Windsor, none of which was true. In Venice, Margot gave Doris a palace on the Grand Canal, a half-built ruin that once belonged to the Marchesa Luisa Casati. Doris poured Margot’s fortune into its restoration, hosting lavish dinners and lending the palazzo to Douglas Fairbanks and Sylvia Ashley.

She wrote to Churchill that she was no longer dangerous, and he believed her. When war was declared in September 1939, the parties ended. Doris was still at Claridge’s in London, watching the city go quiet. In June 1940, she booked passage on the SS Washington, the last American ship to leave wartime Europe.

A German U-boat surfaced and ordered the ship to stop, but the captain radioed that it was the American Washington, and the submarine let them pass. In New York, Doris found that America had changed. Her titled, theatrical glamour looked out of place. Margot’s money was gone.

Her beauty was faltering. She pawned her diamonds and moved into a single room at the Delmonico Hotel on Park Avenue. She wrote to Churchill that she was unwell, lonely, homesick, and miserable. In London, Castlerosse had remarried.

Six weeks after Doris’s death, he married Enid Lindemann, an Australian heiress who had been his lover before the war. Friends of Doris insisted her death was an accident and that she had still hoped to remarry Castlerosse. Doris had once told a friend that making love to dirty old men was not fun, and that if she had to do it to survive, she would think again. What was thrilling in 1922 was vulgar in 1942.

Castlerosse never learned the full story of the interrogation, the diamonds, or the pills. He blamed himself for her death, writing to Beaverbrook that he had loved Doris with a folly and futility that passed belief, and that he had let her die. Nine months after marrying Enid, Castlerosse died of a massive heart attack. Enid claimed she was pregnant, but at 51, Lady Kenmare demanded an abortion, insisting any child born to a woman of that age would be an idiot.

Enid had the abortion. It was a boy. Doris and Castlerosse died nine months apart. He once said that love was the only tremendous force in the world, and that he had loved Doris.

It was foolish, he said, and true, and the only thing that ever made him feel alive. Doris DeVine, the girl from Streatham who signed her name Jessica in secret and whispered spells into mirrors, climbed into the drawing rooms of society with nothing but nerve and charm. She fought to be seen, to be loved, to stay shimmering just a little longer.

In the end, she died alone in a hotel room, unneeded, unheard, and undone by the silence she could no longer fill.