In December 1942, a maid let herself into a suite at the Dorchester Hotel on Park Lane and found the woman inside dead in her bed, a bottle of sleeping pills on the table beside her. She was forty-two years old. Within days, some of the most powerful men in Britain were quietly gathering up her paintings and her letters and carrying them out of that room. She had been a viscountess, a courtesan, a name whispered across two continents, and at the end she owned nothing but the name.
She was born Jessie Doris Devine on the 25th of September 1900 in Streatham, the eldest child and only daughter of a draper named Edward Charles Devine and his wife Jessie. It was a respectable but unglamorous South London upbringing, a world that measured success in shillings rather than acres. But Doris had decided very early that an unremarkable life was not what she intended to have. She was tall, fair, and handsome in the cool, slightly hard style the 1920s would soon make fashionable, and she possessed a complete absence of shame about ambition.
The dress trade was her first ladder. The family business brought her into contact with the theatres, and the theatres brought her into contact with their stars. One of those stars, the actress Gertrude Lawrence, took a liking to the sharp young woman and first drew her up out of the shop and into the rooms where money gathered. She told her friends exactly what she intended to do with her life.
She meant, she said, to climb from flat to flat, each new arrangement a better address than the one before. In the London of the 1920s, there was a name for what Doris became, though polite people preferred not to use it. She was a courtesan, one of a small number of celebrated young women who lived very well on the money of men who were not their husbands. For a brief and dazzling decade, she was perhaps the most famous of them all.
Her early keepers included Tom Mitford, the only brother of the famous Mitford sisters, and the American millionaire Steven Sanford, known to everyone as Laddie. There were others, financiers and aristocrats and men about town, each affair lifting her a little higher and teaching her more about the appetites of powerful men. By the middle of the decade, she had climbed about as high as a courtesan could climb on her own. What she did not yet have was the one thing that would make her untouchable.
She wanted a title. And a title was about to fall in love with her. Valentine Brown was the most feared gossip columnist in London, and against the express wishes of his parents, he married her in secret. By his title he was Viscount Castlerosse, heir to the Earl of Kenmare and to a vast ancient Irish estate at Killarney.
By his trade he was the celebrated society columnist of the Sunday Express. He was enormous, witty, charming, and hopelessly extravagant, and he fell for Doris Devine completely. On the 16th of May 1928, they were married at the register office in Hammersmith, almost furtively, in defiance of his parents and most of his world. The draper’s daughter from Streatham walked in as Miss Devine and walked out as Viscountess Castlerosse.
It was the single greatest leap of her life. The marriage was a sensation. A courtesan who married a viscount was no longer quite a courtesan, but she was not quite a lady either. The hostesses who had refused to receive Doris Devine now had to decide whether they could refuse Viscountess Castlerosse.
Many swallowed their objections because she was extremely good company and because her husband was far too useful and too dangerous to offend. The title was real, and so were the other lovers on both sides of the marriage. Neither of them had married for fidelity. It was an open marriage conducted in plain sight, a scandal the whole of fashionable London had a seat for.
They were two people who understood each other’s nature perfectly and had agreed more or less not to be ruined by it. There were genuine moments of affection, but also furious quarrels, public scenes, separations, and reconciliations. Much of it played out on the Riviera in the 1930s, a glittering, faintly decadent world of white villas and blue water, where Doris belonged utterly. Among the famous names she gathered was the photographer Cecil Beaton, who was linked with her and understood exactly what she was selling.
She had become a kind of living portrait herself, a face that existed to be looked at and discussed. In 1932, she took a lover twenty years her junior. His name was Randolph Churchill, the only son of Winston Churchill, then a politician out of office and out of favor, brooding in the political wilderness. Randolph was twenty-one, headstrong, brilliant, and difficult.
The affair was the kind of liaison Doris’s world took in its stride. What made it matter was where it led. Through Randolph, Doris was drawn into the orbit of the older Churchills on the same sunlit terraces where Winston Churchill spent his long exile from government, painting, writing, and waiting. This is where the documented story begins to blur into the contested one.
That she knew Winston Churchill is certain. That she moved in his circle on the Riviera is certain. That he painted her more than once is certain, for Churchill was a passionate amateur painter, and Doris was exactly the kind of striking subject he liked. Beyond that, the ground grows soft.
In a villa owned by a retired American actress, the Château de l’Horizon near Cannes, Winston Churchill set up his easel and asked Doris to sit. Churchill painting was Churchill at peace, the easel his refuge from the black moods he called his black dog. He painted landscapes, seascapes, the villa, and sometimes the people around him. He painted Doris Castlerosse more than once.
That is not rumor. It is the documented heart of the whole affair. In 1985, a man named John Colville, who had served as one of Churchill’s private secretaries during the war, gave an interview in which he claimed that Churchill and Doris had carried on a love affair for some four years, beginning around 1933. When the claim surfaced publicly decades later, it was electrifying.
But the careful historians who examined it found it troubling. Colville had not become Churchill’s private secretary until 1940, years after the supposed affair was over. Whatever he reported, he reported at second hand. The historian Andrew Roberts rejected the affair outright, pointing out common sense that is hard to argue with: Doris was at the time still married to Viscount Castlerosse, the most waspish and well-informed gossip columnist in Britain.
A cautious adulterer would have chosen very nearly any other woman in England before the wife of the one man certain to find out and to print it. The truth sits in an uncomfortable middle. Churchill knew Doris. Churchill painted Doris.
Whether anything more passed between them cannot now be proved. And yet, whether or not they were lovers, the events that followed her death suggest that someone somewhere in the establishment thought the connection dangerous enough to manage. By 1938, the marriage was over. The union had finally worn through.
They divorced childless after a decade of marriage. The man named as co-respondent was Robert Heber Percy, a flamboyant young aristocrat known throughout society as openly homosexual, a fact that made the naming almost a private joke at Doris’s expense. The story attached to it was that Doris had boasted she could cure such a man of his nature. The choice carried a sneer.
It suggested that the great seductress had been reduced to a punchline. The divorce stripped away the title’s protection. She was once again a woman alone, living on her wits and her fading looks, except that now she was nearly forty, and the looks were the one thing time would not let her keep. She sailed for America in 1940, certain her face would open doors there as it always had, and for the first time it did not.
Part of it was the war, which made a fashionable English woman swanning through American society in the middle of her country’s agony look less like a glamorous exile and more like a deserter. Part of it was that America did not know the old London legend. The largest part was simply time. The jewels began to go, quietly sold and pawned to keep her afloat.
By 1942, she was stranded. She wanted to come back to England, but the Atlantic was a battlefield of submarines. To get back, she needed help from someone with the power to arrange the impossible. She found that someone.
The someone was Winston Churchill, by then the prime minister of a nation fighting for its life. Somehow, in the middle of the war, Churchill’s office arranged for Doris Castlerosse to be brought home. She returned to a darkened, rationed, frightened London and took rooms at the Dorchester Hotel. She was nearly broke.
The jewels were mostly gone, and what remained of her money was tangled in debt. She had attracted the attention of the authorities, for there was a police investigation underway into the illegal selling of diamonds, the very stones she had been quietly disposing of to survive. On the 12th of December 1942, Doris Castlerosse died in her room at the Dorchester from an overdose of sleeping pills. She was forty-two years old.
Whether it was a deliberate act or an accident of too many barbiturates cannot now be known with certainty. The newspapers, which had once devoted columns to her every move, gave her death only the briefest of notices. There was a war on. It should have been the end.
But it was not the end, because of the paintings. Within days of her death, a press baron sat down twice with her grieving brother and came away with the paintings. The press baron was Lord Beaverbrook, one of the most powerful men in Britain, the proprietor of the newspapers that had employed Doris’s husband, a close friend and ally of Winston Churchill, and a man who served in Churchill’s wartime government. He met with Doris’s brother, Dudley Devine, not once but twice.
The grieving brother was persuaded to place the Churchill paintings in Beaverbrook’s care. They passed quietly out of the family’s hands. After the war, a letter from Dudley’s lawyers authorized Beaverbrook to hand over to Captain Dudley Devine the two paintings in his possession belonging to the late Doris, Viscountess Castlerosse. The cold legal language records the essential fact: the canvases the wartime prime minister had painted of a notorious courtesan had spent the war years gathered up and held by his closest political fixer, kept safely away from the eyes of the world.
There is no proof that the paintings were destroyed, and no proof of exactly what was said in those two meetings. But the shape of it is unmistakable. A woman dies, broke, disgraced, and half-forgotten. And yet within days, one of the most powerful men in the country involves himself personally in the fate of her possessions.
Men do not trouble themselves like that over nothing. But one painting was never gathered up, never hidden, never controlled. At Chartwell, the country house in Kent that Churchill loved above all places, among the canvases of a lifetime’s painting, there hung a portrait of Doris Castlerosse, the work of his own hand. The evidence the fixers missed was not buried.
It was on the wall. For decades it hung there quietly. Then, in 2018, a television documentary brought the affair roaring back into the headlines, built around the old claim that Churchill and Doris had been lovers. The newspapers seized on it.
The historians pushed back hard, dismissing the affair as unproven and improbable. The affair is not proven, and the best Churchill scholarship does not believe it. But the suppression is real. It is entirely possible there was no love affair at all, and the frantic gathering of the canvases was the work of cautious men managing a risk that did not in fact exist.
But it is also possible the careful men knew something the historians do not. The honest position is that no one can now be sure, and that the most powerful actors in the story made certain on purpose that it would be so. And through it all, the portrait at Chartwell hung on the wall. A man does not hang on his wall the face of a woman who meant nothing to him.
The draper’s daughter ended with a title, a fortune, and a great man’s portrait, and kept none of them. The marriage ended. The money ran out. The beauty faded.
The diamonds were sold. And the establishment closed quietly over the place where she had been. For a long time, the erasure held. Then, in the 21st century, two young English women rose to international fame as models and actresses, beautiful, talked about, photographed everywhere.
They were the great-nieces of a forgotten viscountess through her brother’s line. Their names were Cara and Poppy Delevingne. And through them, the old story stirred again. What survives of Doris is not the jewels or the title, or even the truth of what passed between her and Churchill, which is gone now beyond recovery.
What survives is the face on the canvas kept by the hand that painted it, the one piece of evidence the powerful men could not gather up. They burned what they could. They hid what they could.
They missed the painting on the wall.