On the morning of December 12, 1942, a maid let herself into a suite at the Dorchester Hotel in London and found Doris Castle Ross 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 celebrated beauty, a name whispered across two continents, and at the end she owned nothing but the name.
Before she was a viscountess, Doris Devine sold secondhand gowns to actresses of the London stage. She was born Jesse Doris Devine on September 25, 1900, in Streatham, the eldest child and only daughter of a draper. The family name had a French ring to it, but there was nothing grand about the life. She grew up among bolts of fabric and the smell of the workroom, in a world that measured success in shillings rather than acres and titles.
It would have been an unremarkable beginning for an unremarkable life, except that Doris had decided very early and very privately that an unremarkable life was not what she intended to have. Her first ladder was the dress trade, which brought her into contact with the theaters and their stars. One of those stars, the actress Gertrude Lawrence, took a liking to the sharp young woman who sold her clothes and drew her up into the rooms where money gathered. Doris understood with an almost unsentimental clarity exactly what she had to sell and exactly what she wanted in return.
She did not drift into the life of a kept woman by accident. She chose it, studied it, and meant to be the best at it London had ever seen. She told her friends without shame what she intended to do with her life, using a phrase that would follow her to the grave. She meant, she said, to climb from flat to flat, a joke and a plan at once, a motto for a career built on the generosity of wealthy men.
In the London of the 1920s, she became 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. The world offered a clever, beautiful woman of the lower middle class exactly one ladder tall enough to reach the life she wanted, and Doris climbed it shrewdly. Her early keepers and lovers were not nobodies. There was Tom Mitford, the only brother of the famous Mitford sisters.
There was the American millionaire Steven Sanford, a polo-playing heir who spent money on a beautiful English woman. There were others, financiers and aristocrats and men about town who paid her bills and competed for the privilege of being seen with her. Each affair lifted her a little higher and taught her more about the appetites of powerful men. She was running a business, and the product was herself.
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 by title Viscount Castlerosse, heir to the Earl of Kenmare and to a vast Irish estate. He was enormous, witty, charming, and hopelessly extravagant, and he fell for Doris completely.
The Kenmares were old Catholic aristocracy, and the idea of the heir marrying a notorious Mayfair courtesan was nearly the end of the world. So the couple married quietly, on May 16, 1928, at a register office in Hammersmith. The draper’s daughter from Streatham walked in as Miss Devine and walked out as Viscountess Castlerosse. The marriage was a sensation because everyone understood what it represented, the rawest kind of social alchemy, beauty and nerve transmuted into rank.
For a brief season, Doris had everything she had set out to win. It should have been the happy ending. It was, in fact, the beginning of the unraveling. From almost the first, the union was an open marriage conducted in plain sight.
Neither of them had married for fidelity. There were quarrels, public scenes, separations, and reconciliations, all played out before an audience that included the gossip writers her husband worked beside. The setting for much of this was the south of France, where the rich and titled of Europe gathered each summer. The Riviera in the 1930s was a glittering, faintly decadent world, and Doris belonged there utterly.
She gathered famous names, including the photographer Cecil Beaton, who understood exactly what Doris was selling. She had become a kind of living portrait, a face that existed to be looked at and discussed. But the surface of all this glamour hid a colder calculation and a deeper loneliness. She had spent her whole life turning herself into something men wanted, and the price of that performance was that almost no one knew the woman underneath it.
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, and he fell into an affair with the famous Lady Castlerosse. What made the affair matter was not the thing itself, but where it led.
Through Randolph, Doris was drawn into the orbit of the older Churchills. On the other side of that door stood the father, easel set up against the Mediterranean light. At a villa owned by a retired American actress, Maxine Elliott, Winston Churchill set up his easel and asked Doris to sit. Churchill painting was Churchill at peace, and he painted landscapes, seascapes, the villa, and sometimes the people around him.
At some point in these years, he painted Doris Castle Ross. This is not rumor. It is the one solid fact from which all the speculation grows, and he painted her more than once. What that painting meant is the question that has launched a thousand arguments.
In 1985, John Colville, who had served as one of Churchill’s private secretaries during the war, gave an interview claiming that Churchill and Doris had carried on a love affair for some four years beginning around 1933. When the claim surfaced publicly, it was electrifying, but careful historians found it troubling. Colville had not become Churchill’s secretary until 1940, years after the supposed affair was over, so whatever he reported was secondhand. The historian Andrew Roberts rejected the affair outright, pointing out that Doris was still married to Viscount Castlerosse, the most well-informed gossip columnist in Britain, and 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.
The honest verdict is that it is possible, that some who knew the circle believed it, and that the historians best placed to judge have largely dismissed it. Yet the events that followed her death suggest that someone somewhere thought the connection dangerous enough to manage. By 1938, the marriage was over. The union had worn through, and they divorced childless after a decade.
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 divorce stripped away more than a husband. It stripped away the title’s protection. She was once again a woman alone, living on her wits and her fading looks, and she was nearly forty.
She sailed for America in 1940, certain her face would open doors 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 during 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 London legend. The largest part was simply time.
There were arrangements, the same kind of relationships that had sustained her in London, but they were thinner, shorter, less generous. The diamonds that were the visible proof of her long success were 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, and that someone was Winston Churchill, by then prime minister of a nation fighting for its life. Somehow, in the middle of the war, Churchill’s office arranged for Doris Castle Ross to be brought home. Why the most overworked man in Britain should have troubled himself with the passage of a fading courtesan has never been fully answered. Doris returned to a darkened, rationed London and took rooms at the Dorchester Hotel.
She was nearly broke, and worse, she had attracted the attention of the authorities, for there was a police investigation underway into the illegal selling of diamonds. On December 12, 1942, she died from an overdose of sleeping pills. Whether it was deliberate or an accident of too many barbiturates cannot now be known. The newspapers gave her death only the briefest notice.
There was a war on, and the death of a faded courtesan was small news. It should have been the end of the story. But the paintings Churchill had painted on the Riviera still existed, and in the days after her death, a quiet and careful operation began. Within days, Lord Beaverbrook, one of the most powerful men in Britain, a close friend and ally of Winston Churchill who served in his wartime government, 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 and stayed out of sight through the remaining years of the war. A letter from Dudley’s lawyers later authorized Beaverbrook to hand over the two paintings in his possession, the cold legal language recording without meaning to essential fact that the canvases the prime minister had painted of a courtesan had been kept safely away from the eyes of the world. Whether anything was burned, whether the operation was ordered from the top or undertaken by a loyal friend acting on his own judgment, cannot be proved.
But the shape of it is unmistakable. Men do not trouble themselves like that over nothing. The very care taken to gather the canvases is itself the strongest evidence that someone believed they mattered. For all the care taken, one painting was never gathered up.
At Chartwell, the country house in Kent that Churchill loved above all places, there hung a portrait of Doris Castle Ross, the work of his own hand, kept and displayed in the heart of his private world. For decades it hung there quietly. And in 2018, a television documentary brought the whole affair roaring back into the headlines, built around the old claim that Churchill and Doris had been lovers. The historians pushed back, 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. The draper’s daughter who set out to climb from flat to flat ended with a title, a fortune, and a great man’s portrait, and kept none of them. For a brilliant decade she had seized everything her birth had denied her, and then one by one, the world had taken it all back. The marriage ended.
The money ran out. The beauty faded. The diamonds were sold. And in the 21st century, two young English women rose to international fame as models and actresses.
The great-nieces of the forgotten viscountess through her brother’s line, their names were Cara and Poppy Delevingne. Through them the old story stirred again, and journalists rediscovered the dazzling, scandalous great-aunt. What survives of Doris is not the jewels or 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, and they missed the painting on the wall.