The Famous Socialite Winston Churchill May Have Had An Affair With

Winston Churchill, the famed British prime minister who led his country through some of its most turbulent periods, including World War II, was known to be fiercely devoted to his wife, Clementine. Though some of his attitudes and actions in his day may not stand the test of time when viewed through the lens of modern ideas, he was never suspected, during his lifetime, of being a philanderer.

However, in 2018, as Time reported, researchers claimed that they had evidence that Churchill carried on an extramarital affair with a friend, a down-on-her-luck British socialite named Doris Castlerosse.

Specifically, historians Richard Toye and Warren Dockter provided audiotape of Churchill's former private secretary, Jock Colville, speaking in 1985, supposedly claiming that his former boss had carried on an affair with Castlerosse.

"[Churchill] certainly had an affair, a brief affair with ... Lady Castlerosse as I think she was called. ... Doris Castlerosse, yes that's right," Colville had said.

Here is what is known, suspected, and implied about the socialite Winston Churchill may have had an affair with.

Doris Castelrosse married into the British aristocracy

As The History Press reported, the future Viscountess Castlerosse was born Doris Delevigne in 1900. If that name sounds familiar, it should: she is the great-aunt of models Poppy and Cara Delevigne, according to The Guardian.

Doris was born into rather humble origins for a future member of the British gentry. Her mother was a homemaker, her father a clothing retailer. But as World War I ramped up, Doris and millions of British women like her saw a way out of their rather limited lives and started looking for adventure.

Eventually, she befriended another young woman with adventure on her mind: Gertrude Lawrence, who was herself the mistress of a prominent British officer. The two women caroused around London, enjoying the finer things in life and, in the process, bedding wealthy men.

When she was 28 years old, she married Valentine Browne, who was known socially by his title of Viscount Castlerosse. Though now married, that didn't stop the newly minted viscountess from continuing to have affairs, including one with Winston Churchill's son Randolph Churchill, according to The Telegraph.

Doris Castlerosse vacationed with Winston Churchill and was the subject of his paintings

For a period of time in the 1930s, Winston Churchill was not working in the British government — a period historians refer to as his "wilderness years." During that time, he would often vacation on the French Riviera, at the home of American actress Maxine Elliot. Castlerosse was known to spend time there as well, according to Time.

During their mutual vacations, Churchill would sometimes paint the Viscountess; according to The Guardian he painted at least two portraits of her. It bears noting that Churchill painted several women, including at least one of his wife, according to The Independent.

When they weren't vacationing together in the south of France, they were carrying on back in London, said Castlerosse's niece, Caroline Delevingne.

"My mother had many stories to tell about [the affair] when they stayed in my aunt's house in Berkeley Square. When Winston was coming to visit her, the staff were all given the day off," she said.

However, Churchill reportedly ended the affair not long after, and the couple went their separate ways.

Churchill might have smuggled his alleged mistress out of the United States

In 1942, according to Time, Churchill made a visit to the United States. Ostensibly, the reason for his visit was to meet with President Franklin Delano Roosevelt, in order to secure U.S. cooperation in British efforts to repel Nazi Germany.

However, there was another matter that required his attention as well. Castlerosse, now aging and running out of money, had come to the States hoping to reverse her fortunes, according to The Mitford Society. Her plan having failed, she was stuck on the wrong side of the Atlantic Ocean and desperate to return to Old Blighty — something that was extraordinarily difficult to pull off while a war was raging.

Churchill, however, allegedly pulled strings to get his purported former lover onto a flight back to London. What's more, she apparently had in her possession one of Churchill's portraits of her, a piece of art that, if brought to light, could end Churchill's social standing, marriage, career, and could even jeopardize the war effort.

Fortunately for the prime minister, the painting wasn't found until after Castlerosse had died, after which one of Churchill's men retrieved it before it could be discovered.

Castlerosse died broke and alone

According to The Telegraph, once Castlerosse returned from the States, her former husband, Viscount Castlerosse, tried to make another go of things in their relationship, only to be rebuffed.

In December 1942, a few months after Winston Churchill successfully secured her return to England, Doris took her own life, according to The Independent, reportedly despondent over her age and her lack of social status. She was also reportedly heavily in debt at the time.

Meanwhile, her alleged affair with Churchill was only a couple of chapters in a well-traveled and well-lived, though short, life. According to The History Press, Castleroose had slept her way across Europe in her quest for fun, status, and money, bedding men and befriending (and possibly bedding) women.

She once said of her lifestyle, which at the time had included traveling the world with a wealthy female companion who lavished gifts upon her, that it beat working.

"I much prefer the life I am leading. Takes half the effort and earns twice the money," she reportedly said.