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Churchill's Secret Affair

Category: News Release


At the height of the Second World War, Winston Churchill visited President Roosevelt in the White House. It was a make-or-break meeting. The UK depended on America's support to defeat Hitler and to ensure the survival of the Western world. But at this crucial moment in history Churchill had something else on his mind: a former lover, stranded in the US was begging him to get her back to Britain. And she had a portrait by the British Prime Minister, which - if revealed - had the potential to wreck his career and damage his country at its hour of greatest need.

This explosive one hour Secret History film reveals the story of Winston Churchill's secret affair, and how it came to haunt him. The story, uncovered by Exeter Professor of History Richard Toye and Warren Dockter, an international historian at Aberystwyth University, will forever cast Churchill in a new light.

In the autumn of 1985, Winston Churchill’s former private secretary Jock Colville gave a frank interview to archivists at Churchill college in Cambridge. For 30 years the tape of that interview lay buried. His words, voiced by an actor in the film, reveal:

“Now this is a somewhat scandalous story and therefore not to be handed out for a great many years. … Winston Churchill was … not a highly sexed man at all, and I don’t think that in his 60 or 55 years’ married life he ever slipped up, except on this one occasion when Lady Churchill was not with him and by moonlight in the south of France, …. he certainly had an affair, a brief affair with … Lady Castlerosse as I think she was called. … Doris Castlerosse, yes that’s right.”

Doris Castlerosse is the great aunt of supermodel Cara Delevingne. In the Delevingne family’s first televised interview about the affair, Doris’s niece, Caroline Delevingne recalls:

“My mother had many stories to tell about … 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. That’s one of the stories my mother told me … and after that, the next day … Doris confided in my mother about it, they were, as I said, good friends as well as being sisters in law, and so , yes, it was known that they were having, having an affair…”

Up until now, Churchill has been revered as a politician who never succumbed to temptation and was always faithful to his wife Clementine. But this intriguing story shows how, at the lowest point of his political career in the 1930s, his 'wilderness years', Churchill spent four holidays in the company of socialite Doris Castlerosse, the great aunt of supermodel Cara Delevingne. During their time in the south of France, Churchill painted three colourful portraits of Doris (he only painted one of his wife) and they continued to meet back London. But when war threatened and Churchill's career revived, the future Prime Minister ended the affair.

Doris moved to Venice, had a relationship with a female American millionaire, before moving to the USA. Her looks - and fortune - declined, and as war came she became increasingly desperate to return home. Churchill's visit to Washington offered her an opportunity, and using her influence on the Prime Minister, she managed to get a rare seat on a flight home.
Doris Castlerosse died of an overdose shortly after her return to London. When her death became known, Lord Beaverbrook, Churchill's fixer, was believed to have quickly moved to retrieve the compromising painting. Churchill's career and reputation were saved and the story of his affair was buried... until now.


Commissioning Editor: Rob Coldstream

Production Company: Menace Films

Executive Producer: Denys Blakeway

Producer/Director: Richard Sanders