Churchill's Secret Affair

Churchill's Secret Affair


Lady Doris Castlerosse was a leggy, soignée professional London high-society mistress who cast such a spell on Winston Churchill that he painted a very tender portrait of her during a brief sexual liaison.

The picture’s existence would come back to haunt Churchill during the darkest days of the Second World War amid fears that it could be used to undermine his position as war leader.

It’s a measure of the hold that Churchill still has on the popular imagination that the story of his short dalliance is so fascinating decades later. Though it has a very modern resonance – Doris’s great-niece is the model/actress Cara Delevingne.


Documentary exploring the secret relationship between the prime minister and a woman he met in the South of France in the 1930s. During an important visit to President Roosevelt at the height of the war, he was reunited with his former lover, now stranded in the US and in possession of a portrait that could have a devastating impact during a dangerous period for the nation.

Cast & Crew

Director Richard Sanders
Executive Producer Denys Blakeway
Producer Richard Sanders