Advertisement

Revealed: Churchill's secret affair and the painting that could have damaged his reputation

Doris Castlerosse and Winston Churchill on a beach near Chateau de la Horizon during the mid 1930s - Production Company. Channel 4 images must not be altered or manipulated in any way. This picture ma
Doris Castlerosse and Winston Churchill on a beach near Chateau de la Horizon during the mid 1930s - Production Company. Channel 4 images must not be altered or manipulated in any way. This picture ma

The year is 1942 and Britain’s wartime Prime Minister is at the White House for a summit with the President of the United States to discuss the progress of the war against Nazi Germany.

Tobruk has just fallen to Germans and Italian troops and Winston Churchill is desperate to retain the support of the American public, many of who are suspicious of their country’s recent intervention in the old world’s quarrels.

But he also has a pressing personal matter on his mind.

At the same time as leading Britain in the war in Africa and Europe, and trying to emphasise the need for the US to stand shoulder to shoulder with this country in the face of totalitarian dictatorship, Churchill is trying to arrange for the return to the UK of an old acquaintance, the beautiful and glamorous London socialite Doris Castlerosse.

Lady Castlerosse in the south of France, at the time of her affair with Churchill
Lady Castlerosse in the south of France, at the time of her affair with Churchill

In fact Lady Castlerosse was an old flame of Churchill’s and the full details of the brief, but passionate affair they enjoyed nearly eight year earlier can now be revealed for the first time.

It has now emerged that arranging for his former lover’s safe passage was not just a matter of sentiment for the Prime Minister.

Historians have discovered that Churchill was particularly keen for her to return to London before the American public got wind of their previous relationship.

Indeed, the last thing he wanted was Lady Castlerosse revealing details of their affair to the newspapers, including the fact that during their relationship he had painted sensuous portraits of her, one of which she had kept in her possession..

The discovery in the Churchill Archives by Dr Warren Dockter, lecturer in international politics at Aberystwyth University, of a taped interview with the Prime Minister’s private secretary, Jock Colville, confirmed the long rumoured affair.

Cara Delevingne, the great niece of Churchill's lover, Lady Castlerosse - Credit: Kirstin Sinclair/Getty Images
Cara Delevingne, the great niece of Churchill's lover, Lady Castlerosse Credit: Kirstin Sinclair/Getty Images

The fling between Churchill and Lady Castlerosse - who happens to be the great aunt of Cara Delevingne, the model and actress - took place when they holidayed together on four occasions between 1934 and 1936 at a chateau owned by an American actress in the south of France.

It was here that Churchill, a keen amateur artist, painted Lady Castlerosse’s portrait. One canvas shows her reclining languidly on a couch.

Churchill’s marriage to his wife Clementine was going through a rocky patch and his political career was in the doldrums and friends say he sought refuge, albeit briefly, in her arms.

Lady Castlerosse’s niece Caroline Delevingne, Cara’s aunt, says: “They had an affair. Both my parents talked about it and knew about it.”

A never before seen letter, discovered by Professor Richard Toye, of Exeter University, lays bare how close the pair were.

In 1934 Churchill wrote to Doris: “What fun we had at Maxine’s. It was beautiful having you there. You were once again a manifest blessing and a ray of sunshine around the pool. I wonder whether we shall meet again next summer.”

They did, but by 1937 the affair had run its course. Churchill threw himself back into front line politics and devoted himself to driving home his warnings about the danger posed by Hitler.

One of the portraits painted by Churchill of Lady Castlerosse - Credit: Channel 4 
One of the portraits painted by Churchill of Lady Castlerosse Credit: Channel 4

Their paths crossed again in the June of 1942, by which point Lady Castlerosse was living in New York but, with no means of supporting herself, was desperate to return to Britain.

With all available ships used to ferry troops and supplies to Britain passage home was hard to find.

During his visit to Washington Churchill sneaks away for a private dinner with his former lover.

Here according to Lady Castlerosse’s husband Valentine, Churchill expresses his concern that the sultry portrait he painted of her might fall into the hands of US gossip magazines and undermine his reputation - at a time when the Anglo-American alliance needs to remain steadfast.

Dr Dockter tells a forthcoming Channel 4 documentary: “He was vulnerable to being blackmailed and must have thought ‘I just have to deal with this and get her back to Britain as soon as possible’.”

Churchill and President Franklin D. Roosevelt pictured during the meeting of the Pacific War Council at the White House in June 1942 - Credit: Corbis
Churchill and President Franklin D. Roosevelt pictured during the meeting of the Pacific War Council at the White House in June 1942 Credit: Corbis

In the summer of 1942 Lady Castlerosse writes to President Roosevelt thanking him for his efforts on Churchill’s behalf to get her safe passage home and shortly after she is found a space on a seaplane for the return flight back to Blighty - taking the portrait home with her.

Churchill and Lady Castlerosse never have the chance to meet again. On December 9, 1942, she died of an overdose of sleeping pills at the Dorchester Hotel, in London’s Park Lane.

There is no record of Churchill’s reaction, but shortly after Churchill’s friend and ally, the newspaper magnate Lord Beaverbrook, met Lady Castlerosse’s brother and took possession of the painting, only returning it to the family at the end of the war.

Dr Dockter says the revelations about Churchill's affair with Lady Castlerosse and his portrait of her she new light on the wartime leader.

“When he’s leading his country in a global war and under enormous pressure, he comes to fear that people might get wind of the affair he’d had with Lady Castlerosse.

“It underscores his greatness that in the midst of all that pressure he can break off to deal with that potential problem,” Dr Dockter told The Telegraph.

“Churchill has been deified, but this story allows us to view him as a far more complex character. He’s still a national hero, but he’s also a guy who has an affair.”

  • Churchill’s Secret Affair is on Channel 4 on March 4 at 8pm