Maxine Elliott: The Maine Starlet and Winston Churchill

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In all the movies, books and histories that explored the life of British Prime Minister Winston Churchill, only a short excerpt from an aide’s long-ignored oral history revealed his tragic affair with British celebrity Doris Castlerosse in the 1930s. It also revealed how Maine’s Maxine Elliott made it happen.

Doris Castlerosse, a British socialite, made a habit of sleeping with wealthy men. She had relationships with both Winston Churchill and his son Randolph. Born in modest circumstances, Castlerosse’s marriage to Richard Castlerosse, a viscount and columnist for England’s Sunday Express, catapulted her to fame.

They had a violent, turbulent marriage that did little to slow Doris’ interest in other men (and probably women). With Richard Castlerosse’s family cutting off his access to the family money, Doris frequently needed money to fuel her globe-trotting lifestyle.

In the 1930s in the south of France, at Cannes, Doris crossed paths with Maxine Elliott, who was then in the final chapter of her eventful life.

Maxine Elliott

Maxine Elliott was born Jessie Dermott, in 1868 to a Rockland, Maine, sea captain. She went to New York as a young woman and married comedian Nat Goodwin. Maxine’s beauty and acting abilities led to a 30-year career as a stage actress, and she skyrocketed to fame. For a time, she also operated a New York theater branded with her name, “Maxine Elliot’s Theatre.”

Maxine’s life was a wild one. Her intimates included J.P. Morgan, British King Edward VII and Charlie Chaplin, among many others. In 1913 she began dating New Zealand tennis star Anthony Wilding.  During World War I she went so far as to donate her money and her time to Belgian war relief. But Wilding was killed in the war.

By 1920, Maxine’s talent, and some help from her wealthy friends, had left her with no need for more money. She retired to a Mediterranean estate in Cannes, France. She wished to age gracefully at her home, Château de l’Horizon. A white art deco villa, it featured a large terrace and a long slide to drop her and her guests from the swimming pool into the sea.

Large parties of libertines assembled at Maxine Elliott’s French estate, and it became notorious. Winston Churchill visited from 1933 to 1939. During these years Churchill fell out of favor with the majority of Britons. He spent his time on the French Riviera, writing and plotting his return to power.

Winston’s wife Clementine had little use for Château de l’Horizon or Maxine and her friends. Clementine viewed them as gossipy and frivolous. Though perhaps her objections were more directly related to a single guest, Doris Castlerosse. It was at Château de l’Horizon that Winston and Doris would begin their affair.

People have long known about Churchill’s connection with Doris. In one letter to her he writes, “What fun we had at Maxine’s. I wonder shall we meet again next summer.”

Dirty Old Men

Yet Churchill scholars defended him for decades, arguing there was no proof of an affair. Then in 2018, someone finally listened to the oral history of his aide, Jack Colville. Colville recorded his recollections in 1985, though they remained un-listened-to for decades. When someone did listen to them, they found the revelation. “He was not highly sexed and I don’t think he ever slipped up, except the once. He had a brief affair with Doris Castlerosse.”

The affair lasted from 1933 to 1937. Churchill once repaid Castlerosse for her affection during the war years by securing a seat for her on an airplane from New York to London. He did it either as an act of kindness or because someone blackmailed him.

Maxine Elliot/Jessie Dermott died at her French estate in 1940 at age 72, far from her Rockland, Maine, beginnings. Her estate now belongs to the Saudi royal family.

Doris Castlerosse died in 1948 of an overdose of sleeping pills. In need of money as always, she was under investigation by Scotland Yard. Detectives were looking into her plans to sell some of her diamonds, illegal during World War II.

Her life as one of Britain’s wildest socialites caused talk in England for decades, though she had some cautions for others who might follow in her footsteps. “You may think it fun to make love,” she once said, “but if you had to make love to dirty old men as I do, you would think again.”

This story about Maxine Elliott was updated in 2022.