Doris Delevingne: The Constant Courtesan

Viscountess Castlerosse

You may think it fun to make love. But if you had to make love to dirty old men as I do, you would think again


The most notorious courtesan of 1930s society, Doris Delevingne boasted that she had reached the height of her profession. Indeed, by the mid ‘thirties, she had risen from humble beginnings in a small terrace house in Beckenham where she lived with her tradesman father, to a swanky address in Mayfair. Advancing on her foundation of beauty, brains and a fancy surname (she fibbed she was descended from a noble Belgian family), Doris set herself up as a one-woman-business, with nothing to trade except her body, and her sparkling wit should her admirer care for conversation. ‘An Englishwoman’s bed is her castle,’ she quipped, quite proud of her achievements. To some it was shameful; but to Doris it was a small price to pay for Rolls Royces, designer shoes, Parisian clothes and baubles from Cartier. She even shortened her name to Delavigne, fearing the original spelling might be too complicated to spell on a cheque. Where most women modestly dismissed their beauty, Doris knew she was beautiful and demanded that her fabulous legs should have a new pair of silk stockings every day, imported from Paris and costing a guinea a pair. She also had a fondness for Italian shoes, buying as many as 250 pairs on a single shopping trip. Anything Doris wanted, she got. Wives of powerful men, and mothers of heirs and spares feared their sons passing Doris’s infamous door on Deanery Street, for they knew one encounter with Doris and they would soon be contributing to her lavish lifestyle. Echoing their qualms, and summing up her scandalous reputation, a society matron snapped: ‘She should write a book and call it around the world in 80 beds.’


Early in her pursuit of riches, Doris met the theatrical actress Gertrude Lawrence who had become the mistress of a Household Cavalry Officer. Becoming flatmates, it soon became clear that both women were intent on climbing to the top. ‘I’m going to be the most celebrated actress in London,’ Gertie announced. ‘And I’m going to marry a Lord,’ Doris replied. An early conquest appeared in the form of Tom Mitford, but this was short-lived and he was not as rich as she had imagined. She soon turned her sights on Cambridge-educated Laddie Sanford, an American multimillionaire known for winning the 1923 Grand National. Setting up home in Park Lane, Doris joined him and found a love-rival in Edwina, Lady Mountbatten. Swiftly moving on from losing her horseman, she snared Sir Edward MacKay Edgar, twenty-five years her senior with enough money and arrogance to buy anything that took his fancy, first a title, and then Doris. But such passing flirtations didn’t last long, and she met the man who would become her husband.


Valentine Castlerosse was working in London as a gossip columnist, but it was his extra-curricular activities that appealed to Doris. He was an heir to an Irish earldom, and he was fat, nasty and broke; though she cared little for his financial status, for she herself had become rich from the money she hoarded off her rich admirers, she set her sights on his title and his castle in County Kerry. The title Lady Castlerosse, she decided, would bring her the type of social acceptance she craved. Quite tellingly, they married in secret, for Castlerosse was too afraid to tell his parents that his wife was a haberdasher’s daughter from Beckenham. Still, marriage meant nothing to Doris and she peddled on with her seduction of rich men – her husband, after all, needed the money. Winston Churchill was so smitten by her charms he painted her portrait three times – or so it was believed. His son, Randolph, too fell under her spell and they began an affair. ‘I hear you’re living with my wife,’ Castlerosse bellowed down the telephone not long after they were married. ‘Yes, I am,’ answered the younger Churchill, ‘which is more than you have the courtesy to do.’ Courtesy did not come into the equation; the couple had tried to live together but to disastrous results. They would kick and punch one another in private, and she would bite and thrash him about in public. Before long, Doris tired of her husband and threw him out of the marital home. Embittered by her rejection, and behaviour, he stood guard across the road, watching well-heeled gentlemen enter and exit the house, often giving them a swat with his blackthorn cane.


When Castlerosse finally plucked up the courage to divorce Doris, he chose to name not one of her many dalliances as co-respondent, but one of the best-known homosexuals of London society, Robert Herbert Percy. But this unusual piece of evidence was not entirely unfounded. Percy had been advised to visit Doris as an attempt to cure him of his homosexuality, and up to the impossible task, she produced a female prostitute and ordered the unsuspecting Percy to cane the terrified wench. Too shy, or perhaps too polite to accept the challenge, Doris gruffly picked up the cane and barked, ‘Here, let me show you how.’ Such antics might have amused her, but it appalled even the closest of her friends. The writer Edith Oliver dismissed her as ‘a common little demi-mondaine…why should one put oneself out for her?’ The high-jinxes were no longer funny; no longer the topic of a risque anecdote. This outsider had outstayed her welcome in Mayfair.


Moving to New York City, Doris lived a semi-gilded existence amongst America’s elite, but at the age of forty she was no longer the high-spirited society girl and her ways and means of getting men into bed for money had become sordid. Two years later, in 1942, Churchill summoned her back to Britain, where she took a suite at the Dorchester. Encountering the old Duke of Marlborough one evening in the hotel’s dining room, she was unnerved by his snide comment about people deserting their country in wartime. The acid remark shook her to the core, for she had gotten into trouble with the police for flogging diamonds in New York – a crime during wartime – to fund her homeward trip. She retired to her bedroom and fixed herself a drink, laced with a fatal dose of sleeping pills.






8 thoughts on “Doris Delevingne: The Constant Courtesan

  1. Valentine Castleross was 15 years younger than Churchill but this article claims Churchill was the younger. Doubtful that she ever lived with Churchill as he was in his 50’s, depressive, not very well off and firmly married.

  2. Pingback: La aventura secreta de Winston Churchill — Blog de Exordio

  3. The Supposed Sexual Relationship Between Winston Churchill & Doris Delavigne
    Clearly for commercial purposes the supposed sexual relationship between Doris Delavigne and Winston Churchill become a very fruitful commercial media platform.
    When in fact this alledged relationship is not supported by anything other than spurious allegations which are at best entirely circumspect. Whereas the relationship between Randolph Churchill was very widely known and subsequently documented.

    As our many of Doris Delavigne’s sexual liaisons which she famously shared with a multitude of leading members of High Society during the 1920’s through the 1930’s internationally.

    It was widely accepted amongst many leading luminaries of London High Society, that her first steps by Doris Delavigne ‘ Along the primrose path ‘ were taken by Doris in company with and arms of one of the handsomest men on England of the 1920’s – 1930’s in international Cafe Society , ex- Calvary Officer and legendary socialite of the period and ‘ Man about town’ in London, New York and on the Côte d’ Azur, Captain Gordon Halsey. The reference for this already published information is to be found within the autobiography of Desmond Young entitled : ‘ Try Anything Twice ‘ see chapter entitled : ‘ An Interlude in Air Street ‘ in which there are various interstin* and illuminating references made concerning less well known aspects of the life of Doris Delavigne during her early steps upon the rungs of the Social Ladder of the day through the skilled employment of her reportedly boundless allure and sexual charms which she shared with so many lovers which have since been so widely ,albeit on occasion inaccurately reported upon by the media.

    Captain Gordon Halsey, would have known Doris Delavigne prior to Doris becoming what might euphemistically perhaps be called ‘ The Toast of London ‘ in the parlance of the period. In particular when Doris worked as ‘ a hostess at The Grafton Galleries Nighclub, which was situated under the famous Grafton Gallery Art Gallery in Grafton Street, off Bond Street in Mayfair in which Captain Gordon Halsey has his first financial interest regarding a fashionable 192O’s London Night Club specifically created for and largely frequented by leading members of High Society in London.

    The Grafton Gallery was subsequently raided by the Police, fined and had it’s licence revoked by the Bow Street Magistrates Court, resulting in the club’s closure.

    Captain Gordon Halsey, then promptly opened his own first upmarket High Society orientated nightclub which quickly became famous, called ‘The Lambs ‘ in Mayfair.
    However, The Lambs became so successful that the club also attracted the unwelcome attentions of th a Police for trangressing the licensing laws by selling alcohol to ‘non members’ which resulted in The Lambs suffering the same fate as The Grafton Galleries Nightclub.

    Following the closure of The Lambs Nightclub, Captain Gordon Halsey purchased a third interest in a financially ailing nightclub called The Quadranr in Air Street sitiuated Regent Street and Picadilly , which was in danger of having to close , as it was making such a loss for it’s gentlemanly owners Desmond Young and his partner Commander Dawes. When Captain Gordon Halsey, offered to buy a third interest in The Quadrant Nightclub Young on the basis that the club must be temporarily closed for total refurbishment and then re-launched at a gala opening both Young and Dawes jumped at the opportunity of having Halsey buy onto their club in the knowledge of having seen the throngs of people from the Tatler and Bystanderr Set of London High Society making their way eagerly and enthusiastically into The Lambs Nightclub prior to it’s untimely closure.

    Captain Gordon Halsey had said to Desmond Young and Commander Dawes, ‘ Let me purchase a third interest in your club and I will then bring all London here ‘ which Desmond Young knew Halsey would be able to do, having seen the erstwhile unparalleled success of The Lambs prior to it’s closure. Halsey was true to his word and The Quadrant became a resounding commercial success from the moment the club re-opened.

    Sadly, Doris Delavigne later became instrumental in The Quadrant Nightclub being successfully prosecute by the Police for transgressing the licensing laws, and being fined a record fine by the magistrates, hitherto never equalled, resulting in the sad demise of The Quadrant which is well documented on by Desmond Young in his autobiography,

    Doris Delavigne and Winston Churchill at Chateau de L’ Horizon
    This fabulous Mediterranean cliffside property at Golfe Juan near Cannes was built by Maxine Elliott a fabulously wealthy American socialite ex-actress and successful business entrepeneur with homes in America, England and on the Côte d’ Azur, L’ Horizon was designed for Maxine by the American architectural residential property genius on the Côte d’ Azur, Barry Diercks in Company with his companion, patron and business partner , a wealthy English socialite and erstwhile Parissien banker Col. Eric Sawyer, who between them were responsible for creating more important residential properties on the Côte d’ Azur than any others ‘ Between the Wars’ .

    I knew both Sawyer and Diercks very well and was often a guest a their famous Villa Le Trident which occupies an entire private headland on L’ Esterel near Miramar. My father Captain Gordon Halsey knew Eric Sawyer from childhood and they were social contemporaries throughout their lives internationally. Hence, my own connection. I was a guest at L’ Horizon as a child during the Post War Years in the early 1950’s when L’ Horizon belonged to the Aly Khan and his wife, Hollywood film goddess Rita Hayworth, where I would habitually meet such luminaries as Gianni Agnelli, Jack Warner of Warner Bros. et al…

    The fact is that the so called revealing shorts that Doris chose to wear at L’ Horizon had been in fashion on the Côte d’ Azur ever since the Mid 1920’s when made fashionable by Americans with villas on Cap d’ Antibes, all largely designed or developed for clients by Barry Diercks and Eric Sawyer.

    What is more the supposed lascivious, suggestive pose adopted by Doris Delavigne for Winston Churchill is an patently absurd description of being in the least suggestive. All anyone has to do is look at the beautiful paintings of ‘ Les Jeunesse d’ Oree ‘ of the 1920’s and 1930’s to be seen adorning the walls of the fabulous Art Deco Hotel Belle Rives at Juan-les-Pins to realise how absurd these allegations of sexual relations between Churchill and Doris Delavigne are.

    Finally, it is beyond the understanding of those unfamiliar with any first hand knowledge of the luminaries 1920’s and 1930’s as to how the wealthy Cafe Society Set of those drawn from High Society behaved right up and until the early 1960’s whereby their generosity and largesse which they extended to those amongst their own rarefied social set defies modern understanding.

    Hence, the absolute nonsense being written about the supposed sexual liaison between Winston Churchill as currently portrayed on Channel 4. And in the latest book on Doris Delavigne..

    The Colleville tape that has been made much of by the media and Caroline Delavigne is not to be relied upon, as of course this allegation by Colleville w@s made to enhance the value of Colleville’s memories of Winston Churchill. I am sure that Colleville would be horrified and aghast at how his comments have been used by others for unworthy spurious percuniary purposes, that are based entirelly supposition and highly circumspect at best..

    Researched, compiled , edited and Written by John Hayden Halsey, only son of Captain Gordon Halsey. See: and click on Nightclub King in list of titles from which to choose..

    • Yes, I agree with the above. I had no part in the documentary and I have my own feelings about it, as I had access to the Churchill archives (amongst others) and I’ve read the letters. The documentary (and family) have taken the letters entirely out of context. But why let the truth get in the way of a good story? My book, the first full length bio on Doris, does not support the claims made by Channel 4.

  4. Dear John Hayden Halsey and The Mitford Society thank you for both writing your information.

    I do hope TV, Radio or Newsprint can hear what you both have mentioned in the near future.

    Thank you for taking the time to write your information.

  5. Pingback: The Churchill Marriage and Lady Castlerosse - Novus Vero

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