Diana Churchill: Winston’s Special ‘Chum’

Posted on January 24, 2022

by Rachel Trethewey

As complex in their own way as their Mitford cousins, Winston and Clementine Churchill’s daughters each had a unique relationship with their famous father. Rachel Trethewey’s biography, The Churchill Sisters, tells their story. Read on for an excerpt.

Firstborn: Clementine with Diana as a baby, 1909.
Photo Credit: Fremantle_Alamy Stock Photo

When Diana was 16, Winston wrote to Clementine that he did not know which one of his daughters he loved most:

But Diana is going to be a great feature in our lives in the next few years. Nature is mysteriously arming her for the ancient conflict. She has a wonderful charm and grace, which grows now perceptibly from month to month.

To gain the polish required to make her debut in society, Diana was sent to stay with a family in Paris. These were carefree days when she was able to develop her own identity away from her overpowering family. Her letters exuded enthusiasm for everything her new life had to offer. Determined to be fashionable, she wrote to her parents telling them she wanted to have her auburn plaits cut off and shingle her hair. The short, curly hairstyle was all the rage and two her Mitford cousins, Nancy and Diana, had done it. Although girls across the country were shingling, it was considered slightly transgressive in upper-class circles. However, Clementine could not preach because she had already shingled hers. Once Diana had done the deed, she wrote ruefully to Winston, ‘I am no longer your Gold Cream Kitten but your Goldless Cream Kitten.’

Enjoying Parisian culture, Diana was stimulated by visits to the theatre, art galleries and museums and, away from her family, she shone. Her host family admired her enquiring mind and thought she was a very intelligent and interesting girl.

Once back in England, Diana continued to have fun. Describing herself to her father as ‘a would-be flapper’, she whizzed around London in her little car, meeting friends and shopping. When she came out as a debutante in 1928, she was featured on the cover of several society magazines, looking chic in a cloche hat and fur-trimmed coat. She was described as ‘picturesque’ with hair ‘like spun gold with a touch of red in it and skin of exquisite cream and roses’ and was likened to her beautiful mother. However, it was noted that she had also inherited her father’s ‘slightly impish smile’.

Planning a party at Downing Street, Diana was full of anticipation. She wrote to Clementine,‘I am so excited for when you come home and for the season and for everything.’ She was determined that every aspect should be perfect for her presentation at court and carefully matched her shell pink dress and shoes, then pirouetted around the drawing room, practising her curtsy in front of an admiring Mary. Believing that she was on the brink of a new life, she seemed more confident than ever before.When Clementine introduced her to the society hostess, Lady Cunard, the old dragon looked Diana up and down and said,‘My, but you are pretty.’ Diana coolly replied, ‘Aren’t I meant to be?’ and swept past her.

Unfortunately, her debutante days turned out to be an anticlimax. Clementine was ill so she could not act as her chaperone and, stepping in at the last minute, Winston made the time to accompany Diana to dances. Once Clementine recovered, neither mother nor daughter enjoyed the endless round of balls and country house parties. 

Shallow society social life never appealed to Clementine or her girls because they had far more intellectual depth than the average aristocratic butterflies who flitted through the season. Nor were they impressed with the supposedly eligible young men on offer. Clementine wrote to Winston that she knew it was her duty to try to find their eldest daughter a suitable husband but, ‘[I] cannot do with these inbred effete sprigs of the ancien regime!’ Understandably, Diana felt uncomfortable in this blatant marriage market which so publicly put to the test a young woman’s attractiveness to the opposite sex.

As the season progressed, Diana’s delicate ego deflated. After being matchmade at one house party with a young man who was a ‘girl hater’, naturally she became timid and, on yet another unrewarding encounter, she admitted to her father that it would be ‘lovely to be home again where one never feels “genee” [embarrassed]’.

At the end of the season Diana remained single. She had failed in the one goal set for her by society. It did not help that yet again she had been upstaged by her glamorous cousin, Diana Mitford. She was one of the debs of the year and immediately found herself a rich husband.

However, the season had not been a complete failure for Diana because it allowed her to get to know her mother better. Clementine had more in common with her girls as they became adults. She was at least as responsible as Winston for her daughters developing into the cultured, well-read women they became. Diana and Clementine went to the theatre regularly together and discussed the latest books. They both found trips abroad stimulating and, spending time alone together in France and Italy, they had ‘the most heavenly time’. While sightseeing and visiting art galleries, Diana discovered her mother was more relaxed when she was away from home. She wrote to her father, ‘Mummie is a completely different person, she is so much stronger and more carefree and better in every way […] If it lasts it will really be too wonderful.’

Clementine also brought her daughters up to have a social conscience and to realise that not everyone was as privileged as themselves. She never forgot the financial hardships she experienced in her youth.While in Venice she taught Diana how to keep her room tidy and darn her own stockings so that she could cope without a maid. She did not want her daughters to expect that they would always be waited on.

Although their relationship improved, mother and daughter never became close. Diana felt that she did not measure up to Clementine’s exacting expectations. Often described as ‘unusual’, she was pretty, but not in the same way as her lithe mother. History was repeating itself and as Clementine had always felt her mother Blanche preferred her more beautiful sister Kitty, Diana was sure Clementine favoured her sister. Sarah had inherited her mother’s strong features and was the most physically like her of the Churchill girls. Diana was more curvaceous and shorter than her mother and sister. As a child she had been slightly plump and throughout her life she was always sensitive about her weight. When Diana was at a dress fitting with Clementine and Sarah she was deeply upset when her mother commented that it was always so much easier to dress her younger daughter. Diana never forgot this casual remark.

Her cousin Anita Leslie remembered finding her in tears at the end of her first season. She told Anita,‘I am so unhappy and Mummy is horrid to me because I haven’t been a success. I have sandy eyelashes.’ Anita claimed that Clementine was ‘downright unkind’ to her eldest daughter. However, the dynamic between them was far more nuanced than that. It seems unlikely her mother ever intended to hurt her, but Clementine’s sharp tongue left lasting scars on Diana’s thin skin. Sadly, Clementine was unable to reach out to her daughter and repair the damage. Perhaps she saw uncomfortable echoes of her own vulnerability in her eldest daughter’s insecurities. When painful emotions were reignited for Clementine, it seems that she blocked them and the person who triggered them out.The rest of the family could only look on with regret as the two sensitive women misunderstood each other.

Wanting her mother and sister to get on, Sarah often acted as peacemaker between them. As they left the dressmakers after Clementine’s thoughtless comment, Sarah squeezed Diana’s hand and said,‘Mama didn’t mean it unkindly. She was trying to bolster me up.’This sisterly solidarity sealed their close relationship. Recognising each other’s insecurities, the two girls developed a mutually supportive relationship which was to survive for the rest of their lives.

There was never any bitchiness between the three Churchill girls – Sarah and Diana’s issues were with their mother, not each other. Clementine’s tart but often truthful remarks are reminiscent of the dialogue between the Mitford girls. They could be razor sharp to each other, too – to a degree, it was witty, a bit of a tease, but it could also be mortally wounding. None of Clementine’s daughters inherited her lacerating tongue; they managed to be amusing without being unkind.

Decades later, when Mary was writing her biography of her mother, she was still wondering what went wrong between Diana and Clementine.Talking to her cousin Peregrine, she asked was their relationship always wrong? Was Clementine always closer to Sarah? Peregrine told her he did not remember any tensions between Diana and her mother when she was growing up. It seems the antagonism developed later, as Diana became a young woman.

Diana was always much closer to her father than her mother. When Clementine was away, Winston’s eldest daughter often kept him company.The newspapers described her as his special ‘chum’ who could always cheer him up. They shared a passion for politics. As a teenager, Diana showed a precocious interest in political ideas. At school she wrote an essay on the complex subject of Tariff Reform versus Free Trade for a competition, and, determined to win, she asked her father for a few hints. Winston later told Clementine that Diana had gained a great deal of information from the newspapers and talked ‘quite intelligently about politics’. She also found campaigning exciting. If Clementine was unavailable, Diana attended meetings with her father. She sat proudly beside him on the platform as he gave his speeches.

When Winston presented his first Budget in 1925, she listened attentively in the parliamentary gallery with her mother and brother, and three years later, she was photographed with her father as he stood on the steps of No. 11 Downing Street holding his red box. Followed by press photographers, she walked with him to the House of Commons where he delivered his Budget. Although she was naturally shy, she began to grow in confidence through her political activity and represented her father at Conservative events and even occasionally made speeches herself.

Women’s roles in politics were changing. Since 1918 many women had the vote and they began to sit as Members of Parliament. The daughters of two of Winston’s Cabinet colleagues, Herbert Asquith and David Lloyd George, were to follow their fathers into Parliament. Diana also had the potential to become a political figure in her own right. She had the connections, the political knowledge and the commitment, but the one thing she lacked was the confidence. It would have taken a woman with a far larger ego than Diana ever had to push herself forward.

Although Clementine had supported votes for women, even when her husband opposed it, the male members of the Churchill family saw politics as a career for men, not women. While he was at Eton, Randolph wrote a derogatory article about women in politics, and decades later, he was still complaining that it had been a great mistake to give women the vote. It was also evident that Winston only thought of his son, not his daughters, following in his footsteps. His view at this time was that women should be attractive adornments to male politicians but not politicians in their own right. Diana’s political apprenticeship, it seemed, was to prepare her to marry a rising star, not to be one herself.

In the 1929 election, all three of Winston’s daughters joined him on the campaign trail in his Epping constituency. He held on to his seat, but the Conservatives lost the election, so the Churchills had to move out of Downing Street.

Later that year, Winston lost a substantial amount of money in the Wall Street Crash and, financially stretched, the Churchills had to shut up Chartwell temporarily. Winston and Clementine moved into a London flat while Mary and Moppet lived in a cottage on the estate. Once he was out of office, Winston was to spend the next decade in the political wilderness, relying on his writing and lecturing for his income.


Photo Credit:
Christopher Kiddey

RACHEL TRETHEWEY has a degree in History from Oxford University, and a PhD in English from Exeter University. At Oxford, she won the Philip Geddes Prize for student journalism. During her subsequent journalist career she wrote features for the Daily Mail and Daily Express and reviewed historical books and biographies for the Independent. The Churchill Sisters is her fourth book.

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