Bringing up Winnie: Winston Churchill’s revealing letters to his mother

It was a relationship that, as Churchill once remarked, was more like brother and sister than mother and son.

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In April 1895, Winston Churchill (aged 20) writes to his mother, Jennie. He wants to buy a polo pony. “My dearest Mamma. . . I am at present very hard up. Would it be possible for you to pay at present so large a sum as £100-£120?… it is an awful bore riding other people’s horses… The sooner the better – as ponies rise in price every day… Unless I give up the game [polo] which would be dreadful. . . With very best love and lots of kisses, I remain, Ever your loving son.”

Churchill had just joined a cavalry regiment, having twice failed to get into Sandhurst. One hundred pounds in 1895 would be £10,000 today – so he’s asking for something really substantial from his recently widowed mother. Furthermore the whole tone is one of expected easy privilege. It’s always worth remembering, when one thinks of Winston Churchill, that he was the quintessential toff: the nephew, and later cousin, of a duke, badly educated at a grand public school, he joined the army as the only prospect of a career. Failing twice to get into Sandhurst is another way of describing someone as either extremely thick or extremely lazy. Always short of funds, he was continually sponging money off his parent. A perfect portrait of a Victorian Hooray Henry.

All the same, this collection of letters is fascinating. Ranging from 1881 (when Churchill was six) to Jennie’s death in 1921, when Churchill was in his late forties and about to enter the so-called Wilderness Years, they shine a piercing light on the man, informed as they inevitably are by benefit of hindsight. And there is no better guide than David Lough, who provides linking commentaries and context to the hundreds of letters, so that the whole volume acts as a kind of hybrid biography/autobiography of the first half of Churchill’s life. Lough wrote a recent, brilliant biography of Churchill called No More Champagne (2015), which sees his life through the lens of his life-long money problems and endless struggle to remain solvent. Much of the correspondence here reflects that perennial theme.

Jennie Churchill was as profligate with money as her eldest son. In 1896 she was swindled by an upper-class con man out of £4,000 (more than £400,000 today). Later in life the tables were turned and she sponged as energetically off her son as he once had off her. “You and I equally thoughtless – spendthrift and extravagant,” he wrote. It was a relationship that, as Churchill once remarked, was more like brother and sister than mother and son. Lough’s commentary is as revealing about Jennie as it is about her famous offspring – a compelling double-portrait steadily emerges from these letters.

Churchill was born in 1874 – he was 27 when the Victorian age ended – and these letters remind us that he was entirely formed as an individual by the 19th century. Its mores, its morals, its diversions, its values, its hierarchies, its assumptions and its rock-solid class boundaries apply as much to Churchill as they did to his aristocratic cousins and his social circle.

Soldiering in India in the 1890s Churchill set out to improve his appalling education. An autodidact, he doggedly read his way to a form of intellectual respectability. In one letter home he outlines his embryonic political credo – at 22 he was already thinking of a career in politics.

I. Reform at home. Extension of the franchise to every male. 2. Imperialism abroad… India must be governed on old principles. 3. European politics. Non Intervention. Keep absolutely unembroiled… 4. Defence. The Colonies must contribute… A mighty navy must keep the seas… There! That is the creed of Tory Democracy.

Evelyn Waugh once said of Churchill that he was a man “always in the wrong”. These letters tend to bear that harsh judgement out – he was violently opposed to home rule for Ireland, for example – and one can see how imperial Britain’s might and sway completely shaped his attitude to “abroad”. And his single-mindedness, his sometimes overweening self-belief and conviction, can be seen as stemming from his absurdly entitled background – as the confidential, unguarded tone of these letters makes clear.

However, there are two instances in his formative years, in particular, that are not really covered by the letters (but emerge through Lough’s expert commentary and footnotes). One is the death of his father, Lord Randolph Churchill, and the other is the extraordinary licentiousness of the life his mother led.

Randolph Churchill – a small fiery man with a huge soup-strainer moustache – effectively destroyed his political career (he was briefly chancellor of the exchequer) through his own vanity and impetuousness. He had a lingering death in his early forties – he died in 1895 – from what was possibly tertiary syphilis (though this can’t be proved). Winston’s letters barely reflect this profound loss, but in fact his father’s example (and failure) as a statesman was the covert driving force behind his own political ambitions. If Winston rose to the top, so would his father’s shame be obliterated and Randolph’s tarnished political reputation somehow re-gilded.

Jennie, for her part, had many lovers, before her husband’s death and after (among them Edward VII). It’s worth recalling that she was only 20 years older than her eldest son and still a beautiful, vibrant woman in her forties in the period when she and Winston were closest, which was before he married. There is an astonishing letter here where we can see that Jennie is actually eyeing up potential future (wealthy) husbands even as her current husband was slowly dying beside her.

Jennie was not only alluring and desirable but also feisty and engagée. After Randolph’s death Winston became the focus of her efforts and ambitions. Through her potent connections in regal, aristocratic and political society she became a super-efficient “fixer” for her son as he tried to advance his career, whether political, literary or journalistic. She often campaigned with him on the hustings. Their relationship lurched a bit when Jennie married George Cornwallis-West, a vapid man-about town, in 1900. George was reputedly the “handsomest man in England” and only 16 days older than her son. It was a fraught society scandal and George was promptly disinherited by his father. The letters about George and Jennie and their rackety, soap-operatic marriage are tactful but full of amusing subtext. It was not what Winston wanted: “I don’t believe you will marry. My idea is that the family pressure will crush George.”

He was wrong. And the tensions of her new marriage (George and Jennie finally divorced in 1914) changed their relationship – she was no longer Winston’s one true confidante, though she remained a constant bulwark of encouragement and support as he sought a wife himself (he was an ardent but unlucky lover until Clementine Hozier arrived on the scene in 1908) and as his political star rose before the First World War and when it dimmed after the Gallipoli debacle in 1915. After Churchill’s post-Gallipoli scapegoating Jennie wrote simply: “Darling old boy I am thinking of you so much & this is only to tell you so.”

Jennie died in 1921, aged 67, from complications arising from a fall down a flight of stairs. She was wearing a new pair of high heels, tripped and broke her ankle badly. Sepsis, amputation and death swiftly followed. She was an indomitable, extraordinary woman and her influence on her son was vital and incalculable. This superb exchange of letters allows us some real understanding of this unique relationship. 

William Boyd’s new novel, “Love Is Blind”, is published by Viking

Darling Winston: 40 Years of Letters Between Winston Churchill and his Mother
Edited by David Lough
Head of Zeus, 610pp, £30

This article appears in the 28 September 2018 issue of the New Statesman, The Tory Brexit crisis