In the half century since he died, there can be no contemporary British figure whose story has been so scrutinized as Churchill’s. Of course he has his critics, and sometimes with good reason. He could be stubborn and impetuous, driven by ego, and sometimes unsympathetic to the plight of others (especially if they were not British, English-speaking or from a ‘Christian civilization’).


The morality of a few of his actions – such as giving permission for the blanket bombing of German cities – continues to divide opinion sharply. But few credibly argue that he was anything other than a giant figure of his age and one who, for all his faults, delivered what the British nation needed at its most acute time of crisis. My book How to Think Like Churchill looks at the personality traits, ideas, beliefs and some of the other key influences that informed his actions at the various stages of his life, and helped define his worldview. There emerges a figure who is nothing if not complex, combining extraordinary strengths and attributes with humbling weaknesses. For a man who had so many distinct phases to his life, it is hard to pin down exactly who the real Churchill was.

About Winston Churchill

Born: 30 November 1874, Blenheim Palace

Died: 24 January 1965, London. He was 90 years old and had suffered a series of strokes | Read more about Churchill's death and the top-secret plans for his funeral

Winston Churchill was a British statesman and author who served two spells as prime minister, notably from 1940–45 when his inspirational leadership and powerful oratory guided Britain through the Second World War.

His writing career earned him a Nobel Prize in Literature in 1953. Widely acclaimed as one of the greatest Britons in history, he was recently portrayed by Gary Oldman on the big screen in the film Darkest Hour.

His childhood did little to suggest his future greatness

Churchill’s childhood did little to suggest he would come anywhere near to matching the achievements of his illustrious predecessors, such as the Duke of Marlborough. He was prone to ill health, had various speech impediments (including a lisp and a stammer), and had an academic record that could at best be described as patchy. A letter from the assistant master at Harrow sent to Churchill’s mother, Lady Randolph, in July 1888, for instance, detailed several of his faults, including forgetfulness, carelessness and a lack of punctuality.

He began his schooling at St George’s in Ascot aged eight, and his various physical frailties made him an obvious target for bullies. It was, perhaps, this experience that made him so determined to stand up to apparently mighty foes in later life.

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Churchill was a voracious reader

Churchill was a voracious reader known for his ability to process vast quantities of text and to quickly grasp its key points. For a man who is quoted in the English language perhaps more than anybody, with the exception of Shakespeare, it is interesting to note that Churchill was a great fan of quotation collections too. They were, he found, a short cut to unending pools of knowledge.

In My Early Life (1930) he notes: “It is a good thing for an uneducated man to read books of quotations… The quotations when engraved upon the memory give you good thoughts.”

He was accident-prone

He was accident-prone, suffering several nasty falls and, in 1931, was involved in an almost deadly accident with a car on a New York street. Sometimes it seemed like fate had something unhealthy in mind for Churchill, but he was never cowed. Indeed, his many close shaves only seemed to further encourage him to tempt destiny and put himself in the way of yet more danger.

In South Africa: London to Ladysmith via Pretoria (1900), Churchill provided arguably the most vivid insight into his attitude to risk: “You must put your head into the lion’s mouth if the performance is to be a success.”

Winston Churchill making the famed ‘V’ for Victory sign. (Image by Bettmann/Getty Images)
Winston Churchill making the famed ‘V’ for Victory sign. (Image by Bettmann/Getty Images)

Churchill invented several words

Like his hero, William Shakespeare, Churchill was known to invent a word or two. For instance, he is credited with inventing the word ‘summit’ in 1950. He is also said to have helped ‘quisling’ come into popular usage as a synonym for a traitor (Vidkun Quisling having been the fascist military officer who became minister-president of German-occupied Norway in 1942).

He was considered for a Nobel Prize several times before he eventually received one

The Nobel Prize awarding committee had considered Churchill for the literature award several times before he eventually received it in 1953. A report for the committee produced in the 1940s deemed him a significant historian but not one, perhaps, whose work was so important or sparklingly literary that it warranted the grandest of all prizes.

So, after years of his name being mooted, he was finally given the great accolade. The official citation proclaimed that the prize had been awarded for “his mastery of historical and biographical description as well as for brilliant oratory in defending exalted human values”.

His first love was not his wife Clementine

Clementine Churchill was undoubtedly ‘the one’, but as strong and enduring as their relationship was, Clementine was not Churchill’s first love. That honour fell to society beauty Pamela Plowden.

Then came Violet Asquith, daughter of prime minister Herbert Asquith, with whom Clemmie somewhat overlapped. Churchill later revealed that he and Violet were not far short of engaged, and he may well have ended up with her if Clementine had refused his marriage proposal. Violet was distraught to find herself, as she saw it, jilted, and she refused to go to Winston’s wedding.

Winston Churchill and his wife, Clementine, 1964. Courtesy of CSU Archives/Everett Collection. (© Everett Collection Historical/Alamy)

Churchill created some 500 artworks

In 1915 Churchill began his painting career, going on to produce some 500 works during his lifetime. He made countless attractive, idealized landscapes, many of which were later reproduced on greetings cards. Pablo Picasso even noted that “If that man were a painter by profession he’d have no trouble in earning a good living.”

In 1947 Churchill had two works accepted by the Royal Academy, which he had submitted under the pseudonym David Winter. By the time he died, Churchill had exhibited no less than 50 of his works at the Academy.

Churchill’s other hobbies included landscaping and, somewhat unexpectedly, bricklaying. He discussed this particular passion in Volume I of The Second World War: “I lived mainly at Chartwell, where I had much to amuse me. I built with my own hands a large part of two cottages and extensive kitchen-garden walls, and made all kinds of rockeries and waterworks and a large swimming pool which was filtered to limpidity and could be heated to supplement our fickle sunshine.”

Churchill loved to smoke and drink

Churchill truly did love the good life, and would brook little compromise when it came to eating, drinking and smoking. When required to travel by aeroplane during the Second World War, he even had his oxygen mask adapted so that he might be able to smoke through it.

He had a formidable appetite from a young age, once receiving a thrashing at school for stealing sugar from a pantry. In the year before he died, Clemmie insisted he go on a diet. His response was to invest in a pair of scales that recorded his weight as lighter than the ones they'd previously employed.

He was an early adopter of the 'onesie'

Churchill was one of the first adopters of the ‘onesie’. Known as the ‘siren suit’, so called because of its suitability in the event of an air raid, it was essentially an all-in-one outfit designed with both comfort and practicality in mind.

The suits made from a variety of materials, including wool and canvas, but Churchill took things a step further: he commissioned the tailors Turnbull & Asser to make him a selection of differently coloured velvet versions (examples of which may be seen today at his family home at Blenheim Palace).


Daniel Smith’s How to Think Like Churchill, published by Michael O'Mara Books Ltd, is on sale now

This article was first published by HistoryExtra in January 2015