Walking with Destiny | Brunswick Group
Brunswick Review The Resilience Issue

Walking with Destiny

Historian and best-selling author Andrew Roberts discusses Winston Churchill’s tortuous political path and the legendary statesman's surprising physical resilience. Churchill survived one house fire, two plane crashes, three car crashes, four bouts of pneumonia during World War II, five wars as a soldier ... and a prison break in South Africa.

There were 1,009 biographies of Winston Churchill before Andrew Roberts published the 1,010th in October last year: Churchill: Walking with Destiny. One of Britain’s best-known and best-selling historians, Mr. Roberts had already written four books with Churchill’s name in the title and his latest work features more pages (1,110) than predecessors. Was there really that much more to be said?

The New York Times titled its review of Mr. Roberts’ book “Is This the Best One-Volume Biography of Churchill Yet Written?” (the Times’ answer: yes). The Sunday Times, Daily Telegraph and The Wall Street Journal gave verbatim assessments in their reviews. The Economist called it one of the best books of 2018.

The Brunswick Review spoke with Mr. Roberts on the US leg of his global book tour, which had featured discussions moderated by political heavyweights—including Karl Rove and Michael Gove—alongside the occasionally bizarre conversation. “A lady in Miami earnestly informed me that she was the reincarnation of Winston Churchill,” Mr. Roberts said. “I inquired a little bit more about this, because obviously I’ve been waiting all my life to meet Winston Churchill. I’ve met him a couple of times in dreams, but then I haven’t actually been able to sort of interview him consciously. Unfortunately, I think she was Churchill’s reincarnation from the last years of his life when, sadly, his mind was wandering a bit, because she didn’t seem to know very much about Winston Churchill when I asked her some questions about him. She did buy three books though, which now that I think about it, might make her self-absorbed.”


The iconic photograph of Churchill, which serves as the cover image of Mr. Roberts’ book, was taken by Armenian-Canadian photographer Yousuf Karsh in 1941. After delivering a speech in Ottawa, Churchill was surprised to find Mr. Karsh waiting to take his picture, but agreed to have one taken. “I offered him an ash-tray for his cigar, but he pointedly ignored it, his eyes boring into mine,” Mr. Karsh recounted. With his camera equipment set up, Mr. Karsh removed the cigar from Churchill's mouth without asking. “His jaw tightened in belligerence; his eyes blazed. I clicked the shutter.” Mr. Roberts wrote it is “the greatest of all the thousands of images of Churchill, capturing his resolution, defiance and solidity ... and his capacity for belligerence.” The scar on Churchill's forehead came from an accident while crossing Fifth Avenue in New York City in 1931—he was hit by a car. The scar was said to glow red when Churchill raged during wartime meetings.

Walking with Destiny features a wealth of new information, including passages from the diaries of King George VI, who held private weekly meetings with Churchill throughout World War II. At these meetings, Churchill aired frustrations—with his American and Russian allies, with British military leaders—which he understandably never voiced in public, giving Mr. Roberts an unfiltered look at Churchill’s thinking and opinions throughout the war. Permission to use those diaries was granted by Queen Elizabeth II, marking the first time a Churchill biographer had been given access to them. 

For a character who has generated a small library’s worth of books—Churchill himself authored more than 6 million words, surpassing Shakespeare’s and Dickens’ combined output—Mr. Roberts’ book feels surprisingly fresh thanks to all its new material. And for a biography that describes a leader who died more than 50 years ago, it also feels strangely timely.

Amid the ongoing drama of Brexit, Walking with Destiny highlights Churchill’s views on what relationship the UK should aim to have with a united Europe. In 1952, he told the House of Commons: “…nor do we intend to be merged in a Federal European system. We feel we have a special relationship [to the rest of Europe]. This can be expressed by prepositions, by the preposition ‘with’ but not ‘of’—we are with them, but not of them.”

However, Mr. Roberts points out that guessing what Churchill’s views on Brexit would be, or what Churchill would have thought of US President Donald Trump’s leadership style, are questions “impossible for anyone short of a necromancer to know.” Though Mr. Roberts added: “I do believe Churchill would have been wonderful on Twitter.” 

Hulton Archive/Getty Images

A young Winston Churchill in uniform of the Fourth Queen’s Own Hussars. Over the course of his military career, Churchill fought in five wars. In an 1898 cavalry charge in Sudan, he killed four men with a 10-shot Mauser automatic pistol.   

Walking with Destiny was also published a few months before the UK’s Shadow Chancellor, John McDonnell, called Churchill a “villain” in an interview, a remark that sparked widespread debate about Churchill’s legacy.

Mr. Roberts’ view of the matter is clear; the book’s final words are “the battles he [Churchill] won saved Liberty.” However, Churchill’s detractors point to his backward stances on Indian independence and female suffrage, and hold him responsible for a 1943 famine in India that saw more than 1 million people starve. Mr. McDonnell based his “villain” assessment on Churchill’s decision as Home Secretary to send troops to control a miners’ strike in 1910; one man was killed. Each charge is addressed—and countered or contextualized—in Walking with Destiny.

Mr. Roberts, who has spent 30 years studying Churchill, wrote the book in 100 days. He did so in his study, a room decorated with cases and frames displaying Churchill memorabilia, including Churchill’s bow tie and hairbrush, as well as an ink drawing of a pig that the amateur painter Churchill created with his eyes shut. 

Had the time studying Churchill and being surrounded by his memorabilia inspired Mr. Roberts to adopt any Churchillian habits himself? “I take a nap every afternoon, and I’m a historian who writes for money, but that’s about it. A friend of mine tried to follow Churchill’s drinking regimen, but after three days his wife complained vociferously. And quite right. I haven’t gone down that route yet, thankfully.”

The portrait of Churchill that emerges in Mr. Roberts’ work is one that defies simplistic stereotypes and embraces Churchill’s endless contradictions, a man who is both a grand strategist yet an at-times infuriating micromanager, loyal but prone to selfishness, demonstrating legendary foresight yet also making decisions that left him on the wrong side of history. This is a treatment of which Churchill himself would have approved. “To do justice to a great man, discriminating criticism is necessary,” Churchill once wrote. “Gush, however quenching, is always insipid.”

The most popular images of Churchill find him overweight and cane-hobbled, yet his life was marked by uncommon physical courage and endurance.

Walking with Destiny also seeks to dispel a number of popular conceptions, arguing that Churchill was neither an alcoholic—“alcohol was always his servant, never his master,” says Mr. Roberts—nor a depressive, two diagnoses often made about Churchill. Mr. Roberts contends Churchill was simply a man with “an ox-like constitution” who drank frequently but functionally—he was noticeably drunk only once during World War II—and a leader who endured dark moments “when any sentient being would be depressed, like after the fall of Singapore or after the Dardanelles catastrophe—but he always bounced back.” Extensive research by Mr. Roberts also reveals no evidence that Churchill knew in advance, and then callously chose to keep silent, about the bombings of Coventry and later Pearl Harbor—two of the many internet-driven conspiracy theories which have been leveled so frequently that they warranted the historian’s rebuttal.

There are few contradictions or misconceptions when it comes to Churchill’s resilience. It was the theme of his greatest speeches, the backbone of his unofficial wartime strategy—“keep buggering on”—and the hallmark of his political career. “If you’re looking for a modern-day equivalent for a business leader, here’s a man whose share price has plummeted and skyrocketed, then plummeted and skyrocketed again and again and again, and he hasn’t let it affect him because he was tremendously resilient.”

Churchill, a war-hero and best-selling author by age 23, lost his first election for MP at the age of 24. He would become Home Secretary, a cabinet-level position, at age 35, and a little over a year later was appointed First Lord of the Admiralty, which ran the navy. While there he oversaw a catastrophic World War I campaign in the Dardanelles, which led to more than 110,000 troops from the British Empire being killed or wounded. He resigned the post in 1915 and went to fight in the war. Even there, he remained undaunted: “My conviction that the greatest of my work is still to be done is strong within me: and I ride reposefully along the gale,” he wrote to his wife Clementine from the trenches.

Churchill lost three elections in two years, but by 1924, had returned as a political force and was named Chancellor of the Exchequer, where he served a five-year term largely defined by a single mistake: returning Britain to the gold standard. By 1929, Churchill had isolated himself from his party and was politically sidelined for most of the 1930s, subsequently enduring what are often called “the wilderness years,” where he vocally opposed German appeasement and advocated for British rearmament—pleas that were fatefully ignored. He occupied no ministerial roles until 1939, when he returned to the post he had resigned 24 years earlier: First Lord of the Admiralty. 

In May 1940, at age 65, Churchill became the country’s Prime Minister and inspired Great Britain to victory in World War II—only for his Conservative party to lose nationwide elections in 1945. He would serve as Prime Minister once more from 1951–1955.


Andrew Roberts, one of Britain’s best-known and best-selling historians, and author of Walking with Destiny.

”Churchill’s sense of destiny is
key to his resilience ... even as
a student at Harrow, he believed
he was going to save London,
save the empire.”

Nor was Churchill’s resilience limited to his political career. The most popular images of Churchill find him overweight and cane-hobbled, yet his life was marked by uncommon physical courage and endurance. He was stabbed in the stomach with a penknife while a student; he survived one house fire, two plane crashes and three car crashes; he nearly drowned in a lake; he partook in the last cavalry charge in British military history—the famed Omdurman charge, in modern-day Sudan; he escaped from prison in South Africa during the Boer War; and he commanded the 6th Battalion from the trenches during World War I. Even when Churchill had become the physically unhealthy figure history largely remembers him as, he worked 120 hours a week throughout World War II and traveled more than 110,000 miles, many of them in a de-pressurized, freezing airplane cabin. Churchill’s private secretary during the war was 41 years younger than him, but remarked how physically exhausting it was to keep up with the PM.

What kept Churchill going? “He was born in a palace, the grandson of a duke, at the apex of Victorian society when the Victorians ruled over one-fifth of the world’s land surface, and this gave him tremendous self-confidence—what we’d call a massive sense of entitlement, which obviously helped,” Mr. Roberts said. “But his sense of destiny is key to his resilience.”

It was a sense of life purpose that bordered on the fanatical. “Even as a student at Harrow, Churchill believed that he was going to save London, save the empire, save England. When he was 16 years old, he told a friend of his [Murland Evans] that he would save Britain from a foreign invasion—and he did truly believe this. Every near-death experience he had throughout his life, and he had quite a few, only reinforced that sense of destiny.”

Which makes it all the more surprising to read of how emotional a leader Churchill was; Mr. Roberts tallied more than 50 recorded instances of Churchill crying during World War II. “Imagine if Theresa May started crying in the House of Commons,” Mr. Roberts said.

Asked if he had become similarly emotional at any points while researching or writing the book, Mr. Roberts pointed to two moments.  “The first came with a letter that Clementine wrote to Lord Asquith [Prime Minister from 1908 to 1916], trying to persuade him not to sack Churchill, or not to force Churchill to resign over the Dardanelles catastrophe. I just thought how incredibly lucky Churchill was to have a wife like that. And I recognized that I, too, actually have a wife like that in Susan [Gilchrist, Brunswick’s Chair of Global Clients] whom I can very easily see doing exactly the same thing: writing this passionate letter to the Prime Minister telling them they’re wrong.

“Then there was another moment at the end of the book, when I was writing about Churchill’s funeral and his interment where I got a sort of huge frog in my throat. I became very emotional writing about the moment they took him down the Thames, the cranes bowing their heads. It was like a punch in a solar plexus, really.”

Andrew Roberts spoke with Edward Stephens, Senior Writer at Brunswick based in New York.


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