Winston Churchill: Walking with Destiny

Here's what you need to know about young Winston Churchill: he was terrible at school. Not "charmingly mediocre"—genuinely bad. He failed the Sandhurst entrance exam twice. His father, Lord Randolph Churchill, wrote him off as a disappointment.

And yet. Born at Blenheim Palace on November 30, 1874, Churchill responded to academic failure by becoming, essentially, his own university. Stationed in India with the 4th Queen's Own Hussars, a bored 22-year-old devoured Plato, Gibbon, Darwin, and Macaulay—giving himself the education Harrow and Sandhurst never provided. He also played polo obsessively, even with a chronically dislocated shoulder.

The adventures came fast. In 1898, he participated in the Battle of Omdurman—the last major British cavalry charge in history. In 1899, captured during the Boer War, he escaped from a POW camp in Pretoria and traveled 300 miles through enemy territory to safety in Portuguese East Africa. The escape made him a national celebrity overnight.

"I am all for the public schools but I do not want to go there one moment longer than is necessary."

— Winston Churchill, on his unhappy schooldays at Harrow

By age 25, he was an MP. By 30, he had defected from the Conservatives to the Liberals—a move that earned him a reputation as an opportunistic turncoat that would shadow him for decades. The pattern was set: Churchill would always be brilliant, always be controversial, and never be trusted by his own side.

The 1930s should have been the end. After the Conservatives lost power in 1929, Churchill spent a decade in political exile—mocked as a warmonger, dismissed as a relic, shouted down in Parliament.

Three issues destroyed his credibility with his own party. First: he opposed Indian independence, attacking Gandhi in terms that alienated moderates. Second: he backed King Edward VIII during the Abdication Crisis of 1936—a catastrophic miscalculation that nearly ended his career when the House shouted him into silence. Third: he warned about Hitler.

From October 1930 onward, Churchill delivered speech after speech about the Nazi threat. In November 1934, he gave a pivotal radio broadcast urging rearmament. The political establishment ignored him. Chamberlain pursued appeasement. Churchill was the madman shouting at clouds.

"The government simply cannot make up their minds, or they cannot get the Prime Minister to make up his mind. So they go on in strange paradox, decided only to be undecided, resolved to be irresolute..."

— Winston Churchill, 1936

Historians now understand this "exile" differently. Churchill wrote constantly—including the massive Marlborough: His Life and Times—honing the historical perspective he would later use to frame World War II not as chaos but as narrative. The wilderness made the war leader.

On May 10, 1940, two things happened. Adolf Hitler invaded France. And Winston Churchill became Prime Minister of Great Britain. He was 65 years old.

What followed was the moment for which his entire erratic, controversial, brilliant life had been preparation. Britain stood alone. The Cabinet—especially Lord Halifax—urged negotiation with Hitler. Churchill refused.

"I have nothing to offer but blood, toil, tears and sweat."

— Winston Churchill, first speech as Prime Minister, May 13, 1940

The speeches are remembered because they worked. Churchill didn't just manage a war; he weaponized the English language. "We shall fight on the beaches." "Never in the field of human conflict was so much owed by so many to so few." These weren't just words—they were actions, shaping British resolve when military reality offered little hope.

Behind the speeches: strategic decisions that shaped the war's outcome. Churchill cultivated FDR relentlessly, securing Lend-Lease supplies before America entered the conflict. He maintained an "uneasy alliance" with Stalin, meeting him in Moscow (1942) and Yalta (1945). He pushed the Mediterranean strategy—North Africa, Sicily, Italy—to delay the cross-channel invasion until 1944, when the Allies were actually ready.

And then, in July 1945, with the war in Europe won but Japan still fighting, British voters turned him out of office. The war leader was not wanted for peace.

The most consequential speech of the Cold War wasn't delivered by a head of state. It was delivered by a man who had just been voted out of office, speaking at a small college in Missouri.

On March 5, 1946, at Westminster College in Fulton, Missouri, Churchill spoke the words that would define a generation's understanding of geopolitics:

"From Stettin in the Baltic to Trieste in the Adriatic, an iron curtain has descended across the Continent."

— Winston Churchill, "Sinews of Peace" speech, March 5, 1946

The phrase "Iron Curtain" hadn't originated with Churchill—but he made it stick. The speech was controversial at the time; the wartime alliance with the Soviet Union was barely cold. But Churchill saw what was coming. Again.

He returned to power in 1951 for a quieter second term as Prime Minister, focused on housing policy and the nuclear deterrent. His health was failing—he'd suffered strokes that the public didn't know about. He resigned in 1955, age 80.

In 1953, he won the Nobel Prize in Literature—not Peace, but Literature—for his oratory and historical writings. The Swedish Academy recognized what Churchill had always understood: words were his weapons.

Churchill called his depression the "Black Dog." It followed him throughout his life. He never hid from it—he managed it.

His primary coping mechanism was painting. He produced over 500 canvases in his lifetime, mostly landscapes and still lifes, working in an impressionist style he'd taught himself. The studio at Chartwell, his family home in Kent, remains filled with his work.

His marriage to Clementine Hozier in 1908 provided the stability his turbulent career required. She was often the only person who could scold him—and the only person whose opinion he truly feared. Their letters reveal a partnership that survived five decades of political upheaval, financial worry, and personal tragedy.

"I am ready to meet my Maker. Whether my Maker is prepared for the great ordeal of meeting me is another matter."

— Winston Churchill, on his 75th birthday

The public image—the champagne, the cigars, the witticisms—was partially performance. Churchill cultivated his own legend carefully. His "drunkenness" was largely exaggerated, often by himself, for effect. He was a night owl, famous for holding Cabinet meetings late into the evening. His daily intake did include Pol Roger champagne and brandy, but spread across long hours.

He died on January 24, 1965—exactly 70 years to the day after his father. He was 90 years old.

Churchill's reputation has never been settled. Hero worship gave way to revisionist critique; the critique has sparked counter-revisions. The debate is not finished.

Modern critics focus on his imperialism—his views on race, his handling of the Bengal Famine of 1943, his opposition to Indian independence. These critiques are not new (his contemporaries made them), but they carry different weight in a postcolonial era.

The definitive modern biography is Andrew Roberts' Churchill: Walking with Destiny (2018), which drew on new sources including King George VI's diary to reveal Churchill's careful management of the monarch during the war. Erik Larson's The Splendid and the Vile offers a narrative non-fiction portrait of his family life during the Blitz.

His advocacy for a "United States of Europe" makes him a contested figure in modern Brexit debates—both Remainers and Leavers claim his legacy. This is fitting. Churchill was never simple, never consistent, never belonging entirely to any faction.

The leadership lesson endures. In crisis, communication is action. Churchill didn't just manage the war; he told the story of it. He understood that before you can fight, people must believe the fight is worth having—and that belief is built with words.