Winston Churchill

Five Days in May

On May 28, 1940, in a smoke-filled room in London, the twentieth century balanced on a single question: should Britain ask what Hitler’s terms might be?

It was not an unreasonable question. France was collapsing. The entire British army — some 400,000 men — was trapped in a shrinking pocket around the French port of Dunkirk, and the planners thought perhaps 45,000 could be saved. The Foreign Secretary, Lord Halifax, a serious and respected man, argued in the War Cabinet that it would be foolish not to at least explore, through Mussolini, what a settlement might look like. Most sober military assessments gave Britain little chance alone.

The new Prime Minister had been in office for eighteen days. For three days he fenced with Halifax in secret sessions, never quite refusing, never agreeing, while the cabinet inched toward the table where such negotiations begin. Then, on the evening of May 28, Winston Churchill went around the War Cabinet to the twenty-five ministers of the outer cabinet and told them where he stood. If Britain’s long island story were to end at last, he said — as one minister, Hugh Dalton, recorded it — let it end “only when each one of us lies choking in his own blood upon the ground.”

The ministers shouted, cheered, some pounded the table and clapped him on the back. The question of terms never seriously reopened. Britain would fight on, alone if it had to.

Nearly everything about Churchill’s first sixty-five years — the recklessness, the romanticism, the obstinacy, the bottomless self-belief — had looked, to the people who worked with him, like a catalogue of dangerous flaws. In the last week of May 1940, they were exactly what the moment required.

The Ghost of Lord Randolph

Winston Leonard Spencer Churchill was born on November 30, 1874, at Blenheim Palace, the vast monument a grateful nation had built for his ancestor the Duke of Marlborough. His father, Lord Randolph Churchill, was a meteoric Tory politician — Chancellor of the Exchequer at 37 — whose career then collapsed in a single misjudged resignation. His mother, Jennie Jerome, was a glamorous American heiress. Both were spectacularly absent parents. The person who actually raised Winston was his nanny, Elizabeth Everest; he kept her photograph beside his bed until the day he died.

Lord Randolph regarded his son with something close to contempt, predicting he would “degenerate into a shabby, unhappy & futile existence.” When he died in January 1895, at just 45, Winston was 20 — and he spent the rest of his life arguing with the ghost. He later calculated that he had had perhaps four or five long conversations with his father in his whole life. Vindicating Lord Randolph, and surpassing him, became the engine of everything.

The young Churchill was in a hurry. Commissioned as a cavalry officer a month after his father’s death, he spent the next five years engineering his way to wherever the shooting was, with a pen in one hand: observing a rebellion in Cuba, fighting on India’s North-West Frontier, riding in one of the last great British cavalry charges at Omdurman in Sudan in 1898 — and filing dispatches and books about all of it, at rates that made him one of the best-paid war correspondents alive.

The Boer War made him famous. In November 1899, an armored train he was riding as a correspondent was ambushed; Churchill, technically a civilian, took charge under fire and was captured. Weeks later he climbed the wall of the prisoner-of-war camp in Pretoria alone and crossed nearly three hundred miles of enemy territory, hiding in a coal train and down a mine shaft, while the Boers circulated his description with a £25 reward. He emerged in Portuguese territory a national celebrity at 25 — and within a year, a Member of Parliament.

He had already told a school friend, the friend later claimed, that he believed London would one day be in danger and that he, Winston Churchill, would save the capital and the empire. It is the kind of story people remember after the fact. It is also exactly what he believed.

A Genius Without Judgment

For the next four decades, Churchill was never boring and rarely trusted. He switched parties twice — Conservative to Liberal in 1904 over free trade, and back again twenty years later (“Anyone can rat,” he said cheerfully, “but it takes a certain ingenuity to re-rat”). As a young Liberal minister he helped Lloyd George lay the first stones of the British welfare state — labour exchanges, unemployment insurance — a fact his later Tory admirers tend to forget. By 35 he was Home Secretary; by 37, First Lord of the Admiralty, where he modernized the fleet, switched it from coal to oil, and championed a strange new machine called the tank.

Then came Gallipoli. In 1915, casting about for an alternative to the slaughter in France, Churchill drove forward a plan to force the Dardanelles strait and knock Ottoman Turkey out of the war. The concept was bold; the execution was a catastrophe of hesitant admirals, mismanaged landings, and trench deadlock on a hostile shore. Tens of thousands of Allied soldiers — Australians and New Zealanders foremost in memory — died for nothing. Churchill, the campaign’s loudest sponsor, became its public face and its scapegoat. He was demoted, then resigned, and went to the Western Front to command an infantry battalion in the trenches. Clementine, his wife, later said she thought the Dardanelles would kill him: “I thought he would die of grief.” He took up painting to keep the despair — his “black dog,” as he called his depressions — at bay.

He clawed his way back, as he always did, and kept making history-sized mistakes. As Chancellor of the Exchequer in 1925 he returned Britain to the gold standard at its prewar rate, throttling the economy and helping trigger the 1926 General Strike; he later called it the greatest blunder of his life. In the 1930s, out of office at his beloved house at Chartwell — writing, painting, laying bricks — he chose causes that seemed designed to prove his critics right. He fought even modest self-government for India with a bitterness that shocked colleagues, sneering at Gandhi as “a seditious Middle Temple lawyer… posing as a fakir.” He backed Edward VIII in the abdication crisis and was howled down in the House of Commons. The settled Westminster verdict on Churchill was that he was a genius without judgment — brilliant, entertaining, and not to be trusted with anything important.

Which is why his other 1930s campaign was so easy to dismiss. From 1933 onward, fed statistics by sympathetic officials, Churchill warned in speech after speech that Germany was rearming at terrifying speed and that Britain was doing nothing. Appeasement was not a fringe policy; it was the overwhelming consensus of a country that had lost a million men a generation earlier. Churchill’s warnings sounded like warmongering from a discredited adventurer. After Munich in 1938, when Chamberlain returned promising peace, Churchill stood up in the Commons and called it what it was: “a total and unmitigated defeat.” His own constituency nearly deselected him.

Within a year, Hitler proved him right. When war came in September 1939, Chamberlain had no choice but to bring him back to the Admiralty. And when the failed Norway campaign — ironically, a fiasco with Churchill’s own fingerprints on it — brought Chamberlain down in May 1940, the establishment’s preferred successor, Halifax, stood aside. On May 10, 1940, the day Hitler’s armies poured into France and the Low Countries, the 65-year-old Churchill became Prime Minister.

“I felt as if I were walking with destiny,” he wrote later, “and that all my past life had been but a preparation for this hour and for this trial.”

The Lion’s Roar

What Churchill actually contributed in 1940 can be stated precisely: he refused, and he spoke.

The refusal came first, in the five days of War Cabinet crisis at the end of May. It was not obvious; it was not even, by cold calculation, clearly rational. It was a decision that Britain would rather risk destruction than test Hitler’s terms — and once made, with the outer cabinet cheering, it closed the question for good.

Then the words. In the summer of 1940 Britain’s armory was thin — the army had escaped at Dunkirk, 338,000 men saved by an improvised fleet, but their equipment lay abandoned in France. What the country had was the Channel, the Royal Air Force, and a Prime Minister who understood that language could be a weapon system. “I have nothing to offer but blood, toil, tears and sweat.” “We shall fight on the beaches… we shall never surrender.” “Let us therefore brace ourselves to our duties, and so bear ourselves that, if the British Empire and its Commonwealth last for a thousand years, men will still say, ‘This was their finest hour.’” When the RAF’s fighter pilots broke the Luftwaffe’s daylight assault that August: “Never in the field of human conflict was so much owed by so many to so few.” The words did not win the war. They did something narrower and indispensable: they made surrender unthinkable during the eighteen months when Britain and its empire stood alone, and they told the world — above all the United States — that resistance was real and worth backing.

Churchill’s larger war was a long, often humiliating exercise in courting stronger partners. He bombarded Roosevelt with some 1,700 messages, traded bases for destroyers, and swallowed the terms of Lend-Lease. When Hitler invaded the Soviet Union in June 1941, the most famous anti-Bolshevik in Britain allied with Stalin overnight. And on the night of Pearl Harbor, he was honest enough to record his real feeling: “So we had won after all.” The defeats kept coming — Singapore’s surrender in February 1942 he called the worst disaster in British history, and he survived censure motions in the Commons — until the tide turned at El Alamein and Stalingrad, and the alliance he had built ground toward victory.

On May 8, 1945, he stood on a balcony above a roaring Whitehall crowd and told them: “This is your victory.” The crowd roared back: it was his. Eleven weeks later, the British electorate — grateful, exhausted, and wanting homes and health care rather than empire and glory — voted him out of office in a Labour landslide. Clementine offered that it might be a blessing in disguise. “At the moment,” Churchill replied, “it seems quite effectively disguised.” Then he accepted the result completely. It was, after all, the thing he had been defending.

The Two Ledgers

Any honest account of Churchill now has to hold two ledgers open at once.

The first records 1940, and it is secure. Without Churchill — without precisely his combination of obstinacy, theatricality, and romantic certainty — it is genuinely hard to construct the history in which Britain does not at least explore terms in 1940, with consequences for the world that are ugly to contemplate.

The second ledger is imperial, and it has grown heavier with each decade of scholarship. Churchill was a Victorian imperialist who never updated his assumptions, and his views on race disturbed even his own colleagues; his cabinet ally Leo Amery wrote in his diary that on the subject of India he could see little difference between Churchill’s outlook and Hitler’s — a sentence all the more startling for coming from a fellow Conservative imperialist in 1942. The gravest entry is the Bengal famine of 1943, in which on the order of two to three million people died under British rule while London repeatedly declined large-scale grain shipments. Historians genuinely disagree about culpability — wartime shipping losses, provincial hoarding, and bad information from Delhi all played roles, and no serious scholar calls it deliberate — but the record of Churchill’s contemptuous remarks about Indians during those very months is documented, and the moral question remains open and live. Alongside Bengal sit Gallipoli’s dead, the Black and Tans in Ireland, and a Middle East map drawn in haste in 1921. When protesters stenciled “was a racist” on his Parliament Square statue in 2020, they were not inventing a grievance; they were reading the second ledger aloud.

Churchill himself expected the argument and tried to rig it, half-jokingly telling the Commons in 1948 that history would treat him well because “I propose to write that history myself.” He did — six volumes of war memoirs that shaped a generation’s memory and helped win him the 1953 Nobel Prize in Literature, awarded for his historical writing and for “brilliant oratory in defending exalted human values.”

He returned to Downing Street in 1951, at 76, an old man chasing one last summit with the Soviets that never came; in 1953 a major stroke was simply concealed from press and Parliament while he recovered. He finally resigned in 1955 and faded slowly — painting, sitting silent in the Commons, the black dog circling — until January 24, 1965, when he died at 90, seventy years to the day after his father. Britain gave him a state funeral, the first for a non-royal in nearly a century. As the launch carried his coffin up the Thames, the dockers along the south bank dipped their cranes, one by one, in salute.

That image is the right place to end, because both ledgers were on the river that day. The cranes belonged to working London, the city that had stood with him under the bombs and then, quite correctly, voted him out. He was the last great believer in an empire whose subjects were already free, and the indispensable man of a fight that had to be won. History is under no obligation to make such people simple. Churchill’s life is the standing proof that it doesn’t.

Sources

1. Churchill Archives Centre, Churchill College, Cambridge — The Churchill Papers (archives.chu.cam.ac.uk/collections/churchill-papers/)
2. International Churchill Society — speech texts and Life archives (winstonchurchill.org)
3. UK Parliament — “Churchill the Orator” exhibition and Hansard records of the 1940 speeches (parliament.uk)
4. Imperial War Museums — “Winston Churchill” and “What makes a Churchill speech?” (iwm.org.uk)
5. Roberts, Andrew — Churchill: Walking with Destiny (Allen Lane, 2018)
6. Jenkins, Roy — Churchill (Macmillan, 2001)
7. Lukacs, John — Five Days in London: May 1940 (Yale University Press, 1999)
8. Mukerjee, Madhusree — Churchill’s Secret War (Basic Books, 2010)
9. Toye, Richard — Churchill’s Empire (Macmillan, 2010)