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How the young Winston Churchill escaped from a prisoner-of-war camp

And what his unlikely tale reveals about imperialism

Winston Churchill after his escape from the Boers on 12 December, 1899
image: Getty Images
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The future prime minister sat at the bottom of a coalmine, clutching a bottle of whisky. He had fled from a prisoner-of-war camp, stowed aboard a train and jumped off in the middle of nowhere. The enemy were hunting for him. If caught, he would be locked up again; those who had helped him would be shot.

Escape would be tricky. He was absurdly conspicuous: a red-headed Englishman in Africa, who knew none of the local languages. “Wanted” posters mocked his “stooping gait” and “almost invisible moustache”.

Yet Winston Churchill did escape, and spun his exploits during the second Anglo-Boer war of 1899-1902 into a tale of derring-do that launched his political career. This improbable story reveals a great deal about war, journalism and history.

British people admire Churchill more than any other prime minister, because he stood up to an aggressive imperial power, Nazi Germany. Of British imperialism, however, he was a lifelong fan. As a young hack he went to cover the war in what is now South Africa convinced that his country, for all its flaws, was in the right. Today, as Britain and France agonise over their imperial history, former colonies try to move beyond it and Vladimir Putin spills lakes of blood trying to recreate Russia’s empire, the tale bears revisiting.

The Anglo-Boer war started because the Boers (descendants of Dutch settlers who began arriving in southern Africa in the 17th century) did not want to submit to British rule and because the British, eager to seize or at least suppress the Boer states, provoked them. The discovery of gold in the Transvaal Republic (one of two Boer states) raised the stakes, attracting British miners. Fearing conquest, the Boers attacked British outposts. The empire struck back. During three years of carnage that followed, neither side spared much thought for the majority of the population of the land they were fighting over: the black Africans.

Churchill arrived in Cape Town in October 1899 with a valet, a supply of fine wines and a contract from the Morning Post for £250 a month (£26,500 or $33,500 today). This rate was “higher, I think, than any previously paid in British journalism to war correspondents,” he later wrote in “My Early Life”.

How did such a whippersnapper secure so fabulous a deal? You might suspect nepotism: his father had been Chancellor of the Exchequer, his cousin was the Duke of Marlborough. But in truth Churchill was not only a great writer (he later won the Nobel prize for literature), but also willing to take extraordinary risks to make a splash for the Post and a name for himself. He had already covered two wars, in India and Sudan, to widespread acclaim. He sometimes sounded as if he did not think a bullet could kill him. “I do not believe the Gods would create so potent a being as myself for so prosaic an ending,” he wrote to his mother.

In wars past he had served both as a journalist and an officer, killing perhaps four men in India and half a dozen in Sudan. This dual role had presented a conflict of interest: that he might favour actions that generated headlines over those that were militarily wise. He also criticised superior officers in print. The War Office found him so insufferable that it banned all correspondents in subsequent wars from being soldiers.

So Churchill began the Boer war as a not-so-humble scribe. He headed straight for the action, dashing to Estcourt, “a tiny tin township of a few hundred inhabitants” near the front line, via Durban.

He started giving officers older than himself “the benefit of his opinion”, as Candice Millard puts it in “Hero of Empire”. Estcourt was in danger of being cut off by 10,000 mounted Boers. The British commander, Colonel Charles Long, wanted to retreat. That would be “a blunder”, Churchill told him. John Atkins, the Guardian correspondent, marvelled at Churchill’s “unblushing self-assurance”. Colonel Long stayed put.

Churchill joined a reconnaissance train, though he thought the mission foolish. “It was only necessary to blow up a bridge or culvert to leave the monster stranded,” he wrote. “This situation did not seem to have occurred to our commander.”

Sure enough, the train was ambushed and partially derailed. Under heavy fire, Churchill led efforts to clear the tracks and send the engine back to safety with wounded men on board. He then ran back to the battle, but found that his comrades had been killed or captured. Two Boers spotted him. Churchill leapt into a shallow ditch. One Boer rode up and levelled his rifle. Intending to kill him, Churchill reached for his Mauser pistol, but he had left it on the train. It was surrender or die, so he surrendered, comforting himself that Napoleon would probably have done the same.

For the next few days Churchill demanded that as a journalist he be released. The Boers refused, citing British newspaper accounts that made clear he had been a combatant during the skirmish. (“MR CHURCHILL’S HEROISM” read one headline.) Also, as one Boer put it: “We are not going to let you go, old chappie...We don’t catch the son of a lord every day.”

Churchill was taken to Pretoria, the capital of Transvaal, and locked up with British officers in a converted school. “I certainly hated every minute of my captivity more than I have ever hated any other period in my whole life,” he wrote. “Luckily it was very short.”

He resolved to break out. Other prisoners were wary of letting him join their escape plans, since he was “unfit, too famous and he couldn’t keep a secret”, as Ms Millard writes. But he was also persuasive. He talked his way into joining a plot that involved hiding in a toilet and scaling the wall when the guards were not looking, on December 12th. Churchill went first, before his co-plotters were ready, and guards prevented them from following. Free but alone and lacking food and a compass, he had to get to the neutral territory of Portuguese East Africa (now Mozambique), 500km away.

Under cover of darkness, he set off on foot, with £75 and four slabs of chocolate in his pocket. “I was in the heart of the enemy’s country…My escape must be known at dawn. Pursuit would be immediate.” He pressed on, reached the railway and waited for a train. When it came, he hurled himself aboard and burrowed in among the empty coal bags.

After Churchill escaped, his fellow prisoners covered for him, stuffing a dummy under his blankets and pretending he was asleep. Unfortunately Churchill had booked a haircut and shave from a Boer barber for the next morning and forgotten to cancel it. His absence was noticed. The Boers were livid, and offered a hefty reward for his recapture.

Churchill slept among the coal sacks. When he awoke, he realised he would have to jump off the train before dawn, or risk discovery. He did so, near a coal town then called Witbank (now Emalahleni).

Study history, study history

John Bird, a local history buff, has mapped exactly what he thinks happened next, based on his knowledge of the landscape and a close reading of Churchill’s works. He showed your correspondent the bend in the tracks where the train slowed down, allowing Churchill to jump off; the pool of water from which he drank voraciously and the hill where he spent the next day hiding among the trees. “My sole companion”, Churchill griped, “was a gigantic vulture, who manifested an extravagant interest in my condition.” Today the hill is part of a not-yet-opened game park.

From the top of the hill Churchill could see a settlement in the distance. When darkness fell, he headed towards it and, desperate, knocked on a door. A man asked “Who’s there?” in Dutch. Churchill replied, in English: “I am a burgher [ie, a citizen of a Boer republic]…I have had an accident…I have fallen off the train. We were skylarking. I have been unconscious for hours. I think I have dislocated my shoulder.”

The stranger invited him in, sat him down and laid a revolver on the table. “I think I’d like to know a little more about this railway accident of yours,” he said, in English. “I think”, said Churchill, “I had better tell you the truth.” “I think you had,” said his host.

It was Churchill’s astonishing good fortune to have knocked on one of the few British doors in the area. His host, John Howard, a manager of a coalmine, fed him and hid him in a mineshaft, with a mattress, blankets and a box of cigars, as well as that bottle of whisky.

The mineshaft today is sealed, and the ground around it is unstable. The local coalfields are excavated at night by illegal miners, known as zama-zama, who sometimes cause tunnels to collapse. When police try to evict them, gunfights erupt.

Howard hatched a plan to smuggle Churchill to the coast in a trainload of wool, setting off on December 19th. The British shopkeeper who was moving the wool, Charles Burnham, was in on the plot and accompanied the cargo. At one hotel along the way, he heard a rumour that Churchill had already passed by that spot, disguised as a Catholic priest. Around the same time Howard met some Boers with a British prisoner who they thought was Churchill. He did not disabuse them.

Arriving in Portuguese East Africa, Churchill walked into the British consulate covered in soot and introduced himself to the startled consul. He took a ship back to South Africa, where he was met by a flag-waving, cheering crowd who demanded a speech. He obliged. For the British, his escape was one of the few scraps of good news to have come out of a war that was going badly. Churchill resolved to join the fight.

Winston Churchill rescued by Trooper Roberts in South Africa during the Boer War in 1899
Churchill, having lost a horse during a battle, is rescued by a comradeimage: Topfoto

He went to see Sir Redvers Buller, the British commander, and asked to re-enlist as an officer, without giving up his newspaper job. This was “very awkward”, he later recalled. The rule against combining journalism with combat had been written because of him. Buller “took two or three tours round the room, eyeing me in a droll manner. Then at last he said: ‘All right.’”

Churchill carried messages at Spion Kop, a gruesome struggle for a strategic hill “with a flat top about as large as Trafalgar Square”. One of the stretcher-bearers during the battle was Mohandas Gandhi, whom Churchill later came to detest (there is no evidence that they met there).

Next Churchill fought to lift the siege of Ladysmith, where a British garrison was hunkered down and running out of food. It gave him some of “the most happy memories” of his life:

“Day after day we rode out in the early morning on one flank or another and played about with the Boers, galloped around or clambered up the rocky hills, caught glimpses of darting, fleeting, horsemen in the distance, heard a few bullets whistle, had a few careful shots and came safe home to a good dinner and cheery, keenly intelligent companions.”

Ultimately, the Boers could not resist superior numbers. In June 1900 British troops entered Pretoria. Churchill went to see the remaining prisoners-of-war. They raised a makeshift Union Jack. Then Churchill went home and was elected to parliament aged 25.

Many Brits thought the war was over when the main Boer cities surrendered. But the Boers resorted to guerrilla tactics and fought on for another two years. The British responded with scorched-earth tactics. They herded Boer civilians into what they called “concentration camps”—a phrase that was to take on a hideous new meaning decades later. Conditions in these camps were atrocious—thousands of women and children died of disease. In time this caused outrage back in London, and tarnished the eventual British victory.

One lesson that can be drawn from the Boer war is that great powers often underestimate smaller enemies. The Boers were mobile, motivated and knew the land. They hid in well-disguised trenches and used smokeless gunpowder. The Brits who thought fighting them would be easy had something in common with Russians today who failed to foresee how ferociously Ukrainians would defend their country.

Another lesson is that military victory does not always bring political triumph. The war created “South Africa as we know it; as a political reality rather than a mere geographical term,” notes Professor Thula Simpson, author of “History of South Africa”. But it came to be dominated by the Boers, not the British, for most of the next century.

The two sides signed a peace deal in 1902 that absorbed the Boer republics into the British empire. It ducked the most important question: whether to give black people the vote. The British Cape Colony had for some time allowed men of property to vote regardless of race. In practice not many blacks qualified, but the Boers regarded this arrangement with horror. They negotiated a clause in the peace treaty stating that the question of the “native” franchise would “not be decided until after the introduction of self-government”.

In 1910 South Africa became a “self-governing dominion”. Its new Boer citizens helped make sure that the black franchise was never extended beyond the Cape. It was gradually curbed and, under apartheid, abolished. Had the British colonies never swallowed the Boer republics, might South Africa’s awful racial history have evolved differently? We will never know.

History will be kind to me

In a YouGov poll, 69% of Britons viewed Churchill positively. That is more than double the 32% who said, in 2019, that the British empire was “more something to be proud of than ashamed”. He is remembered less, and less kindly in South Africa. “In Europe, he was a crusader for democracy and against fascism, but in the South African context, he was opposed to democratic rights and majority rule,” notes Professor Simpson.

History is complicated. Often people’s sense of who they are depends on a simple, moralistic narrative. South African politicians today talk of the evils of colonialism and apartheid; yet many see no problem with Russia’s attempt to carve up Ukraine. Yascha Mounk, author of “The Identity Trap”, writes that “In Britain …some believe that the nation’s character is defined by the cruelties of imperialism, while others think it consists exclusively of the heroism of the Battle of Britain.” As Churchill’s life reminds us, a fair account must include both strands, and many more besides.

The young Churchill’s belief in empire was challenged, a little, by one of his boyhood heroes. During a speaking tour of America he met an ageing Mark Twain. “Of course we argued about the [Boer] war. After some interchanges I found myself beaten back to the citadel ‘My country right or wrong’. ‘Ah,’ said the old gentleman, ‘when the poor country is fighting for its life, I agree. But this was not your case.’”

This article appeared in the Christmas Specials section of the print edition under the headline "From prisoner to prime minister"

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