Churchill’s Great Escape: Britain’s Bulldog outwitted the Boers with good manners and chocolate

Winston Churchill led the most adventurous life of any British Prime Minister. His wartime premiership was notable not just for his bullish defiance of the Nazi-led Axis powers but also for his energetic and deliberately swashbuckling approach to conducting the war and securing victory. It is often forgotten that when Churchill became Prime Minister he also appointed himself as Minister of Defence.

That this should be the case was largely due to his extensive military adventures decades before in the last days of the Victorian era. The most famous of these exploits was his daring escape from a prisoner of war camp during the Second Boer War (1899-1902).

Churchill had joined the British Army in 1893 and had served as a lieutenant in the cavalry. On one occasion he took part in the last significant British cavalry charge at the Battle of Omdurman in 1898. By this time he had developed an interest in war correspondence and some of his earliest literary works were reports on various military campaigns.

By 1899 he was writing for The Morning Post and he was sent to cover the unfolding Boer War in South Africa. Soon after his arrival, Churchill accompanied a scouting expedition in an armoured train that was reconnoitring between Frere and Chievely in the British Natal Colony on 15 November. The train was ambushed and partially derailed by a Boer commando force that then attacked the expedition for over an hour. Throughout this bombardment Churchill helped to organise and load wounded soldiers onto the still operational locomotive, which then managed to escape.

However Churchill found himself alone in a gully near the track and was captured by a Boer who aimed his Mauser rifle at him. This Boer was later rumoured to be Louis Botha, the future Prime Minister of South Africa.

Churchill was captured by the Boers during an attack on a British armoured train.
Churchill was captured by the Boers during an attack on a British armoured train.

Despite the fact that Churchill was technically a civilian he was treated as a prisoner-of-war by the Boers, mainly because he came from an elite aristocratic family and could be used as a bargaining tool but also because he had taken an active part in enabling British soldiers to escape during the train ambush.

He was taken to Pretoria and imprisoned in a converted school with British officers but Churchill soon became restless and made plans to escape. He initially planned a mass breakout but soon realised that it was impractical and began to collude with two other officers to escape to Portuguese East Africa (now Mozambique). He closely monitored the Boer guards and saw a gap in their routine when no one was watching the 10-feet wall that surrounded the camp.


Churchill (far right) was photographed during his captivity in Pretoria. Imprisonment did not suit him.
Churchill (far right) was photographed during his captivity in Pretoria. Imprisonment did not suit him.

He also got into a revealing exchange with one of the guards about the nub of the dispute with between Britain and the Boers, which he recounted in his 1900 memoir, London to Ladysmith via Pretoria.

According to Churchill the guard asked him:

“Is it right that a dirty Kaffir (native) should walk on the pavement without a pass? That’s what they do in your British colonies. Brother! Equal! Ugh! Free! Not a bit. We know how to treat Kaffirs…They were put here by God Almighty to work for us. We’ll stand no damned nonsense from them. We’ll keep them in their proper places.”

Churchill wrote in retrospect:

“He and I had no more agreement….Probing at random I had touched a very sensitive nerve. What is the true and original root of Dutch (Boer) aversion to British rule? It is the abiding fear and hatred of the movement that seeks to place the native on a level with the white man.”

Though by no means a modern advocate for racial equality, Churchill’s words put him at a direct contrast with most of his contemporaries.

Having sussed out the guards, Churchill paid his bill with a Pretoria shopkeeper who had sold him tobacco and then wrote a note to the Boer Minister of War declaring:

“I have the honour to inform you that as I do not consider that your Government has any right to detain me as a military prisoner, I have decided to escape from your custody.”

After being in captivity for only four weeks, he made his bid for freedom on the night of 12 December 1899 by waiting for the gap to appear and then silently raced forward and scaled the wall. He successfully landed in some shrub and waited for his fellow escapees for some time but they eventually called out to him that the guards had become suspicious.

This was an immediate problem for Churchill. His colleagues had the map, compass and over the half the rations for the 300-mile journey to Portuguese East Africa. He only had £75 and some chocolate but despite this handicap Churchill set off into the dark streets of Pretoria and started life as fugitive.

After his escape Churchill spent time hiding on freight trains in the Transvaal.
After his escape Churchill spent time hiding on freight trains in the Transvaal.


After wandering through Pretoria he came across a railway track and boarded the next freight train by clambering up the buffers onto empty coal sacks. Once he was in the truck he discovered that he was sharing space with a vulture that reputedly took a great interest in Churchill’s condition.

Eventually he jumped from the train from hunger and thirst and walked for hours through long grass and avoiding swamps. In desperation Churchill decided to knock on a door to ask for food in what he later discovered was Witbank in the Transvaal Highveld. By a great stroke of luck the person who answered the door was John Howard, one of the few Englishmen for miles around.

Howard was the manager of the Transvaal and Delagoa Bay Colliery. One of his colleagues was another Englishman from Oldham called Mr Dewsnap. By coincidence Churchill had unsuccessfully stood for the parliamentary seat of Oldham the previous year.

The Boers put a price on Churchill's head to be recaptured dead or alive.
The Boers put a price on Churchill’s head to be recaptured dead or alive.

Howard and Dewsnap fed Churchill and hid him in a mine while they planned how to safely get him to friendly territory. Churchill spent days down the mine, supplied with food and cigars and spent hours reading by candlelight. On one occasion he was told that the Boers had a price on his head of £25 to be captured dead or alive.

Eventually he was moved and lodged in one of the pithead offices where he read the Robert Louis Stevenson novel, Kidnapped. After six days it was arranged that Churchill would be hidden on a train loaded with wool, which was heading for Delagoa on the frontier of Portuguese East Africa. He was bundled into the trucks and spent the next two and a half days hiding amongst the woolsacks. On the third day the train was stopped and searched but to Churchill’s great relief he heard the men were speaking Portuguese. He had escaped from the Transvaal on 21 December. Howard received a cable two days later that simply said, “Goods arrived safely”.


Churchill pictured soon after his successful bid for freedom.
Churchill pictured soon after his successful bid for freedom.

Churchill went on to return to the front and took part in the Battle of Spion Kop and the relief of Ladysmith. In the closing stages of the war he rode with his cousin the Duke of Marlborough into Pretoria and demanded and received the surrender of the guards of the prison camp. He then held his hat in the air and announced to the British prisoners that they were now free.

It was a neat end to his South African adventures and Churchill returned to Britain as a celebrity and quickly started his political career.

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