Churchill’s Great Escape

2 mins read
A young Winston Churchill in uniform.
A young Winston Churchill in uniform.

Patrick Boniface examines the lives of history’s most daring wartime captives.

In November 1899, the 25-year-old Winston Leonard Spencer-Churchill was travelling in an armoured train transiting between Frere and Chieveley, in the British colony of Natal in South Africa. The soldiers were making a fast reconnoitre of the territory, and Churchill was there to send news back to Great Britain to those eager for information about this important but under-reported mission.

The conditions were horrendous. The train rattled and rolled, and within the steel-clad carriages the air was hot and sticky. Churchill, however, loved it – to him it was dangerous and exciting. The young man was soon on the edge of his seat: a Boer commando-laid trap was sprung not long into his journey.


The Boers had placed a large boulder on the railway track, forcing the train to stop. Within seconds, it came under withering attack from field-guns and rifle-fire. Injured soldiers tried to move their colleagues to safety while attempting to uncouple the carriages, but within 70 minutes of the start of the onslaught the Boers had closed in.

In the mayhem, Churchill found himself in a ditch, covered in sweat, blood, and dust. A Boer got off his horse and raised his Mauser pistol to shoot him, and Churchill, who was unarmed, surrendered. (The officer Churchill surrendered to was General Louis Botha, who would later become Prime Minister of South Africa.) Churchill and the other prisoners were route-marched and put on a train to Pretoria. The future British Prime Minister eventually found himself in a prisoner-of-war camp housed in what was originally a school. It is now a national monument.

The long road to freedom

During his time in captivity,  Churchill and the other captured  men drew maps of battles and military movements from the scant information they received from  their colleagues. These maps were fashioned in pen and pencil, with  red used for British movements and blue for those of the Boers.

On the evening of 12 December 1899, after four weeks in captivity, Churchill scaled a 10-foot wall and made his way through Pretoria. Although he walked under cover of darkness, he was not yet free. His aim was to find the railway line that headed east to Delagoa Bay. When he did so, he followed the course of the railway, either walking along it or hitching rides on steam trains ferrying freight.

He survived by stealing food and drink along the way. By sheer luck, he met fellow Englishman John Howard, manager of the Transvaal and Delagoa Bay Colliery, and with Howard’s help and hospitality Churchill managed to evade capture.

After an epic 300 miles on the run, Churchill finally reached Delagoa Bay on a freight train laden with wool. The Boers had wanted Churchill dead or alive, but he managed to reach the border with Mozambique at Lourenço Marques (now Maputo), where he was safe once again.

Propaganda Value

Churchill was an ambitious man who was eager to make a name for himself. It was hardly surprising that, when he presented himself to the local British consul, he and the British authorities sought to squeeze every last ounce of propaganda from his escape. Churchill travelled by steamer to Durban, where he was greeted by a large crowd and treated like a hero, something that must have gratified his already considerable ego.

Early the following year, Churchill retraced his steps to resume his work as a war correspondent. On arrival at the army camp in Natal, an officer took him to his tent, which Churchill found standing just 50 yards from where he had been captured six weeks earlier.

Churchill soon abandoned his journalistic ambitions and joined a Boer cavalry regiment, taking part in the Siege of Ladysmith. But his military career did not last long – he travelled back to Britain to pursue his interest in politics later that same year. Meanwhile, the Anglo-Boer War wore on until the signing of the Treaty of Vereeniging in 1902.

This article was published in issue 79 of Military History Monthly. To subscribe to the magazine click here. To access the digital edition click here.

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