In 1899, Churchill headed to South Africa as a journalist for the Morning Post to cover the Boer War. He was captured in an ambush of an armored train but escaped with £75 and four slabs of chocolate in his pocket in hopes of finding the Delagoa Bay Railway. This from our archives, 30 December 1899 (link here).
The Morning Post of Wednesday contained a characteristic telegram from their correspondent, Mr. Winston Churchill, describing his escape from Pretoria.
Mr. Churchill, who had been taken prisoner after showing great gallantry in the armoured train action near Chieveley on November 15th, was confined at Pretoria. Despairing of his application for release (on the disputable ground of his having been a non-combatant) being granted,

Churchill’s diagram of the State Model School where he was held prisoner, from his 1900 book on his adventure.
he scaled the wall of the State Schools Prison on the night of the 12th, made his way through the pickets of the Town Guard, and managed to board a goods train outside the first station on the Delagoa Bay Railway, hiding himself under some coal sacks in a truck.
Jumping from the train before dawn, he spent the day in a small wood “in company with a huge vulture, who displayed a lively interest in me,” resuming his walk along the railway at dusk. This mode of progress he maintained for five days, making wide detours to avoid all stations, bridges, and huts, subsisting mainly on chocolate, and on the sixth day contrived to board a train beyond Middleburg, whence there was direct communication with Delagoa Bay. There he arrived after “sixty hours of misery,” “very weak, but free,” and declares that he will avail himself of every opportunity from this moment…
“to urge with earnestness an unflinching and uncompromising prosecution of the war.”
We congratulate Mr. Churchill on his courage and perseverance – as well as his good fortune.
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