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Posted on Sep 26, 2007 in Carlo D'Este, Front Page Features

Winston Churchill’s Great Escapade

By Carlo D'Este

This month, I’m providing another extract from my forthcoming new book, Warlord: A Life of Winston Churchill at War, 1874-1945 (to be published in June 2008 by HarperCollins and in the UK by Penguin), a biography of his astonishing military career from his youth through World War II.

As a young man, Churchill was highly ambitious and while he believed that his future lay in politics, he had a lifelong love-hate relationship with soldiering – love for fighting men and disdain for most generals who commanded them. He was commissioned a 2nd Lieutenant of cavalry in 1895 and served in India until 1899, when he resigned his commission in order to pursue a political career. Then came the Boer rebellion in 1899 and Churchill hastened to South Africa to cover the war for a London newspaper, the Morning Post. His destination was the Natal city of Ladysmith where considerable fighting was taking place. The British garrison there had come under siege by the Boers and was already cut off from the outside world by the time Churchill arrived in November at the small hill town of Estcourt on the Durban-Ladysmith-Johannesburg railway line.


Inaction was decidedly not Churchill’s style and he began to chafe in frustration at being unable to find a way into Ladysmith. Although he thought fleetingly about attempting to make a dash by horseback through enemy lines the forty miles to Ladysmith, common sense prevailed. Soon, however, Churchill began searching for someone able and willing to escort him through the Boer lines to Ladysmith and is reputed to have offered as much as the enormous sum (in those days) of £200. An able young cavalryman of the Natal Carbineers named William Park Gray volunteered for the task, but his commanding officer refused him permission to escort Churchill. “I was told he could not spare a single man, let alone me, to lead a bloody war correspondent into Ladysmith.” Churchill soon found another volunteer who accepted the assignment for a mere £5. He planned to slip away from Estcourt the following morning but for the intervention of what in hindsight can only be described as one of the most fateful events of his life.

The date was November 15, 1899, a day in which Churchill became a prisoner of the Boers – and shortly thereafter a national hero in Britain. The events of that amazing day in what has been called the armored train incident are the subject of this month’s article.

Churchill as a correspondent for the Morning Post
during the Boer War, 1899


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