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Posted on Oct 25, 2006 in Carlo D'Este, Front Page Features

Churchill’s Early Escapades as a Soldier

By Carlo D'Este

This article is another in a series on Winston Churchill and offers a brief sampling from my forthcoming new book, Warlord, a biography of his astonishing military career – from his youth through World War II.

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Churchill fought in many wars as a soldier and a war correspondent. In each of them he narrowly escaped death, sometimes more than once, usually because he deliberately exposed himself to enemy fire. It is rather miraculous that he survived these numerous brushes with death to become Britain’s war leader in 1940. During World War II he drove his frustrated handlers to sheer distraction by repeatedly venturing into the night during German air raids on London to see and be seen by the men and women defending the British capital.


As a newly commissioned cavalry lieutenant, Churchill traveled to Cuba in 1895 to observe the guerrilla war between Spain’s colonial army and Cuban revolutionaries and to see for himself what war was all about. In 1897, while serving with his regiment in India, he managed to finagle his way into a border war with the Pathan tribesmen in the Northwest Frontier in what was then (and still is now) very dangerous territory. In Churchill’s time it was the home of various rebellious tribes; today it is a sanctuary for Taliban and Al Qaeda terrorists. In a small unit action, Churchill came under fire and narrowly escaped wounding and possibly, death.

In 1898, despite being persona non grata on the express orders of the British commander-in-chief in Egypt, Gen. Horatio Kitchener, Churchill used his influence to gain an assignment to Kitchener’s expeditionary force that was formed to recapture the Sudan and avenge the death of Maj. Gen. Charles “Chinese” Gordon, who was killed during the siege of Khartoum in 1885. During one of the last charges by British cavalry, Churchill again narrowly escaped death at the battle of Omdurman.

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In the autumn of 1899, Britain became embroiled in the Boer War in southern Africa, a conflict that it expected to win handily in a matter of months, but which instead turned into a deadly battle of attrition and bloodshed. Britain’s war against the loosely organized Boers – descendants of Dutch farmers – became the forerunner of a new century of warfare that changed the whole concept of how future wars would be fought.

Churchill during the Boer War

Eager to report on the war and gain glory for himself, Winston Churchill sailed to South Africa in October 1899. Once there he found far more than he ever bargained for. Captured by the Boers after heroically saving an armored train near Ladysmith (where the British garrison was surrounded and under siege), Churchill was incarcerated in Pretoria, only to make a dramatic escape and make his way across hundreds of miles of enemy territory toward Portugese East Africa. By good fortune he encountered several friendly British citizens who risked their lives to smuggle him to freedom. For the first time the name of Winston Churchill was flashed around the world as news of his escape was reported.

His great escapade earned him celebrity status throughout Britain. Not only did Churchill become a heroic example of British courage, but his escape also served as about the only encouraging news for Britain in what had become a lengthy and costly war. Not surprisingly, tales about Churchill became embellished from fact into folklore, thus conferring a cult status upon Britain’s hero du jour. Thirsting for positive news, the press shamelessly exploited exaggerated tales of his heroics. Music-hall comedian, T.E. Dunville, who performed in Lancashire, incorporated this in his routine:

You’ve heard of Winston Churchill;
This is all I need to say –
He’s the latest and the greatest
Correspondent of the day.

After his escape, Churchill returned to reporting the war. His dispatches skewered the idiotic battlefield tactics of a British Army befuddled by the Boers, who consistently won major battles, ambushed columns and killed hundreds of soldiers in a war than became Britain’s “Vietnam.” Churchill insisted on reporting directly from the front lines and time and again barely escaped death.

War has a way of humbling those that disrespect its devastating unpredictability. On the basis of his combat experience he should have appreciated that bullets do not discriminate, and at least once even he had good reason to question his overconfidence while atop a hill observing and writing when the Boers began shelling it. “I was very nearly killed two hours ago by a shrapnel,” he wrote to his distraught girlfriend, Pamela Plowden. “But though I was in the full burst of it, God preserved me. Eight men were wounded by it. I wonder whether we shall get through and whether I shall live to see the end.” Churchill wrote to his aunt that he had been under fire “in forty separate affairs” in the Boer War, and “one cannot help wondering how long good luck will hold.” Somehow it did.

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