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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

On November 14, the alarm was raised when Boers were seen in the hills outside the town. The garrison went to full alert and everyone became jumpy in the expectation an attack might be imminent, although as the day passed an attack seemed increasingly unlikely. It was in this atmosphere that on the morning of November 15, Churchill’s friend, Captain Aylmer Haldane, was ordered to take 120 troops aboard an armored train on a reconnaissance probe toward Colenso (a town on the railway line about half way between Estcourt and Ladysmith). The armored train was a creature of the Boer War and although the premise was sound, in practice it was clumsy and vulnerable to attack and disablement without warning. It also ran to a predictable schedule, usually every other day at roughly the same time. Moreover, the rail lines were not only the logistical lifeblood of the British and the only means by which they could move men, equipment and supplies over the vast expanse of southern Africa, but they were equally the prime target of the Boers – for the very same reason. One of Churchill colleagues scornfully called it “that futile contrivance” belching black smoke and loudly announcing its presence to the Boers, almost as if inviting an ambush.


The train consisted of an engine, a tender and six cars, arranged as follows: a flatcar upon which was mounted a 7-inch naval gun manned by a crew of sailors that Churchill described as “an antiquated toy,” two armored cars, the engine and its tender in the middle, followed by two more armored railcars and in the rear, a fifth railcar containing a breakdown crew complete with tools and equipment. There was also a telegraphist aboard to signal messages back to Estcourt. The railcars were without roofs and to gain access, troops had to climb up and over its sides, which was often an ordeal for smaller men. Like the warships of old, these railcars contained steel gun ports along each side through which riflemen could fire at the enemy. Soldiers of the Dublin Fusiliers and the Durban Light Infantry (a unit of Natal volunteers) were crammed inside much like cattle and due to the short height of the car’s walls, they had to sit or crouch to avoid becoming exposed targets for a Boer marksman.

Boer activity had increased around Estcourt thus persuading the garrison commander to order yet another reconnaissance using the armored train. Even this early in the war such trains had already been dubbed “Wilson’s deathtrap” in dubious honor of their creator. The folly of employing such a sitting duck was that a handful of cavalry would have had the advantage of speed and flexibility to accomplish the same task with far less risk and a far greater chance of survival.

Churchill learned of the reconnaissance the previous night from Haldane. Never able to resist the lure of an adventure, he was not about to pass up a chance to report the war, and accepted Haldane’s invitation to accompany him.

Churchill arrived at the station armed with a Mauser semi-automatic pistol, several clips of ammunition tucked into his tunic, and his field glass, and awaited Haldane outside the headquarters building. He later explained that he elected to accompany Haldane, “Out of comradeship, and because I thought it was my duty to gather as much information as I could for the Morning Post.” He also admitted, “because I was eager for trouble, I accepted the invitation without demur.” And trouble was precisely what Churchill got that fateful morning, setting into motion a series of events that would change his life forever.

The chill in the air and a damp mist aptly fit the mood of the British garrison as the armored train bearing Churchill rumbled out of the Estcourt station at 5:30 a.m. toward a fiery reception from the Boers. Steaming cautiously north toward Colenso, the train passed through the village of Frere and arrived in Chieveley (fourteen miles north of Estcourt) without incident or any sign of Boer activity. It stopped briefly while the telegraphist reported their safe arrival, noting also that an estimated one hundred Boers were observed north of the town but appeared to pose no threat. Haldane was ordered to proceed no farther north but instead to take the train back to Frere, a town halfway between Chieveley and Estcourt, and once there to remain “in observation guarding your safe retreat.” The train then began to reverse itself toward Frere, at one point stopping briefly while Churchill, at Haldane’s request, climbed a hill to reconnoiter. An unflatteringly accurate account written by Churchill’s friend and Harrow classmate, Leo Amery, the chief Times correspondent in South Africa, in the aftermath of that November morning noted: “It is typical of British military methods that though the train had been running up to Chieveley almost daily, the officer selected to command [Haldane] had never been up the line before. That the train was certain to be caught in a trap, sooner or later, was the outspoken conviction of every officer in Estcourt, but no precautions were taken to accompany it by a few mounted men to scout on both sides of the railway.”

Before it could complete the return journey to Frere, a Boer force of unknown size was spotted occupying a high hillside situated where the train had to negotiate a long downward slope, then a sharp curve before a half-mile run to Frere station. It was clear that for the train to safely reach the town, Haldane’s small force would have to fight its way through this potential danger. Although there would certainly be a skirmish, no one expected it to be a serious problem. As Churchill watched through his field glasses, the train passed below the hill, then a thunderous sound of guns suddenly erupted as the Boers opened fire on the train with rifles, Maxims and two field guns.

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