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Winston Churchill wore medals during World War I he had earned since joining the army in 1895 (National Archives).

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Winston Churchill first heard a shot fired in anger at him on the morning of his 21st birthday, in 1895. A newly commissioned second lieutenant with Queen Victoria’s army, he spent a two-month leave observing Spanish troops trying to quell an insurrection by Cuban colonists. During that day’s early morning march, gunfire sounded from afar, but it did not faze the young Churchill. He was, he wrote in his memoirs, like the optimist “who did not mind what happened, so long as it did not happen to him.” Later that morning, however, as Churchill gnawed on a chicken drumstick during a break in the march, a volley rang out nearby. A slug passed within a foot of his head and hit a horse just behind him between the ribs, leaving a dark red circle a foot wide on its bright chestnut coat. Watching the horse struggle for life, Churchill wrote, “I began to take a more thoughtful view of our enterprise.” Over the next five years, Churchill would see battle in three very similar wars: against the tribesmen on the North-West Frontier of India (now the border of Pakistan and Afghanistan); against the Dervishes in the Sudan; and against the Boers in the Anglo-Boer War of 1899–1902. Serving simultaneously as a cavalry officer and newspaper correspondent during much of that time, he proved an acute observer and a prodigious chronicler, turning out dozens of articles and four books, some still relevant to modern conflicts.

"I am more ambitious for a reputation for personal courage," Churchill told his mother, "than [for] anything else in the world," and a couple of decorations would help to "beat my sword into an iron dispatch box," a reference to the place from which ministers give their speeches in the House of Commons.

Equally important, these experiences helped mold one of the most influential men in modern history. Thirsting for fame and glory, Churchill during those years went through a literal baptism of fire. What he saw and learned in the field sparked what would become a lifelong fascination for battle and war. At the same time, his writings forced him to confront questions of grand strategy and the nature of conflict.

The British Empire at the end of the 19th century still covered one-quarter of the world’s land surface, with 380 million subjects scattered on every continent. Inevitably, Churchill’s combat tours exposed his powerful and impressionable mind to most of the forces that were to shape the future: war itself, Great Power politics, religious fanaticism, and nationalism. And while he was devoted to the empire and convinced of its power for good in the world, we can see a generous mind at work, adamantly resisting any departure from its benign principles, but increasingly conscious of man’s capacity for evil.

Churchill’s path to glory was littered with oddly propitious turns. An indifferent student, he entered the army because his father did not think he was bright enough for the law. At age 20, he graduated from the Royal Military College at Sandhurst, and was commissioned as a lieutenant in the 4th Hussars on February 20, 1895, just nine months before he saw action in Cuba.

As he was to do throughout his career, Churchill went to people at the top to achieve his objectives. Of course, it did not hurt that he was the son of Lord Randolph Churchill, the former chancellor of the exchequer, and his beautiful and well-connected American wife, the former Jennie Jerome of New York City. In a bid to be seconded to the staff of the commander in chief in Cuba, Winston wrote to a former parliamentary ally of his father, Sir Henry Drummond Wolff, then British ambassador to Madrid, as well as to Lord Garnet Wolseley, the commander in chief of the British Army. To help pay his way and make his name, he arranged with the Daily Graphic to file occasional dispatches at five guineas each.

In Cuba, his assignment to the staff of General Álvaro Suáres Valdés introduced him to the finest cigars and meals, rum cocktails, and the siesta, but it was not an unmitigated privilege. The general often rode to within 500 yards of the enemy line and, with his white uniform and gold lace, was the target of every sharpshooter, diminishing the life expectancy of his staff members.

Neither the privileges nor the danger blinkered Churchill’s judgment. “There is no doubt,” he reported in a dispatch to the Daily Graphic, that the insurgents “possess the sympathy of the entire population, and hence have constant and accurate intelligence.” The only uniform an insurgent wore was a badge; when removed it was “impossible to tell a rebel from an ordinary peasant.” The island was overtaxed, all offices were reserved for Spaniards, and the administration was corrupt. It was not surprising, he reported, that the demand for independence was “national and unanimous.”

He found many of the Spanish army operations pointless. For 10 days, he told his readers, he had accompanied 2,000 of the best Spanish troops under a general who marched hard in search of enemy troops, attacked, and drove them out of their position. Then, honor seemingly satisfied, the general returned to his cantonments, having taken a low grassy hill of no importance and killed 30 or 40 rebels. The Spanish officers, he reported, “anticipate a speedy end to the war…[but] I confess I do not see how this is to be done.” As long as the insurgents adhered to the tactics they had adopted, “they can neither be caught nor defeated.”

Churchill did not have high expectations for the rebels either, saying they offered at best “a bankrupt Government, torn by racial animosities and recurring revolutions.” The outlook for Cuba, he concluded in his last dispatch, was a somber one. Churchill delivered this judgment at age 21, after just 16 days in Cuba. Yet its balanced assessment of the insurgents, the futility of the Spanish strategy, and the ultimate result was an accurate reflection of countless insurgencies to come.

As happened throughout Churchill’s career as a war correspondent, his presumption annoyed the authorities and some of the press, who wondered what could possibly impel a British officer to get mixed up in such a dispute. The answer, of course, was ambition, fame, adventure, and the love of danger, or at least the desire for a reputation for courage in the face of danger, which, he confessed frankly to his mother, would help him as he pursued his political career.

“I am more ambitious for a reputation for personal courage,” he told her, “than [for] anything else in the world.” A couple of decorations, he added, would help to “beat my sword into an iron dispatch box,” a reference to the place from which ministers give their speeches in the House of Commons. Not surprisingly he was seen by some as bumptious and—accurately—as a medal hunter. This didn’t bother him. If he was seeking medals, it was his own life that he was risking.

What did concern Churchill after his return to London was getting another opportunity for action. That came in September 1896 when he joined his regiment in India, then departed again to be a war correspondent in a pending war between Greece and the Ottoman Empire. As the Thirty Days’ War looked to have been averted by the Great Powers—and did not break out until April 1897—Churchill returned to England for a vacation when trouble flared on the North-West Frontier.

“I was on the lawns of Goodwood [a race course] in lovely weather and winning my money,” he wrote later, “when the revolt of the Pathan tribesmen on the Indian frontier began.” He had extracted a promise from Brigadier Sir Bindon Blood, in command of the Malakand Field Force on the frontier, that he would employ him on his staff in such a contingency, and Blood wrote to tell him that if he could get press accreditation, he would do so. By modern journalistic standards, this may seem an obvious conflict of interest, and it was unusual even then, but it served to circumvent the bureaucracy. Churchill demanded $50 a dispatch from the Daily Telegraph and full attribution, but to his annoyance, after his return to India his mother negotiated only $25 and anonymity.

“Stingy pinchers,” he grumbled, but what really hurt was the lack of a byline. How was he to gain fame and fortune if nobody knew he was there? He need not have worried. Though the “letters” were attributed only to “a young officer,” Lady Randolph took care to ensure that everyone of note, including the Prince of Wales, knew who had written them. (He also wrote dispatches for the Allahabad Pioneer.)

General Blood attached Churchill to Brigadier P. D. Jeffreys, who had been directed to conduct a punitive expedition. This was a relic of the mid-century policies of the British authorities in India, who used such forays to discourage incursions from warlike tribes in the north. The operations irritated the tribesmen and did not improve the situation, so they were succeeded by a “forward policy” of pacification, which relied on forward outposts, a civilizing presence, educational and economic advantages (such as building roads while protecting and encouraging trade), and payments to local grandees.

A warrior-writer of some repute by the end of the Boer War, Churchill formed lifelong impressions, later writing, "Never believe any war will be smooth and easy, or that anyone who embarks on that strange voyage can measure the tides and hurricanes he will encounter." (Library of Conress).The forward policy has obvious analogies to current U.S. policy in Afghanistan. So do its drawbacks. The mullahs simply saw the British as a threat to their faith and power, and the policy began to fail. Then, in 1897, the Turks defeated the Greeks, a book was published on jihad, Islam welcomed a new caliph, and a new “Mad Mullah” emerged in India, convinced of his divine mission against the infidel British. In response, Britain reverted to its traditional punitive expeditions.

As always, Churchill in his dispatches was generous to his opponents. The “brave and warlike” Pathan tribes exhibited great military skill, he wrote. They followed “a code of honor not less punctilious than that of old Spain…supported by vendettas as implacable as those of Corsica.”

But the tribal society showed all the consequences of such a code. As he put it in The Story of the Malakand Field Force, his first book, which he wrote in two months upon his return from the campaign, “Except at the times of sowing and of harvest, a continual state of feud and strife prevails throughout the land. Tribe wars with tribe….To the quarrels of communities are added the combats of individuals….Every tribesman has a blood feud with his neighbor. Every man’s hand is against the other, and all against the stranger.”

Churchill confronted physical danger and death more directly in this campaign than ever before. In his letters, dispatches, and books, the thought of death is never far away. In a letter to Lady Randolph he confessed that in one skirmish he was perhaps “very near my end.” Referring to his dispatch to the Telegraph, he wrote: “If you read between the lines of my letter, you will see that this retirement was an awful rout in which the wounded were left to be cut up horribly.” He and another subaltern carried a wounded sepoy some distance: “[My] pants are still stained with the man’s blood….It was a horrible business. For there was no help for the man that went down.” In his book he was more insouciant: “Nothing in life is so exhilarating as to be shot at without result.”

In this campaign Churchill developed a philosophy of glory that he adhered to throughout his life, combining an ardent pursuit of fame, an extraordinary belief in his luck, and a phlegmatic acceptance of death. The pursuit of a military career, he reflected in his writings, differs from all others:

The only way [a soldier] can hope to rise above the others is by risking his life in frequent campaigns. All his fortunes, whatever they may be, all his position and weight in the world, all his accumulated capital, as it were, must be staked afresh each time he goes into action. He may have seen twenty engagements and be covered with decorations and medals….And yet each time he comes under fire his chances of being killed are as great as, and perhaps greater than, those of the youngest subaltern….The statesman, who has…made a great miscalculation, may yet retrieve his fortunes. But the indiscriminating bullet settles everything.

As for the campaign itself, the tribesmen, he reported, “have been punished, not subdued; rendered hostile, but not harmless. Their fanaticism remains unshaken….The riddle of the frontier is still unsolved.” As the campaign wound down, Churchill returned to the 4th Hussars and peacetime duties in India.

The Story of the Malakand Field Force was received with almost universal enthusiasm. The reviewer in the Athenaeum called it “a literary phenomenon.” Richard Harding Davis, perhaps the greatest American war correspondent, wrote several years later that it was Churchill’s “best piece of war reporting…and to writers on military subjects it is a model. But it is a model very few can follow, and which Churchill himself was unable to follow, for the reason that only once is it given a man to be twenty-three years of age….[The actions] which he witnessed and in which he bore his part, he never again can see with the same fresh and enthusiastic eyes.”

For those who study Afghanistan and Pakistan today, the book is still significant. Although Churchill, judging the conflict by the standards of European wars of the day, was somewhat dismissive of the issues and the scale of operations, some 120 years later we have become far more conscious of the power of the Islamist ideology driving such conflicts, and of the capacity of small, fanatical groups to strike disproportionately damaging blows.

Churchill next covered the war against the Dervishes in the Sudan, which arose from the same Islamic zeal Churchill had encountered on the North-West Frontier. In 1883, the followers of Mohammed Ahmed, who called himself the Mahdi, or messiah, and had proclaimed a holy war against foreigners, annihilated an army of 10,000 Egyptians led by an English officer. Sent to Khartoum with vague instructions to restore order and evacuate Europeans, Major General Charles Gordon dispatched 2,600 women and children to Egypt before he found himself besieged. After more than 300 days, the city fell and Gordon was killed. In the decade that followed, the government in Egypt accumulated the money, intelligence, and force to meet the 60,000 men on whom Khalifa Abdullah al-Taaisha, who had succeeded the Mahdi, could call.

Churchill had long coveted the chance of glory in the Sudan. He had made unavailing efforts to attach himself to the forces of Sir Herbert Kitchener, the sirdar, or commander in chief, of the Egyptian army, which was then led by both British and Egyptian officers. Kitchener saw no reason to encourage a brash young subaltern who, without the experience of his seniors, criticized their judgment.

In truth, Churchill had been full of praise for Sir Bindon Blood in India, but he had commented freely on military policy, and that behavior from a subaltern was equally unacceptable. Kitchener firmly rejected the appeals of all the grand names mobilized by Lady Randolph.

Then, with that luck to which Churchill frequently referred, he was saved by the prime minister, Lord Robert Salisbury, who had read the Malakand Field Force and invited its author to 10 Downing Street. A courteously worded request from Salisbury eventually received a grudging acquiescence from Kitchener, and on August 15, 1898, Churchill filed his first dispatch from Atbara, which lay at the end of a 400-mile railroad built across waterless desert to enable the British to strike at the Dervishes.

Churchill was attached to the 21st Lancers. The celebrity achieved by his dispatches from India, and then by his book, meant there was no lack of interest in his reports. Unfortunately, Kitchener’s dislike of war correspondents meant that they had to be sent to the Morning Post in the form of a series of letters to a friend. Once again, Churchill’s dispatches recognized the bravery and fanaticism of the opponent—the Dervishes were “as brave men as ever walked the earth”—and that the Khalifa represented both the religious and the nationalistic aspirations of his followers. The Khalifa had announced his intention to destroy the infidels. “Allah,” wrote Churchill sardonically, “is said to have fully approved of his plan.”Winston Spencer Churchill, the famous war correspondent, in Bloemfontein, South Africa, c. 1900 (Library of Congress).

The most memorable passage concerned Churchill’s participation in what was probably the last classic cavalry charge of the British Army, at Omdurman. The charge arose in part from a misapprehension, since the great mass of the Dervishes was concealed by a fold in the ground, and the British rode into a trap. The long column of Lancers began to move against what seemed to be a row of crouching blue figures, firing frantically. Churchill, whose shoulder had once been dislocated, clutched a Mauser pistol rather than a sword. As the Dervishes came into full view, he realized that they were 10 or 12 deep.

Suddenly he was in their midst, but they were not so thickly packed that he collided with any of them. The Dervishes were hacking at the horses, firing their rifles, pressing the muzzles into the very bodies of their opponents. Some Lancers were dragged from their horses. Churchill saw a gleam of a curved sword and fired. Then suddenly he was through the mass, with horses spouting blood, men clutching arms and faces cut to pieces, “gasping, crying, collapsing, expiring.” He was untouched. “It passed like a dream,” he told his mother, “and some part I cannot quite recall.”

The charge won extravagant praise and three participants were awarded Victoria Crosses. But it was, wrote the Marquess of Anglesey in his History of the British Cavalry, “the most futile and inefficient part of the battle.”

The Mahdists left some 15,000 of their dead and wounded on the battlefield. Churchill reported that they “strewed the ground in heaps and swathes.” The battle opened the way to the fall of Khartoum. It was, Churchill wrote in The River War, published in two volumes in 1899 to almost universal approbation for its honest assessments of the British Army at war, “the most signal triumph ever gained by the science of arms over barbarians.”

Churchill admired Kitchener’s cool precision, his careful planning, and the magnitude of his achievement in conquering the Sudan. But he wrote scathingly of the shooting of wounded Dervishes, and of the treatment of the Mahdi’s corpse. “The corpse of the Mahdi was dug up,” Churchill wrote in The River War. “The head was separated from the body, and, to quote the official explanation, ‘preserved for future disposal’—a phrase which must in this case be understood to mean, that it passed from hand to hand till it reached Cairo.”

Even before the book was published, Churchill resigned his commission and returned to England to run for Parliament for the Conservatives, in Oldham, Lancashire. In this case his usual good luck came in disguise. He lost, but the defeat led to his traveling to South Africa as a war correspondent. In hindsight the Boer War seems a minor prelude to the Great War, but it was the first conflict since the Crimean War to be waged by Britain against a modern army. It was also the war that made Churchill an internationally known figure, and opened up the political career of which he dreamed.

The Morning Post agreed to pay Churchill’s expenses: $5,000 for four months’ work and $1,000 a month thereafter, probably the most lucrative contract won by a newspaper war correspondent up to that time. He took with him a letter of introduction from the colonial secretary, his personal valet, a new adjustable Ross telescope, a Voigtlander field glass, ample wine, and 18 bottles of 10-year-old Scotch whiskey, among other refreshments.

The story of the South African campaign is the story of Churchill’s adventures, though from the start his judgment of the Boers and the probable length of the war was far sharper than that of the military authorities. Three days after his arrival, he wrote his mother: “We have greatly underestimated the military strength and spirit of the Boers. I very much doubt whether one army Corps will be enough.”

That insight clearly contributed to Churchill’s lifelong recognition of the perils of going to war. “Let us learn our lessons,” he wrote many years later, reflecting on the Boer and other wars. “Never, never, never believe any war will be smooth and easy, or that anyone who embarks on that strange voyage can measure the tides and hurricanes he will encounter.”

The Boers, mostly farmers from the two independent inland states of the Transvaal and the Orange Free State, had invaded the Cape Colony and Natal, Britain’s two coastal colonies in Southern Africa. Perhaps the finest mobile mounted infantry in the world, they had attacked a British advance column in Natal, killed the commander, Major General Sir Penn Symons, rounded up several thousand of his troops, and were besieging 9,600 British soldiers in the garrison town of Ladysmith in Natal, as well as Kimberley and Mafeking in the Cape Colony.

Churchill hastened to the Natal front, some hundred miles from the east coast port of Durban, and at once destiny took him firmly in its grasp. An old friend from India, Captain Aylmer Haldane, invited Churchill to join him on an armored train containing a company of the Dublin Fusiliers and another of Durban Light Infantry, with an antiquated 7-pounder muzzle-loading naval gun. These troops were to reconnoiter along the tracks to the railroad junction town of Colenso. Reports indicated no enemy within the next few miles.

The train completed its reconnaissance and on its return, as it rounded a corner, they could see newly made entrenchments. The Boers waited until the train was within 600 yards of their position, then opened fire with two field guns, Maxim machine guns, and a large number of rifles. The driver put on full steam, ran down a steep gradient, and crashed into a pile of stones artfully placed across the line to derail the train.

The three cars ahead of the locomotive were flung onto the embankment or across the track. The Boers’ fire was intense, if not particularly accurate. As Haldane noted in his later report, Churchill offered to help clear the line while the captain, dazed from the crash, organized those in the armored cars to return fire. The first thing was to detach the car that was half off the rails. Volunteers were called for, and after much pushing, the locomotive giving a shove, the car fell off the line. But it became jammed in the derailed car and Churchill had to search for a chain that could be used to pull back the obstruction.

There was still not enough room for the locomotive to get past. For 70 minutes Churchill and the other volunteers struggled, amid “clanging, rending iron boxes with the repeated explosion of the shells and the artillery, the noise of the projectiles striking the ears…the grunting and pulling of the [locomotive]—poor, tortured thing, hammered by at least a dozen shells, any one of which, by penetrating the boiler, might have made an end to all.”

At length, it cleared the obstruction, so Haldane permitted the driver to retire slowly, putting as many of the wounded as possible aboard the locomotive. Churchill ran back to help extricate the other unwounded men, and found himself in a railroad cutting almost alone. Unbeknownst to him, two soldiers, without authority, had waved white handkerchiefs in surrender. The Boers were rounding up prisoners and Churchill turned to escape. Several Boers began firing at him. One, just 40 yards away, took careful aim. “Death stood before me, grim sullen Death without his light-hearted companion, Chance,” he reported later. He slowly held up his hands.

“I cannot speak too highly of his gallant conduct,” wrote Haldane in his official report. A wounded officer, interviewed by a local newspaper, described his conduct as “that of as brave a man as could be found.”

A youthful-looking Prime Minister Churchill inspecting Civil Defense personnel in London at the outbreak of the Second World War (National Archives).But Churchill was now in the humiliating position of being a prisoner of war in Pretoria, the Boer capital. The account of his escape is crowded with the same daring and extraordinary luck that characterized his conduct on the train. He climbed over a well-lighted fence surrounding the prison. With no map, he guided himself by the stars, then leapt onto a passing train, jumping off as it approached the border with Portuguese East Africa. He stumbled—by chance—into one of the few houses owned by an Englishman, who helped conceal him on a train bound for the coast. He arrived back in Durban just as the British had suffered the last of three terrible defeats during the so-called Black Week. But tales of his exploits quickly traveled the world. As his son later wrote, like Lord George Byron after the publication of Childe Harolde, Churchill awoke one morning, at the age of 25, and found himself famous.

There was much more to report. He wrote two books based on his dispatches: From London to Ladysmith via Pretoria and Ian Hamilton’s March. Far earlier than most, he understood that this would be a long and arduous war—in truth Britain’s Vietnam. It was the culmination of a series of experiences given to few young men, and few young men would so comprehensively have understood them, and put them to such world-shaping use some 40 years on. Time and again we read in his dispatches accounts of the passionate nationalism of the Boers, both young and old. It was a powerful lesson in the dangers of underestimating an enemy, a mistake he did not make when confronted with the rise of Adolf Hitler, who was also tapping into resentful nationalism, in this instance of the Germans.

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