Prologue
 
Crouching in darkness outside the prison fence in wartime southern Africa, Winston Churchill could still hear the voices of the guards on the other side. Seizing his chance an hour earlier, the twenty-five-year-old had scaled the high, corrugated-iron paling that enclosed the prison yard. But now he was trapped in a new dilemma. He could not remain where he was. At any moment, he could be discov­ered and shot by the guards or by the soldiers who patrolled the dark, surrounding streets of Pretoria, the capital of the enemy Boer repub­lic. Yet neither could he run. His hopes for survival depended on two other prisoners, who were still inside the wall. In the long minutes since he had dropped down into the darkness, they had not appeared.

From the moment he had been taken as a prisoner of war, Churchill had dreamed of reclaiming his freedom, hatching scheme after scheme, each more elaborate than the last. In the end, however, the plan that had actually brought him over the fence was not his own. The two other English prisoners had plotted the escape, and agreed only with great reluctance to bring him along. They also car­ried the provisions that were supposed to sustain all three of them as they tried to cross nearly three hundred miles of enemy territory. Unable even to climb back into his hated captivity, Churchill found himself alone, hiding in the low, ragged shrubs that lined the fence, with no idea what to do next.



Although he was still a very young man, Churchill was no stranger to situations of great personal peril. He had already taken part in four wars on three different continents, and had come close to death in each one. He had felt bullets whistling by his head in Cuba, seen friends hacked to death in British India, been separated from his regiment in the deserts of the Sudan and, just a month earlier, in November 1899, at the start of the Boer War, led the resistance against a devastating attack on an armored train. Several men had died in that attack, blown to pieces by shells and a deafening barrage of bullets, many more had been horribly wounded, and Churchill had barely escaped with his life. To his fury and deep frustration, however, he had not eluded capture. He, along with dozens of Brit­ish officers and soldiers, had been taken prisoner by the Boers—the tough, largely Dutch-speaking settlers who had been living in south­ern Africa for centuries and were not about to let the British Empire take their land without a fight.

When the Boers had realized that they had captured the son of Lord Randolph Churchill, a former Chancellor of the Exchequer and a member of the highest ranks of the British aristocracy, they had been thrilled. Churchill had been quickly transported to a POW camp in Pretoria, the Boer capital, where he had been imprisoned with about a hundred other men. Since that day, he had been able to think of nothing but escape, and returning to the war.

The Boer War had turned out to be far more difficult and more devastating than the amusing colonial war the British had expected. Their army, one of the most admired and feared fighting forces in the world, was astonished to find itself struggling to hold its own against a little-known republic on a continent that most Europeans consid­ered to be theirs for the taking. Already, the British had learned more from this war than almost any other. Slowly, they were real­izing that they had entered a new age of warfare. The days of gallant young soldiers wearing bright red coats had suddenly disappeared, leaving the vaunted British army to face an invisible enemy with weapons so powerful they could wreak carnage without ever getting close enough to look their victims in the eye.

Long before it was over, the war would also change the empire in another, equally indelible way: It would bring to the attention of a rapt British public a young man named Winston Churchill. Although he had tried again and again, in war after war, to win glory, Churchill had returned home every time without the medals that mattered, no more distinguished or famous than he had been when he set out. The Boer War, he believed, was his best chance to change that, to prove that he was not just the son of a famous man. He was special, even extraordinary, and he was meant not just to fight for his country but one day lead it. Although he believed this without question, he still had to convince everyone else, something he would never be able to do from a POW camp in Pretoria.



When Churchill had scrambled over the prison fence, seizing his chance after a nearby guard had turned his back, he felt elated. Now, as he kneeled in the shrubs just outside, waiting helplessly for the other men, his desperation mounted with each passing minute. Finally, he heard a British voice. Churchill realized with a surge of relief that it was one of his co-conspirators. “It’s all up,” the man whispered. The guard was suspicious, watching their every move. They could not get out. “Can you get back in?” the other prisoner asked.

Both men knew the answer. As they stood on opposite sides of the fence, one still in captivity, the other achingly close to freedom, it was painfully apparent that Churchill could not undo what had already been done. It would have been impossible for him to climb back into the prison enclosure without being caught, and the punish­ment for his escape would have been immediate and possibly fatal.
 
 

In all the time he had spent thinking about his escape since arriv­ing in Pretoria, the one scenario that Churchill had not envisioned was crossing enemy territory alone without companions or provisions of any kind. He didn’t have a weapon, a map, a compass, or, aside from a few bars of chocolate in his pocket, any food. He didn’t speak the language, either that of the Boers or that of the Africans. Beyond the vaguest of outlines, he didn’t even have a plan—just the unshak­able conviction that he was destined for greatness.

Part One

Pushful, the Younger

Chapter 1 - Death by Inches

From earliest childhood, Churchill had been fascinated by war, and dreamed of gallantry in battle. “There is no ambition I cherish so keenly,” he had confided to his younger brother, Jack, “as to gain a reputation for personal courage.”

As a boy, he had collected a miniature army of fifteen hundred toy soldiers and spent hours sending them into combat. “From very early youth I had brooded about soldiers and war, and often I had imagined in dreams and day-dreams the sensations attendant upon being for the first time under fire,” he wrote. “It seemed to my youthful mind that it must be a thrilling and immense experience to hear the whistle of bullets all around and to play at hazard from moment to moment with death and wounds.” At Sandhurst, the Royal Military College, from which he had graduated in 1894, Churchill had loved nothing more than to participate in war games, regretting only “that it all had to be make-believe.”

To be an aristocratic Englishman in the late nineteenth century meant being surrounded not merely by the lavish benefits of imperial power but by its equally vast responsibilities. Covering more than a fifth of the world’s land surface, the British Empire had come to rule about a quarter of the human race—more than 450 million people living on every continent and on the islands of every ocean. It was the largest empire ever known, easily outranking the once mighty Spanish Empire, which had been the original object of the awe-filled description “the empire on which the sun never sets.” It was five times the size of the Roman Empire at its zenith, and its influence—over people, language, money, even time, for the clocks in every time zone were set to Greenwich mean time—was unrivaled.

By the time Churchill reached adulthood, the greatest threat to the empire no longer came from the other major powers—Spain, Portugal, Germany or France—but from the ever-expanding burden of ruling its own colonies. Although long the object of admiration, envy and fear, the British army had been stretched impossibly thin as it struggled to keep the empire intact, crisscrossing continents and oceans to put down revolts everywhere from Egypt to Ireland.

To Churchill, such far-flung conflicts offered an irresistible opportunity for personal glory and advancement. When he entered the British army and finally became a soldier, with the real possibility of dying in combat, Churchill’s enthusiasm for war did not waver. On the contrary, he had written to his mother that he looked forward to battle “not so much in spite of as because of the risks I run.” What he wanted most from his life as a soldier was not adventure or even battlefield experience but a chance to prove himself. He wanted not simply to fight but to be noticed while fighting.

For a member of Churchill’s high social class, such bold, unabashed ambition was a novelty, if not an outright scandal. He had been born a British nobleman, a direct descendant of John Churchill, the 1st Duke of Marlborough, his parents personal friends of the Prince of Wales, Queen Victoria’s oldest son and heir. Yet in his open pursuit of fame and popular favor, Churchill seemed far less Victorian than Rooseveltian. “The immortal Barnum himself had not a greater gift for making himself and his affairs the talk of the world,” his first biographer, Alexander MacCallum Scott, would write just a few years later. “Winston advertises himself as simply and unconsciously as he breathes.”

In a world in which men were praised not just for their stiff upper lip but for extreme modesty when it came to their own achievements, Churchill was widely criticized for being that most offensive of creatures, the medal hunter. He was called a “self-advertiser,” a “young whippersnapper,” even, by a reporter for the Daily Chronicle, “Pushful, the Younger.” He was not unaware of these criticisms and even years later, bewildered by the viciousness with which he was attacked, would admit that it was “melancholy to be forced to record these less amiable aspects of human nature, which by a most curious and indeed unaccountable coincidence have always seemed to present themselves in the wake of my innocent footsteps.” He was not, however, about to let them slow him down.

Churchill knew that the surest and quickest route to recognition, success and perhaps, if he was lucky, fame was a military medal. It was “the swift road to promotion and advancement in every arm,” he wrote, “the glittering gateway to distinction.” Distinction, in turn, could be parlayed into political clout, opening a door onto the kind of public life that he longed for, and which he believed was his destiny. So while the military was not, for Churchill, an end in itself, it was certainly a very useful means to an end. What he needed was a battle, a serious battle, one that would be talked about, would be remembered, and, with a good dose of courage and a little showmanship on his part, might propel him to the forefront of the military stage. For that, he was willing to risk anything, even his life.

Churchill had seen real fighting for the first time in 1895. Instead of spending his leave playing polo or foxhunting like most young officers, he had gone to Cuba as a military observer, joining a fighting column of the Spanish army during an uprising that was a prelude to the Spanish-American War. It was here that he began smoking cigars, giving birth to a lifelong habit and a distinct preference for Cubanos. It was also here that on his twenty-first birthday he heard for the first time “bullets strike flesh.” In fact, he had very nearly been killed by a bullet that, by the capriciousness of fate, had sailed just a foot past his head, striking and killing the horse standing next to him. In Cuba, however, he had been only an observer, not an active participant, and for Churchill that would never be enough.

Churchill’s true education in the harsh realities of Britain’s colonial wars began the next year, in the remote mountains of British India’s North-West Frontier, modern-day Pakistan, whose sweeping vistas, unforgiving beauty and lethal conflicts would later suggest powerful parallels to those of southern Africa. For the British army, no colony had been more difficult to subdue than India, the jewel in the empire’s crown, and no part of India had proved more deadly for British soldiers than the tribal lands of the Pashtun, an ethnic group renowned for their military skill and unyielding resistance to outside control.

It was, in fact, the Pashtun’s unmatched ferocity in battle that drew Churchill to India, and to the Pashtun heartland known as Malakand. In October 1896, Churchill had arrived in India with his regiment, the Fourth Queen’s Own Hussars. He had come hoping to find himself quickly at the center of action. Instead, he had spent month after frustrating month in Bangalore, which he irritably described to his mother as a “3rd rate watering place.”

The incredible luxury in which he lived had made little difference. Left to find their own lodgings, Churchill and two fellow officers had chosen what Churchill described to his mother as “a magnificent pink and white stucco palace in the middle of a large and beautiful garden.” They paid for this lavish abode by combining their salaries, given to them in silver rupees poured into a string net bag “as big as a prize turnip,” with any allowance they managed to pry from dwindling family fortunes.

Like some of his fellow officers, Churchill came from a family that was rich in titles and grand estates, but little else. The Churchill family palace, Blenheim, was, like most great houses in England at the end of the nineteenth century, hovering on the brink of collapse. The 5th and 6th Dukes of Marlborough had lived lives of such extravagance that when Churchill’s grandfather inherited the title and the palace, he had been forced to sell not just land but some of the treasures that the family held most dear. In 1875, when Churchill was not yet a year old, the 7th Duke sold the Marlborough Gems, a stunning assortment of more than 730 carved gemstones, for more than £36,000. A few years later, despite the protestations of his family, he sold the Sunderland Library, a vast and historically significant collection.

The most effective means the Churchills had found of keeping the palace from going under, however, had been to marry the successive dukes off to “dollar princesses,” enormously wealthy heiresses whose families longed for an old British title to burnish their new American money. Soon after becoming the 8th Duke, Churchill’s uncle George Spencer-Churchill, whose first wife divorced him in the wake of an affair, married a wealthy New York widow named Lillian Warren Hamersley. His son, now the 9th Duke, dutifully followed in his footsteps, marrying a dollar princess of his own, the American railroad heiress Consuelo Vanderbilt, in 1895.

Despite his family’s financial failings, Churchill was accustomed to a lavish lifestyle, and he hired a veritable army of servants while in India. “We each have a ‘Butler’ whose duties are to wait at table—to manage the household and to supervise the stables: A First Dressing Boy or valet who is assisted by a second DB: and a sais [syce] to every horse or pony,” Churchill had coolly explained to his mother. “Besides this we share the services of 2 gardenders [sic]—3 Bhistis or water carriers—4 Dhobies or washermen & 1 watchman. Such is our ménage.”

When a Pashtun revolt began in the mountains of Malakand the next year, Churchill, bored and restless, had been on leave in London, at the world-famous Goodwood Racecourse. It was a perfect day, the racecourse was so beautiful that the Prince of Wales referred to it as a “garden party with racing tacked on,” and Churchill was “winning my money.” As soon as he learned of the revolt, however, Churchill knew that this was the opportunity he had been waiting for, and he was not about to waste a moment or wait for an invitation.