To say Winston Churchill was an ambitious young man would be a classic example of English understatement. By the age of 25, the freckled-faced redhead had already written three books, run unsuccessfully for Parliament and participated in four wars on three continents. Nicknamed “Pushful, the Younger” by a newspaper reporter, Churchill hungered for fame and glory and was hardly shy in sharing the belief that he would one day become prime minister. “I have faith in my star that I am intended to do something in the world,” he wrote to his mother.

A photo of Churchill shortly after his escape in 1900. (Credit: Imperial War Museum)

“Churchill knew he would do extraordinary things—but not everyone else did,” Candice Millard, author of the new book “Hero of the Empire: The Boer War, a Daring Escape, and the Making of Winston Churchill,” tells HISTORY. “He knew he needed to prove it to a broader audience, and he thinks war is his vehicle to political power.”

Chasing the ghost of his distant ancestor John Churchill, the great British general whose figure literally loomed over the family’s estate at Blenheim Palace from atop a triumphant column, young Winston “threw himself into unbelievably dangerous situations,” Millard says. While working as a newspaper correspondent and military observer with the Spanish army during an uprising in Cuba, a bullet whistled just a foot past his head and killed a horse standing next to him. In British India, he survived a bloody battle in which he had seen friends mutilated by the enemy. Churchill believed greater forces than simple luck were at work. “I do not believe the Gods would create so potent a being as myself for so prosaic an ending,” he wrote to his mother.

Churchill during the Boer War. (Credit: Universal History Archive/Getty Images)

When Britain went to war with the Boers in southern Africa in 1899, the future prime minister saw a chance to once again make a name for himself. Confirming Churchill’s assessment that “my literary talents do not exist in my imagination alone,” the London Morning Post won a fierce bidding war for his pen by agreeing to pay him $150,000 in present-day money for just four months’ work—a sum that exceeded those paid to either famed authors Rudyard Kipling or Sir Arthur Conan Doyle for similar work covering the Boer War.

“Churchill was an excellent reporter. He understood history, so his analysis was insightful and brilliant, and his prose was incredibly beautiful,” Millard says. “I read a lot of coverage of the Boer War and his was head-and-shoulders above that of everyone else. It’s smart, incredibly readable and feels very modern.”

Churchill (far right) with his fellow POWs. (Credit: Doubleday)

With his valet and a vast liquor cabinet that included 18 bottles of scotch whiskey in tow, Churchill arrived in Cape Town in October 1899. A few weeks later, he was aboard an armored train carrying British troops on a reconnaissance mission when it was suddenly ambushed by the Boers and tossed from the tracks. As shells roared around him and bullets pinged the sides of the armored train, the war correspondent’s instincts took over. Acting like a decorated commander, Churchill braved the line of fire for more than an hour as he directed the soldiers to free the train. While some of the British fighters were able to flee to safety, the war correspondent was among those captured by the Boers and transported to a prisoner-of-war camp in the enemy capital of Pretoria.

“There is no ambition I cherish so keenly as to gain a reputation for personal courage,” Churchill had confided to his younger brother, Jack, two years earlier. As tales of his bravery reached London, that reputation was finally his, but it came at the price of his freedom. Although the Boers allowed prisoners-of-war to purchase newspapers, cigarettes and beer, the future prime minister despised his imprisonment “more than I have ever hated any other period in my whole life.” What frustrated Churchill even more than the loss of control was the possibility that he was missing out on further opportunities for glory. “I had only cut myself out of the whole of this exciting war with all its boundless possibilities of adventure and advancement,” he lamented.

A “Wanted” poster featuring Churchill and the reward for his return. (Credit: Hulton Archive/Getty Images)

On the night of December 12, 1899, while the guards weren’t watching, Churchill scaled the prison fence and made a break for freedom. The fugitive may have had no map, no ability to speak the local language and just “four slabs of melting chocolate and a crumbling biscuit” in his pocket, but he still possessed a seemingly superhuman level of self-belief that he could safely navigate the 300-miles journey through enemy territory.

As the Boers launched a massive manhunt—posters offered a reward for his capture, “dead or alive”—Britain became captivated by Churchill’s saga. “To their shock and horror, the British were losing the war,” Millard says. “When Churchill escaped, they had lost huge battle after huge battle, and they needed a hero. Here they had this young son of a lord who had humiliated the Boers. Everyone and Churchill knows the Boers are scouting the terrain, and if they catch him, there’s a real risk they would kill him. Everyone’s mesmerized.”

Returning from the Boer War on the RMS Dunottar Castle, July 1900. Churchill is seated, second from right .

Hiding by day and traveling at night, Churchill stole food and drank from streams. When hunger had nearly consumed him, the escapee took a chance and knocked on the door of a coal mine manager. Once again, luck was looking out for young Churchill as the man who answered the door was an Englishman, John Howard. “I felt like a drowning man pulled out of the water,” Churchill recalled. For days he hid in the total darkness of the coal mine, with the patter of the rats scurrying around his pillow his only company, until Howard was able to smuggle his countryman onto a freight train that carried him to freedom in Portuguese East Africa.

Although Churchill had finally achieved the glory he had always sought, he opted to continue covering the war—and fighting in it as well. He participated in the Battle of Spion Kop where a bullet severed a feather on his hat. When Pretoria fell in June 1900, Churchill rode into the city on horseback and led the liberation of the 180 soldiers remaining in the prison where he had once been confined.

A 1916 portrait of Churchill. (Credit: National Portrait Gallery)

Churchill returned to Britain that summer as the imperial hero he had always hoped to be. The country finally saw the greatness in the ambitious young man that he had seen in himself. He once again ran for a seat in Parliament. This time he won. “Nothing but personal popularity arising out of the late South African War carried me in,” he wrote the day after the election. “This is the launching pad for Churchill’s political career. This is what he had been trying again and again to happen. This is what made him a household name in Great Britain,” Millard says.

The story of Churchill’s exploits in the Boer War is not a coming-of-age story. As Millard points out, he had already come of age by the time he arrived in southern Africa. “He knew in his heart of hearts that he was destined for greatness. If you look at a photograph, you wouldn’t necessarily recognize him, but inside he was already fully formed. His determination, audacity, arrogance, ingenuity and grit were all there on full display.”