1. Winston Churchill’s mother was an American.

In the late 19th century, it was rather common for British aristocrats to marry U.S. heiresses. One such relationship matched Lord Randolph Churchill, the third son of the seventh Duke of Marlborough, with Jennie Jerome, the Brooklyn-born daughter of a wealthy financier. The couple had two children together: Winston in 1874 and Jack in 1880. Yet the relationship purportedly soured, and Jennie was frequently absent. She remained in England following Lord Randolph’s death in 1895 and would marry twice more, in both instances to men two decades her junior.

2. Churchill almost didn’t make it into military school.

As a student, Churchill performed poorly in virtually every subject except history and English composition. He was particularly inept at foreign languages. In a memoir, he described taking a two-hour-long Latin test that he left completely blank apart from his name and the number of the first question, along with “a blot and several smudges.” His plan to attend the Royal Military College at Sandhurst suffered a setback when he twice failed the entrance examinations. With the help of a military tutor, he finally qualified the third time around, but only for the cavalry class, which had lower standards than the infantry.

3. A daring escape from prison camp earned him instant fame.

After graduating from Sandhurst, Churchill took leave from the army and traveled to Cuba, where he reported on an uprising for a London newspaper. He subsequently served as a war correspondent and military officer, a dual role then permitted, in India, Sudan and South Africa. Upon arriving in South Africa in 1899, his armored train was ambushed by Boers, the descendants of Dutch settlers who were fighting the British at the time. Churchill was captured and marched to a prison camp, which he soon escaped from by scaling a wall at night, even as two of his fellow prisoners turned back. With no precise plan, Churchill luckily stumbled upon the house of a British coal mine manager, who hid him in a mineshaft for three days and then sent him on a wool-filled rail truck into Mozambique. From there, Churchill caught a ship back to South Africa and rushed to the front a newfound hero.

4. He organized a massive World War I attack that failed spectacularly.

Churchill’s political career began in 1900 when he was elected to Parliament, a position he would hold for more than 60 years. He secured his first cabinet post in 1908, and by 1911 had advanced to become First Lord of the Admiralty (the British equivalent of U.S. Secretary of the Navy). In this capacity, he prepared an amphibious assault during World War I against the crumbling Ottoman Empire. Churchill believed such action would allow the British to link up with their Russian allies, put added pressure on Germany’s eastern front and possibly even tip the balance of the entire conflict. But when Allied battleships entered the Dardanelles strait, located near present-day Istanbul, in March 1915, Ottoman fire sank three of them, severely damaged three others and sent the remainder into retreat. Allied troops similarly failed to gain ground during months of fighting on the adjacent Gallipoli Peninsula, suffering over 250,000 casualties in the process. Although Churchill lost his admiralty post as a result of the failure, he was eventually able to rehabilitate his reputation.

5. Churchill was no fan of Gandhi.

Throughout much of his life, Churchill opposed any form of autonomy for India. He reserved particular dislike for nonviolent independence leader Mohandas Gandhi, at one point calling him “a seditious Middle Temple lawyer now posing as a fakir of a type well known in the East,” and he even favored letting Gandhi die during a hunger strike. Churchill’s imperialist attitude came through with regards to other British colonies as well. He once asserted, for example, that Zulus, Afghans and Dervishes were “savages and barbarous peoples.”

6. Most of his famous speeches came within a few months of each other.

Churchill took over as prime minister in May 1940 after a disastrous start to World War II in which Nazi Germany conquered much of Europe. A master orator, he did his best to rally the nation in the face of near-certain attack, giving six major speeches in four months. During the first of those, he told Parliament that he had “nothing to offer but blood, toil, tears and sweat.”

On June 4, he similarly declared, “We shall defend our island, whatever the cost may be. We shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills. We shall never surrender.” And on June 18, as France prepared to submit to the Nazis, he told his countrymen to “brace ourselves to our duties and so bear ourselves that if the British Empire and its Commonwealth last for a thousand years, men will still say, “This was their finest hour.’”

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7. Churchill was voted out of office before World War II’s end.

In July 1945, after Germany had surrendered but not Japan, Britain held its first general election in a decade. To the surprise of many, Churchill’s Conservative Party lost in a landslide, having been successfully portrayed by the Labour Party as anti-worker and anti-welfare. “They have a perfect right to kick us out,” he purportedly said upon hearing the news. “That is democracy. That is what we have been fighting for.” He returned to the premiership in 1951, remaining there until ill health induced him to resign three-and-a-half years later.

8. Churchill popularized the term “iron curtain.”

Despite his misgivings about communism, Churchill gladly allied himself with the Soviet Union during World War II. Afterward, however, he began to harbor serious misgivings about the Soviet Union’s aims. In a March 1946 speech, he spoke of “an iron curtain [that] has descended across the continent.” “Behind that line,” he said, countries are subject “to a very high and, in many cases, an increasing measure of control from Moscow.” From that point forward, Western officials continuously mentioned the “iron curtain” when talking about the USSR.

9. He was an award-winning author.

Churchill wrote volumes of books over the course of his life, the first of which detailed his army experiences in India, Sudan and South Africa. He later penned a biography of his father, a biography of the first Duke of Marlborough, numerous volumes on World War I and World War II, a history of English-speaking peoples and one novel that he urged his friends not to read. In 1953, while serving his second term as prime minister, he received the Nobel Prize in Literature for “his mastery of historical and biographical description as well as for brilliant oratory in defending exalted human values.”

10. Churchill was extremely accident-prone.

As a youth, Churchill once suffered a concussion and ruptured a kidney while playfully throwing himself off a bridge. Later on, he nearly drowned in a Swiss lake, fell several times from horses, dislocated his shoulder while disembarking from a ship in India, crashed a plane while learning to fly and was hit by a car when he looked the wrong way to cross New York’s Fifth Avenue. None of these incidents left him debilitated. He lived until age 90 before finally succumbing to a stroke.