Commanding Facts About Winston Churchill

December 9, 2023 | Stephanie Kelsey

Commanding Facts About Winston Churchill

“History will be kind to me for I intend to write it”.—Winston Churchill

Everyone knows Winston Churchill as the British Prime Minister who was in office during the WWII, and who provided us with a bevy of quotable quotes. But what do we know about him as a person? Keep reading to find out 45 commanding facts about this fascinating man.

45. Just Wrap Him in Bubble Wrap

Churchill lived to a very respectable 90 after suffering a stroke, but he put his body through a lot over the years. When he was young, he threw himself from a bridge in a game, suffering a concussion and rupturing a kidney. When he was older, he nearly drowned in a lake, dislocated his shoulder while getting off a ship, fell from a number of horses, crashed a plane and was hit by a car. Maybe he was a cat and had nine lives?

winston churchill

44. Getting Schooled

He wasn’t the greatest in school. In fact, he was only really good in history and English composition. He was also pretty terrible with foreign languages, and once said he only wrote two things down for a two-hour long Latin exam: his name and the first question’s number. Yeah, that’s pretty rough.

Winston Churchill factsGetty Images

43. Third Time’s the Charm—Barely

He had desired to enroll in the Royal Defence College at Sandhurst, but his academic performance was insufficient. He failed the entrance exams twice and only passed the third time after hiring a tutor experienced in defense education. Even then, he only just managed to qualify for the cavalry class because they had lower standards than the infantry.

Winston Churchill factsWikimedia Commons

42. Winston the Writer

Churchill took leave from the army after graduating from Sandhurst, first ending up in Cuba. He worked for a London newspaper and reported on the uprising happening in the country. Shortly thereafter, he was appointed as a front-line journalist and armed forces official, covering events from places such as India, Sudan, and South Africa.

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41. And So It Begins

A year after this ordeal, he returned to England to start a political career. He had his first cabinet post in 1908 and became the First Lord of the Admiralty in 1911. This role was essentially like being the Secretary of the Navy in the US.

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40. Royal Rulings

Over the span of his political career, there were six monarchs to reign over the Commonwealth: Victoria, Edward VII, George V, Edward VIII, George VI and the current Queen, Elizabeth II.

Winston Churchill factsFlickr, Levan Ramishvili

39. Fourth Time’s the Charm

Before proposing to Clementine Ogilvy Hozier and marrying in 1908, Churchill proposed to three other women. Three! They all declined. Do you wonder if they ever regretted that decision?

Winston Churchill factsGetty Images

38. #OMG

Speaking of modern discourse, Churchill is believed to be the first recipient of the term “OMG.” It was used in a letter from Lord Fisher to Churchill in September 1917.

Winston Churchill factsChurchill (2017), Salon Pictures

37. Tank You Very Much

The British first used the tank in battle in September 1916 and Churchill is widely known as helping in its development.

Winston Churchill factsWikimedia Commons

36. A Prominent Post

Churchill was made Prime Minister in May 1940—after WWII had begun. He did his best to rally his country, and keep spirits high. In just four months, he delivered a number of speeches, with many quote-worthy moments. Just one month into his post, he said: “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.”

Winston Churchill factsDarkest Hour (2017), Perfect World Pictures

35. Winthton

And while he was famous for his speeches, he actually had a speech impediment. He particularly had a hard time with the letter “s.”

Winston Churchill factsWikimedia Commons

34. Keeping up With the News

Because of this impediment, he studied all current issues and any possible interactions and conversations that could be raised by them. That way, he would be prepared and help prevent the impediment from coming through.

Winston And The KingGetty Images

33. Thanks, but No Thanks

Churchill and his Conservative Party were voted out of office in 1945, before Japan's surrender and while the hostilities were still ongoing. “They have a perfect right to kick us out,” he said after being defeated by a landslide. He was voted back into power in 1951, but had to step down less than four years later due to health concerns.

Winston Churchill factsFlickr, Levan Ramishvili

32. Soviet Struggles

During WWII, Churchill allied his country with the Soviet Union, but wanted nothing to do with them once it was over. He even brought about the term “Iron Curtain” as a way of describing them. He believed Moscow was in control of the entire Soviet Union, and made sure everyone knew his opinion. The term was used by most Western nations after that.

Winston Churchill factsGetty Images

31. Futuristic Flyer

He had an interesting way of getting around during WWII: a pressurized chamber. His health wasn’t that great, so the “Life Pod” had to be used when he had to fly. It had a phone, ashtray and air circulation system so that he could still smoke. Priorities!

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30. Machine Firepower Winston

He was also considerably resolute when it came to traveling by boat during the same conflict. His lifeboat was equipped with a machine weapon, enabling him to "resist capture at all costs."

Winston Churchill factsGetty Images

29. Winston the Writer, Take Two

Despite not being the best in school, Churchill wrote quite a number of books as an adult. He wrote a biography about his father, Lord Randolph Churchill, who was the Duke of Marlborough, and a number of works on both World Wars. He also wrote a novel that he didn’t want his friends to read, and told them as much. Was it a crisis of confidence or was he writing bad things about them?

Winston Churchill factsGetty Images

28. That Could Have Been a Disaster

There’s one photo in particular of Churchill where he looks pretty grumpy. The reason? The photographer, Yousef Karsh, had just taken a cigar right from Churchill’s mouth.

Winston Churchill factsWikimedia Commons, Yousuf Karsh

27. Don’t Get Between a Man and His Wants

He didn’t like being told he couldn’t drink in front of the Saudi King because of his religious beliefs. Churchill declared, "my belief instituted a strict observance, which involved partaking in spirits before, after, and if necessary, during all meals and the breaks between them." In essence, there was no separating the man from his indulgences or libations.

Winston Churchill factsDarkest Hour (2017), Perfect World Pictures

26. A Mother's Inducement

His mother hated that he smoked. She even composed a letter to him at the age of 15, promising him a pony and a piece of personalized weaponry if he abstained from it for six months. He did, and as soon as the six months was up, he quickly picked his habit back up again.

Winston Churchill factsGetty Images

25. An Exceptionally Good Honor

He was so recognized for his fondness for a certain habit that they even named one item after him. The Cuban “Churchill” cigar is about seven inches long and 19 millimeters wide.

Winston ChurchillNational Archives and Records Administration, Wikimedia Commons

24. American Ancestry

Though his father was among British nobility, his mother was an American socialite from New York. This probably had something to do with Churchill being made an honorary American citizen in 1963, the first person to earn this distinction. Maybe they were also inspiration for the Earl and Countess of Grantham in Downton Abbey?

Winston Churchill factsWikimedia Commons

23. Luck of the Irish

He may have been born in Oxfordshire, England, but Churchill actually grew up in Dublin, Ireland. His grandfather employed his father in the area.

Winston Churchill factsFlickr, Ron Cogswell

22. He Sees Departed Souls

Churchill claims to have seen the ghost of American President Abraham Lincoln in the White House. He wasn’t the only one, though. Ronald Reagan’s daughter and Theodore Roosevelt also say they saw Lincoln’s spirit.

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21. He’s Too Sexy for His Clothes

Maybe this is the reason why he saw ghosts? During his stay at the White House in 1941, Churchill seemingly spent most of his personal time unclothed and frequently indulged in alcoholic beverages. To each his own!

Winston Churchill factsGetty Images

20. Comfort and Style

If he wasn't unclothed, you may have found him wearing a onesie. Or, at least, a one-piece outfit designed for conflict periods. It was known as a “siren suit,” and was used for practical reasons in case of an air raid. He had them made in a few materials like wool, canvas and even velvet.

Winston Churchill factsGetty Images

19. Did He Keep His Own Quotes?

He was a bookworm and a collector of quotations. He was known for his ability to find all the key points in long bodies of text, too. “The quotations when engraved upon the memory give you good thoughts,” he said.

Winston Churchill factsGetty Images

18. Nobel and Nobility

Roughly halfway through his second go-around as Prime Minister, Churchill received the Nobel Prize in Literature. He received the prestigious honor for “his mastery of historical and biographical description as well as for brilliant oratory in defending exalted human values.” He had been considered a number of times prior to this one actually sticking. The same year, he was knighted by the Queen.

Greta Thunberg FactsShutterstock

17. Wordy Winston

He’s credited with creating a couple words. The first being “summit” in 1950, and the second being “quisling” to describe a traitor. He wasn't very inventive with the latter, with its origin being Vidkun Quisling, a leader known for his authoritarian regime.

Winston Churchill factsWikimedia Commons

16. It’s Never Too Late to Start Something New

He must have had a creative brain because he took up painting when he was in his 40s. In 48 years, he painted more than 500 works! He once said, “when I get to heaven I mean to spend a considerable portion of my first million years in painting.”

Winston Churchill factsGetty Images

15. The Struggles Were Very Real

He suffered from depression his whole life, calling it the “black dog.” Mental health issues also impacted his children, with one daughter tragically losing her life, and another struggling with alcoholism. His personal mental health suffered as he got older, and his overall health became worse after suffering from a number of strokes.

Depression factsPixabay

14. Oh, the Controversy

Churchill favored eugenics—the now completely debunked belief that things like criminality and intelligence were based in genetics, so breeding should be restricted to only those with the best genes. He contributed to the Mental Deficiency Act of 1913 where he tried to incorporate that those who were feeble-minded should be sterilized instead of hospitalized. Thankfully, this was changed before the law actually came into effect.

Winston Churchill factsGetty Images

13. Even the Best of Us Break Down

Although he was known for being opinionated and staunch in his demeanor, he was very emotional. If he was given bad news, he was known to break down crying, and sometimes would have to hold back tears when delivering speeches.

Winston Churchill factsChurchill (2017), Salon Pictures

12. Always on the Go

A couple other interests of his including bricklaying and landscaping. “I built with my own hands a large part of two cottages and extensive kitchen-garden walls, and made all kinds of rockeries and waterworks and a large swimming pool,” he said.

Winston ChurchillUnknown Author, Wikimedia Commons

11. Chart-Topper

Not once, but twice has Churchill made it onto the music charts, just not while he was alive. The first was a compilation of speeches he made and was released posthumously in 1965. The second time was part of a 70th anniversary compilation for the Battle of Britain.

Winston Churchill factsDarkest Hour (2017), Perfect World Pictures

10. G.O.A.T. Brit Edition

In a poll conducted in 2002 by the BBC, Churchill came in first in a list of greatest Britons of all time.

Winston Churchill factsShutterstock

9. No Other Like Him

He was also honored with his own coin posthumously. It’s pretty rare for a statesman to be honored in such a way, but due consideration was given. He was also honored again, 50 years later. Another accomplishment, given that he is the only statesman to be revered twice in such a way.

Winston Churchill factsShutterstock

8. Telling His Story

Churchill has been portrayed on screen (both big and small) a number of times, by a number of actors. Richard Burton, Christian Slater, John Lithgow and Gary Oldman are all among those to depict the late Brit whether on TV or on film.

Winston Churchill factsDarkest Hour (2017), Perfect World Pictures

7. Paying Tribute

Upon his passing, the Queen declared that Churchill's body would be exhibited at Westminster Hall for three days, a privilege usually only granted to members of the royal family. He also had a state funeral, one of the largest ever held in British history. Representatives from 112 countries were invited, with China being the only one to decline. Over 350 million people watched from around the world, with the American audience being larger than the one who tuned in for the funeral of US President John F. Kennedy. Churchill was buried in his family’s plot alongside both of his parents.

Aphra Behn factsPixabay

6. No Longer a Captive

Things took a bit of a turn for the worse in 1899 when he arrived in South Africa. The train he had been traveling on was ambushed by Boers, who were descendants of the Dutch settlers and took up arms against the British. Churchill was taken to a confinement camp, but he managed to break free pretty quickly. During the night, he climbed over a wall and kind of just traveled, since he didn’t have any concrete plans for his escape.

Winston Churchill factsGetty Images

5. Can’t Keep Him Away

Luck was with him, and he came across the home of a British coal mine manager. He was hidden in a mine shaft for three days before getting put on a rail truck headed to Mozambique that was filled with wool. After arriving there, he hopped back onto a ship for South Africa and back to the front lines.

Winston Churchill factsShutterstock

4. An Epic Fail

As First Lord, Churchill organized an attack against the Ottoman Empire during the WWI that proved costly. It was supposed to get the Brits to meet up with their Russian allies, but the Ottoman Empire ended up sinking three of their ships at Gallipoli near present-day Istanbul. Three other ships were damaged, and all others retreated. Churchill lost his role because of this failed assault, but would eventually regain his reputation.

Winston Churchill factsFlickr, Archives New Zealand

3. Opinions Are Entirely His Own

At least, that’s what he would put on his Twitter biography if he was around today. He was pretty opinionated, especially when it came to Gandhi. Of the Indian leader, Churchill said he was “a seditious Middle Temple lawyer now posing as a fakir of a type well known in the East.” Churchill also would have allowed Gandhi to succumb during a hunger strike. He didn’t hold contempt just for Gandhi, either. He also called Zulus, Afghans and Dervishes “savages and barbarous peoples.”

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2. Not One of His Best Moments

Despite the exceptional reputation that Churchill garnered posthumously, his legacy wasn't solely built on leadership and speeches during periods of conflict. Churchill was one reason why millions of Indians suffered from fatal starvation in 1943. He exported food from India instead of releasing food rations, one of the factors that made the manmade famine so horrible.

Winston Churchill factsWikimedia Commons

1. Attribute It to the Conflict

He was pretty upset with Prohibition when it was in place in the US. He called it “an affront to the whole history of mankind.” Ol' Churchy definitely could be a little dramatic when it came to the hooch.

Winston Churchill factsGetty Images

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12

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