1. Winston’s teachers described him as unambitious, rebellious, and violent, and said that he could not be trusted to behave himself in any situation.
2. Even though he was known for his remarkable ability to make stirring speeches, he actually suffered from a speech impediment which he made great effort to hide.
3. At his house in Kent, England, he stocked between 3,000 and 4,000 Cuban cigars at a time.
4. Churchill acquired his taste for cigars during his visit to Cuba in 1895. He traveled there because the Cuban uprising against the Spanish empire was, to him, the only interesting war going on at the time.
5. While fighting in the Anglo-Boer war in 1899, he was captured by the Boers and thrown into a POW camp. One night, he was able to make a dramatic escape by vaulting the prison walls. Once out, he stole food and hitched rides until he finally reached safety in Mozambique.
6. In 1904, during his first term in the British Parliament, Churchill helped draft a piece of legislation which mandated the sterilization of those who were referred to at the time as “feeble minded.” He was acting on what he had said years earlier to his cousin: “The improvement of the British breed is my aim in life.”
7. He suffered from intense bouts of depression which he called his “Black Dog” periods. It is now believed that he had bipolar disorder.
8. When justifying his support of the Soviet Union, Churchill famously said, “If Hitler invaded hell, I would make at least a favourable reference to the devil in the House of Commons.” He was expressing his belief that the enemy of your enemy is your friend.
9. In 1953, Churchill was awarded the Nobel Prize in Literature and was knighted by Queen Elizabeth II to become Sir Winston Leonard Spencer-Churchill. During the same year, he had a stroke. Funeral plans were made and called Operation Hope Not.
10. Upon Churchill’s death in 1965, his funeral saw the largest gathering of members of the public and statesmen since 1852, when the Duke of Westminster was buried.