The Wit & Wisdom of Sir Winston Churchill

Some people claim that Sir Winston Churchill was one of the most intelligent people of his generation. His epoch-making speeches inspired the British during World War II, while he was Britain’s Prime Minister, and are credited with raising British morale through its darkest days. His fluid expression and acerbic wit have been regarded as the model of English usage. In 1963, during a ceremony granting US citizenship to Sir Winston, President John F. Kennedy observed, “Churchill mobilized the English language and sent it into battle. 

Yet, throughout his school years, Winston was regarded by his teachers as a poor student and a behavior problem. He did poorly on his tests and barely passed the entrance exams to the prestigious Harrow School. While there, he developed an interest in history and wrote some poems and letters that were published in the school magazine. In spite of his writing prowess, Churchill never felt he was sufficiently educated. “It’s a good thing for an uneducated man to read books of quotations,” he said, “The quotations when engraved upon the memory give you good thoughts and make you look for more.” To this end, he studied the Bartlett’s Familiar Quotations assiduously and developed a talent for expressing ideas with wit and brevity. Later in life, suggesting that his poor performance at school may have been an advantage, he noted, “By being so long in the lowest form [grade] I gained an immense advantage over the cleverer boys…I got into my bones the essential structure of the normal British sentence–which is a noble thing.” Churchill’s use of colorful metaphor enabled him to convey lasting images. In describing his disdain for Joseph Stalin and Communism, he explained:

Trying to maintain good relations with a Communist is like wooing a crocodile. You do not know whether to tickle it under the chin or beat it over the head. When it opens its mouth, you cannot tell whether it’s trying to smile or preparing to eat you up. 

Through his tireless study of language he acquired the turn of phrase so vital to witty discourse. At a reception when Churchill was seated beside a Methodist minister, an attractive young waitress approached with a tray of glasses filled with sherry. Churchill eagerly seized a glass, while the staunch minister, drawing himself into a posture of self-righteous indignation, responded, “Young lady, I’d rather commit adultery than take an intoxicating beverage!” There was a silent pause, and then as the waitress departed, Churchill called out, “Come back miss–I didn’t know we had a choice.”

Later in life, Churchill’s achievements, enhanced by his oratory skills, brought him numerous honorary degrees. On one such occasion, when accepting an honorary Doctor of Law degree, he announced with great humility, “Perhaps no one has ever passed so few examinations and received so many degrees.”

Beginning at the 9:07 mark in the YouTube video below, Orson Welles shares a telling anecdote about Churchill and his wit.