In this week’s Leading Thoughts, I want to offer a short piece from one of my books. I’m doing this because the piece deals with humor in the life of Winston Churchill. It is hard to exaggerate how important humor is in a leader’s arsenal. I’m not referring to the silly, giggly brand of humor common these days, but rather to the higher humor that both wrings a laugh and imprints an enduring message. Churchill was a master at this, so forgive the length and the presumption of quoting my own work, and enjoy this chapter from The Character and Greatness of Winston Churchill.


“In my belief, you cannot deal with the most serious things in the world unless you also understand the most amusing.”

“Man,” said English essayist William Hazlitt, in The English Comic Writers, “is the only animal that laughs and weeps: for he is the only animal that is struck by the difference between what things are and what they ought to be.” If this is true, then genuine humor arises from something akin to a largeness of soul, an inner breadth so all-encompassing as to embrace both the commonplace and the ideal, both life’s ugliness and its stunning beauty, both the normal and the absurd. Such is the soul of great leadership, and such was the soul of Winston Churchill.

Wit, which Webster defines as “the ability to relate seemingly disparate things so as to illuminate or amuse,” flowed effortlessly from Churchill. His was not the humor of the comedian, that of the joke or the anecdote. Instead, he combined a non-conformist’s perspective with an awe-inspiring command of language to produce an often disarming and sometimes shattering effect that always extended his meaning.

Once when visiting the White House, Churchill emerged from his daily bath just as President Roosevelt was wheeled into his room. Roosevelt was deeply embarrassed and apologized profusely while beating a hasty retreat. Astutely, Churchill seized the moment for a larger cause. Holding up a detaining hand, he solemnly proclaimed, “The Prime Minister of Great Britain has nothing to hide from the President of the United States.” When the cliché “familiarity breeds contempt” was once used in an argument against him, he thundered, “I would like to remind you that without a degree of familiarity we could not breed anything.” When Pygmalion was beginning at His Majesty’s Theatre, George Bernard Shaw wired Winston: “Am reserving two tickets for you for my premiere. Come and bring a friend—if you have one.” Churchill, who could give as good as he got, wired Shaw back: “Impossible to be present for the first performance. Will attend the second—if there is one.”But Churchill’s wit could be quite acidic, as well. He was unwilling to suffer fools, had a fiery temper, and was not adverse to making “a few remarks of a general character, mostly beginning with the earlier letters of the alphabet.” He said of John Foster Dulles that he was “dull, duller, Dulles.” He called Clement Attlee a “sheep in sheep’s clothing” and “a modest man with much to be modest about.” Lady Astor, a constant thorn in Churchill’s side, once said in exasperation, “Winston, if I were your wife I’d poison your soup.” He replied without hesitation, “Nancy, if I were your husband, I’d drink it.” To another woman who said that she liked neither his politics or the new mustache he was sporting, he retorted, “Madam, I see no earthly reason why you should come into contact with either.” And in a manner typical of his style, he fired a broadside against one despised breed by simply defining them for ages to come. “A fanatic,” he jibed, “is one who can’t change his mind and won’t change the subject.”

He was not a stone-faced wit, though, and he enjoyed the occasion of a laugh as much as anyone. Friends noted that he had a habit of “throwing back his head and laughing heartily.” His fellow members of Parliament learned to look for the signs that a classic “Churchillism” was on its way.

“One always knew it was coming. His own laughter began somewhere in the region of his feet. Then a leg would twitch; the bubble of mirth was slowly rising through the body. The stomach would swell; a shoulder heave. By this time, the audience would also be convulsed, although it had no idea what the joke was going to be. Meanwhile, the bubble had ascended a little further and had reached the face; the lips were as mobile and expressive as a baby’s. The rich, stumbling voice would become even more hesitant. And finally there would be the explosion, the triumphant sentence of ridicule.” 

Yet, he took wit seriously, even as he did language and the spoken word. His secretary recorded that while once touring slums he remarked, “Fancy living in one of these streets, never seeing anything beautiful, never eating anything savory, never saying anything clever.” Churchill’s wit is similar to that found in many great leaders. It sprang from a yearning to find acceptance, certainly, but it also found its origin in a kind of compassion, in a genuine affection and a hope of touching more than the mind with the power of truth. Herbert Elliston, editor of the Washington Post, perhaps better than anyone understood the impact of Churchill’s wit and, through it, the wit required of leaders in difficult times.

Churchill will live if only in his witticisms. And these will be the stock of conversation in all countries for a long time to come. They are as much a revelation of character as anything he said or did—as much, also, of an influence among men. In wartime they passed by word of mouth all over the world wherever men were struggling with the aggressor and planning a new life in liberty. They lightened the burdens of the dispirited and were quoted as the words of a champion.