Weird History
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What Winston Churchill Was Really Like, According To The People Who Knew Him

Updated September 1, 2020 2.0k votes 280 voters 13.2k views16 items

List RulesVote up the most surprising details about Winston Churchill.

Winston Churchill is now almost deified as the man who stood between the Western world and utter darkness in that terrifying summer of 1940, and who helped shepherd the Allies to victory over the next five years. His achievements have been hailed in books and on film. In his lifetime, his reputation was much more complex. Many viewed him as a jingoistic imperialist with an antiquated concept of the British Empire. He made plenty of enemies in his long and storied career, and Churchill's personality traits, enchanting to some, were equally galling to others.

Here's a collection of descriptions of Winston Churchill from before, during, and after his glory days of WWII.

  • 1

    He Had A Weak Handshake

    Of his 1954 meeting with Churchill, Richard Nixon later observed:

    Like so many Englishmen, his handshake was more of a pressureless touch than a firm grasp.

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  • 2

    He Figured How To Win The War While Shaving

    He Figured How To Win The War While Shaving
    Photo: United Kingdom Government / Wikimedia Commons / Public Domain

    In Finest Hour, Churchill's son Randolph was quoted describing the morning of May 18, 1940, when France was collapsing before the German offensive:

    I went up to my father's bedroom. He was standing in front of his basin and was shaving with his old fashioned Valet razor. He had a tough beard, and as usual he was hacking away.

    "Sit down, dear boy, and read the papers while I finish shaving:" I did as told. After two or three minutes of hacking away, he half-turned and said: "I think I see my way through." He resumed shaving.

    I was astounded, and said: "Do you mean we can avoid defeat? (which seemed credible), or beat the b*stards?" (which seemed incredible).

    He flung his razor into the basin, swung around, and said: "Of course I mean we can beat them."

    Me: "Well I'm all for it, but I don't see how you can do it."

    By this time he had dried and sponged his face and turning around to me, said with great intensity: "I shall drag the United States in."

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  • 3

    He Wouldn’t Speak On Radio For Less Than $500

    He Wouldn’t Speak On Radio For Less Than $500
    Photo: Unknown / Wikimedia Commons / Public Domain

    In 1938, when Churchill was still out of government, journalist William Shirer tried to get him to discuss the recent German annexation of Austria as a radio talking head for CBS:

    CBS, for which I was a correspondent in Europe, asked me to get Churchill to broadcast on the crisis, but it would pay him only fifty dollars, which was a ridiculous sum. From the way he talked I concluded he would accept five hundred dollars. But [Shirer's boss] William Paley was adamant. He would not pay more than fifty, and we lost the broadcast.

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  • 4

    He Delivered A Major War Update With His Hands In His Pockets

    On April 10, 1941, the Manchester Guardian described a speech Churchill gave before Parliament:

    He was as masterful as ever. Indeed, he was masterful enough at times as to be quite casual. Think of Hitler addressing his Reichstag with both hands thrust deep in his trouser pockets! Yet that was Mr. Churchill. It was in this way that he announced that the Germans had entered Salonika at four o'clock this morning. He almost did it in an aside. Intended or not, the manner took a lot of the force out of the blow.

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