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.

  • 5

    He Looked Shorter Than He Was

    In his memoir Leaders, Richard Nixon, who met Churchill in 1954 while Vice President, wrote:

    I was rather surprised that he looked so short. Perhaps it was because his shoulders slumped and his large head seemed to rest on his body as if he had no neck at all.

  • 6

    His Judgment Was Questionable

    In 1942, Noel Coward wrote:

    I feel that he is losing his touch. He is fine when making stirring speeches but on major issues I doubt his judgement. His prophecies just before the war, when he was a voice in the wilderness, were wonderful but he seems less good in judging strategy and men.

  • 7

    He Could Make A Joke But Not Take One

    Herbert Morrison wrote:

    His sense of humour was uncertain. He excelled at making pithy comments about events [...] and about some of his colleagues, whether they were present or not. There was rarely anything vicious about these jokes: they were leg pulling jokes which only the sensitive and pompous found annoying.

    But he had to be the joker, and not the victim. Once or twice I essayed a joke at his expense. Immediately his smile vanished. He gave a perfect masculine version of Queen Victoria's "We are not amused". The aristocratic Churchill came to the fore; there was a frown on his face, and then he would move to the business of the meeting.

  • 8

    He Was Personally Offended By Bad Weather After D-Day

    He Was Personally Offended By Bad Weather After D-Day
    Photo: Parnall, C H (Lt), Royal Navy official photographer / Wikimedia Commons / Public Domain

    John Eisenhower, son of Supreme Allied Commander Dwight D. Eisenhower, was working as an aide for his father at the time of the Normandy Invasion. He remembered:

    The date was June 20, 1944, two weeks after the Allies had landed in Normandy, on June 6. Outside his window the worst storm in fifty years was raging over Great Britain and the English Channel, a storm so violent that it could conceivably destroy the Anglo-American OVERLORD beachheads on the coast of Normandy. The fruits of years of preparation were in greater peril that day than they had been on the better-remembered D-day itself.

    In Churchill's office, for a short visit, was my father, General Dwight D. Eisenhower, with me present as an aide. Dad and I had been planning to visit OMAHA Beach, in Normandy, the day before. Now we found ourselves marooned in Dad's "Telegraph Cottage" south of London, incapable of taking any action whatsoever. Frustrated at his enforced isolation, Dad decided to drive up to London to see Prime Minister Winston Churchill.

    After minimal greetings, all three of us sat down at the large table in Churchill's office and said little except for Churchill's fretting over the situation. He slouched in his chair, glaring at the floor. "They have no right," he growled, "to give us weather like this!" So sure was he of the rightness of the Allied cause that he took this storm as a personal affront on the part of the Almighty to himself.