Weird History
317 voters

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

Updated September 1, 2020 2.3k votes 317 voters 14.6k 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.

  • 9

    He Resembled “A Rumpled Bed”

    He Resembled “A Rumpled Bed”
    Photo: Lyn Ott / Wikimedia Commons / Public Domain

    Spy novelist Eric Ambler, who was an artilleryman during the war, wrote:

    The Prime Minister enjoyed Hollywood films…there was a roomy projection theatre upstairs at Chequers and off-duty officers from the guard company and our battery would sometimes be invited up for the weekly film shows. … Under the projection beam and in the flickering reflections from the screen he looked like a rumpled bed.

  • 10

    He Was A Bad Listener

    Air Chief Marshal Sir Arthur "Bomber" Harris wrote of Churchill:

    He has, in fact, developed to a perhaps extreme degree this rather unfortunate trait of the man who has almost absolute power, knows his own mind, and really does not want to be bothered with everybody else's ideas. He is a bad listener, and frequently interrupts anyone who is expressing views, whether they are opposed to his own or not, halfway through a sentence; then he is off at a tangent, holding forth, always with interest and generally on sound lines, on some other aspect of the subject under discussion, or even on some entirely different subject.

  • 11

    He Was Extremely Conceited

    He Was Extremely Conceited
    Photo: Elliott & Fry / Wikimedia Commons / Public Domain

    Ted Morgan's biography of the young Churchill quotes this comment which Henry Cabot Lodge made to then-president Theodore Roosevelt:

    I have met him several times. He is undoubtedly clever but conceited to a degree which it is hard to express either in words or figures.

  • 12

    He Was Respected But Not Loved In Parliament

    Conservative MP and diarist Henry "Chips" Channon described Churchill coming to Parliament in 1944:

    He came in just before 11.30 and smiled. The House cheered and rose, a courteous, spontaneous welcome which under the dramatic circumstances was legitimate, but curiously cold. Churchill is not loved in the House. He has never had any ovation to equal several of Mr Chamberlain's, and this morning's performance proved it. I thought he looked disappointed, but his health and colour have returned.