Churchill travelled extensively precisely because he was an ardent believer in face-to-face, real, live human relationships. That's the way he wanted to get to know other world leaders -- up close and personal. In this way, listening and responding, he sought to understand both friend and foe alike. And Churchill went to great lengths to plan every detail of the meals he shared during these many discussions -- meals and discussions that went well into the night.
Sir Winston was an extremely confident person and he placed unlimited trust and confidence in his own powers to charm, cajole and persuade others. If all this sounds familiar, it's because Donald Trump (who also requires little sleep and works well into the night) appears to be cut from the same mold. Extravagance characterizes both leaders and, like Churchill, Trump does not close the door to any eventuality if he's given the chance to meet with someone face-to-face and often over a fine meal. Churchill used 10 Downing or Chartwell or The Savoy or even far flung locals for these meetings just as President Trump uses the White House or Camp David or Mar-a-Lago or Trump Tower or any one of a number of Trump holdings throughout the world.
You couldn't tell Churchill that he could not cozy up to Stalin and bend the Soviet leader his way just as you cannot convince Trump that he doesn't have a shot of gaining concessions from Putin. Yes, Russia and England were thrown together by necessity during WW II. They were nominally allies and it was a different time, to be sure. But even after the war and even after much of eastern Europe was ceded to the Soviet block and even into the advent of the Cold War, Churchill was still convinced he could charm Russia via Stalin's successor, Khrushchev and begin to win new concessions. To that end, Churchill met with President Eisenhower in Bermuda in 1953. Sir Winston wanted peace; he wanted to at least try to avert a nuclear arms race; he wanted to open up a crack of sunlight in the Iron Curtain that he said had descended across Europe. Like Trump, he set aspirations high and remained ever hopeful.
And, in Dinner With Churchill you will also discover this: when Churchill was Prime Minister, even during the war, underlings who were part of Britain's administrative state tried to dissuade Churchill or tone down his rhetoric or the size and scope of his often audacious plans. In fact, Churchill's Principal Private Secretary at one point privately referred to his boss as "a lunatic: he gets in such a state of excitement that the wildest schemes seem reasonable." The Private Secretary was hopeful that "the Cabinet and finally The King" would "restrain" Churchill. Here again, dramatic similarities to the era of Trump.
It's amazing what history can teach you -- if you pay attention and if you're perceptive.
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