The Donald Trump Winston Churchill Overlap

James M. Ridgway, Jr.
3 min readJan 21, 2017

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To many Americans, especially conservative Americans, the late Sir Winston Churchill is seen as a great World War Two hero. And of course in many respects he was of that ilk.

But the truth of Churchill is much more complex than this popular notion of the British statesman. Heading toward the Second World War Churchill was viewed by most in England as a washed-up political hack, who, being rooted in a fast fading British aristocracy, seemed out of step with modern times.

Unlike Donald Trump, our current accidental president, Churchill was a prolific reader and writer with a profound sense of history. With the rise of Hitler and the Nazis in Germany, the egocentric Churchill saw a window of opportunity for a political comeback. He commenced an endless campaign of rants against the German chancellor, which for a time made little impression on the people of Britain. However, as war with Germany began to appear inevitable, Churchill’s stock with the people rose as well.

And so by the time war manifested itself between England and Nazi Germany, without hesitation the political establishment turned to Churchill as the nation’s natural leader. Like Trump, under certain conditions, Churchill’s political cheerleading and salesmanship could be marvelously effective. He rallied a desperate people through a perilous time when all seemed lost. Trump, on the other hand, created a sense of perilous times that only he could rectify, notwithstanding the nation having already been rescued from the brink of disaster by President Obama.

But when it came to practical matters of military strategy Churchill was hopelessly flawed. During World War One he was the First Lord of the Admiralty until he was forced out upon horrendous Allied losses during the Gallipoli campaign, an operation brought about at Churchill’s insistence.

Again leveraging his great political influence in World War Two, Churchill pushed hard for the Italian campaign, calling Italy the Axis’ soft underbelly It was a campaign that needlessly cost British and American force tens of thousands of lives, as they fought up the rugged mountains of the Italian peninsula toward Rome. Yes, Rome was a valuable prize, but grinding toward the Italian Capitol from the base of the mountainous peninsula that heavily favored German defensive positions was a needless bloody mess that did little to speedup winning the war. Had those same resources that were applied to the slogging Italian campaign been put into a campaign up the Rhone Valley of southern France (the true soft underbelly of the Axis powers) in conjunction with the Normandy landings of 6 June 1944, many thousands of lives would have been saved and the war enormously speed up. This of course is military minutia that has been lost to the general public.

Also, like the extravagant Trump, Churchill wallowed in luxury at all times. While his people were being severely rationed when it came to food and minor pleasures, Churchill traveled to the various battlefronts attended to by a huge personal staff that keep him well supplied with the world’s finest cigars, booze and cuisine.

And like Trump pretending to care about the common man, Trump’s personal hero, Winston Churchill, never refrained from living like a king even in the worst of times. Yes, as the days of Trump’s presidency roll along I think there will be a great deal of overlap between the behind the scenes ways of Trump and Churchill. Each will have projected grandiosity while causing needless havoc.

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James M. Ridgway, Jr.
James M. Ridgway, Jr.

Written by James M. Ridgway, Jr.

Jim Ridgway, Jr. military writer — author of the American Civil War classic, “Apprentice Killers: The War of Lincoln and Davis.” Christmas gift, yes!

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