Churchillian Trump?

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In July, I wrote an article that included some of Winston Churchill’s famous quotes and titled the article, “Winston Churchill Would have Loved Twitter, Just Like President Trump“,  After watching the latest movie about Churchill, “Darkest Hour”, which I highly recommend, I was struck again with the wit and sharp tongue similarities between President Trump and Prime Minister Churchill.  Below are some pairings that I found to be most similar in style, delivery and sharpness.


President Trump:  “As long as you’re going to be thinking anyway, think big.”

Winston Churchill:  “The POSITIVE THINKER sees the INVISIBLE, feels the INTANGIBLE, and achieves the IMPOSSIBLE.”


President Trump:  “Many people are afraid to fail, so they don’t try. They may dream, talk, and even plan, but they don’t take that critical step of putting their money and their effort on the line. To succeed in business, you must take risks. Even if you fail, that’s how you learn. There has never been, and will never be, an Olympic skater who didn’t fall on the ice.”

Winston Churchill:  “Success consists of going from failure to failure without loss of enthusiasm.


President Trump:  “Sometimes by losing a battle you find a new way to win the war.”

Winston Churchill:  “Success is not final, failure is not fatal: it is the courage to continue that counts.”  

Non-PC Personal Observations!!

President Trump:  “Do you mind if I sit back a little? Because your breath is very bad. 

Winston Churchill:  “I may be drunk, Miss, but in the morning I will be sober and you will still be ugly.”


President Trump: “I’m asking the American people to rise above the noise and the clutter of our broken politics, and embrace the great faith and optimism that has been the central ingredient in the American character.”

Winston Churchill:  “The pessimist sees difficulty in every opportunity. The optimist sees the opportunity in every difficulty.”

Future Success

President Trump:  “No dream is too big. No challenge is too great. Nothing we want for our future is beyond our reach.”  

Winston Churchill:  “Success consists of going from failure to failure without loss of enthusiasm.”


President Trump:  “In the end, you’re measured not by how much you undertake but by what you finally accomplish”

Winston Churchill:  “It is no use saying, ‘We are doing our best.’ You have got to succeed in doing what is necessary.”

On America

President Trump:  “When America is united, America is totally unstoppable.”

Winston Churchill:  “You can always count on Americans to do the right thing – after they’ve tried everything else.”

The Legacies of Churchill and Trump

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Winston Churchill’s legacy is pretty much set in history.  President Trump’s is still unfolding.  Based on his first year in office as the President of the United States, you can bet his legacy will include tenacity, outspokenness, strength, and an unlimited pursuit to make America the best it can be.  If President Trump is tested in wars, his legacy will be colored by his prosecution of those events.

Regardless of Trump’s final legacy, there is no doubt that they have more in common than  not.  Their drive for success is unquestioned.  Churchill’s response to the adversities and challenges of war was to say. “We shall defend our island, whatever the cost may be, we shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills; we shall never surrender.”  Trump’s response to challenges, adversities, and our potential was equally as prophetically sound when he said, “No dream is too big. No challenge is too great. Nothing we want for our future is beyond our reach.”

There is no doubt the world and America are living in a period of global challenges that are equal to or even greater than anytime in the past.  The threat of war is visible on many fronts and its drums are audible nearby.  Will the world and the US succumb to the weaknesses that plagued the world in Chamberlain’s appeasement views or follow the resolve of Churchill and overcome these many threats? 

When tested, will President Trump take his seat in history as the protector of freedom around the world or will he join the ranks of the appeasers that have created past and current challenges in opposing tyrannical evil in distant capitals and at home?  My hope is that President Trump will recall his own words that he uttered, “When somebody challenges you, fight back. Be brutal, be tough.”, and cling to his realistic assessment, “In the end, you’re measured not by how much you undertake but by what you finally accomplish.”

RD Pierini



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