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Sir Winston Churchill, King Henry the Eighth, and Donald Trump

Written By | Mar 26, 2017

COLORADO SPRINGS, Colo., March 25, 2017 — The self-proclaimed supreme deal-maker of our times, President Donald Trump, has failed. His first legislative foray into the repeal and replacement of Obamacare went down in flames on Friday.

Was Trump, a political neophyte, a clueless victim? Was he a hapless bystander? Did he trust too much in his legislative consigliere, Paul Ryan?

No, no, and no. The man who swept aside the entire Republican establishment to become America’s businessman-president is the last thing from naïve. Trump’s life in its totality is a lesson in shrewdness, a litany of correct decisions, and a demonstration of his ability to move up, down and through complex problems to reach solutions.

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 As many decry the president’s chances going forward, they do so using traditional Washington power standards. But in Trump, we have a wholly different breed of cat in action. Everyone would do well to stand well back, watch and learn.

Because Trump may well have sacrificed a battle on his long march to his “Draining the Swamp” war.

Professional prognosticators are claiming that establishment Washington has taught this man a lesson. The impulsive businessman has been given a reality check by checks and balances.

The truth may be the reverse. Our “Mr. Trump Goes to Washington” plays chess and majors in the long game. If the movie’s Mr. Smith won over the town through good-hearted earnestness, watch for Trump to accomplish much the same through cunning and the wisdom of a true deal-maker.

An example of a leader of extraordinary effectiveness and longevity is one of the 20th century’s most forceful and effective leaders, Sir Winston Churchill. Named the Greatest Briton of all time in a 2002 poll, Churchill’s complex legacy continues to stimulate intense interest among historians, yet in a career spanning some 70 years, he had more than his share of controversy and enemies.

No less complex a man than our current president, Churchill was an idealist and a pragmatist; an orator and a soldier; an advocate of progressive social reforms and an unapologetic elitist; a defender of democracy as well as of Britain’s fading empire.

Churchill served as prime minister of the United Kingdom from 1940 to 1945, crucial years in the history of the modern western world. After becoming prime minister in 1940, he helped lead a successful Allied strategy with the U.S. and the Soviet Union during WWII to defeat the Axis powers and craft post-war peace.

Voted from office following the war, this galvanic statesman returned to lead Great Britain again from 1951 to 1955. He was a leader of strong will who is credited for motivating mottoes still in common use today, including, “Never give up,” and “You have enemies? Good. That means you’ve stood up for something, sometime in your life.”

Now, a century later, America’s 240-year-old democracy experiment is yet in its infancy as compared to many other cultures and civilizations, including the British Empire. The times have changed and most kings and dictators have fallen. America has lost blood and treasure, again, and again, to ensure that people around the world retain liberty and freedom. With the exception of the Civil War, America’s great battles have been waged against outsiders.

Churchill was faced with a time when the international order was threatened by a mad man in Germany. As Hitler marched across Europe, Great Britain saw they were next. They engaged the United States in efforts to stop the German threat. But Churchill’s steadfast leadership against appeasers in his own country and against great odds won the day.

Germany is no longer a threat to the world order. An international march toward creating an Islamic Caliphate is our new challenge, providing leaders with similar choices to those of Britain before World War II. Engage the enemy? Ignore him, and hope he goes away?

Today’s world battle against Islamic radicals is far more insidious and dangerous than it was against the Nazis. Today’s enemy sits upon his religion, challenging the West’s egalitarian views against religious prejudice. The Islamists hide behind our own constitutional systems as they plan their attacks.

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Even more problematic, in WWII, the Nazis fought from their own home base. Today’s warriors have embedded themselves into the West. They live among us. They have jobs, and they wait until their number is called.

Every President of the United States has had his own trials to overcome, and his own battles to achieve results. Those battles have most often been fought out in the open. Presidents have always had a loyal opposition, sometimes even within their own parties.

Today, President Trump, no less than Prime Minister Churchill, is faced by a fierce enemy he knows has the power to destroy everything America stands for. As he fights with leftist judicial activists over his constitutionally granted Executive Privilege to enforce border restrictions, as ugly as that battle may seem, at least one can say it is being fought in the courts, and the media, in the open, where adversaries are self-identified.

But Trump’s war in the past weeks has become far more complex than Churchill’s. He came into office a mere two months ago, thinking he knew his enemy. That was then, and this is now. More than at any time in the nation’s history, America’s ‘Secret State,’ a world of spies, wire-taps, and faceless enemies, has come to the fore. President Trump, unwittingly, now is faced with internal intrigues that rival the Tudors. Yet, he is not empowered, as the late King Henry the Eighth was, to smoke out his enemies and chop off their heads.

He must engage within the rule of law. On his way out of town, his predecessor, no fan of Trump’s, widened the circle of potential enemies within, granting many more national security agencies here the power to see national security-sanctioned phone, computer and God knows what else traffic. Did the former president hope for his embedded colleagues to disseminate secrets detrimental to the incoming president? Who knows? But, as crime solvers anywhere know, look for motive.

Since January 20, the truth of the existence of a secret “Deep Government,” is being revealed in a steady daily drip, drip, drip of revelations. What appears clear is that unnamed sources “at court” would overturn our president through nefarious spying and under handed tactics. To address this new reality, the man who came to Washington to drain the swamp must first locate the alligators in that swamp.

Much of his opposition is well hidden, cowering behind convenient presidential orders made by his predecessors. As President Trump discovers the truth about those who would oppose him, no less than King Henry the VIII, he must stand alone, trusting few save his most loyal consiglieres. He came to Washington believing his enemies to be out in the open, ready to do him battle. Instead, he finds himself blind-folded and operating as though inside a dark paper bag, lacking the necessary knowledge even of who and where his enemies are.

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He came to Washington believing his enemies to be out in the open, ready to do him battle. Instead, he finds himself blind-folded and operating as though inside a dark paper bag, lacking the necessary knowledge even of who and where his enemies are.

President Trump, like Sir Winston Churchill and King Henry the VIII before him, is alone. He must realize that hard fact now more than ever before. His battle to renew America, and to make it great again, clearly is not shared by everyone. He is surrounded by those who smile to his face, but who undercut his orders.

In his Washington White House residence, as President Trump stands and looks out upon the National Mall, at the well-kept grounds of the White House, and at the jets landing off in the distance at National Airport, he may feel isolated and beset by enemies. Welcome to the Swamp!

However, our president would do well to train his gaze beyond Washington, to the people of the United States who elected him, who placed their faith in him, and for whom a surveillance state, a “Deep State” must not endure. He, and he alone, can change things. Like King Henry the VIII and Sir Winston Churchill before him, he guides the ship of state. May he rule long and wisely. May God always be with him.

Karen Hagestad Cacy

Karen Hagestad Cacy, of Colorado Springs, is a former Washington speechwriter and transportation lobbyist. Raised in Portland, Oregon, she holds a BA degree in Russian and Middle East Studies from Portland State University (and American University in Cairo.) Her four novels are available on She is also the author of two plays.