Born November 30, 1874, Sir Winston Leonard Spencer Churchill possessed the determination of a bulldog. And well might he, for he was descended from one of Britain’s greatest generals, the daring, cunning, master-leader John Churchill, Duke of Marlborough (1650-1722).  

Of Winston Churchill, historian Paul Johnson writes, “No man did more to preserve freedom and democracy and the values we hold dear in the West.” 

Though Winston Churchill certainly had his faults, he must be ranked as one of history’s greatest leaders and profiles of courage. We named our son after this remarkable man, praying that our Winston will demonstrate the same attributes as he serves Christ. Here are five lessons from the life of Winston Churchill. 

1. Leadership Follows Preparation

British Prime Minister Benjamin Disraeli once said, “The secret of success in life is for a man to be ready when his time comes.” Winston Churchill aptly illustrates this powerful truth. In his early days, Churchill honed the character and skills that prepared him to lead the British Empire and the free world through their darkest hour. 

Like many of history’s great leaders, Churchill experienced a somewhat difficult childhood. Though his parents had status, Churchill’s father, as the second son of the seventh Duke of Marlborough, had little money. Most of Churchill’s growing up years were spent in a boarding school, away from home, where he chafed at the strict regimen. Churchill also struggled with a speech impediment, likely a lisp or stutter. Yet Churchill developed a love for History and English, subjects in which he excelled, and which were to serve him well in the future.

In India, Sudan, and South Africa, Churchill, first as a military officer and then as war correspondent, demonstrated the courage that came to define the rest of his life. Churchill actively participated in World War I, overseeing the disastrous Gallipoli invasion, which he learned from, and helping to develop the tank. When he became Prime Minister, at age 65, Churchill stated, “I felt as if I were walking with destiny, and that all my past life had been but a preparation for this hour and this trial.”

2. Leadership Demands Courage

In their darkest hour, when the British people were on the verge of making a deal with Hitler, Churchill inspired them to continue on. Perhaps we can better appreciate his legendary quotes if we understand that Britain’s epic struggle was the context in which many of them were delivered. To the British people, Churchill exhorted, “Never, never, never give up,” and “Success is not final, failure is not fatal, it is the courage to continue that counts.”

In his 20s, during the Boer War, Churchill helped an armored train out of an enemy ambush, although he was later captured himself. Subsequently, he escaped from prison, with a “dead-or-alive” bounty placed on his head. 

In World War II, Churchill became associated with the famous V for “victory” sign. In his “Finest Hour” speech, Churchill said, “Let us therefore brace ourselves to our duties, and so bear ourselves, that if the British Empire and its Commonwealth last for a thousand years, men will still say, ‘This was their finest hour.’” 

As Churchill believed, “Without courage, all other virtues lose their meaning.”

3. Leaderships Requires Communication

Churchill’s communication may be measured by the fact that today he is one of the most quoted individual in the English language. Unlike many leaders, Churchill wrote all of his speeches (roughly 2500) himself. 

Words like the following gave Great Britain hope and reassurance and impelled them to action. 

• “We shall fight them on the beaches…” 
• “Victory at all costs, victory in spite of all terror, victory however long and hard the hard may be; for without victory there is no survival.” 
• “Do not let us speak of darker days; let us speak rather of sterner days. These are not dark days: these are great days – the greatest days our country has ever lived. ”

Not only was Churchill a master speaker, he was also one of the most celebrated authors of his day. By some estimates, his prolific writings include a staggering 20 million words. For this, Churchill was awarded the Nobel Prize in literature, in 1953.

Churchill’s voracious reading contributed greatly to his success as a communicator. He made a practice to read widely, and then filed away interesting quotes. He admonished, “Employ your time in improving yourself by other men’s writings so that you shall come easily by what others have labored hard for.”

4. Leadership Necessitates Perspective 

George Santayana said it best, “Those who do not remember the past are condemned to relive it.” Long before WWII began, Churchill was only one of a few to foresee the threat of Nazism. In 1938, Prime Minister Neville Chamberlain returned triumphantly from appeasing Hitler at Munich proclaiming to a large crowd “peace with honor,” and “peace for our time.” 

Though a minority voice, Churchill understood the fatal consequences of Chamberlain’s appeasement. Churchill, whose warnings had gone unheeded for years, rightly stated, “We have sustained a total and unmitigated defeat.” In hindsight, most historians agree that, had the British and French stood with the Czechs, Germany might possibly have quickly squashed, and Hitler deposed. As Churchill stated, “An appeaser is one who feeds a crocodile – hoping it will eat him last.”

As Churchill demonstrates, understanding history allows us to make better choices today that impact the future. In 1948, Churchill wrote to his grandson, “Learn all you can about the past. For how else can anyone make a guess about what is going to happen in the future.” 

5. Leadership Entails Teamwork

We know much about Winston Churchill, but what about the men who helped him achieve victory, those whom Churchill called his “inner circle?” 

Churchill’s team was capable, working together for a common purpose. While all carried an equal voice in discussion, Churchill had the final decision. Yet when a decision had been made, Churchill trusted his subordinates to carry it out as they best saw fit. While Churchill delegated, Hitler often micromanaged, a fact which Paul Johnson believes contributed in large part to the Allied victory. As the 1941 Russian campaigned bogged down, Hitler made poor decisions over the better advice of his generals, decisions which cost him dearly.  

No great men or women in history have accomplished great things on their own. And history teaches us that a dedicated minority working together can accomplish remarkable things. As Churchill proclaimed, “Never in the field of human conflict was so much owed by so many to so few.”

Though Churchill is considered one of the greatest wartime leaders of history, he would not have been a great leader without his team. In his own words, “I have never accepted what many people have kindly said, namely that I have inspired the nation. It was the nation and the race dwelling all around the globe that had the lion heart. I had the luck to be called upon to give the roar.”

Churchill and Today

We live in difficult, yet exciting times. Throughout history, there have always been battles to fight, and today is no exception. Ephesians 6:12 tells us that we fight a spiritual battle “against principalities, against powers, against the rulers of the darkness of this world.” 

Against this rising tide of evil, the world needs spiritual leaders to rise to the call, with eternal vision and a firm resolve. We must recognize, as Churchill did, that crisis always spells opportunity. “A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty.”

We pray that our son Winston would be prepared to be a leader for God’s glory, in the home, the church, business, the public square, or wherever God places him. May he be a courageous man of God, living with hopeful assurance in the ultimate triumph of God’s kingdom. As Maltbie Davenport Babcock said, “It matters not how deep intrenched the wrong… Faint not—fight on! Tomorrow comes the song.” 

More Resources on Churchill and His Times

Their Finest Hour Speech by Winston Churchill

We Shall Fight On the Beaches Speech by Winston Churchill

Blood, Toil, Tears, and Sweet Speech by Winston Churchill

Churchill by Paul Johnson

Churchill’s Trial: Winston Churchill and the Salvation of Free Government by Larry Arn

The Rise and Fall of the Third Reich by William L. Shirer

Winston Churchill and Statesmanship Free Online Course by Hillsdale College