The Best Books on Winston Churchill

I’ve heard there are still over a hundred books a year published on Winston Churchill. Rightfully so. He was the greatest man of the 20th century and deserves to be studied, remembered, imitated, and revered for ages to come.

Now Churchill wasn’t perfect. He had considerable flaws. As someone said about him, “The first time you meet Winston, you see all of his faults, and the rest of your life you spend in discovering his virtues.” He was wrong about race, imperialism, and the welfare state. He was involved in, party to, and downright responsible for several political and military disasters. He was a hard charger, and he often didn’t care who got in his way.

But he was also a hero, and there’s something to be said for flawed heroes. Churchill was a giant of a man, but he was very human. His struggle to make something of himself, his ironclad determination to rise again after a fall, and the sheer force of his will against all odds and every opponent give you the sense that maybe you too can aspire to greatness.

I began reading about Churchill several years ago, and I’ve been absolutely hooked ever since. He is a man of endless appeal. Without any of his other accomplishments, he could have been world class as a statesman nearly three times over, a prime minister, an orator, a journalist, a historian, a builder and bricklayer, a soldier, and a painter, each in their own right. Because of his super-human suite of gifts, nearly everyone can find something to relate to. I think everybody should spend some time with the old lion, and here are the best books I’ve read:

To Begin:

Churchill by Paul Johnson

Johnson’s biographies are all good, and most importantly, they’re short. Napoleon, Socrates, and George Washington are all excellent. His 200-page introduction to Churchill is the perfect place to begin a lifelong friendship with the great man of Britain. Johnson chronicles his colossal life with speed and intrigue and gives a great defense of Churchill in the end.

Churchill: A Life – Martin Gilbert

This is the abridged version of the authorized biography, which is eight sprawling volumes! Gilbert began this project alongside Churchill’s son, Randolph, and after volume two, carried the load himself. He went on to write about Winston for over 40 years. The last volume he published, Churchill: The Power of Words is a selection of WSC’s best articles, historical writing, speeches, and letters. Gilbert had access to everything available about Churchill, including his private papers, extensive interviews with family members, and a free run of Chartwell, Churchill’s country home. This is the gold standard for Churchill biography and scholarship.

Churchill Style: The Art of Being Winston Churchill – Barry Singer

This book is about Churchill’s eccentricities. From the kinds of hats he wore (he never met a hat he didn’t like), to his favorite brand of Champagne (Pol Roger), to the kinds of pens he used, this book gives you access to all of Churchill's stuff. The text of this book is really well done and gives a great overview of his life, but the real value is in the pictures. This is one you can spend an hour looking at, poring over the hundreds of photos, ads, and cartoons showing Winston in his element. It is a fitting tribute to the man who said, “I have the simplest tastes. I am always satisfied with the best.”

The Churchill Factor – Boris Johnson

This is the most recent book I’ve read on Churchill and it has become one of my favorites. It is not technically a biography, so I would suggest you have a couple books under your belt before you jump into this one. Boris Johnson, a Churchill-like figure in his own right for better or worse, has produced the greatest ode to Churchill I’ve come across. He defends him against his critics, vindicates his military blunders, and imagines what the world would be like today if it weren’t for this greatest of men. This is one of the most enjoyable books I’ve read. Johnson somehow found a few new stories and details, and he packaged it all in his trademark wit and persuasiveness.

Hero of the Empire – Candice Millard

In 1899, Churchill was taken captive by the Boers in South Africa. As one of the nation’s most famous soldiers and war correspondents, he knew he needed excitement and intrigue, and he got it. In her quick, flowing prose, Millard tells the story of his escape and daring journey through enemy territory. Although the book only covers a few weeks of Churchill’s life, it presents a snapshot of his quintessential character. He is bold, reckless, charming, and driven by his unwavering sense of his own destiny.

The Churchill of Churchill Biographies:

The Last Lion by William Manchester

If you’re looking for the best of the bunch, The Last Lion is your choice. There are three thousand-page volumes in this series, but they are easily worth the time. It took me all of 2015 to read this set, and I’ve read two of the volumes again since then. The 50-page introductions in the first two volumes are worth the price of the series. The reason I like Manchester better than Gilbert is his writing. He perfectly embodies what historians and biographers should be; tour guides to the best of their subject. Manchester’s writing is as grand as Churchill’s and he understands the great currents running along his monumental life. Working through Manchester’s three volumes is time well spent; delightful, inspiring, and weighty. Churchill said, “we are all worms. But I do believe that I am a glow-worm.” The Last Lion will show you this is true.

Cole Feix is the founder of So We Speak and a regular writer. Follow him on Twitter, @cfeix7.

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