The most recommended Winston Churchill books

I first read this book half a century ago and still enjoy rereading it. Churchill’s style is modeled on the great historians of the 18th and 19th centuries. He argues with conviction and clarity that war could have been prevented.

However, I find myself echoing a 19th century prime minister who said of the historian Macaulay: ‘I wish I were as sure of anything in this world as [he] is of everything.’

It will take some digging, but do try to hunt this down. Thompson was assigned as Churchill's bodyguard just a week before the 1921 Cairo Peace Conference began. His account of his boss's attitudes and habits is refreshingly irreverent. (While smoking a cigar, Churchill “looked like an upholstered toad, slowly incinerating himself.”) Thompson also provides an important contemporaneous description of how T. E. Lawrence was regarded by Arabs in 1921, before either he or Churchill became enveloped in mythology.

I did not love this one at first. This is the life story of Richard Hillary, a would-be poet who happened to fly Spitfires in the Battle of Britain. His first attempts to tell what it feels like to be in the cockpit engaged in a life-or-death dogfight at 15,000 felt self-absorbed.

But then he reveals what it’s like to be shot down and the harrowing aftermath of a cockpit fire. All pretense is set aside as Hillary battles to return to the sky and be a pilot again. It’s a lovely, lovely book.

I write stories about famous people and moments in history. I like to strip down the narrative and make history read like a top-notch thriller. But to do that, I need to stand on the shoulders of authors who devoted ten or a dozen years to researching and writing the detailed lives of a subject they adore. I do not have the attention span to spend so long on one character.

I love this book because William Manchester (and Paul Reid, who stepped in to finish the book when Manchester died) loves Winston Churchill. What he wore, how he spoke, who he loved, what he drank. It is hundreds of pages of gorgeous detail, waiting for a long winter’s reading night. 

Meant to be entertaining as well as informative, this book romps without reverence through the lives and writings of historians, some from beyond the Western world, from ancient Greece to today. That’s 2500 years of written history!

You'll discover that, rather than being just the sober history that teachers may have taught you, historians have come in all forms and with all kinds of minds. They’ve argued with each other, sometimes been fools, showed themselves entirely human—and yet left us some of the world’s greatest texts of religion, literature, and learning.

Cohen defines “historian” controversially as well as liberally, to include Shakespeare, novelists, political figures, and television personalities. But then, as humans, don’t we all have a past and think historically? Food for thought—and fun along the way.

Already a published expert on air power, armour, and the Normandy campaign, Buckley went on to produce a well-considered and ably researched evaluation of the British army in 1944-5, one that rescued it from the deeply-flawed criticism by Max Hastings of its relative effectiveness.

The late politician Lord Jenkins made a name for himself with his political biographies. Churchill: A Life was the culmination of a critically successful career as a writer. Jenkins leaves no stone unturned in assessing Churchill’s thirst for political glory. Andrew Roberts called the book ‘a masterpiece.’

As part of an international project comparing imperial retreat and the wars of decolonization (or national liberation), I had to do extensive reading in this growing field.

Although there have been some important works, including a recent Pulitzer Prize winner, Martin Thomas’s book was one of the first and remains one of the best. The book’s title summarizes the choice facing post-World War 2 British and French leaders: did they attempt to defend colonial rule or abandon their overseas empires?

In both countries, the overseas colonies were seen as essential both economically and for national prestige. With impressive research and even more impressive fairness, Thomas challenges long-held interpretations that emphasized British moderation and managed decolonization with alleged French repression.

He also covers the anticolonial movements in both empires, emphasizing both their local roots, their shared international connections, and how the liberation movements played such an important role in Cold War… show more.

The authors work for the Sunday Times Insight team and the book they have produced is, you might say, a public inquiry of the kind we won’t be getting from any government, now or in the future. We’ve all been living through this nightmare and the concept of journalism being a first rough history of events is more than adequately demonstrated by this excellently researched text.

Unless you’ve been asleep, or visiting another planet during the past 15 months, you’ll be painfully aware of how badly the pandemic has been handled in the UK. Coming on the back of Brexit, the big event that caused the Government to never have its eye on the Coronavirus ball at the critical moments in January and February, 2020, the pandemic was at first ridiculed, then fatally downplayed by Boris Johnson.

Worse, as we all know to our personal and collective cost, was to… show more.

Why would I include a book on rhetoric right after a set of recommendations of titles covering philosophy, given the two-thousand-year rivalry between those two ancient disciplines? In contrast to other people who teach critical thinking, I place great value on persuasive communications, commonly referred to as rhetoric, given the need to see through the rhetoric of others when analyzing their arguments, and the ability of persuasive language to turn valid and sound arguments into unstoppable ones. In his recently updated bestseller Thank You for Arguing, author Jay Heinrich lays out a powerful case for why effective argumentation can bring people together to solve problems, providing potential offramps from today’s polarized, destructive pseudo-debates. Heinrich’s book is accessible and entertaining, drawing from pop culture and his own life experiences, alongside the wisdom of Aristotle and other great thinkers from history, to demonstrate how to productively argue out our disagreements,… show more.