The most recommended Winston Churchill books

Leave it to Churchill to sum up the events of 1941 that determined the ultimate outcome of the war. In his words, the theme of this volume of his epic account of the war is “How the British fought on with Hardship their Garment until Soviet Russia and the United States were drawn into the Great Conflict.” Much of this consists of letters, reports, speeches, and other original documents from that period, woven together by its skillful narrator. Little wonder that Churchill was later awarded the Noble Prize in Literature "for his mastery of historical and biographical description as well as for brilliant oratory in defending exalted human values.”

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.

William Manchester was such a great writer that I felt the loss keenly when he announced he couldn’t finish the 3rd book.

A writer that made the mundane soar and takes the already amazing life and speeches of Winston Churchill and frames them in a story that seems timeless. Churchill wasn't perfect, but he had seen WWII approaching, predicted what would happen, and then managed to get into power at the crucial moment to keep the UK alive.

Manchester's prose sings, and the story ends at the darkest hour. I think Britain's experience in WWII is a very good example of how a future war could look. A country fighting on multiple fronts, with insufficient resources as the forces of evil encroach ever closer.

Manchester's book finishes at a point that makes the reader ask how is this winnable?

The fate of Singapore was sealed long before the Japanese attack on Malaya in December 1941. The blame lay with British Prime Minister Winston Churchill who refused to listen to warnings from military advisers to reinforce defences in Singapore and Malaya. Her was convinced the Japanese would never dare to attack a white power. Obsessed with beating Rommel, Churchill poured into the Middle East massive resources that should have gone to the Far East. However, when inevitably Singapore fell to the Japanese in February 1942, Churchill attempted to deflect criticism by accusing the defenders of spineless capitulation.

"I find Hornblower admirable, vastly entertaining," said Winston Churchill in the best short review ever written. Forester takes you back 200 years to an age of wooden ships and iron men. Here you smell the powder, see the mainsails strain, hear the roar of cannon and the clang of steel – and learn more about the Napoleonic Wars than any textbook could convey. The Hornblower books are all electrifying, but to my mind, this is the best.

The first in the Bandy Papers series, and the best. Jack was a Canadian who served in the air force and managed the difficult task of providing a comedy about flying in WW1 with, once again, realistic, and well-researched flying scenes. This book is a comedic tour de force, wringing belly laughs from war without belittling the surrounding terror and angst. It won several Canadian comedy awards, and you can understand why. It made me laugh so hard in places, that it hurt. But I repeat, the flying scenes are first-rate, and the characters are a hoot as they blunder through the war.

Churchill is perhaps best remembered for his bulldog premiership during the Second World War. Max Hasting’s excellent study graphically portrays the enormous political and strategic stresses and strains endured by Churchill. Coalition warfare was one of vigorously competing interests and Hastings shows how Churchill achieved a quite remarkable juggling act.

Henry Goulding was commander of the WW2 Special Boat Service. There is a dark, incomplete story here. The real drama is hidden between the lines and yet to be proven. Henry Goulding was a friend of Churchill, accomplished spy, fiercely patriotic, yet he did something out of character when he hid a briefcase packed with top-secret documents in his attic. He was summoned to a hospital in Scotland, despite being fit and healthy, escaped after a scuffle, telephoned his wife, was returned to the hospital where he died shortly after, apparently of natural causes. His medical records have never been released. I was contacted by his granddaughter, who years later found the briefcase, and asked if I might write a more detailed book tackling the mystery behind his death, a book begun by Sir Paddy Ashdown who died before completing a chapter. 

This book is currently out of print.

Hornblower is a fantastic character, and the entire series is worth a read, but C.S. Forester got more accomplished throughout the series. Meticulously researched - and recently wildly popular, thanks to a TV series - the books are still much deeper, more resonant, and better!! Hornblower is in constant turmoil, too sensitive for his own good or for the crises every Admiral probably had to face, he is also so self-conscious that even in love - and he is very passionate - he can't quite let go. Combine that with a number of vivid females and still more interesting fellow officers - all with their own crosses to bear - and the Napoleonic war on the seas and... could not have been written better.

In 1940 London, Maggie Hope, a brilliant mind who graduated top of her class, is recruited by Number 10 Downing Street to be…a typist. Of course. She’s a woman. She’s also a crackerjack code breaker. I think you know where this is going. The character is wonderful, the writing strong, the story tight. A highlight for me was when Maggie –a young, virginal, cerebral type—pulls off a daring motorcycle jump with a man on the back because she has to. I don’t know, I think there’s a life lesson somewhere in there.