The best Winston Churchill books

4 authors have picked their favorite books about Winston Churchill and why they recommend each book.

Soon, you will be able to filter by genre, age group, and more. Sign up here to follow our story as we build a better way to explore books.

Shepherd is reader supported. When you buy through links on our website, we may earn an affiliate commission (learn more).

Churchill

By Martin Gilbert,

Book cover of Churchill: A Life

“I esteem biography,” Samuel Johnson once said, “as giving us what comes near to ourselves, what we can turn to use.” None of us is ever likely to be called upon to save Western democracy, as Winston Churchill was. But democracy can use some help these days, and all of us can be inspired by the absolute boldness Churchill showed when Great Britain was facing its darkest hour.

Who am I?

I’m a man who has led two lives. The first was as a junk dealer’s son from Buffalo, New York, who worked his tail off in school, won a full scholarship to Columbia University in 1958, and began dreaming of entering politics and someday becoming governor of New York State. The second life arrived suddenly during the third semester of my junior year when blindness seemed to rob me of my dreams. It didn’t, and along with dear friends and a loving family, these biographies have played a central role in keeping my dreams alive.


I wrote...

Hello Darkness, My Old Friend: How Daring Dreams and Unyielding Friendship Turned One Man's Blindness into an Extraordinary Vision for Life

By Sanford D. Greenberg,

Book cover of Hello Darkness, My Old Friend: How Daring Dreams and Unyielding Friendship Turned One Man's Blindness into an Extraordinary Vision for Life

What is my book about?

It’s a memoir built around a tragic event—the day in February 1961 when a Detroit surgeon blinded me ironically to save my eyes—but it is far from a tragic tale. My future wife, Sue, my college roommate Art Garfunkel, and others got me back on my feet and helped me find my way from there. Today, I consider myself, as did Lou Gehrig in his distress, “the luckiest man in the world.” That’s the story I tell, in part to understand my own life and in part to encourage others. It's also available in a Young Adult edition.

Churchill

By Roy Jenkins,

Book cover of Churchill: A Biography

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.’


Who am I?

Anthony Tucker-Jones, a former intelligence officer, is an author, commentator, and writer who specializes in military history, with well over 60 books to his name. His work has also been published in an array of magazines and online. He regularly appears on television and radio commenting on current and historical military matters.


I wrote...

Churchill, Master and Commander: Winston Churchill at War 1895-1945

By Anthony Tucker-Jones,

Book cover of Churchill, Master and Commander: Winston Churchill at War 1895-1945

What is my book about?

This book assesses what in his formative years shaped Winston Churchill as a military commander, and then examines how in high office he got it both right and wrong. From his earliest days, he was an extreme risk-taker and he carried this into adulthood. Today Churchill is widely hailed as Britain’s greatest wartime leader and politician. Deep down though, he was foremost a warlord. Just like his ally Stalin, and his arch enemies Hitler and Mussolini, Churchill could not help himself and insisted on personally directing the strategic conduct of the Second World War. For better or worse throughout his long career, he insisted on being both a political master and a military commander.

Winston's War

By Max Hastings,

Book cover of Winston's 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.


Who am I?

Anthony Tucker-Jones, a former intelligence officer, is an author, commentator, and writer who specializes in military history, with well over 60 books to his name. His work has also been published in an array of magazines and online. He regularly appears on television and radio commenting on current and historical military matters.


I wrote...

Churchill, Master and Commander: Winston Churchill at War 1895-1945

By Anthony Tucker-Jones,

Book cover of Churchill, Master and Commander: Winston Churchill at War 1895-1945

What is my book about?

This book assesses what in his formative years shaped Winston Churchill as a military commander, and then examines how in high office he got it both right and wrong. From his earliest days, he was an extreme risk-taker and he carried this into adulthood. Today Churchill is widely hailed as Britain’s greatest wartime leader and politician. Deep down though, he was foremost a warlord. Just like his ally Stalin, and his arch enemies Hitler and Mussolini, Churchill could not help himself and insisted on personally directing the strategic conduct of the Second World War. For better or worse throughout his long career, he insisted on being both a political master and a military commander.

I Had a Black Dog

By Matthew Johnstone,

Book cover of I Had a Black Dog

Sometimes pictures express depression better than words, and that’s the case in this beautiful, powerful and hopeful little book. Depression can be hard to describe, hard to find the words to tell other people how you feel. Matthew Johnstone uses Winston Churchill’s image of depression as a black dog and in 48 pages reveals what depression can do to you. 

This book is especially good to show to your loved ones when you’re finding it hard to express the pain of your depression.


Who am I?

I’m a Brighton based writer. I’ve lived with bloody depression and frigging anxiety, since a child. I’m the founder of The Recovery Letters project, which publishes online letters from people recovering from depression, addressed to those experiencing it. It was published as a book in 2017 and Cosmopolitan named it "One of the 12 mental health books everyone should read". I also edited What I Do to Get Through: How to Run, Swim, Cycle, Sew, or Sing Your Way Through DepressionMy fourth book, How to Tell Anxiety to Sod Off, is due out in 2022.


I wrote...

How To Tell Depression to Piss Off: 40 Ways to Get Your Life Back

By James Withey,

Book cover of How To Tell Depression to Piss Off: 40 Ways to Get Your Life Back

What is my book about?

Trying to manage the range of symptoms that depression throws at you is like navigating the dark ocean floor when you are without a torch and don't know how to swim. How do you manage something that feels utterly unmanageable? How do you get through each day when depression is telling you you're a worthless lump of camel spleen? What you need is a guide. A really good one. You need to know what works and what to do.

This book gives you 40 ways to get to a better place with depression. They are born out of the author's personal experience of clinical depression and his many years of working as a counsellor helping people with their mental health. James lives with depression and knows its lies, the traps it makes and how to dodge when it starts spitting bile in your face. Nice, eh?

Three Cheers for Me

By Donald Jack,

Book cover of Three Cheers for Me: Volume One of the Bandy Papers

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.


Who am I?

My father was a pilot in WW2 and I learned to fly in Africa when I was 17. Subsequently I flew biplanes, some of them like the ones in these books, made of wood, glue, and fabric. Since childhood, I've been fascinated by flying in WW1. It was a time of incredible change. The dawn of aviation, when designers and pilots barely understood what they were doing. Biographies written at the time are typically laconic, “emotionally repressed” might be modern. So these novels help us understand today some of those stresses and joys of these remarkable adventurers who dared to undertake what mankind had never done before; fight in the heavens.


I wrote...

Knights of the Air, Book 1: Rage

By Iain Stewart,

Book cover of Knights of the Air, Book 1: Rage

What is my book about?

Action, loyalty, valor, and blood make Stewart’s series kicker in the Knights of the Air series a remarkable historical novelA sharp and effective blend of WWI aviation action and adventure, a hefty dose of emotion and human drama, plus a dash of romance keep the pages flying. Finely written and vividly imagined, this is a complex, gritty novel delving into the brutalities of war. Stewart is an author to watch." Bookview gold award

Assignment

By Walter Henry Thompson,

Book cover of Assignment: Churchill

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.


Who am I?

Mary Doria Russell is the New York Times best-selling and award-winning author of The Sparrow, Children of God, A Thread of Grace, Dreamers of the Day, Doc, Epitaph, and The Women of the Copper Country. Widely praised for her meticulous research, fine prose, and compelling narrative drive.


I wrote...

Dreamers of the Day

By Mary Doria Russell,

Book cover of Dreamers of the Day

What is my book about?

A novel about the making of the modern Middle East. A schoolteacher still reeling from the tragedies of the Great War and the influenza epidemic travels to the Middle East in this memorable and passionate novel. With prose as graceful and effortless as a seductive float down the Nile, Mary Doria Russell illuminates the long, rich history of the Middle East with a story that brilliantly elucidates a few pivotal days in Cairo that changed the world.

The Grand Alliance

By Winston S. Churchill,

Book cover of The Grand Alliance: The Second World War, Volume 3

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.”


Who am I?

Award-winning journalist and historian Andrew Nagorski was born in Scotland to Polish parents, moved to the United States as an infant, and has rarely stopped moving since. During a long career at Newsweek, he served as the magazine's bureau chief in Hong Kong, Moscow, Rome, Bonn, Warsaw, and Berlin. In 1982, he gained international notoriety when the Kremlin, angered by his enterprising reporting, expelled him from the Soviet Union. Nagorski is the author of seven books, including The Nazi Hunters and Hitlerland.


I wrote...

1941: The Year Germany Lost the War

By Andrew Nagorski,

Book cover of 1941: The Year Germany Lost the War

What is my book about?

By the end of 1940, Nazi Germany ruled most of Europe, but by the end of 1941 Hitler had already squandered his chances for victory in World War II. He repeatedly gambled on escalation: by invading the Soviet Union, by making mass murder and terror his weapons of choice, and by driving Churchill and Roosevelt into a de facto alliance even before the United States formally entered the war. All of which set the stage for Germany’s ultimate defeat.

But, as Nagorski explains in his fast-paced chronicle about this pivotal year, there was nothing inevitable about this sequence of events.

The Second World War

By Martin Gilbert,

Book cover of The Second World War: A Complete History

This 900-page history is a vivid account of WWII across all fronts. Though the research is meticulous and covers the length of the war, the explanations are clear and fascinating and the chronology makes it feel like a guided tour through time. Along the way, Gilbert interposes a human face and a very personal account, revealing upheaval and atrocities, but ensuring that there is a permanent record of those civilians, particularly Jews, who died without just cause. And the examples and conditions endured are at times difficult to read and heartbreaking. The book covers all aspects, from battle lines to partisan attacks, to numbers killed, to firsthand accounts, to Hitler’s inners circle, and more. This is an outstanding read and this book is just one of Gilbert’s many significant contributions as a historian.


Who am I?

Gemma is the bestselling author of historical fiction novels, translated into several languages. Set against the backdrop of war in Europe, her fifth book in this genre will be released later this year. She has combined the war experiences of family members in WWI and WWII, information collected during her research and travels, and her academic studies in writing and history, to create the authentic scenes and characters for her books.


I wrote...

The Road Beyond Ruin

By Gemma Liviero,

Book cover of The Road Beyond Ruin

What is my book about?

August 1945. As Stefano, an Italian POW, heads toward home across war-ravaged Germany, he encounters a young child beside his dead mother. Unable to leave him to an unknown fate, Stefano takes the boy with him, finding refuge in a seemingly abandoned house in a secluded woodland. But the house is far from vacant. Stefano wakes at the arrival of its owner, Erich, a former German soldier, who invites the travelers to stay until they can find safe passage home. Stefano cautiously agrees, intrigued by the disarming German, his reclusive neighbor Rosalind, and her traumatized husband, Georg. Stefano is also drawn to Monique, the girl in a photograph on Rosalind's wall, who went missing during the war. But when he discovers letters written by Monique, a darker truth emerges. This place of refuge could be one of reckoning, and the secrets of the past might prevent the travelers from ever getting home.

The Guns of August

By Barbara Wertheim Tuchman,

Book cover of The Guns of August

If you want one book to understand how the first month or so of World War 1 played out, there is only one place to turn. Tuchman’s book is beautifully written, with a rich tapestry of characters and events, it covers the major events in Europe in August and early September 1914. It is largely seen through the eyes of ‘great men’the military and political leaders of the daywhich makes it slightly dated by today’s standards, but the skill and humanity of the reader and the sheer scope of the narrative will keep you in their thrall.


Who am I?

Narrative history isn’t about dates, kings, and queens. It’s about deeds, actions, experiences, decisions of people great and small. It’s about putting the reader in the middle of a drama and watching events unfold around them as if they were there so they can understand, observe, and perhaps ask: what would I have done? The best history writing shouldn’t just inform, but inspire you, make you feel: laugh, cry, feel angry, flinch at horrific sights, cheer the heroes, boo the villains, because history is made by ordinary people, good and bad, who possess many similar traits to the reader.


I wrote...

Hitler's Final Fortress: Breslau 1945

By Richard Hargreaves,

Book cover of Hitler's Final Fortress: Breslau 1945

What is my book about?

Hitler’s Final Fortress is the story of the battle of Breslau—today Wrocław in Poland—at the end of World War 2, a siege that lasted as long as Stalingrad but is little known in the West. It is told through the eyes of the city’s residents, the scratch German units who sought to defend it, the Nazi leaders who reduced it to rubble, the Red Army troops who sought to capture it. By the time Breslau surrendered on May 6, 1945—four days after Berlin had fallen—the city was a wasteland and 25,000 soldiers and civilians had died.

Hitler's Final Fortress is the first full-length account of the siege in English, based on official documents, newspapers, letters, diaries, and personal testimonies.

In Command of History

By David Reynolds,

Book cover of In Command of History: Churchill Fighting and Writing the Second World War

“Another book on Churchill?” asks Reynolds on the first page. “Can there be anything new to say?” Yes, is the emphatic answer. Churchill’s magisterial memoir shaped how many readers came to understand World War II. In this equally magisterial book, Reynolds dissects how Churchill wrote his memoir, exploring how the politics of the post-war era were often as important in shaping Churchill’s judgments as the events of the war itself. Methodologically sophisticated and elegantly written.


Who am I?

Steven Casey is Professor in International History at the LSE. A specialist in US foreign policy, he is the author of ten books, including Cautious Crusade, which explored American attitudes toward Nazi Germany during World War II; Selling the Korean War, which won both the Truman Book Award and the Neustadt Prize for best book in American Politics; and When Soldiers Fall which also won the Neustadt Prize. In 2017, he published War Beat, Europe: The American Media at War against Nazi Germany, which won the American Journalism Historians Association 2018 book of the year, the panel judging it “a landmark work.” 


I wrote...

The War Beat, Pacific: The American Media at War Against Japan

By Steven Casey,

Book cover of The War Beat, Pacific: The American Media at War Against Japan

What is my book about?

The definitive history of American war reporting in the Pacific theater of World War II, from the attack on Pearl Harbor to the atomic bombings of Hiroshima and Nagasaki. After almost two years slogging with infantrymen through North Africa, Italy, and France, Ernie Pyle immediately realized he was ill-prepared for covering the Pacific War. As Pyle and other war correspondents discovered, the climate, the logistics, and the sheer scope of the Pacific theater had no parallel in the war America was fighting in Europe.

The War Beat, Pacific shows how foreign correspondents ran up against practical challenges and risked their lives to get stories in a theater that was far more challenging than the war against Nazi Germany, while the US government blocked news of the war against Japan and tried to focus the home front on Hitler and his atrocities.

Or, view all 36 books about Winston Churchill

New book lists related to Winston Churchill

All book lists related to Winston Churchill

Bookshelves related to Winston Churchill