May Book Chain: Winston Churchill & World Leadersfrom WWII through the Cold War Reading Challenge - Book covers arranged in Collage.

May 8th is Victory in Europe (VE) day; on this date in 1945, world leaders formally accepted Germany’s unconditional surrender, and WWII ended. As events unfold in Russia and Ukraine in 2022 – 77 years later – it’s impossible not to look back at what the last major conflict in Europe cost the world. 

Our minds are naturally drawn to the people involved, great leaders such as Churchill and Roosevelt, as well as villains like Stalin and Hitler. Reading the stories of these leaders is eye-opening and often reveals critical nuances and complexities that increase our understanding of pivotal moments in history.

Our May book chain is all about these leaders. Once you read about Churchill, you’ll want to wander out and explore Roosevelt, and then you’ll need to satisfy your curiosity about leaders on the other side. Inevitably, this will lead to questions about Truman, the war in the Pacific, and how the Cold Ward started and ended. You know how it goes.

So, let’s get reading.


Thousands and thousands of pages have been written about Winston Churchill, many by the man himself. (He did enjoy telling his own story, something you’ll discover as you get to know him better.) Here are two notable books to get you started:

Hero of the Empire: The Boer War, a Daring Escape, and the Making of Winston Churchill

Candice Millard, 2017

Hero of the Empire: The Boer War, a Daring Escape, and the Making of Winston Churchill Book Cover

Most of the books about Mr. Churchill focus on WWII, but Ms. Millard chose to focus her history on Churchill’s early military career. Mr. Churchill always aspired to be prime minister. He felt that military heroics were an essential stepping stone toward that goal, so he set out for the Boer Wars to distinguish himself on the battlefield. His experience is the stuff of great stories – frustrated goals, heroic persistence, captured by the enemy, a daring escape, an epic train crash – it’s all in here, and it’s all true. The man who led Britain during the Blitz was made in these moments.

Candice Millard is a brilliant writer, and you’ll be captivated by this fabulous story.

Churchill: Walking with Destiny

Andrew Roberts, 2018

Churchill: Walking with Destiny by Andrew Roberts book cover

Churchill: Walking with Destiny is unique in that it tells the story of Churchill by using his personal thoughts and feelings about the events in his life. If you’re looking for more than a chronological history, this book is for you. 

The author accessed Churchill’s papers and diaries and many others to humanize and give dimension to this remarkable man. Many believe this is the best single-volume comprehensive biography of Churchill ever written. If you’ve read a lot already about Churchill, this book will still delight you.


Once you read about Churchill, chances are you will be curious about Roosevelt. You’ve got dozens of books to choose from to learn more about FDR. He was elected president four times and is credited for bringing the United States out of the Great Depression and directing American forces worldwide in opposing Axis powers during WWII. Here are two of our favorite books about Roosevelt.

Franklin and Winston: An Intimate Portrait of an Epic Friendship

John Meacham, 2003

Franklin and Winston: An Intimate Portrait of an Epic Friendship by John Meacham book cover

Alone, these great leaders did remarkable things; together, they changed the world. The friendship between Churchill and Roosevelt was rare. John Meacham gives readers a peek inside their relationship and the chance to reflect on each man’s character and how they worked together to end the war. 

Churchill and Roosevelt exchanged thousands of messages, spent over 100 days together during the war, had secret meetings, and triumphed over skeptics to overcome one of the greatest challenges of the 20th century. 

No Ordinary Time

Doris Kearns Goodwin, 1995

No Ordinary Time by Doris Kearns Goodwin book cover

Ms. Goodwin’s knowledge of history and the presidency and her talents for research and writing are on full display in this Pulitzer Prize-winning biography. Aside from the author’s abilities, what sets this biography of FDR is the inclusion of parallel stories of Eleanor Roosevelt and her relationship with her husband. 

This book is an intimate portrait of the Roosevelt White House. You won’t get an exhaustive history of this power couple, but you will get a close look at the home front during WWII with all its meanings.


Harry Truman entered the world stage after the passing of FDR in early 1945. For all the work Roosevelt did on ending the conflict, Truman was the one who was able to see it through. While his name is not the first to come to mind when thinking of this era, he certainly made a lasting impact.


David McCullough, 1992

Truman by David McCullough book cover

Truman was an ordinary man from Missouri who rose to lead the United States in extraordinary times. This book is another Pulitzer Prize winner, and rightfully so. 

Yes, this history is about Truman, but it’s also about WWII, the birth of the nuclear age, the start of the Cold War, the Korean War, the recognition of Israel, and so much more. If you want to understand how we got from the end of WWII to where we are now, this book is the perfect place to start, and Truman was in the middle of it all.


Joseph Stalin is one of the bloodiest, most ruthless dictators in all history, and yet he was one of the “good guys” in WWII. He worked with Roosevelt and Churchill to oppose the Axis powers. 

While most Allies in WWII were fighting evil, Stalin was mostly getting the competition out of the way. To understand Russia’s current leader and his view of history, you’ll need to learn about Stalin.

Stalin: The Court of the Red Tsar

Simon Sebag Montefiore, 2003

Stalin: The Court of the Red Tsar by Simon Sebag Montefiore

No western author has managed to get as close to the life of Stalin as Mr. Montefiore. While you might be familiar with the basic facts about Stalin – 20 million lives purged, Gulags, WWII, etc. –it’s likely you don’t know much about Stalin himself. 

Mr. Montefiore did exhaustive research and paints a portrait of evil that includes personal details such as favorite books and movies and insider info on the workings of the Kremlin. He also shares Stalin’s point of view on the Yalta meeting with Churchill and Roosevelt, a perspective you won’t get anywhere else. Stalin: The Court of the Red Tsar is invaluable reading.

Red Famine: Stalin’s War on Ukraine

Anne Applebaum, 2018

Red Famine: Stalin's War on Ukraine by Anne Applebaum book cover

The road to understanding Putin’s war on Ukraine passes through Stalin’s war on Ukraine. In the early 1930s, Russia forced peasants onto collective farms, a decision that led to a catastrophic famine and the deaths of at least five million people from starvation. Three million of those deaths were deliberate and occurred in Ukraine after Russia sealed Ukraine’s borders and seized all its food. Ukrainian independence was a threat to Stalin, and starving the peasantry was the solution. As Ukrainian independence is in Russia’s crosshairs once again, making this book a must-read.


The pear-shaped man with the ridiculous mustache is universally recognized but also, as it turns out, still kind of a mystery. There are two biographies of Hitler that compete for being the most reliable. They are the following:

Hitler by Ian Kershaw book cover
Adolf Hitler by John Toland book cover

There’s also always Mein Kampf, Hitler’s autobiography.

Going Deeper

As is the case with serious readers, one book leads to another and then another. With your appetite whetted for non-fiction information about WWII and the events that followed, here are three titles to take you further:

The Rising Sun: The Decline and Fall of the Japanese Empire, 1936-1945

John Toland republished in paperback in 2003

The Rising Sun: The Decline and Fall of the Japanese Empire  by John Toland

John Toland won the Pulitzer Prize for this work about the Japanese Empire and WWII told from the perspective of the Japanese. In the author’s words, this book is a “factual saga of people caught up in the flood of the most overwhelming war of mankind, told as it happened—muddled, ennobling, disgraceful, frustrating, full of paradox.” 

A singular account of the Japanese Empire during the global conflict that is not as well understood as the conflict in Europe.

The Cold War: A World History

Odd Arne Westad, 2019

The  Cold War by Odd Arne Westad book cover

When WWII ended, what exactly followed? Mr. Westad makes the case in his history of the Cold War that this was not a time of peace but of continued bloody conflict; Koreans, Vietnamese, Americans, and others were killed during this “peace.” 

The author contends that this was not a conflict between the US and the USSR but was, in fact, a global ideological conflict that engulfed the entire 20th century. Westad presents an engaging history and provides a close-up look at the world as we know it.

Reagan and Gorbachev: How the Cold War Ended

Jack Matlock, 2005

Reagan and Gorbachev: How the Cold War Ended by Jack Matlock

We started our reading challenge with books about two remarkable men – Churchill and Roosevelt. It seems fitting to end the challenge with another pair of noteworthy leaders, Reagan and Gorbachev, whose leadership abilities, vision, and relationship likewise yielded peace. 

The author, Jack Matlock, served as an advisor to Reagan and as an ambassador to the USSR. His personal experiences allow him to share a first-hand account of the sophisticated diplomacy that led to the end of the Cold War and the fall of communism.

Bonus Book: One cannot tell the story of the end of the Cold War without mentioning Margaret Thatcher. There Is No Alternative: Why Margaret Thatcher Matters by Claire Berlinski is a brilliant look at another powerful, visionary world leader. We highly recommend including this book in your reading list. 

There Is No Alternative: Why Margaret Thatcher Matters by Claire Berlinski book cover

Margaret Thatcher was sometimes called “TINA” (there inalternative) by her inner circle. Sometimes, there really is no alternative, and leaders simply have to make the hard choice, a reality that’s important to remember in today’s world of conflict.

Take a Deeper Dive into WWII and Cold War Leaders

Yearning to expand your understanding of the world, past and present? Add these titles to your cart today and dive into the May reading challenge from Discover Books. We love books about fascinating people and history, and we know you do too. 

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