Taking the Churchillian Plunge

Diving into a Churchill biography can be a daunting task, especially for a first-timer. His life was enormous, his influence sweeping. It is only natural that he is perhaps the most written-about figure in modern history. When historian Andrew Roberts published his single volume Churchill biography, Walking with Destiny, in 2018, Roberts noted his was the 1,010th Churchill biography to hit the market.

With so many choices, where does one begin? The answer somewhat depends on what you’re looking for. It’s hard to beat Churchill’s own books, especially his autobiography My Early Life (1930), which covers his youth and early adulthood up to 1902; The World Crisis (1923-1931), his account of World War I; and The Second World War (1948-1953), his six-volume history of World War II (originally published by HMH!). There is also the eight volume “official” biography, Winston S. Churchill, the first two volumes of which were written by Winston’s son Randolph. After Randolph died, the task fell to his research assistant Martin Gilbert, who finished the following six.

But if eight volumes (each coming in at well over 1,000 pages) is just too much (don’t worry, it is for just about everyone), here’s what I recommend:

Best single volume biography:

  • Walking with Destiny by Andrew Roberts (2018) is, in my opinion, the perfect place to start if you are new to Churchill and want one book to give you the full picture of his vast life. Roberts’ writing is sharp and vibrant; it’s a true tour de force. It’s still a sizable endeavor, but the 1,000 pages will fly by. (Anything shorter simply cannot do Churchill justice.) It also makes a great gift!

If you enjoyed The Daughters of Yalta:

  • Hero of the Empire: The Boer War, a Daring Escape, and the Making of Winston Churchill by Candice Millard (2016) will introduce you to a young Winston Churchill on the verge of etching his name into the annals of history. It is a thrilling tale of war and adventure that illuminates a man on the rise brimming with the energy and confidence that will ultimately propel him to the great heights of his career. This is a fantastic piece of narrative nonfiction about just a few days in the life of Winston Churchill, but what a formative few days they were.

  • The Splendid and the Vile: A Saga of Churchill, Family, and Defiance During the Blitz by Erik Larson (2020) is the most recent work from the author of the immensely popular Devil in the White City, Dead Wake, and In the Garden of Beasts. It takes you behind the scenes of the most consequential year in the life of Winston Churchill and introduces you to some of the figures closest to him, meanwhile revealing just how desperate the situation was for Britain in the first year of World War II, when they faced the Nazi menace alone.

Happy reading!

CGK

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