Military historian and author Peter Caddick-Adams joins Underground Strategy for a wide-ranging conversation on leadership, legacy, and the life of Winston Churchill.

We explore Churchill’s wartime decisions, his eccentric personality, his genius for messaging, and the long arc of a career that spanned cavalry charges to the nuclear age. Peter also shares firsthand insights from his time as a NATO historian and discusses how battlefield experience, archival research, and media strategy all shaped Churchill’s story—and continue to influence how we study and remember war.

This episode covers everything from Churchill’s infamous boiler suit to his complex relationship with Roosevelt, his financial struggles, and whether Volodymyr Zelensky truly deserves the label of a “modern Churchill.”

Peter Caddick-Adams’ Work

X (Twitter) – https://x.com/militaryhistori

Winston Churchill: The Prime Ministers Series – https://amzn.to/43v15r1

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Winston Churchill with Peter Caddick-Adams