The podcast episodes discuss various aspects of Winston Churchill's political career, including his defeat in the 1945 general election despite leading the country to victory in the war, his subsequent return to power, and his influence on British politics and the global stage.

For example, the episode UK General Elections: 1945 delves into the surprising defeat of Churchill's Conservatives and the rise of the Labour Party under Clement Attlee, while the episode Who is Teaching Your Kids? Live from The People's Convention ft. Hillsdale President Larry Arnn features a scholar discussing Churchill's views on the importance of free elections and the strength of a sovereign people.

The episode The Plan Dog Memorandum (Encore) also touches on Churchill's efforts to ensure US involvement in the European front during World War II, highlighting his strategic vision and diplomatic acumen.