Churchill’s The Second World War, Part Twenty-Two

In this episode of Hillsdale Dialogues, Hugh Hewitt and Hillsdale College President Dr. Larry Arnn dive into Winston Churchill’s The Gathering Storm, focusing on the early naval battles of World War II and the strategic mindset that defined Britain’s wartime leadership. The conversation centers on the dramatic confrontation between the British ships Ajax and Achilles and the German pocket battleship Graf Spee, a battle Churchill recounts with the vividness of a thriller. Hewitt draws striking parallels between this 1939 naval engagement and modern U.S.-Iran tensions, emphasizing how symbolic victories—like Churchill’s insistence on towing the damaged Exeter back to Britain—mattered as much as military outcomes. The episode also explores Churchill’s ruthless pragmatism: his willingness to violate Norwegian neutrality preemptively, his cold-eyed refusal to aid Finland despite public sympathy, and his infamous 1941 declaration that he’d support the devil if Hitler invaded hell. These moments reveal a leader who judged alliances not by ideology but by survival, a lesson Hewitt argues is urgently relevant today, especially as he identifies China—not Russia—as the modern equivalent of Germany in Churchill’s calculus. The discussion underscores the enduring power of leadership, symbolism, and strategic clarity in times of crisis.