Hillsdale Dialogues — Churchill’s The Second World War, Part Twenty Two

Podcast: Hillsdale Dialogues
Host: Hugh Hewitt with Dr. Larry P. Arnn (President, Hillsdale College)
Date: April 6, 2026

Episode Overview

This episode delves into Winston Churchill’s account of the early years of World War II, primarily through the lens of his first volume, "The Gathering Storm." Hewitt and Arnn analyze Churchill’s leadership, the challenges Britain faced at sea, the significance of various naval battles, and the moral and strategic dilemmas encountered by Allied leadership. Throughout, parallels are drawn to contemporary wars and political decisions, exploring how lessons from Churchill’s era remain relevant.

Key Discussion Points & Insights

1. Early Leadership and British Naval Heroism

• Naval Battles Set the Tone:
  The episode opens with the sinking of the Royal Oak at Scapa Flow, a blow to British morale, followed by the story of Captain Kennedy and the converted freighter Walla Pindi. Churchill’s admiration for such heroism highlights a legacy of risk-taking and resolve in the Royal Navy (00:29–02:26).
  • Dr. Arnn on naval leadership:
    “Admiral Nelson... said a captain can never go far wrong by placing himself alongside the ships of his enemy.” (02:26)
• Comparisons With Past and Present:
  Discussion of the Royal Navy’s past glory versus its diminished presence in modern times. (00:29–03:47)

2. The Battle of the River Plate & The Graf Spee

• Pocket Battleships and Naval Strategy:
  Dr. Arnn explains the technical and tactical edge of German "pocket battleships" like the Graf Spee—fast and heavily armed, they threatened British control of the seas. (04:09)
• Narrative Quality of Churchill’s Writing:
  Hewitt notes Churchill’s gripping, almost fictional approach to recounting the battle, likening it to classic naval novels. (05:22–06:16)
  • Hewitt:
    “Churchill somehow slips into fiction writing almost in this chapter. I don’t know if you reread it... but it’s a thriller.” (05:22)
• Symbolism and Ship Names:
  Reflection on the significance of ships named Ajax and Achilles, drawing connections to Homer’s Iliad and the symbolism of heroism. (07:32–08:25)
• The Role of Symbolism in Warfare:
  Churchill’s deliberate decision to tow the damaged Exeter back to Britain rather than scuttle it underscored psychological resilience for the nation. (08:25)
  • Hewitt:
    “Churchill wouldn’t let them scuttle it... because of the symbolism that they didn’t lose a ship in it. It’s a small detail, but it matters.” (08:25)

3. Churchill’s Leadership Style and Communication

• Eloquence and Optimism:
  Churchill’s speeches were pivotal for morale—delivered with candor regarding challenges yet imbued with confidence and tenacity (13:25–15:06).
  • Dr. Arnn:
    “Churchill would give his speeches on the radio and they remain the most popular things, the most percentage of the audience ever broadcast on British radio.” (13:25)
• The Importance of Victories:
  The British faced years of setbacks before any significant victories. When success finally came, it was deeply appreciated by the public. (13:25–15:06)

4. Modern Reflections: Churchill’s Legacy and British Identity

• Currency and Cultural Memory:
  Discussion of the Bank of England’s removal of Churchill from banknotes; Arnn laments the shift away from celebrating great figures, noting a loss of shared identity. (15:06–16:08)
  • Dr. Arnn:
    “They’re putting animals on there now. Right. Which means the only thing they’ve got in common now is the land and not the people. ...A society can be reversed.” (15:20)

5. Parallels Between WWII and Present Day

• Technology and Ruthlessness in War:
  Analysis of the “magnetic mine” crisis—how the British obtained, disarmed, and reverse-engineered German technology, underscoring the necessity of innovation and ruthlessness to survive in war. (16:56–19:04)
  • Dr. Arnn (quoting Churchill and Lincoln):
    “Lincoln said you don’t fight wars by building rose water through elder stalk squirts. Churchill said, we have not traveled all this distance across the oceans... because we are made of sugar candy.” (18:03)
• Maintaining Morale:
  Importance of having “something positive coming along on your side” in both peace and war. (19:04–20:33)

6. Strategic Dilemmas: Norway and the Winter War

• The Norwegian Campaign:
  Churchill’s advocacy for preemptive action in Norway was overruled by the Cabinet; the Germans acted first and took Norway, a strategic failure for the Allies. (23:05–26:19)
  • Dr. Arnn:
    “From the point of view of principle, if you’re in a death struggle with a violating enemy who threatens your survival, and you think they’re going to do that, you can do it.” (23:52)
• Winter War in Finland:
  The episode closes with Churchill’s pragmatic approach—reluctance to intervene in Finland, despite sympathy, because strategic priorities lay elsewhere. (27:13–32:01)
  • Dr. Arnn on alliances:
    “Churchill never really believed in his heart of hearts that the alliance between Germany and Russia... was going to stick. He thought that... the Soviets might join up with the Allies.” (32:01)

7. Diplomacy, Realism, and the Necessity of Allies

• Shifting Alliances:
  Churchill’s realism allowed for alliances with former adversaries, most notably the Soviet Union, when survival demanded it.
  • Churchill (quoted):
    “If Hitler invaded hell, I would at least make a favorable reference to the devil here in this House.” (32:01–33:58)
• Lessons for Today:
  Arnn and Hewitt apply Churchill’s insights to contemporary strategy and diplomacy—emphasizing the importance of clear-eyed realism regarding both enemies and allies. (35:12–36:06)

Notable Quotes & Memorable Moments

• On heroism and risk:
  “A captain can never go far wrong by placing himself alongside the ships of his enemy.” — Dr. Arnn quoting Admiral Nelson (02:26)
• On symbolism in war:
  “Churchill wouldn’t let them scuttle it... because of the symbolism that they didn’t lose a ship in it.” — Hugh Hewitt (08:25)
• On Churchill’s communication:
  “He repeats some of the speeches in this gathering, in this and the next volume, Finest Hour. And... the nature of the speeches was to explain the situation. Let me tell you what's going on. And it carried conviction in part because he was clear and admitted the difficulties.” — Dr. Arnn (13:25)
• On ruthlessness:
  “You got to be ruthless if you’re going to win.” — Hugh Hewitt (31:08)
• On alliances and hard choices:
  “If Hitler invaded hell, I would at least make a favorable reference to the devil here in this House.” — Churchill, quoted by Dr. Arnn (32:01–33:58)

Key Timestamps for Important Segments

• 00:29–03:47: Early challenges for the British Navy and the Royal Oak
• 04:09–08:25: Graf Spee, naval strategy, and symbolism of ship names
• 13:25–15:06: Churchill’s speeches and impact on morale
• 15:06–16:08: British currency and legacy
• 16:56–19:04: Magnetic mine crisis and innovation in warfare
• 23:05–26:19: The Norwegian campaign’s missed opportunity
• 27:13–32:01: The Winter War in Finland and Churchill’s realpolitik
• 32:01–33:58: Alliance with the Soviet Union and necessity in alliances

Tone and Style

The episode is both analytical and conversational, combining detailed historical narrative with wit and irony reminiscent of Churchill himself. Both speakers move fluidly between reflections on historic events and their relevance to contemporary geopolitical challenges, embodying the dialogic spirit of the podcast’s “Great Books, Great Men, and Great Ideas.”

Summary Takeaway

Churchill’s early leadership in WWII, particularly through naval strategy and morale-building rhetoric, offers enduring lessons on the value of risk, symbolism, realism, and adaptability in times of national crisis. The episode illustrates how history’s complexities inform today’s challenges, underscoring the significance of moral conviction, clarity in communication, strategic alliances, and the enduring need for courage—both on the battlefield and in policymaking.