Hillsdale Dialogues: Churchill’s The Second World War, Part Twenty-One

Podcast: Hillsdale College Podcast Network
Date: March 30, 2026
Host: Hugh Hewitt
Guest: Dr. Larry Arnn, President, Hillsdale College
Book in Focus: Winston Churchill’s The Second World War, Volume I: The Gathering Storm (Chapters 26–29)

Overview

This episode resumes the ongoing series dissecting Winston Churchill’s monumental six-volume history of WWII, focusing on the opening stages of hostilities as depicted in The Gathering Storm. After a hiatus, Hugh Hewitt and Dr. Larry Arnn discuss the outbreak of war in France (1939–1940), Allied and Axis strategic decision-making, lessons about leadership and miscalculation, the psychology of war, and parallels to current geopolitical situations, particularly concerning Iran and American foreign policy.

Key Discussion Points & Insights

1. The Opening of War in France & Allied Planning

(00:29–05:32)

• Deployment of the British Expeditionary Force (BEF):
  • Churchill's critical task at war’s start was moving the BEF to France, an operation made possible by a period of relative calm ("the Phoney War").
  • “They had the ships to do it and they got them over and so they joined the French.”
    — Dr. Arnn (01:56)
• French Strategic Thinking and the Maginot Line:
  • France’s defensive posture was shaped by trauma from WWI.
  • They constructed the Maginot Line expecting a repeat of the German offensive from WWI, not considering alternative invasion routes.
  • “If you’re trying to dance and you start off with the wrong foot… you’re always wrong-footed.”
    — Dr. Arnn (01:56)
  • Germans, led by tacticians like Rommel and Guderian, exploited weak points by coming through the Ardennes—an unexpected move France hadn’t anticipated.

2. The Perils of “Fighting the Last War”

(05:02–07:05)

• Churchill’s Critique:
  • The British and French prepared for the wrong kind of conflict, neglecting lessons from recent strategic shifts.
  • Quote: “It is a joke in Britain to say the War Office is always preparing for the last war. It was certainly true of the French army.”
    — Churchill, quoted by Hewitt (05:02)
• The “Short War Illusion”:
  • Both Napoleon and Germany in WWI believed in rapid, decisive victories—a folly repeated, with Germany finally succeeding in 1940 due to new tactics.

3. The Rapid Fall of France

(07:05–09:32)

• The Germans succeeded in rapidly conquering France in weeks in 1940, contrary to prevailing beliefs that modern armies would not collapse so quickly.
  • “You can’t imagine a modern army of several million men being conquered in a matter of weeks. And then… the French army was so. Conquered.”
    — Dr. Arnn (08:56)

4. The Limits of Perceived Behavior and Strategic Surprise

(09:32–12:39)

• Churchill on Intellectual Inertia:
  • Quote: “The human mind, except when guided by extraordinary genius, cannot surmount the established conclusions amid which it has been reared.”
    — Churchill, quoted by Hewitt (09:32)
• Discussion of unpredictability in leadership, tying Churchill’s points to more contemporary figures, especially Donald Trump.
  • “Trump is very unpredictable. And my own view is that that’s because he chooses to be.”
    — Dr. Arnn (12:39)

5. Modern Leadership, Law, and Misconceptions

(12:39–16:06)

• Trump and Accusations of Authoritarianism:

  • Even when angered by court decisions, Trump abides by constitutional limits, a distinction from true authoritarian behaviors.
  • “To anyone who calls him an authoritarian or a fascist... He cares the most about his tariff power. It's been taken away from him by the court that he appointed and he’s mad and he's accepting their ruling. And that is the end of the argument…”
    — Hewitt (14:13)

• Historical Precedents:

  • Comparisons to Lincoln’s restraint during the Civil War when faced with adverse Supreme Court decisions.

6. The Advantage of the “Lawless Aggressor” and the Power of Democracy

(16:24–19:44)

• Aggressive First Moves in War:
  • Aggressors gain short-term advantage by striking first—parallels drawn with recent and past conflicts (Hamas, Japan at Pearl Harbor).
  • “On the other hand, unless the victory of the aggressors is absolute and final, there may be a day of reckoning.”
    — Churchill, as discussed by Hewitt (16:27)
• The Democratic Response:
  • Once rallied, democratic societies are capable of powerful, sustained response (Pearl Harbor, post-9/11).
  • The fragility of autocratic regimes as public support erodes (Iran, Soviet Union, Cuba).

7. Lessons from Late-Stage Regimes

(19:44–21:21)

• Dr. Arnn reflects on the collapse of the Soviet Union’s “nomenklatura" and draws analogies to the current Iranian regime, suggesting autocracies are inherently brittle.

  • “Everybody can see it.”
    — Dr. Arnn (19:44)

• Ethnic and Social Complexity in Iran:

  • Recognition that Iran is multi-ethnic; underlying tensions are brewing, eroding regime stability.

8. Hitler’s Strategic Calculations and Allied Resilience

(21:21–23:58)

• Hitler rightly judged the weakness in French politics but underestimated British resilience—a miscalculation with long-term consequences.

• “He quite accurately estimated the French. He underestimated the Brits…”
  — Hewitt (21:21)

• The role of personalities such as de Gaulle in reviving French national pride during the occupation.

9. Naval Setbacks and the British Response

(26:01–28:40)

• The Sinking of HMS Royal Oak at Scapa Flow:

  • British naval pride was shaken when a German U-boat penetrated Scapa Flow and sank a battleship.
  • “What are we going to do? Surrender? So that was… that factor that Churchill loves. Consensual governments operate on consent.”
    — Dr. Arnn (27:04)

• The critical importance of unity in the face of adversity.

10. Neville Chamberlain’s Character and Legacy

(28:40–31:36)

• Chamberlain, often maligned, is described as having “steel in his spine” after Hitler’s betrayal.

  • “He was mad and he had to deal with this guy. So that. And Churchill respected him for that...”
    — Dr. Arnn (29:43)

• Baldwin—predecessor blamed for Britain’s lack of preparedness.

• War as revelatory of leaders’ inner strengths, learning under pressure.

11. American Isolationism—A Blessing and a Risk

(34:23–36:00)

• The U.S. enjoys geographical isolation but this leads to a persistent isolationist instinct, which isn’t possible for countries like France.
• Modern threats (ballistic missiles, surprise attacks) mean America can no longer depend solely on distance for safety.
  • “Everything is changing so fast in the world. Just remember, the United States could be devastated in the course of 20 minutes…”
    — Dr. Arnn (34:49)

Notable Quotes & Memorable Moments

• On Military Miscalculation:
  “They had the ships to do it and they got them over and so they joined the French. And the beginning of the war is the opposite of the First World War...”
  — Dr. Arnn (01:56)
• On Strategic Surprise:
  “He got Rommel and Guderian...to make a different plan… they decided they could get tanks through the Ardennes forest… and they did get through.”
  — Dr. Arnn (03:00)
• On Democracy Awakening:
  “If you get a democratic people angry, that's a mighty force.”
  — Dr. Arnn (17:22)
• Comparing Autocracy and Democracy:
  “In the last years of the Soviet Union, nobody believed in the Soviet Union...they were wedded to their principles. I mean, their privileges.”
  — Dr. Arnn (20:31)
• On American Isolationism:
  “We have had the luxury of not having that...but everything is changing so fast in the world.”
  — Dr. Arnn (34:23)

Important Timestamps

| Timestamp | Segment/Topic | |-----------|--------------| | 00:29–01:56 | Setting the scene: resuming the WWII series; BEF deployment | | 01:56–05:32 | French war planning, Maginot Line, German strategy | | 05:02–07:05 | Churchill on “preparing for the last war” | | 07:05–09:32 | The swift collapse of France; the illusion of protracted war | | 09:32–12:39 | Leadership unpredictability; Churchill’s remarks on genius | | 12:39–16:06 | Trump, the Constitution, and comparisons to Lincoln | | 16:24–18:37 | The dangers—and limits—of aggression and democratic reaction | | 19:07–21:21 | The decay of revolutionary zeal and regime fragility in Iran/Soviet context | | 21:21–23:58 | Hitler’s misreading of Allies; de Gaulle’s role | | 26:01–28:40 | Scapa Flow disaster and British endurance | | 28:40–31:36 | Neville Chamberlain’s character; leadership under pressure | | 34:23–36:00 | Isolationism: American safety and global change |

Final Thoughts

This episode deftly weaves together historical analysis of WWII, the psychology of strategic leadership, and contemporary analogies—especially around unpredictability and response to aggression. Dr. Arnn’s insights, supported by Churchill’s wisdom, invite listeners to reconsider not just how the Second World War unfolded but how its lessons remain urgently relevant in today’s volatile world.