Hillsdale Dialogues
Episode: Churchill’s The Second World War, Part Twenty One
Date: March 30, 2026
Episode Overview
This episode of the Hillsdale Dialogues features host Hugh Hewitt and Hillsdale College president Dr. Larry P. Arnn delving into Winston Churchill’s The Gathering Storm, specifically chapters 26 through 29. With renewed urgency, they discuss the outbreak of WWII, the rapid fall of France, and Churchill’s reflections comparing WWII to WWI. The episode also draws parallels to modern geopolitical events, including discussions about leadership, unpredictability in statecraft, and the strategic advantages of democracies versus aggressive regimes.
Key Discussion Points & Insights
The British Expeditionary Force and Early WWII Strategy
[00:29-01:56]
- Hewitt introduces the situation at the start of WWII: Britain’s urgent task of moving the British Expeditionary Force (BEF) across the channel to France.
- Dr. Arnn discusses the logistical advantage Britain had in the early weeks, transporting troops with little resistance, but notes the contrast between WWI and WWII French strategies.
“The beginning of the war is the opposite of the First World War... In the First World War ... they marched into machine guns... Now they go into the second war and they're on the defensive and they built a wonderful line of fortifications called the Maginot Line... and they didn't extend it all the way...”
— Dr. Larry Arnn [01:56]
- The Maginot Line’s failure: French built it assuming a repeat of Germany’s WWI tactics. Germans innovate by moving through the Ardennes, previously thought impassable for tanks.
Strategic Miscalculations and the “Short War Illusion”
[05:02-07:05]
- Churchill's quip about “preparing for the last war” applies to both British and French planning.
- Dr. Arnn references Harold Rood's Short War Illusion—the mistaken belief that war will be a quick, decisive affair.
- Germany, learning from past failures, achieves rapid conquest of France in just six weeks in 1940, contrary to Allied assumptions.
“The Germans succeeded at that in the west. They attacked on 10 May, and by what, 25 June, France was entirely conquered.”
— Dr. Larry Arnn [06:05]
- Churchill’s surprise at the speed of France’s defeat highlights the dangers of entrenched assumptions.
Limits of Intelligence and the Fog of War
[06:33-07:05]
- Hewitt notes how limited wartime reconnaissance hindered Allied understanding of enemy movements compared to today.
- Dr. Arnn notes, “war is a fog” and draws analogies to both historical and recent conflicts.
Leadership, Unpredictability, and Comparative Statecraft
[09:33-14:15]
- Quoting Churchill: "the human mind, except when guided by extraordinary genius, cannot surmount the established conclusions amid which it has been reared" [09:33].
- Hewitt and Arnn discuss Trump’s unpredictability as an asset in foreign policy, contrasting with more predictable American presidents ("Trump is very unpredictable. And my own view is that that's because he chooses to be." – Dr. Larry Arnn [12:58]).
“If you were... the supreme leader of Iran, would you prefer Joe Biden, Barack Obama or Donald Trump to be here?”
— Dr. Larry Arnn [13:11]
- Debate whether unpredictability and willingness to ignore convention are key advantages in war and diplomacy.
The Accusation of Authoritarianism
[14:15-16:25]
- Hewitt refutes the notion of Trump as authoritarian, noting Trump’s respect for Supreme Court decisions limiting his power—contrasting with what an actual authoritarian would do.
- Dr. Arnn points to Abraham Lincoln’s constitutional restraint during civil war, arguing Trump displays similar respect for legal boundaries.
The “Advantage of the Lawless Aggressor” & Responses in Democracies
[16:43-18:56]
- Churchill’s observation: Aggressors often hold initial advantages, but democracies, when aroused, represent a “mighty force.”
- Modern parallels drawn to 9/11, Japanese attacks in WWII, and current Middle East events.
“If you get a democratic people angry, that's a mighty force.”
— Dr. Larry Arnn [17:43]
Revolutionary Zeal, Regime Durability, and Inevitable Decline
[18:56-21:40]
- Discussion of the Iranian regime’s waning zeal, paralleling the Soviet Union in its later years.
- Dr. Arnn emphasizes that regime longevity is challenged when the population loses faith, referencing insights from Solzhenitsyn about the ‘nomenclature’ who maintained Soviet power for their own interests.
Misjudgment of National Character: Hitler, Chamberlain, and De Gaulle
[21:40-24:18]
- Churchill’s appraisal: Hitler underestimated Britain’s resolve while accurately judging internal French weakness.
- Parallels between French defeat, de Gaulle's resistance, and the role of stubborn national character in eventual resurgence.
Scapa Flow and “Absorbing Defeat”
[26:34-29:18]
- Revisiting the shocking German U-boat attack at Scapa Flow (the sinking of HMS Royal Oak).
- Arnn highlights how national unity in adversity is the strength of democracies:
“They're in the war. It's a big war. Nobody wanted the war... but now, you know, if you want to know who caused the Second World War, his name is Adolf Hitler, secondarily Joseph Stalin. But now they're in it, right?”
— Dr. Larry Arnn [27:43]
- Arnn and Hewitt draw parallels to modern crises, arguing that unity and strategy are essential for endurance.
Reevaluating Neville Chamberlain
[29:18-32:15]
- Arnn defends Chamberlain as a tougher figure than history often credits:
"Neville Chamberlain was a hard man... Hitler betrayed him. He didn't like it and he got really tough."
— Dr. Larry Arnn [30:21]
- Chamberlain’s post-Munich resolve is highlighted, along with Churchill’s gracious eulogy.
War as a Revealer of Character
[32:15-33:41]
- Hewitt asks if current conflicts reveal strengths and weaknesses in leaders—Arnn credits Trump with building a strong, resilient team, especially in security.
- Uncertainties of current events (Straits of Hormuz, Iran) acknowledged.
America’s “Isolationist Streak”
[35:01-36:38]
- Episode closes with a discussion on the American tendency toward isolationism—an enduring feature rooted in geography and history, but one increasingly challenged by global threats:
“...the people who rely on the relative isolation of America make a really good argument that it's deeply embedded in American history... but everything is changing so fast in the world.”
— Dr. Larry Arnn [35:39]
Notable Quotes & Memorable Moments
- “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 Hugh Hewitt [05:02]
- “The human mind, except when guided by extraordinary genius, cannot surmount the established conclusions amid which it has been reared.” — Churchill, quoted by Hugh Hewitt [09:33]
- “If you get a democratic people angry, that's a mighty force.” — Dr. Larry Arnn [17:43]
- “War is a fog. Of course.” — Dr. Larry Arnn [07:05]
- “Neville Chamberlain was a hard man... Hitler betrayed him. He didn't like it and he got really tough.” — Dr. Larry Arnn [30:21]
Timestamps for Key Segments
- 00:29–01:56 Introduction; review of the strategic context in France, British Expeditionary Force
- 01:56–05:02 French mistakes and the Maginot Line
- 05:02–07:05 The “Short War Illusion”; rapid German victory
- 09:33–12:37 Leadership qualities, unpredictability in war, referencing Churchill and modern examples
- 12:37–16:25 Trump, unpredictability, Supreme Court, and accusations of authoritarianism
- 16:43–18:56 Democratic response to aggression; lawless advantage
- 18:56–21:40 Lessons from revolutionary regimes: Iran and the Soviet Union
- 21:40–24:18 National character and leader misjudgments: Hitler, Chamberlain, de Gaulle
- 26:34–29:18 Scapa Flow, unity in adversity, Churchill’s insights
- 29:18–32:15 Reappraising Neville Chamberlain
- 32:15–33:41 War revealing character; current US military leadership
- 35:01–36:38 America’s isolationist tradition and present-day challenges
Main Takeaways
- Both the victors and the vanquished in WWII were often hampered by assumptions rooted in past conflicts.
- The speed of France’s defeat in 1940, contrasted to WWI, was due to a combination of German innovation and Allied misjudgment.
- Unpredictable leadership can unsettle adversaries, offering strategic advantages.
- Democratic societies, though sometimes slow to anger, are powerful once mobilized.
- Authoritarian regimes lose legitimacy and effectiveness over time as populations grow weary.
- Leadership under pressure—whether Chamberlain in war or Trump in modern crises—reveals inner character and resilience.
- America’s isolationist instinct has been a protective luxury, but modern technology and global politics necessitate new strategies.
This episode provides a thorough, historically grounded analysis of early WWII strategy and leadership, consistently connecting the lessons of the past to present geopolitical challenges, all delivered in the engaging and reflective style characteristic of the Hillsdale Dialogues.