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

Podcast: Hillsdale Dialogues
Host: Hugh Hewitt
Guest: Dr. Larry P. Arnn (President, Hillsdale College)
Date: February 16, 2026
Theme: Reflections on Churchill’s account of WWII, with a special focus on Poland, Russia, the nature of power, and great strategic dilemmas.

Episode Overview

In episode 20 of their series on Churchill’s Second World War memoirs, Hugh Hewitt and Dr. Larry Arnn analyze the "tragedy of Poland," the enduring nature of Russia, the challenges of alliance, and the practical difficulties of political and military leadership in times of crisis. Along the way, they connect Churchill’s dilemmas to contemporary global challenges, offer insights on tyranny and freedom, and reflect on lessons in leadership.

Key Discussion Points & Insights

The Tragedy of Poland and the 1939 Carving-up (01:22–04:22)

• Both hosts reflect on brief visits to Poland and its unique historical burden.
• Dr. Arnn summarizes Poland's fate, pointing out how it oscillated between Russian and German domination.
• The Molotov-Ribbentrop Pact is discussed as a cynical agreement to divide Poland—Hitler and Stalin agreeing to partition the nation.
  • “The immediate point of the deal was Poland. They agreed to split it up between them.” — Dr. Arnn (03:32)
• The Soviets opportunistically wait for Germany to defeat much of Poland before seizing their share.

Churchill’s “Riddle Wrapped in a Mystery” & Russian National Interest (04:22–06:47)

• Hewitt reads one of Churchill’s most famous lines on Russia:
  “I cannot forecast to you the action of Russia. It is a riddle wrapped in a mystery inside an enigma. But perhaps there is a key. That key is Russian national interest.” (04:45)
• Dr. Arnn affirms that Russian national interest remains a central, enduring theme in interpreting Russian policy.
  • Russia is "made out of very strong material, and it ain’t going anywhere." (05:06)
• Communism is seen as alien to Russia’s core identity; Russia, like China, is fundamentally ancient and resilient, more so than transient ideologies.

Enduring Patterns: Russia, China, and Tyranny (06:47–09:04)

• The apparent continuity of Russian and Chinese character regardless of ideological overlays is discussed.
• Hewitt draws parallels between Putin and the czars, as well as Xi's increasingly "emperor-like" rule in China.
• References to Tolstoy and Dostoevsky emphasize Russia's "cosmic tragedy" and depth.

Dostoevsky, The Grand Inquisitor, and the Nature of Freedom (11:23–15:22)

• Dr. Arnn describes Dostoevsky’s Brothers Karamazov and the famous “Grand Inquisitor” chapter.
  • The Grand Inquisitor rebukes Jesus for granting people freedom instead of material security:

    “We have taken away their freedom and now they’re happy... We tell them what to do and because we excuse them from their sins, we bear the world's burden of sin. Now you refused to do it. You left them free and we're going to burn you tomorrow.” — Dr. Arnn paraphrasing Dostoevsky (13:19)

  • Christ’s miracles in the gospels often come with a command to "tell no one"—illustrating the gospel's respect for human freedom.
  • Dr. Arnn: “He’s leaving us free... there has to be a teaching, and you have to believe it... and there have to be suffering by me. You have to believe that.” (14:49)

Great Powers: Tocqueville, Endurance, and Casualty Tolerance (15:22–17:49)

• Hewitt recalls Tocqueville's prophecy that Russia and America would dominate world affairs.
• Discussion of Russia’s enormous WWII casualties and contemporary resilience in the Ukraine conflict.
  • Dr. Arnn notes, “1.1 million [casualties]... compared to their casualties in this First and Second World War—that's nothing.” (16:25)
  • Soviet losses in WWII: 20–25 million dead, up to 50 million including civilians.

Tyranny: Stalin, The Bolsheviks, and Contingency (17:49–19:35)

• Stalin’s intentional starvation of Ukraine and mass killings are detailed.
  • “Stalin is in some ways the beau ideal of a tyrant because his way of killing more people than Hitler killed... all he did was ship all the food out of Ukraine... and let them starve...” — Dr. Arnn (17:15)
• The Bolshevik Revolution is presented as contingent, not inevitable.
  • “If you just read the history, you see that it was not [inevitable].” — Dr. Arnn (18:38)

Churchill, Poland, the War Cabinet, and Strategic Leadership (21:54–29:06)

• Churchill’s dilemma after Poland’s fall: balancing long-term strategies versus immediate needs.
  • “There is the usual conflict between long term and short term policy which rises in intensity in wartime.” — Dr. Arnn paraphrasing Churchill (22:57)
• Dr. Arnn relates this to leadership at Hillsdale during COVID, emphasizing focus on essentials—“I need to know if the kids are gonna die.” (26:53)
• Role of expert advisors: Churchill’s recruitment of Prof. Lindemann to focus on realities rather than what others are doing. (27:53)
  • “He wants them thinking about what to do, not watching what other people are doing. Real things.” — Dr. Arnn (28:04)

Destroyers, Food, Independence, and British Vulnerability (29:06–31:33)

• Churchill immediately recognizes the need for more destroyers to protect vital supply routes from German U-Boats.
  • “Step one, get dinner. We’re getting hung here.” — Dr. Arnn (29:50)
  • Britain’s dependence on food imports is a longstanding strategic vulnerability.
  • “His main case against socialism was it will starve us to death. We won’t be able to produce, we won’t have anything to train and we cannot grow our own food.” — Dr. Arnn (30:27)

Alliance with France & The Necessity of Strategic Promises (31:33–36:22)

• Discussing whether Churchill’s assurances to France (on providing 55 divisions) were prudent or misleading.
  • Dr. Arnn cautions: “You promise them what you can best contribute... That’s if we can get there...” (35:08)
• Churchill did not want to "continue the war single handed," preferring to avoid isolation.

Contemporary Reflections: Defense Spending & Lessons for Today (36:22–38:05)

• Possible US conflict with China—limitations of current military production.
  • “We would start running out of vital stuff in three weeks and they would start running out of vital stuff in a year.” — Dr. Arnn citing a new study (37:10)
• Calls for increased US defense spending echo Churchillian logic—preparing for both present and future threats.

Notable Quotes & Memorable Moments

• Churchill on Russia:
  “It is a riddle wrapped in a mystery inside an enigma. But perhaps there is a key. That key is Russian national interest.” (04:45)

• Dr. Larry Arnn:
  “Russia is a thing made out of very strong material, and it ain’t going anywhere.” (05:06)

• On Soviet Atrocities:
  “Stalin is in some ways the beau ideal of a tyrant because [he killed through] the simplest means: ship all the food out... and let them starve over the winter.” (17:15)

• On Freedom & Dostoevsky:
  “You were too interested in their freedom. So we, we have fixed that. We have taken away their freedom and now they're happy.” (13:19)

• On Immediate vs. Long-Term Decision-making:
  “There’s always a war between the immediate and the long term. The immediate is easier to see...” (22:57)

• Pragmatism in Crisis:
  “I need to know if the kids are gonna die. That’s it. Everything else is, you know, I don’t need to know if the grownups are gonna die...” (26:53)

• On Britain’s Strategic Vulnerability:
  “Let me think of the first time longer than that. He’d been saying, Britain is in an artificial situation... and it cannot grow its own food.” (30:27)

• On Allies:
  “We need allies that can contribute so we don’t subsidize because we can’t afford to just subsidize them.” (33:19)

Timestamps for Key Segments

• 00:29 — Introduction to episode, Churchill’s memoirs, and Poland
• 01:22 — Polish history, Molotov-Ribbentrop Pact
• 04:22 — Churchill’s “Riddle” quote, Russian national interest
• 06:47 — Russian character: continuity, communism as distortion
• 11:23 — Dostoevsky, Russian tragedy, the Grand Inquisitor
• 15:22 — Russia & America as great powers, Ukraine war
• 17:49 — Stalin, engineered famines, contingency of history
• 21:54 — War cabinet, long-term vs. short-term decision making
• 26:53 — Leadership during COVID: focus on essentials
• 28:04 — Churchill brings in Prof. Lindemann for hard truths
• 29:06 — Destroyers, U-boats, necessity of securing food supply
• 31:33 — Alliance management, promises to France
• 36:22 — Modern defense challenges, lessons from history

Takeaways & Reflections

• The plight of Poland in 1939 illuminates the moral and strategic complexities of alliance, guarantees, and great power politics.
• The unchanging patterns of Russian and Chinese statecraft suggest the primacy of national character over ideology.
• Political and educational leadership, in both war and crisis (e.g., COVID), requires balancing the urgent and the important.
• Churchill’s approach—focus on the real, the immediate, and the necessary—remains relevant, especially in times of threat or uncertainty.
• Modern parallels abound: sustaining allies, defense readiness, and the necessity of hard choices rooted in reality, not wishful thinking.

For more episodes and information, visit Hillsdale Dialogues.