Hillsdale Dialogues: Churchill’s The Second World War, Part Eleven
Podcast: Hillsdale College Podcast Network Superfeed
Host: Hugh Hewitt
Guest: Dr. Larry Arnn, President of Hillsdale College
Date: November 17, 2025
Episode Overview
In this episode, Hugh Hewitt and Dr. Larry Arnn continue their deep dive into Winston Churchill's The Second World War, focusing on Churchill’s lowest political point in 1936 and his remarkable resurgence as the threat of Nazi Germany intensified. They explore the internal politics of Britain, the rise (and limits) of key figures like Baldwin, Chamberlain, and Eden, and reflect on the crucial interplay of character, leadership, diplomacy, and military readiness during Europe’s drift to war. Through stories from Churchill’s memoir, they discuss how history hinges on the decisions and qualities of individuals, and draw timely lessons about statesmanship, historical contingency, and the ongoing importance of both military and diplomatic strength.
Key Discussion Points and Insights
1. Churchill’s Low Point and Fight for Influence (00:30–04:18)
- In 1936, Churchill was politically isolated and considered a "spent force" after being booed in Parliament and losing meaningful government influence (00:30).
- Dr. Arnn explains Churchill’s resurgence:
- He used his skills as a writer and orator “in the House and out of doors” to inform and persuade (01:32).
- Churchill formed the Focus, an all-party group advocating for rearmament, uniting diverse political factions: “Anybody who wants our country to be strong enough to prevent, if possible, and if not to win a war with Germany, you are invited.” (02:38)
- His speeches (sometimes using confidential information) pressured the government toward rearmament, even without winning formal votes (03:38).
- Notable wisdom: "There are two ways to get on with somebody. One is to talk and write and the other is to fight. Talking and writing are better." (Dr. Arnn, 01:42)
2. Government Transitions: Baldwin to Chamberlain, Eden’s Role (04:18–08:51)
- When Baldwin retires, Chamberlain becomes Prime Minister, but does not bring Churchill into government, despite Churchill’s accurate warnings about Germany (04:18).
- Dr. Arnn explains the dynamics of forming a British cabinet: balancing allies, rivals, competence, and mistakes (05:22).
- Churchill's view: Eden would be more valuable at the military-administrative Admiralty than as Foreign Secretary, foreseeing that negotiation alone with Germany was futile (07:20).
- Dr. Arnn recalls Churchill’s ominous dinner with Hitler’s aide Ribbentrop, foreseeing German expansionism and Britain’s future resistance (07:46).
3. Britain’s Grand Strategy & Churchill's Warnings (08:40–09:23)
- Churchill reiterates Britain’s long-standing policy: never allow a single dominant power in Europe (08:40).
- Quote:
“Evil man, you must not underestimate England... If you plunge us into another great war, she will bring the whole world against you like the last time.”
— Churchill to Ribbentrop, cited by Hugh Hewitt, (09:23)
4. The Resignation of Anthony Eden (12:15–16:22)
- Anthony Eden resigns as Foreign Secretary on Feb 20, 1938, a moment Churchill describes with poetic sorrow.
- Quote (Churchill in his memoir):
“Consumed by the emotions of sorrow and fear, there seemed to be one strong young figure standing up against the long dismal drawling tides of drift and surrender... Now he was gone. I watched the daylight slowly creep in through the windows and saw before me... the vision of death.” (13:27) - Dr. Arnn: Eden was trusted by Churchill and his resignation signaled the weakening of principled opposition within government (13:49–16:22).
5. Private Intelligence and Rearmament (17:19–18:18)
- Churchill’s independent information network revealed vast German military spending, far greater than previously admitted (17:19).
- Chamberlain’s response: he would confirm the German figures if raised in Parliament, showing prior knowledge but little action.
6. The Limits and Character of Leaders (18:18–21:03)
- Dr. Arnn: Churchill’s analysis of Baldwin (devious, weak) and Chamberlain (overconfident, stubborn) highlights how personal character and choices, not historical inevitability, shape events (18:18–21:03).
- Leadership choices can change the course of history; fatalism is a mistake.
7. Diplomacy, Military Power, and International Affairs (24:13–25:01; 27:03–28:03)
- Example: Eden’s effective diplomacy with France and the threat of force curbed Italian aggression at sea.
- Dr. Arnn: “Come to find out, you got to have both [diplomacy and military power].” (25:01)
- In a shifting world order, diplomacy grows more important, but strength remains essential.
“Military power is the price of getting in the room.” (27:53)
8. The Munich Crisis and "Peace For Our Time" (29:53–31:46)
- Chamberlain’s personal intervention in 1938 aimed to avoid war at the cost of sacrificing Czechoslovakia’s defenses.
- Dr. Arnn: By 1938, Germany was “very hard to stop,” and opportunities to avert disaster were rapidly diminishing.
9. The Power and Limits of Historical Study (31:46–36:42)
- Churchill’s conviction: History is shaped by choices at pivotal moments.
- Studying these moments helps current and future leaders avoid fatalism and understand the value of practical judgment.
- Churchill, despite gaining glory from WWII, saw the war itself as a preventable catastrophe.
Memorable Quotes & Moments
-
On the power of individual leadership:
“It's what we do. If Baldwin and Chamberlain messed up the situation in ways that terrified Churchill and compromised England, the fact that they could do that means that somebody else might have done better, and then we can try to do better. Choices matter very much.”
— Dr. Arnn, 21:03 -
On reading history:
“Reading history is like reading the newspaper, except the picture is more complete because you know what happened later... Churchill is questing for the places where better choices might have made better things happen.”
— Dr. Arnn, 32:44 -
On diplomacy and military power:
“You gotta have both. And unfortunately, sometimes America forgets that lesson.”
— Dr. Arnn, 25:01 -
On the meaning of Churchill’s memoir:
“His account of this war... is that it could have been and it should have been prevented. And his account is that it was a disaster, that it was not.”
— Dr. Arnn, 36:28
Timestamps for Key Segments
| Segment Topic | Timestamp | | ------------------------------------------------------------- | ----------- | | Churchill’s lowest point, revival through writing/speaking | 00:30–04:18 | | Cabinet government and why Chamberlain passes over Churchill | 04:18–08:51 | | Britain’s grand strategy: never allow domination of Europe | 08:40–09:23 | | Anthony Eden's resignation and Churchill’s reaction | 12:15–16:22 | | Churchill’s private intel, Nazi armaments revelation | 17:19–18:18 | | Leadership character as a factor in historical outcomes | 18:18–21:03 | | Diplomacy, military force, and realpolitik | 24:13–25:01, 27:03–28:03 | | The narrowing window to stop Hitler, Munich Crisis | 29:53–31:46 | | Lessons from Churchill’s historical method | 32:44–36:42 |
Concluding Thoughts
The dialogue closes by reinforcing Churchill’s belief in contingency—critical decisions by individuals can avert or trigger catastrophe. For audience members, the episode models how deeply engaging with history, particularly through the eyes of great statesmen like Churchill, equips contemporary leaders and citizens alike to better understand, judge, and influence the world around them.