Hillsdale Dialogues – "Churchill’s The Second World War, Part Nineteen"

Date: February 9, 2026
Guests: Dr. Larry P. Arnn (President, Hillsdale College), Hugh Hewitt (Host)

Episode Overview

This week’s episode continues the in-depth exploration of Winston Churchill’s memoirs on World War II, focusing on Churchill’s return to the Admiralty at the outset of the war and the profound burden of leadership in times of conflict. Dr. Arnn and Hugh Hewitt discuss Churchill’s experiences, attitudes toward war, the necessity of personal observation, the importance of ceremony, Churchill's relationships with soldiers and statesmen, and the evolving alliance with Franklin D. Roosevelt. The conversation is rich with historical insight, reflections on leadership, and parallels to both personal and institutional life.

Key Discussion Points & Insights

1. Churchill’s Burden and Experience in War

• Churchill’s return to the Admiralty (First Lord from September 1939 to May 1940) is marked with sorrow and determination, reflecting both his extensive personal involvement in prior wars and a deep sense of foreboding.
• Dr. Arnn: “He was not a whiner… he could see this is going to be really bad… They begin in warning and they proceed through urgent warning to ‘too late now; we got to get ready to fight.’ He very regretted that last condition.” (03:33)
• Churchill’s personal history: fought or reported in Cuba, Afghanistan, South Africa, "the River War," and the trenches of World War I.
• He understood both the personal and societal costs of modern warfare.

2. Importance of Personal Observation and Leadership

• Churchill’s visit to Scapa Flow, the Royal Navy’s stronghold, underscores his belief in “seeing for oneself.”
• Dr. Arnn: “You want to see. I mean, I have learned the most about students and running a college in the dining hall at lunch at Hillsdale College. ... If you go sit down and talk to them, it is amazing what you learn.” (09:22)
• Parallels to Lincoln visiting Grant at the front during the Civil War; importance for leaders to understand conditions on the ground.

3. Technological and Tactical Innovations

• Churchill’s willingness to try all possible means to defend Britain:
  • Supported technological advances (radar, anti-aircraft defenses)
  • Employed measures like barrage balloons against German raids, some effective, others less so.
  • “They tried everything.” (04:28)

4. Realism, Mourning, and Steeling Oneself to Loss

• The sinking of HMS Courageous soon after Churchill's return is noted:
  • Churchill: “We can’t expect to carry on a war like this without that sort of thing happening from time to time. I’ve seen lots of it before.” (18:09, quoting Churchill)
  • More than 500 lost, illustrating the scale and acceptance of wartime sacrifice.
  • Dr. Arnn: “That doesn’t mean you don’t mourn while you do it, but you do, as you say, steel yourself…” (18:57)

5. The Scope of the Second World War

• The unprecedented scale of WWII naval action; no historical precedent compares.
• Hewitt: “There’s never been a years-long war at sea that goes on with this many ships… It’s extraordinary, the scope of this war.” (21:01)

6. Ceremony and Ritual in Dark Times

• Churchill is buoyed by the Navy’s “perfect discipline, style and bearing.”
  • Dr. Arnn: “Our lives go by much faster than we think. And so there are great things and small things that happen in them. And the great things need to be marked… so people can mark them together.” (23:05)
• Parallels to academic ceremonies at Hillsdale, emphasizing communal recognition and rites of passage.

7. The Holocaust: A New Horror

• Discussion moves to when Churchill discovered the full extent of Hitler’s crimes.
  • Dr. Arnn: “The evil of Hitler was very well known, but that breaks new ground.” (20:16)
  • Factories for mass murder were unprecedented, shocking even those familiar with wartime atrocities.

8. Churchill, Shakespeare, and Reflection

• Churchill’s use of Shakespeare’s Richard II ("For God’s sake, let us sit upon the ground and tell sad stories of the death of kings") signals both deep reflection and the personal cost of resumed conflict.
  • Context: Picnic in Aberdeen after visiting Scapa Flow; acknowledges the loss of comrades and looming casualties. (17:44)

9. Leadership and Communication: Churchill and FDR

• FDR reaches out directly to Churchill, bypassing formal diplomatic protocols:
  • Compliments Churchill’s book Marlborough, signs as “a former naval person.”
  • Dr. Arnn: “Roosevelt had been spurned by Chamberlain when he offered help… To get a letter from the President… you don’t write him back and say, ‘well, I’m okay.’” (33:10)
• Their correspondence becomes the backbone of Allied leadership during the war.

10. Learning from the Past: War Planning and Disagreement

• Churchill’s experience allowed him to recognize the scale of required production, urging the Americans to triple their output (22:35).
• Disagreements later arose over grand strategy, e.g., Churchill favoring the North African campaign over a direct channel crossing in 1942.
  • Hewitt and Arnn agree Churchill’s caution was justified, given U.S. military inexperience at that stage. (36:49)

Notable Quotes & Memorable Moments

• Dr. Larry Arnn on Personal Observation:
  “If you’re giving orders to troops, should you not meet them, should you not see what they’re like? Will that not help you estimate what they can do?” (13:53)
• Churchill on Enduring Loss:
  “‘We can’t expect to carry on a war like this without that sort of thing happening from time to time. I’ve seen lots of it before.’” (18:09, Churchill quoted by Hewitt)
• On the Holocaust:
  “The evil of Hitler was very well known, but that breaks new ground.” (20:16, Dr. Arnn)
• Ceremony’s Importance:
  “And the great things need to be marked, and they need to be a customary way to do it so people can mark them together.” (23:05, Dr. Arnn)
• On Strategic Foresight:
  “In the meeting, Churchill shocked them. He said … ‘At least triple this. You can do more than that.’ And they did.” (22:35, Dr. Arnn)

Timestamps for Important Segments

• [01:48-04:10] – Churchill’s war experience, foreboding at the Admiralty
• [05:59-09:22] – Scapa Flow, “power of personal observation,” leadership analogies
• [13:49-16:45] – Direct engagement with workers/troops; the necessity of real-world understanding
• [17:44-18:09] – Picnic in Aberdeen, invoking Richard II, confronting loss
• [18:09-18:57] – Sinking of Courageous, realism regarding sacrifice
• [20:16-21:01] – Churchill learning of the Holocaust, shock at industrialized mass murder
• [22:35-22:37] – Churchill pushes Americans to triple wartime production
• [23:05-23:50] – Marking ceremonies, rites of passage, and their importance
• [33:10-33:24] – FDR’s political acumen, direct outreach to Churchill
• [36:49] – Allied strategy, North Africa campaign chosen over Normandy in 1942

Episode Tone and Style

The conversation is scholarly but accessible, laced with Dr. Arnn’s affectionate wit and historical perspective. Both speakers draw frequent analogies between Churchill’s leadership and contemporary issues, making the discussion relatable even as it remains firmly rooted in Churchill’s writings and historical record.

Summary

In this episode, Dr. Larry Arnn and Hugh Hewitt explore the depths of Churchill’s burdens in 1939 as he resumes leadership in a world once again at war. Churchill’s realism, based on unmatched personal experience, guides his approaches to leadership, innovation, and sacrifice. The hosts underscore the importance of seeing things firsthand—whether in war or running a college—and mark the necessity of ceremony and custom in turbulent times. The correspondence and alliance between Churchill and FDR are traced as foundational for the war effort, and thoughtful parallels are drawn to both past and present leadership challenges. The dialogue concludes with insights into grand strategy, learning from past errors, and the critical value of practical experience, echoing the enduring lessons of Churchill’s life and writings.