Hillsdale Dialogues

Episode Title: Churchill’s My Early Life, Part Three – March 24, 2025
Hosts: Hugh Hewitt & Dr. Larry P. Arnn (President, Hillsdale College)

Episode Overview

This episode continues the ongoing discussion between Hugh Hewitt and Dr. Larry Arnn about Winston Churchill’s autobiography, My Early Life, focusing on his years in India, his approach to luck and adversity, the beginnings of his real education, and how his formative experiences shaped his philosophical and public outlooks. The hosts also respond to contemporary criticisms of Churchill, defending his legacy and recounting key moments from Churchill's early career and self-education.

Key Discussion Points & Insights

1. Responding to Anti-Churchill Rhetoric

• [01:35-03:34]
  • Hewitt raises recent trends of anti-Churchill sentiment, particularly among young audiences who lack historical context.
  • Dr. Arnn clarifies misconceptions—such as Churchill’s role in Iraq and Afghanistan—highlighting Churchill’s actual policies and thinking on democracy and colonial rule:

    “He specifically refused to take a long-term British rule in Iraq and Afghanistan. He didn’t labor to build democracy there because he didn’t think they wanted it.” (Dr. Arnn, 02:26)

2. Early Military Career and the Role of Luck

• [04:43-08:38]
  • Discussion centers on Churchill’s military experience, focusing on his injury in India and the consequential circumstances of the Battle of Omdurman.
  • Churchill’s dislocated shoulder forced him to fight with a pistol instead of a saber, which possibly saved his life.
  • Hewitt cites Churchill:

    “You can never tell whether any bad luck may not, after all, turn out to be good luck… My story might never have gotten so far in the telling.” (Hewitt quoting Churchill, 07:54)

  • Dr. Arnn connects Churchill’s attitude to adversity to his broader worldview:

    “Churchill was not at all a stoic, but he did have that stoic attitude lots of times in his life.” (08:38)

3. Churchill’s Political “Wilderness” and Use of Setbacks

• [08:38-11:19]
  • They recount how Churchill’s political isolation mid-career, when not given a cabinet position, ultimately protected his reputation.
  • Dr. Arnn paraphrases Churchill:

    “But if I had joined the government at that time, I would have been complicit in the policies that led to the outbreak of the war. Yeah, above me, above me beat the invisible wings, he said.” (11:07)

4. Churchill in India – Active Life and Self-Education

• [14:08-15:36]
  • Churchill both relished and tired of India, using hot afternoons for studious self-improvement, reflecting his restless, driven spirit.

    “Everybody else took a long nap in the afternoon in India… what he did in those times was he started seriously, his education.” (Dr. Arnn, 15:02)

5. The “Curiosity Bulb” and the Education of a Leader

• [15:36-18:59]
  • Churchill described a sudden hunger for learning at age 22. Dr. Arnn emphasizes this as a defining moment for many students—where learning transforms from duty to love.
  • Dr. Arnn shares:

    “I wish I had been as eager to know when I was a freshman as I am now, because a light goes on… you don't really begin to learn until that happens.” (16:37)

  • Churchill’s characteristic humility about his education is discussed, noting that his supposed shortcomings in classical languages belied significant knowledge.

6. The Challenge and Danger of Autodidacticism

• [18:59-27:18]
  • Churchill immerses himself in the works of Gibbon, Macaulay, Plato, Aristotle, and more, occasionally adopting their prejudices uncritically.
  • Hewitt points out:

    “So it’s the danger of being an autodidact, right?” (26:02)

  • Dr. Arnn concurs but balances the value of great teachers versus active, self-motivated thinking:

    “An excellent teacher is one of the blessings of life… but it’s partly chance… Churchill kept thinking, right, and he read a lot of things.” (27:18)

7. Churchill’s Religious Views and Comparisons to Lincoln

• [28:33-31:47]
  • Churchill’s statements reveal a mixture of skepticism and reverence toward religion—what Dr. Arnn identifies as a belief in “protecting Providence.”

    “He believed that that Providence was especially interested in him.” (Dr. Arnn, 29:25)

  • Churchill and Lincoln are contrasted:

    “They were both very respectful of Christianity and… believed in God very much… but they were not doctrinaire theologians.” (Dr. Arnn, 30:55, 31:13)

8. Physical Daring and the Spirit of Adventure – Churchill as Polo Player

• [32:42-33:31]
  • Churchill’s vigor is captured in his passion for polo, which he played into his fifties, illustrating both his physical courage and tendency to downplay his own achievements.

9. Self-Education and Evaluating Historical Claims

• [33:31-34:38]
  • Dr. Arnn encourages listeners to study Churchill critically by comparing different authors’ interpretations:

    “If you really want to learn about him… write down [critics’] main claims and then you would go look up in Martin Gilbert whether they're true or not.” (33:48)

10. War and Modernity – Churchill’s Realism about Violence

• [37:10-39:50]
  • Churchill’s evolving perception of war, from adventure to mass industrial slaughter, and the dangers of technological escalation, are discussed.
  • Dr. Arnn follows up with reflections on contemporary warfare’s changing nature and references Churchill’s essays on science and the future.

    “Now it’s manufacturing, it’s industrial, and the death… the best way to prevent it is to be in a position to win it and make that known.” (Dr. Arnn, 37:58)

11. Technology & the Perils of AI

• [39:50-40:52]
  • The dialogue ends with contemporary concerns about AI, linking Churchill’s predictions about technology’s disruptive impact.
  • Dr. Arnn summarizes the uncertainty:

    “We don’t know what that’s gonna do.” (39:50)

Notable Quotes & Memorable Moments

• On Luck’s Double-edged Nature

  “You can never tell whether any bad luck may not, after all, turn out to be good luck… life is as a whole and luck is as a whole, and no part of them can be separated from the rest of it.”
  — Churchill, quoted by Hewitt, 07:54

• On Political Setbacks

  “If I had joined the government at that time, I would have been complicit in the policies that led to the outbreak of the war… above me beat the invisible wings.”
  — Dr. Arnn paraphrasing Churchill, 11:07

• On the Need for Teachers & Self-Reliance

  “An excellent teacher is one of the blessings of life… but in another way, [education is] not at all [chance]. Because Churchill kept thinking, right, and he read a lot of things.”
  — Dr. Arnn, 27:18

• Churchill’s Religious Sentiment

  “He believed that that Providence was especially interested in him.”
  — Dr. Arnn, 29:25

• On War’s Changing Character

  “When war was snapping flags and cavalry charges and sabers and the casualties were light, it was the grandest adventure… but then it changes… now it’s manufacturing, it’s industrial…”
  — Dr. Arnn, 37:58

Suggested Timestamps for Key Segments

• Churchill’s Early Critics & Public Memory: 01:33–03:34
• Battle of Omdurman & The Value of Luck: 04:43–08:38
• Political Exclusion & “Invisible Wings”: 08:38–11:19
• Churchill Discovers His Intellectual Appetite: 15:36–18:05
• Self-Education, Teachers, and Autodidacts: 24:05–27:18
• Churchill’s Religious View (and Comparison with Lincoln): 28:33–31:47
• Physical Daring (Polo) and Downplaying Achievement: 32:42–33:31
• The Dangers of Modern War & Technology: 37:10–39:50

Conclusion

This episode stands as a rich, nuanced discussion of Churchill’s youthful formation—his intellectual awakening, responses to adversity, a pragmatic religious outlook, and a hands-on approach to self-improvement. Dr. Arnn and Hewitt not only showcase Churchill’s complexity and humanity but also defend the value of historical understanding against modern revisionism. The dialogue offers timeless lessons on education, resilience, and the risks inherent in both war and unexamined progress.

For listeners seeking to understand Churchill, or the nature of great leadership and the search for knowledge, this conversation is essential.