Hillsdale Dialogues: Churchill’s My Early Life, Part Five

Date: April 14, 2025
Host: Hugh Hewitt
Guest: Dr. Larry P. Arnn, President, Hillsdale College

Overview

In this episode, Hugh Hewitt and Dr. Larry Arnn continue their exploration of Winston Churchill's memoir My Early Life, focusing on chapters 13 through 15, which briefly recount Churchill's Sudan campaign and his relentless pursuit of adventure and military distinction. The conversation also connects Churchill’s personal qualities to broader themes of ambition, envy, anxiety, chance, and the enduring lessons for contemporary society. Parallels are drawn with modern figures like Elon Musk and current geopolitical and economic issues, such as tariffs and trade policy, linking Churchill’s era to the present day.

Key Discussion Points

Churchill’s Adventurous Spirit and Relentless Ambition

• Churchill’s drive for adventure: Hugh Hewitt opens with Churchill’s eagerness "to share in the Sudan campaign," noting his restless and daring youth (01:13).
  • Quote: “He loved adventure, and it's an adventure story. The young Churchill is just as dashing as any young British soldier can be.” – Hugh Hewitt (01:36)
• Modern equivalents: Dr. Arnn argues this spirit is alive today in young people and entrepreneurs like Elon Musk, who pursue grand visions.
  • Quote: “Sure we do. Yeah, of course we do. They're rising up all the time … that's the spirit, right? That's the thing that gets it going.” – Dr. Arnn (02:46)
  • Musk’s ideal of “sustained abundance for everyone” is contrasted with Churchill's more grounded humanity (03:39).

Envy, Criticism, and Reputation

• Churchill criticized as a ‘self-advertiser’: Both Musk and Churchill faced resentment for their outsized ambition.
  • Quote (Churchill’s memoir): “It is melancholy to be forced to record these less amiable aspects of human nature. He's being called a medal hunter and a self advertiser.” – Hugh Hewitt (05:20)
• Navigating criticism: Churchill’s willingness to push boundaries in the British military and in journalism attracted both detractors and supporters, illustrating the double-edged sword of public ambition (06:12, 11:23).

The Power of Connections and Persistence

• Securing a place in the Sudan campaign: Churchill leverages personal and family connections (notably his mother and Prime Minister Lord Salisbury) to push for his assignment, despite resistance from General Kitchener.
  • Quote: “Churchill gets in to see Lord Salisbury, because he wrote an interesting book … and Churchill gets him to write a telegram to Kitchener which effectively says, please take Churchill. And Kitchener says no.” – Dr. Arnn (08:22)
• Navigating military bureaucracy and persistence: Evelyn Wood’s intervention finally gets Churchill to the front, highlighting the interplay of individual agency and institutional politics (17:24-18:52).

Anxiety and the Management of Worry

• Churchill’s personal struggle with anxiety: The memoir reveals Churchill’s anxiety during his journey to Sudan—the fear that orders would arrive to cancel his mission (18:52-19:32).
  • Quote: “When I am overcome with worry, I write down on a piece of paper a list of the things that I’m worried about. … I can concentrate on the ones that I can do something about.” – Dr. Arnn (19:33)
• Generalizing the lesson: Dr. Arnn notes that Churchill’s practical method for managing anxiety is universally useful.

The Role of Chance in Life’s Outcomes

• Luck, fate, and missed disaster: Churchill narrowly avoids a deadly cavalry charge (the position he wanted was given to another, who was killed), leading to a reflection on luck and risk (29:34-31:40).
  • Quote (Churchill’s Memoir): “Chance is unceasingly at work in our lives, but we cannot always see its working sharply and clearly defined.” – Read by Hewitt (31:23)
• Philosophical perspective: Dr. Arnn connects Churchill and Aristotle—arguing that people of “many purposes” multiply their opportunities for fortunate outcomes by taking more risks (31:40-33:02).

Broader Historical and Contemporary Parallels

• Military criticism then and now: The tradition of military officers avoiding political criticism is contrasted with Churchill’s habit of openly criticizing superiors (13:53-14:22).
• Trade, tariffs, and the modern world: Drawing parallels to present debates, Hewitt and Arnn discuss the global disadvantage of American industry under current trade arrangements, connecting it to Churchillian themes of national self-preservation and resilience (22:20-25:15).
• The British Empire’s unity and lessons for the West: The episode closes with a discussion of how the common feeling and voluntary loyalty of the Empire—particularly from dominions like New Zealand—mirrored the unity needed in the West today (36:34-37:45).

Notable Quotes & Memorable Moments

• On Churchill’s bold pursuit of action
  “He is the most published author on these wars in which he fought, and he’s the second lieutenant and he is critical of the generals. Now, that’s outrageous.”
  — Dr. Larry Arnn (11:23)

• On dealing with setbacks and anxiety
  “Churchill lived with a lot of anxiety … when I am overcome with worry, I write down on a piece of paper a list of the things that I’m worried about. … I can concentrate on the ones that I can do something about.”
  — Dr. Larry Arnn (19:33)

• On luck and purpose
  “Somebody like Churchill, a person of many purposes, the chance tends to favor such people because they have so many purposes that breaks in chance are more likely to favor one of them.”
  — Dr. Larry Arnn (31:40)

• On the unity of the Empire
  “It was united by fellow feeling and common loyalty, even placing New Zealand in peril by its own choice.”
  — Dr. Larry Arnn (37:35)

• On tariffs and free trade
  “Our trading partners, so to speak, have had consistently higher tariffs than we have for 50 years…if all [Trump] achieves is he equalizes those tariffs … that should be a gain.”
  — Dr. Larry Arnn (22:20)

Timestamps for Key Segments

| Timestamp | Segment/Theme | |-----------|-------------------------------------------------------------------------| | 01:13 | Introduction to Churchill’s Sudan adventure and his adventurous mindset | | 05:20 | Churchill on envy and being criticized as a self-advertiser | | 08:22 | Churchill’s lobbying for the Sudan campaign and influence of connections | | 13:53 | Churchill’s habit of critiquing military superiors; comparison today | | 18:52 | Churchill’s anxiety over reaching the front; methods of managing worry | | 29:34 | The story of Robert Grenfell and the role of luck and chance | | 31:40 | Philosophical discussion: Purpose, risk, and fortune | | 22:20 | Parallels with contemporary tariffs and global trade policy | | 36:34 | Unity and sentiment in the British Empire and lessons for the West |

Conclusion

This episode is a nuanced and lively exploration of Churchill’s formative experiences—his audacity, drive, and struggles with anxiety—set against a broader backdrop of leadership, fate, and lessons both historical and contemporary. Dr. Arnn and Hewitt provide not only insight into the historical Churchill but also draw connections to the dilemmas and ambitions that continue to shape personalities and nations today.

Next episode: “I Leave the Army”—exploring Churchill’s transition from soldier to statesman.