Hillsdale Dialogues — "Churchill’s My Early Life, Part Two"
Date: March 17, 2025
Participants: Hugh Hewitt (Host), Dr. Larry P. Arnn (President, Hillsdale College)
Episode Overview
The second installment in a multi-week series examining Winston Churchill’s autobiography, My Early Life, this episode continues to follow Churchill’s formative years as recounted in his vivid 1930 memoir. Host Hugh Hewitt and Dr. Arnn delve into Churchill’s military adventures, his thoughts on empire and luck, and the social mores of late Victorian and Edwardian Britain. The discussion foregrounds Churchill’s role in the colonial wars, the unique society he inhabited, and the character traits emerging in his youth.
Key Discussion Points & Insights
1. Setting the Historical Table: The Boer Wars and Imperial Context
[01:12–05:55]
- Churchill’s Early Adventures:
Dr. Arnn outlines Churchill’s participation in four major conflicts prior to WWI: Cuba, the Indian Northwest Frontier, Sudan, and South Africa—each shaping his early worldview and writing career. - Battle of Majuba Hill and British Prestige:
- Hewitt: The British defeat at Majuba Hill (1881) is described as a major stain on imperial honor. “The Brits didn’t lose, much less to a young 19-year-old farm boy.” [03:05]
- Dr. Arnn: The British had a habit “to always win the last battle,” but the Boers proved a persistent challenge.
- South African (Boer) Wars:
The Boers are praised for their guerrilla tactics and horsemanship, likened to the “Comanches” for their mobility and marksmanship. [05:55]“He calls them the greatest horseback fighters ever that they can shoot and ride. I’m thinking the Comanches.” — Hewitt, [05:55]
2. Churchill’s Dramatic War Stories
[06:12–09:36]
- Armored Train Incident (Preview):
Dr. Arnn relates the famous episode of Churchill’s escape from an armored train ambush, praising his initiative under fire—though the hosts note the book's narrative hasn’t reached this episode yet.
“He records that it was like being in front of an iron target in a target range, people shooting at him ... and he walks around and looks and he studies the situation...” — Dr. Arnn, [08:07]
- Famous Churchill line to wounded civilian engineer:
“Buck up, man. In war, no one is ever wounded twice in the same battle. And you are going to get a medal.” [08:45]
- Famous Churchill line to wounded civilian engineer:
3. The Jameson Raid, Cecil Rhodes, and Pre-War Politics
[09:36–17:21]
- Churchill’s Social Sphere:
Story of an awkward dinner featuring Churchill, John Morley (a “Little Englander” and Cabinet member), and Sir John Willoughby (fresh from the bungled Jameson Raid). The complexity of British imperial politics and society is highlighted.“But blood had been shed. And that makes a different tale.” — Hewitt quoting Churchill, [15:26]
- Dr. Arnn contextualizes Cecil Rhodes as a “tremendous human being ... out there, you know, building the British Empire” and the raid as symptomatic of the chaotic nature of imperial expansion. [14:02]
- Society and Manners:
The hosts marvel at the rigid etiquette of the day, noting that powerful men could share a table and refuse to speak.“It’s a weird society from which Churchill emerges … Pre World War I Britain is different from post World War I Britain in many significant ways.” — Hewitt, [16:57]
- On British manners:
“The British would be very good at chopping each other up politely if that’s what they wanted to do.” — Dr. Arnn, [17:21]
- On British manners:
4. Churchill and the British Aristocracy
[17:51–20:33]
- Manners, Gender, and Hierarchy:
Discussion of the British royal family, the accuracy of portrayals in the TV series The Crown, and Churchill’s respectful conduct toward women and superiors.“Churchill was very courteous to women ... He was not risqué. He was not discourteous, except in the parliamentary way, to important people.” — Dr. Arnn, [19:14]
- Churchill as a Boss:
Churchill’s secretaries reportedly adored him despite his brusqueness during stressful times.“We’re all toads under the Harrow.” — Churchill’s phrase when comforting a crying secretary, as related by Dr. Arnn, [21:42]
- Anecdote of Churchill’s distraction-prone budgerigar bird in his home office.
5. Reflections on Leadership and Relationships in WWII
[22:10–24:53]
- Masters and Commanders:
Comparisons drawn from Andrew Roberts’ account of Churchill’s relationships with American and British generals. - Alan Brooke's Disappointment:
Dr. Arnn explains how rivalry and disappointment played out in Britain’s top brass, influenced by the rise of American power.
6. Churchill’s Voyage to India: Benefits of Long, Slow Travel
[24:53–26:57]
- Long Voyages as Intellectual Retreat:
Churchill made use of sea voyages for study and writing, surrounded by boxes of books and papers.“The long voyages were thinking times ... And he was an immensely productive man all his life.” — Dr. Arnn, [25:33]
- Early Life in India:
Churchill (stationed in Bangalore) found much of idle colonial life stifling, seeking out “relief” through war, polo, and self-education.
7. The Colonial Experience in India
[29:50–34:52]
- Military Hierarchy and Luxury:
Descriptions of the privileges even junior British cavalry officers enjoyed:"Every cavalry subaltern ... gets a butler, a dressing boy, and a groom ... Princes could live no better than we.” — Churchill, as recounted by Hewitt [31:39]
- Churchill’s Restlessness:
- India as a place of ease and authority, but Churchill was “impatient” and craved challenge and significance.
- Social Status and Reception:
Churchill’s arrival in India was noticed but not glamorous; he was of a well-connected family but not yet truly prominent in his own right.
8. Financial Straits and the Realities of Empire
[35:10–36:59]
- Polo on Credit:
Churchill and his fellow officers purchased horses by borrowing at exorbitant monthly interest rates—“They only charged 2%, a month.” [35:10]- Hewitt notes Churchill’s flair in writing and self-mockery:
“He knew it was to be written, not to be read, and he knew he wanted to…” [35:25]
- Hewitt notes Churchill’s flair in writing and self-mockery:
9. Character Formation and the Luck of Life
[36:59–39:52]
- Restless Ambition:
Dr. Arnn notes Churchill’s emerging “impatience” with comfort and desire for action—traits shaping his later life. - Luck and Adaptation:
Anecdote involving Churchill’s dislocated shoulder: it forced him to use a pistol instead of a saber in battle, perhaps saving his life at Omdurman.“Life is a whole and luck is a whole, and no part of them can be separated from the rest.” — Churchill, p.102 (quoted at [38:38])
- Dr. Arnn connects Churchill’s belief in “luck” with Aristotle’s notion that “people with a lot of purposes have more luck than people who have few.”
Notable Quotes & Memorable Moments
-
On Early Military Writers:
“He’s probably the most popular author. … And he’s just a kid, you know, and he’s pining about strategy and generals and the rights and wrongs of the war.” — Dr. Arnn [07:35]
-
On British Social Protocol:
“You can get along with anyone in the aristocracy, unless one of them is charged with murder, in which case you can’t be nice to him.” — Hewitt, paraphrasing Churchill [15:26]
-
On Luck:
“Life is a whole and luck is a whole, and no part of them can be separated from the rest.” — Churchill (quoted), [38:38]
“People with a lot of purposes have more luck than people who have few.” — Dr. Arnn, adapting Aristotle, [39:52] -
On Restlessness:
“He is not fit to settle into a life of ease and authority. Yes, he’s impatient. He’s impatient with that.” — Dr. Arnn [36:59]
-
On Churchill’s Conduct:
“Churchill was very courteous to women and he was, what would you call it, he was not risqué. … if it’s a person to be respected, he would argue with them with respect.” — Dr. Arnn [19:14]
Timestamps for Important Segments
- Churchill’s Early Military Service & the Boers: [02:25–06:12]
- Armored Train Incident Preview: [06:12–09:32]
- Jameson Raid, Morley and Rhodes: [09:36–17:21]
- British Manners & Churchill’s Social Skills: [17:51–20:33]
- WWII Leaders, Diaries, and Legacy: [22:10–24:53]
- Long Sea Voyages and Self-Improvement: [24:53–26:57]
- Life for a Cavalry Officer in India: [29:50–34:52]
- Financial Realities (Polo & Loans): [35:10–36:59]
- Luck, Fate, and Omdurman: [38:08–39:52]
Overall Tone & Style
The dialogue is lively, scholarly, and affectionate toward its subject, with both participants relishing the anecdotal richness of Churchill’s memoir. Dr. Arnn provides context and scholarly insight, while Hugh Hewitt keeps the pace brisk and accessible, often referring to “Steelers fans” as a stand-in for listeners who may not know all the historical details.
Final Thoughts
This episode sets the tone for a deeper examination of Churchill’s early life, connecting colorful anecdotes with broader themes of character, ambition, empire, and luck. The conversation is accessible but rich in reference, inviting listeners to read My Early Life alongside the hosts as they continue to draw lessons relevant to leadership, adversity, and the shaping of 20th-century lions.
Recommended: Start reading or rereading Churchill’s My Early Life for full engagement with upcoming episodes!