Hillsdale Dialogues — Churchill’s My Early Life, Part One

Date: March 10, 2025
Host: Hugh Hewitt
Guest: Dr. Larry P. Arnn, President of Hillsdale College

Overview

This episode launches a multi-part discussion series on My Early Life, Winston Churchill’s memoir recounting his first thirty years. Hugh Hewitt and Dr. Larry Arnn analyze the formative influences in Churchill’s upbringing, the political and familial context of his youth, and the early character traits and experiences that would later shape one of history’s most significant leaders. Central themes include Churchill’s family background, education, early military adventures, and the Victorian values and political world in which he came of age.

Key Discussion Points & Insights

1. Context and Background of Churchill’s Early Life (01:12 – 04:29)

• Churchill’s Career Overview: Before delving into the book, Hewitt summarizes Churchill’s rapid ascent through various political and military roles — from a string of government ministerships to a wide-ranging military record.
• Churchill’s Versatility: Dr. Arnn notes the singularity of Churchill’s career path:

  “Churchill, we will learn in this book, had the gift of doing about what he wanted to, about all the time. … he went where there was action and advancement and he went fast.” (03:15)

2. Family Background: Lord Randolph and Jenny Churchill (03:56 – 06:02)

• Lord Randolph Churchill: A brilliant, ambitious Tory Democrat with a meteoric (but ultimately self-sabotaged) political career; architect of new Tory policies in the tradition of Disraeli; known for wit and an acerbic tongue.

• Jenny Churchill: From a wealthy American family, daughter of Leonard Jerome, known for beauty and social dynamism.

• Impact on Winston: Dr. Arnn clarifies both parents’ influences and explores their limitations in nurturing their son, including Lord Randolph’s neglectful tendencies.

  “The worst thing Lord Randolph did to Winston Churchill… Churchill writes him two plaintive letters saying, please, can you come and see me? And Churchill never got an answer to those letters, nor saw him, and that was not good.” (23:27)

3. Political Backdrop: Salisbury, Chamberlain, and Trade Politics (05:28 – 09:58)

• Lord Salisbury: The last real aristocrat to be Prime Minister, described as “stolid, implacable, large, and brooding over all of British politics for 25 years.” (05:28)
• Trade Debates: Discussion of free trade vs. protectionism (imperial free trade), and how these shaped party alliances and splits, including Joseph Chamberlain’s industrial union vision for the British Empire — “It actually was like the European Union… free trade among the members, tariffs on everybody else.” (08:44)
• Churchill’s Political Breaks: Churchill’s eventual split and realignment from Conservative to Liberal, then back again, reflect both inherited and opposed positions from his father’s generation.

4. Parliamentary Culture: Courtesy and Conflict (09:58 – 11:19)

• Parliamentary Decorum: Examples of mutual respect between political opponents (Gladstone’s compliment to Chamberlain), contrasted with contemporary politics’ loss of such traditions.
• On Churchill’s Career Risks:

  “Churchill, when Churchill left the conservatives in 1904, and then he did come back in 1924, there are conservatives who never lived to forgive him for that. But they were by and large courteous to him.” (10:46)

5. Churchill’s School Days and Reputation as a “Dunce” (14:25 – 16:55)

• Academic Struggles: Churchill’s own depiction (possibly overstated) of his poor performance at Harrow as part of his self-mythology — “He actually calls himself a dunce in this book, but he was not a dunce.” (15:08)
• Exceptional Memory: His feats in recitation at school, particularly of Macaulay’s “Horatius,” reveal extraordinary memory and mental discipline.

6. Early Military Ambitions and Training at Sandhurst (18:04 – 21:46)

• Military Training: Churchill’s lack of affinity for conventional education gave way to passion for the more physical and “real world” challenges at Sandhurst.
• Punctuality and Social Life: Amusing anecdote about Churchill’s lateness to a dinner with the Prince of Wales, and lessons in royal etiquette.
• Adventuresome Spirit:

  “[Churchill] rode horses and he shot stuff and wielded a saber and that's just the coolest thing in the world.” (21:08)

7. Churchill as Journalist and Subaltern (18:57 – 20:35)

• Simultaneous Careers: Churchill cultivated a public reputation by writing about wars he fought in — “He would resign his commission and then write a bunch of articles and then join back up. So you couldn't stop him.” (19:49)

8. Parental Shadows and Social Class Complexities (23:27 – 26:18)

• Lord Randolph’s Fallibility: Emphasized the “shadow” cast by a difficult, distant father, whose political stature didn’t translate to good parenting.
• Marlborough Lineage: Churchill’s noble ancestry, his lack of inheritance, and the economic realities of his upbringing.

9. Early Travel and Military Intelligence: Cuba Adventure (30:29 – 33:28)

• Cuban Campaign: Churchill’s resourcefulness and connections let him arrange to observe combat in Cuba at 21 — reportedly gathering intelligence for the British War Office, though this episode isn’t described in his memoir.
• Nontraditional Military Life: The flexibility and privilege of aristocratic military service — repeatedly obtaining permission for overseas adventure, which would be inconceivable in today’s armed forces.
• Humor and Humility:

  “I have never had a prejudice against fat men.” — Churchill’s quip about hiding behind a corpulent comrade during an attack (33:28)

10. Themes of Luck, Destiny, and Belief (37:56 – 39:02)

• Luck as a Motif: Churchill refers often to luck, viewing good and bad fortune as cyclical — “He believes in luck and he also believes it evens out.”
• Glimpses of Faith: Dr. Arnn asserts Churchill also believed in destiny and, particularly later, in God — “He did believe in God, too. … It’s not an orthodox account of God, but… he did believe in God very much.” (38:18, 38:54)

Notable Quotes & Memorable Moments

• “Churchill, we will learn in this book, had the gift of doing about what he wanted to, about all the time.” — Dr. Arnn (03:15)
• “It actually was like the European Union... free trade among the members, tariffs on everybody else.” — Dr. Arnn on Chamberlain’s imperial policy (08:44)
• “Churchill called himself a dunce in this book, but he was not a dunce.” — Dr. Arnn (15:08)
• “Churchill had a tremendous memory.” — Dr. Arnn describing reciting Macaulay’s lines (16:55)
• “He would resign his commission and then write a bunch of articles and then join back up. So you couldn't stop him.” — Dr. Arnn (19:49)
• “One of the things that comes out in this book is that Churchill, in his military career up until 1900, is also a journalist. And he becomes the leading journalist and then best-selling authority on three wars.” — Dr. Arnn (18:57)
• “I have never had a prejudice against fat men.” — Quoting Churchill retelling a firefight in Cuba (33:28)
• “[Churchill] did believe in his destiny. He did believe in God, too.” — Dr. Arnn (38:18)

Timestamps for Core Segments

• Churchill’s Career Overview: 01:12 – 04:29
• Family Background: 04:29 – 06:02
• Political Backdrop: 05:28 – 09:58
• Parliamentary Culture: 09:58 – 11:19
• School Days & “Dunce” Myth: 14:25 – 16:55
• Sandhurst & Military Training: 18:04 – 21:46
• Journalism and Subaltern: 18:57 – 20:35
• Parental Shadows & Social Class: 23:27 – 26:18
• Cuba and Early Intelligence Work: 30:29 – 33:28
• Themes of Luck and Destiny: 37:56 – 39:02

Closing Thoughts

Churchill’s My Early Life emerges in this dialogue as a book of youthful adventure, familial tension, and self-mythology—but also as an inspiration for spirited young people. Hewitt and Arnn repeatedly urge listeners to read, not just listen to, the book, emphasizing that its humor, insight, and candor are best experienced firsthand. Dr. Arnn closes with Churchill’s advice that it’s never too early to seek greatness—urging young people to read Churchill’s memoir for both its wisdom and its exhilarating sense of possibility.