Podcast Summary: Old School with Shilo Brooks

Episode: The Old Man and the Sea with Admiral James Stavridis
Date: October 9, 2025
Host: Shilo Brooks
Guest: Admiral James Stavridis

Episode Overview

This episode of Old School features a conversation between host Shilo Brooks and Admiral James Stavridis—retired four-star U.S. Navy Admiral, former NATO Supreme Allied Commander, prolific author, and lifelong reader. The episode centers on Ernest Hemingway’s classic novella The Old Man and the Sea, its impact on Admiral Stavridis's life, and broader themes of mentorship, resilience, ambition, leadership, and the enduring value of reading great books.

Key Discussion Points & Insights

Admiral Stavridis’s Journey Into Reading

• Childhood in Greece (01:55):

  • Developed a love of books because there was no television in Athens, Greece, in 1963.
  • Weekly trips to the English language library cemented his reading habit.

    "When a lot of my contemporaries were developing the television habit...I was reading books because there were no options." —Stavridis [01:55]

• Personal Library (02:58):

  • Owns over 5,000 books, with 1,000 collectible first editions (e.g., Atwood, McCarthy, Hemingway).
  • His wife calls his passion "a gentle madness."

    "My wife, for Christmas last year, gave me a coffee mug. On one side of it says, yes, I need all these books, and on the other side, it says, I have actually read these books." —Stavridis [03:43]

Military Life and the Life of the Mind

• Balancing Reading & Naval Command (04:01):
  • Not the stereotypical “brawny” officer; sports were tennis and squash.
  • Experienced a sense of not fitting neatly in either world—sometimes “not military enough” for military peers, “too military” for academia.

    "I've always had a foot in both camps. Life of the mind and the life of the military. Others would say, I never actually fit in anywhere." —Stavridis [05:31]

Why The Old Man and the Sea?

• First Encounter & Lasting Impact (06:59):

  • Read in high school, drawn to the sea as a budding naval officer and to the mentorship between Santiago and the boy, Manolin.

    "When I first read it, what caught me was the ocean, the sea... Even as a teenager, I knew I would be a Navy officer." —Stavridis [07:36]

  • Has reread the book at least 10 times.

• Summary of the Novella (09:24):

  • Admiral Stavridis recaps the plot and highlights the emotional power of the ending—the old man returns with only the skeleton of the marlin, but is supported by the loyal boy.

    "At the end of the novel. He comes back into port and all that is on his skiff is a skeleton. Everything has been eaten by these sharks." —Stavridis [10:54]

Thematic Deep Dives

1. The Old Man and the Boy—Mentorship and Generational Duty

• The Value of Mentorship (12:37):
  • The story demonstrates “what generations owe each other”—the elder generation must lead and teach; the younger must be loyal in return.

    "An older generation is required to teach and to help and to lead and to mentor... What the younger generation owes is loyalty." —Stavridis [12:43]

  • Parallels with his own naval mentorship and career shift into teaching.

    "What I loved was taking care of sailors, mentoring them, guiding the trajectory of their lives." —Stavridis [15:36]

2. The Old Man and the Fish—Ambition, Respect, and Sacrifice

• Duality of Love and Struggle (17:37):

  • Santiago both loves and must conquer the marlin, analogous to the tension between empathy and the need to achieve.
  • Links to Christian and literary themes—sometimes to achieve greater good, an individual must “kill the thing we love.”

    "At times we have to kill the thing we love in order to achieve something higher." —Stavridis [17:37]

  • The marlin as a symbol of ambition; everyone needs a rival or a worthy challenge.

    "The fish is also ambition. It is what we want desperately." —Stavridis [18:37]

• Testing Manhood (20:44):

  • Santiago’s quest is about proving himself against a worthy adversary; shallow victories don’t satisfy.

    "If a man who is strong overcomes a weak thing, that's somehow not a proof that one is a man. But a man needs to take a risk...he's trying to prove something to himself." —Brooks [20:02]

  • Stavridis extends the metaphor to rivalries in sports (tennis) and personal push for greatness.

3. The Old Man and the Sea—The Arena of Existence, Resilience, and Mortality

• The Indifference and Infinity of the Sea (23:47):

  • The ocean represents the eternal, impersonal vastness in which our struggles play out.

    "The sea is this vast eternal arena in which it happens. And here's the point. The ocean could care less." —Stavridis [25:16]

  • Perspective: Our achievements may be transient, so humility and focus on what matters—relationships, purpose—are essential.

• Perseverance in the Face of Defeat (29:25):

  • Notable quote:

    "Man is not made for defeat. A man can be destroyed, but not defeated." —Hemingway, read by Stavridis [29:38]

  • Interpretation: The true virtue is resilience; continuing to strive even as outcomes are lost.

The Value of Rereading

• Growth with Rereading (46:51):
  • The meaning of The Old Man and the Sea—or any great book—evolves with life experience.

    "The Old man and the Sea that I read when I was 15, is a completely different book than the Old man and the Sea when I read it in my 50s." —Stavridis [47:16]

Notable Quotes & Memorable Moments

• On Reading and Leadership:

  "I do think reading and leading actually go together in very important ways." —Stavridis [05:40]

• Father, Mentor, and the Value of Loyalty:

  "I believed deeply in what an older generation owes that younger generation. What the younger generation owes is loyalty." —Stavridis [13:10]

• Santiago’s Resilience:

  "A man can be destroyed but not defeated." —Hemingway, read by Stavridis [29:41]

• Perspective from the Sea:

  "I'd look at that line where the sky meets the sea. And then in my 40s, I thought, you know what I'm looking at? I'm looking at eternity." —Stavridis [24:19]

• Relating Personal and Literary Ambition:

  "The fish that I feel the most bound to is writing... I would love to write a book a tenth as great as the Old Man." —Stavridis [32:44]

Important Timestamps & Segments

• Admiral’s Childhood & Reading Habit: [01:55–02:46]
• Personal Library and Collectibles: [02:58–03:43]
• Stereotypes in Military and Academia: [04:01–05:31]
• First Encounter with The Old Man and the Sea: [06:59–07:36]
• Summary of Novella: [09:24–11:56]
• On Mentorship and Loyalty: [12:37–14:33]
• Leadership Lessons & Career Transition: [15:32–16:20]
• The Fish as Ambition & Rivalry: [17:37–22:37]
• The Sea as Eternity and Context for Action: [23:47–27:37]
• Key Passage Reading (Resilience): [28:21–29:41]
• On Rereading & Personal Development: [46:51–47:29]
• Lightning Round (Favorite Military History Book): [49:08–49:42]
• On What Civilians Miss About Military: [50:21–52:08]
• "What Keeps You Up at Night?" [54:07–56:54]
• Closing Compliments & Mutual Thanks: [56:54–57:27]

The Relationship Between Reading and Leadership

• Reading functions as a "simulator" for leadership, allowing you to place yourself in the shoes of others and ask, "What would I do?" [40:01]
• Great books provide perspective, making real-life challenges more manageable.
• Reading unlocks creative solutions and provides practical advice, even from fiction like The Godfather or classics like The Prince.

The Purpose and Medicine of The Old Man and the Sea

• As Medicine for Aging and Loss:

  "The Old man and the Sea is ultimately a very hopeful book about, you know, don't worry about whether you caught the fish or not. What you ought to worry about are those relationships in your life." —Stavridis [37:36]

• For those feeling lost or diminished by age, or struggling with grief or failure, the novella offers hope, resilience, and a reminder to dream of lions—to maintain inner vitality regardless of outward loss.

Concluding Reflections

• Admiral Stavridis advocates for reading not only for pleasure and enrichment but as essential training for better leadership, deeper empathy, and perspective.
• Both speakers highlight the lasting transformative power of great books and the importance of returning to them throughout life.
• Stavridis ends on a hopeful note: despite fears about geopolitics and global conflict, he finds optimism in technology, the rising influence of India, and most significantly, the ongoing rise of women into positions of power.

Selected Notable Quotes with Timestamps

• “A man can be destroyed, but not defeated.” —Ernest Hemingway, read by Stavridis [29:41]
• “I would love to write a book a tenth as great as The Old Man. A truly great novel would be my fish.” —Stavridis [32:44]
• “Every book is a simulator. Every book is a chance to put yourself into the book and say, hmm, what would I do?” —Stavridis [40:01]
• “Reading and leading actually go together in very important ways.” —Stavridis [05:40]

Recommended Further Action

• Check out Admiral Stavridis’s The Admiral’s Bookshelf for more in-depth book recommendations and wisdom distilled from the great works in his extensive personal library.
• Reread (or read for the first time) Ernest Hemingway’s The Old Man and the Sea and reflect on the nature of ambition, resilience, mentorship, challenge, and surrender.

This episode is an engaging meditation on what it means to strive, to fail, to endure, to teach, and to dream—through the lens of literature, leadership, and the life of the sea.