Podcast Summary: Old School with Shilo Brooks Episode: America’s Most Righteous War Produced Its Best Anti-War Novel Guest: Elliot Ackerman | Date: January 15, 2026

Episode Overview

In this episode of Old School, host Shilo Brooks sits down with Elliot Ackerman—bestselling author, Marine Corps and CIA veteran, and contributor to The Free Press—to discuss Joseph Heller’s iconic novel Catch-22. The conversation explores why Catch-22, though based on World War II widely considered "America’s most righteous war," stands as the greatest anti-war novel, unpacking its absurdist humor, devastating truths about war, and its resonance for both past and present conflicts. Ackerman and Brooks delve into the novel’s themes, its place in military and literary culture, and how it shaped Ackerman’s own views on war.

Key Discussion Points & Insights

Discovering Catch-22 and Its Initial Impact

• Ackerman’s First Encounter: Ackerman first read Catch-22 at age 26 while deployed as a Marine lieutenant aboard the USS Iwo Jima during an American evacuation operation in Lebanon (00:55).

  • “Being on the ship every day was a little bit like Groundhog Day...the postmodernism, absurdism of Catch 22, it made it like the perfect time to read this book.” [B, 01:18]

• Why It Resonated in the Military: The book upends traditional military tropes, highlighting the fundamentally self-contradictory and absurd nature of war.

  • “War itself ultimately is a catch 22. It's a system that contradicts itself.” [B, 02:14]
  • Quoting George Carlin: “Fighting for peace is like screwing for virginity.” [B, 02:20]

• Civilization's Contradiction: Ackerman notes civilizations are built on the commandment "Thou shalt not kill," but war enacts state-sanctioned killing for preservation—an illustration of the book’s core contradiction.

Absurdity, Comedy, and the Truths of War

• Comedy as Survival: Brooks and Ackerman discuss Heller’s use of comedy to make sense of horror. Comedy, Ackerman insists, is vital in coping with war’s tension and horror.

  • “One truth I could never dodge was like, war's funny. It's funny because it's so serious. You can't take it serious and stay sane.” [B, 06:10]
  • “Most of the time when I get around...with buddies of mine from that time, usually the stories we're telling are...the funny ones. And they're often funny stories that occur in the most tense situations, because we needed the joke in that moment.” [B, 06:29]

• Even WWII—the ‘righteous war’—is not exempt from absurdity:

  • “Even in a war like World War II...those comedic and absurd strains continue to exist.” [B, 07:10]

Characters, Structure, and the Dilemma at the Heart of Catch-22

• Plot Fundamentals & Yossarian’s Journey (07:16–09:00)

  • Yossarian is a bombardier desperate to survive; as mission numbers keep increasing, survival grows uncertain.
  • The novel features a non-linear structure with recurring, traumatic episodes (e.g., the death of Snowden).
  • The ensemble cast is “trapped” in their own versions of the catch.

• The "Catch-22" Itself ([10:25–13:20])

  • Ackerman reads a key passage defining the paradox:
    • To avoid dangerous missions, one would have to be insane; but requesting removal is evidence of sanity, forcing continued participation.
  • "Anyone who wants to get out of combat duty isn't really crazy...which specified that a concern for one's own safety...was the process of a rational mind.” [B, 12:40]

• Bureaucratic Absurdity vs. Human Suffering

  • Brooks: Comically absurd military bureaucracy (e.g., moving strings to rewrite history, fake flight logs) is juxtaposed with graphic, real tragedies (e.g., Kid Sampson’s death) (21:49).
  • Ackerman: Institutions can erase individual humanity, yet the best comedic writing (as in Heller’s) sharpens our sense of the tragedy by investing us in the characters through laughter (22:00-24:30).
    • “Comedy is like a booster...you start to love these folks. But the payload at the tip is the tragedy.” [B, 23:55]

The Modern and The Postmodern

• Postmodern Perspective in Catch-22

  • Heller strips out “good guys and bad guys,” heroism, and meaning—presenting war as senseless contradiction (14:12).
    • “There are really no villains...there's just Yossarian and his heroic act is sort of just trying to survive and exist.” [B, 14:50]
    • “The longer you can stay in [war], the more untethered a person can feel from these grounding moralistic concepts...we are kind of adrift.” [B, 15:09]

• The “Organization Man” and Existential Dread

  • The book’s existential terror (fear of being just a cog) feels timely in contemporary, bureaucratic America. Ackerman sees this as true to his own experience of post-war America, drawing parallels between service members returning home and Heller’s advertising career (25:35–27:00).
    • “You start in your 20s, you're like, free basing the crystal meth of purpose...then eventually you have to come home...and a sort of like, kind of depression will set in and a sense of being unsettled.” [B, 26:19]

• Modern Form: Brooks observes that Catch-22’s short, episodic chapters resemble modern television or digital storytelling (28:04).

War and Profit: Milo Minderbinder & “War is a Racket”

• Milo as Satire of War Profiteering
  • Milo creates a mess-hall-syndicate making profit from all sides, including bombing his own base if the price is right. Ackerman draws a direct connection to real-world history and current events in Venezuela.
    • “War is a racket. It's waged for the benefit of the few at the expense of the many.” (Quoting Smedley Butler) [B, 32:17]
    • “Heller interrogates that [profit motive]...he's showing all of these economic cross currents...there's truth in that. That doesn't mean that's the only reason wars are fought.” [B, 33:12]
  • The economic motivations for war remain ever-present, echoed both in history and in coverage of contemporary conflicts.

Literature, Cynicism, and Dangerous Books

• Should Soldiers Read Catch-22? Is It Dangerous?

  • Ackerman encourages soldiers to read Catch-22 as part of a larger constellation of war literature—not to be shielded from its cynicism, but challenged by it (43:38).
    • “Any book that makes you think is dangerous because it's going to knock you off your center.” [B, 43:43]
    • Recommends carrying “contradictory ideas” by reading across genres and perspectives on war.

• Brooks’ Teaching Philosophy: A book offers “a perspective among many on an enduring question.” Even “dangerous” or mocking perspectives are essential for anyone seeking wisdom (45:07–46:29).

War, Society, and American Moral Hazard

• America’s Changing Relationship to War
  • Ackerman warns that America’s "insulation" from the costs of war (since 9/11) encourages careless engagement due to lack of existential sacrifice or disruption.
    • “The challenge is that when you go to war, when you roll the iron dice of war, the enemy always gets a say...that psychology really puts us in peril today and quite possibly puts us in a position of moral hazard as a nation.” [B, 53:13]

Notable Quotes & Memorable Moments

• CATCH-22 Paradox:

  • “Anyone who wants to get out of combat duty isn't really crazy… which specified that a concern for one's own safety…was the process of a rational mind. Orr would be crazy to fly more missions, insane if he didn’t. But if he was sane, he had to fly them. If he flew them, he was crazy and didn’t have to. But if he didn’t want to, he was sane and had to. Yossarian was moved very deeply by the absolute simplicity of this clause of catch 22...” [B, 12:40–13:12]

• War’s Absurdity:

  • "War itself ultimately is a catch 22. It is a system that contradicts itself." [B, 02:14]

• Necessity of Comedy:

  • “War's funny because it's so serious. You can't take it serious and stay sane.” [B, 06:10]

• Survivor’s Humanity:

  • “What redeems Yossarian as a character is he never turns his back on his humanity.” [B, 16:48]
  • The climactic moment: "You just have to say...that you like us." [B, 17:52]

• On Military Purpose and Existential Crisis:

  • “Purpose is sort of the drug that induces happiness, you start in your 20s, you're like, free basing the crystal meth of purpose...then eventually you sort of have to come home...and a sort of like, kind of depression will set in and a sense of being unsettled.” [B, 26:19]

• Books as Alloys in the Forge of Understanding:

  • “How do you make steel? You take a bunch of alloys and you heat them and you fold them together and you bang them out and that makes something that's truly strong and truly enduring. I think catch 22 is an important alloy to fold into your understanding of war.” [B, 46:33]

• The Paradox of Command:

  • “As a combat leader...what you are asked to do in ordering your men to execute these missions...is to destroy the thing that you love. And that paradox sends people home with a certain degree of heartbreak. And your heart can't break unless you are in love.” [B, 49:05]

Timestamps – Important Segments

• 00:55–01:39: Ackerman describes reading Catch-22 for the first time as a Marine
• 02:02–03:35: Why the book resonated with him—war as a systemic contradiction
• 05:54–07:16: Role of comedy and laughter in understanding war’s gravity
• 10:25–13:20: Ackerman reads and analyzes the iconic “Catch-22” paradox passage
• 14:12–15:48: Discussion on Catch-22 as a postmodern anti-war novel and the erosion of moral concepts
• 21:48–24:30: Juxtaposing absurd bureaucracy and real tragedy in the novel, and what it means
• 25:35–27:05: Ackerman draws parallels between military service, post-war civilian life, and existential purpose
• 32:14–33:12: Satire of profit and war (“War is a racket”)
• 43:38–45:07: Should Catch-22 be recommended to soldiers? The case for reading dangerous books
• 49:05–50:23: The catch-22 of command—having to send men you love into harm’s way
• 50:37–52:02: The one book Ackerman assigned to his first platoon (Starship Troopers) and why

Rapid-Fire (“Lightning Round”) – [47:21–54:22]

• Top Influential Writers: Graham Greene, Rizard Kapuczynski, and his wife, Lee Carpenter [B, 47:45]
• Enduring Lesson from Combat: The paradox of commanding men you love [B, 48:43]
• If Soldiers Should Read One Book: Robert Heinlein’s Starship Troopers [B, 51:04]
• Biggest Concern about Modern War: Moral hazard from an insulated society [B, 52:09]
• Grade for Trump’s Foreign Policy: “Incomplete” [B, 54:14]

Final Takeaways

This conversation underscores the timeless relevance of Catch-22—not just as a scathing anti-war satire but as a guide to understanding the contradictions, absurdities, and moral weight of war in any era. Both Ackerman and Brooks advocate for reading widely, including “dangerous” books, to forge a nuanced, resilient intellect. Their discussion ultimately makes a powerful case for classic literature as an essential tool for personal growth, informed citizenship, and enduring wisdom.

Notable Quote for Reflection:
“A book is a perspective on an enduring question...even the dangerous ones, even the ones that make cynicism or mockery of the things you hold dear, are valuable to you and you should not run away from, nor should you be censored from.” [A, 45:07]

Listen to the full episode for even deeper insights and personal stories connecting literature and life, war and peace, cynicism and hope.