The Irregulars

Summary

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The Secret World of Roald Dahl – Episode: The Irregulars

Date: January 19, 2026
Host: Aaron Tracy

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Overview

This episode dives deep into one of the wildest, lesser-known chapters of Roald Dahl’s extraordinary life: his time as a British spy in America during World War II as a member of "the Irregulars." Host Aaron Tracy peels back the familiar image of Dahl as a beloved children’s author to reveal an adventurer, secret agent, and controversial figure. The episode explores how Dahl’s covert wartime experiences influenced his later writing, shaped his worldview, and contributed to both his literary genius and complex legacy.

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Main Themes and Purpose

• Roald Dahl’s Secret Life as a Spy: The episode reveals how Dahl—best known for stories like Matilda and Charlie and the Chocolate Factory—served as an MI6 agent tasked with gathering intelligence, influencing U.S. policy, and even seducing high-profile women.
• The Irregulars: A clandestine group of British agents operating in the U.S., whose methods blurred the lines of conventional espionage.
• Interplay between Darkness and Creativity: Tracy examines how the darkness and danger in Dahl’s life seeped into the tone and themes of his children’s books.
• Moral Complexity and Legacy: Dahl’s charm, arrogance, and personal flaws—including accusations of antisemitism—are discussed, questioning how much we really know (or want to know) about our cultural icons.

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Key Discussion Points & Insights

1. Roald Dahl: Familiar Image vs. Hidden Reality

• Perceptions from Friends and Public

  • Most Americans recognize Dahl for his children’s books, describing him as an eccentric, grandfatherly figure.
  • Some are aware of his controversies: “I think… he was an antisemite.” (03:14, Guest)
  • Almost no one knows about his days as a British spy.

• Breaking the Mold

  • “Forget the Roald Dahl in your head… Because the Roald Dahl I’m about to introduce you to operated in the shadows of World War II as a dashing British spy.” (04:09, Aaron Tracy)

2. Formation of the Irregulars: Spies in America

• Unlikely Recruitment

  • Dahl, fresh out of a broken flying career, meets Major Harold Balfour at a London cocktail party. Balfour recruits him for what Dahl thinks is a diplomatic post—but he’s actually being conscripted into British military intelligence. (08:24-09:15)

• Espionage Mandate

  • Britain, desperate to bring the U.S. into the war, will stop at nothing, using “secret British agents in America that called themselves the Irregulars” (04:27)
  • Their job? “All that was not being done and could not be done by other means… a license to operate in the gray areas if I’ve ever heard one.” (24:49, Aaron Tracy)

• Remarkable Company

  • The Irregulars include Roald Dahl, Ian Fleming (James Bond’s creator), and David Ogilvy (the father of modern advertising): “Picture Roald Dahl, James Bond, and Don Draper all hanging out drinking and seducing their way through a foreign capital during wartime…” (24:19)

3. Dahl’s Double Life: From Fighter Pilot to D.C. Socialite & Spy

• Strange Lodgings

  • Dahl moves into an apartment with a bloody history, unbothered by the macabre details: “The future author of tales filled with darkly comic violence isn’t remotely bothered by the apartment’s bloody history. If anything, there’s a flicker of fascination…” (17:52, Aaron Tracy)

• Espionage by Charm and Storytelling

  • Dahl’s specialty? Enchanting, seducing, and gathering secrets from America’s power elite—particularly through his skill with storytelling and his “astonishing” social confidence.
  • “He spends his time at Hyde Park swimming, birdwatching, barbecuing, and drinking with the President and First Lady… making mental notes on everything, desperate to report it all back…” (30:06)

• Key Missions & Early Successes

  • Writing a story called The Gremlins brings him to the attention of Eleanor Roosevelt, leading to weekends with the First Family and privileged access for intelligence gathering.
  • “Are you kidding me? For a spy, just befriending a staffer or an intern in the Roosevelt administration would be giant. Dahl… becomes pals with the first family.” (30:06, Aaron Tracy)

4. Seduction and Influence: The Claire Boothe Luce Assignment

• Mission: Influence Henry Luce (media mogul) by seducing his influential wife, Congresswoman Clare Boothe Luce.

  • Clare, a celebrated playwright, journalist, war correspondent, and congresswoman, “about as influential as it gets.”
  • Dahl engages in an affair with Claire and “complains to his superiors about Claire’s appetite”—using his charm for both intelligence gathering and shifting opinions in powerful circles.
  • “Dahl confides… that he just can’t take another night with Clare; she’s completely worn him out… ‘The things I’ve done for England.’” (40:48, Aaron Tracy)

• Direct Impact

  • Dahl’s insights help shape British propaganda and eventually sway the editorial line of Life magazine toward supporting Britain in the war.

5. Legacy, Controversy, and the Genesis of Dahl’s Fictional Universe

• Bleeding Darkness into Children’s Literature

  • Tracy draws explicit lines between Dahl’s espionage, penchant for the macabre, and the “nastiness” of his fiction: “So much of Dahl’s fiction pulls the reader towards scenes of fear and dread… He’s able to conjure these scenes so well because they’re part of his fabric. Dahl sees darkness everywhere, which means he barely notices it anymore.” (19:36, Aaron Tracy)

• Controversy and Complications

  • Tracy frankly acknowledges Dahl’s dark side and prejudice, reading from Dahl’s Washington Post obituary:
    • “No children’s author… has regularly sparked more controversy… books larded with gratuitous violence. Bigotry, sexism, vulgarity, greed and all manner of foulness.” (09:00, Host quoting Washington Post)

• The Dilemma of Admiration

  • On reconciling Dahl’s dark traits with his genius:
    • “It’s a strange, super complicated thing to admire so much about Dahl with the knowledge that he wouldn’t have come to my Hanukkah party.” (10:20, Aaron Tracy)

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Notable Quotes & Memorable Moments

• On the Unlikely Combo of Writer-Spy

  • "We would never expect a writer like, say, Stephen King to secretly conduct espionage, or Jason Bourne to retire…to pen 49 beloved books that change children’s literature forever. The combination simply should not exist in one human being. But then how do you explain Roald Dahl?" (05:05, Host)

• Dahl recalling his White House days:

  • “I was only a young chap of 26 in an RAF uniform and had no business around there, really.” (29:41, Roald Dahl [Archive])

• On the legacy of darkness in Dahl’s work:

  • “There’s so much nastiness there. Leaks off the page, staining your fingers.” (09:28, Host)

• On Dahl's seduction assignment:

  • “Dahl is trying to figure out what it means to be a man in this uncertain period. Should he be a macho playboy or a more sensitive man of letters? He’s 26. This is when you figure out who you are…which isn’t easy when you’re lying about your identity to almost everyone you meet.” (41:55, Host)

• On the unresolved nature of Dahl’s story:

  • “In espionage, access is everything, and Dahl has it. But he’s still far from achieving all his goals. He still has a lot of work left to do, and… he's going to have to do it with a ton of obstacles in his way.” (43:15, Host)

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Important Segments & Timestamps

• Public Perception of Dahl & the enigma of his legacy (02:41–04:09)
• Introduction to the Irregulars & the WWII context (04:09–08:24)
• Dahl’s recruitment at a London party & his first espionage experience (08:24–13:20)
• The American isolationist sentiment and necessity for covert British action (13:20–15:40)
• Life in D.C., dark apartments, and fascination with the macabre (17:52–19:29)
• The Gremlins story and access to the White House (27:51–30:06)
• Epic seduction: Clare Boothe Luce & the politics of desire (34:28–41:55)
• Host’s reflection on Dahl’s complicated impact and enduring mystery (09:00–10:20 and throughout)

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Language & Tone

Aaron Tracy maintains a conversational, lightly irreverent, and highly analytical tone—mixing awe, skepticism, and respect for the subject’s complexity. His language is engaging, witty, and rich with cultural references (“Picture Roald Dahl, James Bond, and Don Draper all hanging out…”), making the espionage era come alive while never losing track of the serious questions embedded in Dahl’s legacy.

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Final Thoughts

This episode masterfully reframes Roald Dahl not merely as the creator of cherished childhood stories, but as a figure of immense contradiction—a man whose daring, shadowy World War II exploits both enriched his creative universe and complicate his legacy. Tracy’s exploration of the Irregulars contextualizes Dahl’s darkness and ingenuity, setting the stage for deeper explorations in episodes to come.

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Transcript

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[Guest or Interviewee]

Definitely the bfg, that was a classic. Charlie and the Chocolate Factory. And I think there was a series of the glass. Great Glass elevator. Love those.

[Aaron Tracy (Host/Narrator)]

When you picture Dahl in your mind, what does he look like?

[Guest or Interviewee]

Well, he's definitely older. Gentleman, I would say 70ish. Kind of big guy. Not fat, certainly not fat. Who doesn't like fat people? But like, you know, a tall man, big cardigan sweater, a beard, sitting in a big kind of comfy reading chair. Kind of like Masterpiece Theater style.

[Aaron Tracy (Host/Narrator)]

When I mention the name Roald Dahl, what do you think of?

[Guest or Interviewee]

So I think of Charlie and the Chocolate Factory, Matilda James and the Giant Peach. And that he was, I think, an anti Semite

[Roald Dahl (Archive or Voice Actor)]

dad.

[Aaron Tracy (Host/Narrator)]

What do you know about Roald Dahl? Almost nothing. I think I know how to spell his name.

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[Aaron Tracy (Host/Narrator)]

did, I don't think I could tell you anything about him. Did you know that Dahl was a spy for British Intelligence?

[Guest or Interviewee]

No way. I did not know that. That's wild.

[Aaron Tracy (Host/Narrator)]

He worked for MI6.

[Guest or Interviewee]

Very surprising. I'm very curious. Was this before he wrote his stories?

[Aaron Tracy (Host/Narrator)]

It must have been during the war. Roald Dahl was a spy for British Intelligence. What? His job was literally to seduce the wives of powerful Americans. And he was really good at it.

[Guest or Interviewee]

Okay, I don't think that's true.

[Aaron Tracy (Host/Narrator)]

I'm telling you, the guy was a spy. I talked to a lot of people about Roald Dahl and none of them knew even a fraction of his full story. And the full story is bananas. Forget the Roald Dahl in your head. The one who's the most successful children's author of all time. Forget the image you have of him, which, if it's like mine, is a disheveled BFG lookalike grandfather figure in a worn out cardigan and shaped like a spoon. Because the Roald Dahl I'm about to introduce you to operated in the shadows of World War II as a dashing British spy. Honestly, we could do a whole 10 part series just about the spy unit Dahl was recruited into during the war. A group of secret British agents in America that called themselves the Irregulars. A name they took from the informal network of child spies in Sherlock Holmes. Which also tells you how they see themselves. Young men operating in the shadows where traditional agents can't go. So picture a handsome 25 year old doll 4,000 miles from home. Thrust into this world without a single day of espionage training. Imagine how intimidated he feels walking into a room with this collection of remarkably, almost suspiciously handsome and charming men who seemed born for this work. Dahl, on the other hand, feels like an imposter in way over his head. Let's hear from the man himself, Roald Dahl, describing his unlikely employment goals.

[Roald Dahl (Archive or Voice Actor)]

My job was to try to help Winston Churchill to get on with FDR and tell Winston what was in the old boy's mind in America.

[Aaron Tracy (Host/Narrator)]

I mean, how cool is he playing it there? As if he's just setting a lunch with some old pals and not orchestrating an alliance between the two most powerful leaders in the free world. As you'll hear, Dahl's whole life is one surprise after another. It defies all expectations. We would never expect a writer like, say, Stephen King to secretly conduct espionage or Jason Bourne to retire from his spy work to pen 49 beloved books that change children's literature forever. The combination simply should not exist in one human being. But then how do you explain Roald Dahlia? Impossibly, implausibly real. Welcome to his deeply bizarre universe. I promise it'll only get stranger from here. For my Heart podcasts, Imagine Entertainment, and Parallax. This is the secret world of Roald Dahl. I'm your host, Aaron Tracy. I also teach in the English department at Yale, so books have always been a huge part of my life, and Dahl's were the foundation, the first ones I ever cracked open and read on my own. Dahl's stories are what turned me on to reading, but that's only part of why I've spent decades obsessed with Roald Dahl. I'm even more fascinated by what an enigma he is. He tries on all these different masks, kind of like Bob Dylan. He's impossible to nail down. The man is a total cipher, which is maddening when you think about the fact that we offer him up to our most impressionable population. I have two young kids. They're going to grow up reading Doll like millions of others. Now, when my wife and I hire a babysitter, you better believe we do a little digging into who she is first. But we just happily bring Doll into our children's rooms. And not to get too precious about it, but into their hearts and minds, letting him worm directly into their ears night after night. Shouldn't we have some idea of who this guy is? Well, I promise you, you don't, but you're about to. Another reason I'm really obsessed with Dahl is because he lives the noisiest craziest, most adventurous life you've ever heard as a writer. I'm a writer. Literally, no one would describe me as adventurous. I write a ton of TV and audio dramas. But it's 11am As I record this, and I'm still in my bathrobe. The most adventurous I ever am is changing up my smoothie recipe by adding peppermint. That's what being a writer is. But no one told Roald Dahl. You may only know Dahl for his books, but when we're done with this series, you're going to feel like his writing is about the 19th most interesting thing about him, which is especially bananas when you look at the numbers. The man has sold over 300 million books. He's been translated into 63 languages. And let me put that 300 million copies sold into context. Herman Melville, Henry James, Virginia Woolf, Toni Morrison, Philip Roth, fellow children's author Shel Silverstein. Add up all of their sales of all of their books, and it equals about 25% of Dahl's. That's a nutty number. Here's another one. In 2018, the Hollywood Reporter wrote that Netflix spent around $1 billion for the rights to Dahl's works. But of course, his impact is so much bigger than the stats. The man has permeated our collective consciousness. I have never in my life unwrapped a candy bar without part of me wondering, even for just a millisecond, if there might be a golden ticket in there. Which isn't to say I don't have my issues with the Man. He can be difficult, sometimes incredibly nasty to those he's closest to. Kind of like some of his characters. It's easy to forget how he actually treats the kids in his books, especially the ones who aren't the heroes. Take Mrs. Gloop straight to the Fudge Room. But look sharp, or her little boy's liable to get poured into the boiler. You boiled him up.

[Guest or Interviewee]

I know it.

[Aaron Tracy (Host/Narrator)]

Goodbye, Mrs. Gloop. Adieu. Yup, all those children on the Choco tour get tortured in gruesome ways. Same in the Witches. Same in Matilda. There's so much nastiness there. Leaks off the page, staining your fingers. When he died in 1990, the Washington Post, my hometown newspaper, did not mince words. Quote, no children's author of the past 30 years has regularly sparked more controversy than Roald Dahlia. On the one hand, kids consistently name him their favorite writer. On the other, our best critics maintain that his books are larded with gratuitous violence. Bigotry sexism, vulgarity, greed and all manner of foulness. And that's not some hit piece or social media takedown. It's his obituary. Dahl's nastiness and his controversies have sucked up a lot of oxygen the past few years. I now look at the spines of his books on my shelf not that differently than I look at J.K. rowling's, which is to say kind of queasily. We'll definitely get into all that. It's fascinating, sometimes ugly stuff from a guy who helped shape generations. But for now I'll just say it's a strange, super complicated thing to admire so much about Dahl with the knowledge that he wouldn't have come to my Hanukkah party. My friend, the writer Ben Dolnick captures the dilemma perfectly in a short essay he wrote. He writes about watching his daughter fall headlong, quote into that extraordinary, silent, inexpensive, schedule disrupting passion of reading. Ben wrestles with watching her cherish books written by a man who may have been repelled by her very existence. I wanted to start the show off by talking to friends about their perceptions of Dahl because the weirdness that people see in him is really telling. Here's the opening of a BBC profile from 1982. This is how a venerable respected network introduces one of the world's most famous authors. The man who lives in this house makes very good orange marmalade. He also breeds orchids. He has never eaten a dish of tripe in his life and he wishes that his dog could speak to him. He's Roald Dahl. Who else in the world would be introduced like that? He makes very good orange marmalade and has never eaten tripe. But that's how people talk about Dahl. He's a curiosity, a character, not a man. Honestly, I think it's at least partly due to his appearance. A real Life Giant at 6 foot 6. Plus, he's got that name that's so unusual for most people. And his creativity is just so off the charts. So with all that, he can't possibly be like you and me, right? He must be some fantastical creature that just wandered into our world. People are desperate for him to be a real life BFG or Ms. Trunchbull or Willy Wonka, which, fine, is not that unfair or unusual. We definitely imagine Hemingway was as haunted as his characters. We'd feel cheated if Phoebe Waller Bridge wasn't as raw or hilarious as hers. But here's the crucial those other writers characters operate within the boundaries of recognizable human behavior. Dahl's creations exist In a universe where children turn into blueberries and giants roam the countryside collecting dreams. So was Dahl really as mischievous and outlandish, whimsical and grotesque as his characters? Sort of. Now, I'm incredibly excited to tell you about Dahl's very strange life as a very real secret agent. Picture Dahl in his early 20s, that critical moment when most of us are fumbling to find our path. Not long before, he'd been soaring through the skies as a fighter pilot for the Royal Air Force. But a series of catastrophic crashes had left him broken. His flying career abruptly terminated. So now he's at a crossroads. The war continues to rage, but his part in it has been stripped away and he's looking for what to do with his life. Dahl finds himself at a cocktail party in London that a date has dragged him to. He towers awkwardly above the crowd, nursing a drink, contemplating an early exit. It's an elite crowd, but it's a lot of rehearsed anecdotes and performative laughter. Then something catches his eye. A solitary figure standing apart. Not a film star or socialite, but someone far more intriguing to a political obsessive like Dahl. Major Harold Balfour, a member of Churchill's war cabinet, one of the men literally deciding the fate of Britain as German bombs fall on London. Dahl senses this could be his chance. Impressing the major might lead to something, though he has no idea that this conversation will alter the trajectory of his entire life. Let me pause here for a quick sec to set the scene for what's going on in the world, because it's crucial to what Dahl is about to become part of. The late 1930s and early 40s are one of those rare times that it's not an exaggeration to say the fate of the world is at stake. Hitler isn't just winning battles, he's winning the war. Mostly because the US is sitting on the sidelines. The British ambassador warns his government that 9 out of 10Americans are determined to stay out of the war. In other words, to not help Britain. The most famous of these is Charles Lindbergh. It is now obvious that England is losing war. And I have been forced to the conclusion that we cannot win this war for England, regardless of how much assistance we send. That is why the America First Committee has been formed. And this is while Germany is sweeping through Europe, The Nazis take Austria, Czechoslovakia, Poland, Denmark, Norway, Belgium, the Netherlands, Luxembourg and France and America. We're just watching it unfold. Many, if not most, Americans are still traumatized from the first. First time we joined in a world war 20 years earlier. The memory of American boys coming home in coffins or not coming home at all remains raw. The thinking is simply that Hitler is not our problem. The public isn't yet aware of what's going on with the Jews of Europe. The reports of them being rounded up and sent to concentration camps is just too impossible to believe. So we choose not to. Britain, of course, is on the brink. You know this. You've seen the movies, read the books, listened to the podcasts. Think Churchill pacing war rooms by lamplight. Britain's darkest hour. If FDR doesn't send help, and fast, England is done. So put yourself in Winston Churchill's position. Your island nation stands as one of the last flickering lights of democracy in Europe. Your cities are being bombed into rubble, your people are sleeping in subway tunnels. And across the Atlantic sits powerful, untouched, and so stubbornly unwilling to join the fight. What wouldn't you do to change their minds? At that point, is anything off the table? This is where espionage becomes not just an option, but a necessity. Okay, so back to our cocktail party. Dahl spots Major Balfour, a man whose signature on documents can move troops and redirect warplanes. Dahl takes a deep breath, and with that peculiar confidence that will define him throughout his life, he crosses the room, introduces himself, and simply begins to chat. Dahl gives great chat. His conversation has all the hallmarks of his later fiction. Wickedly funny, wildly creative, a little dirty, totally compelling. Dahl is one of those people who just instinctively knows how to captivate. I'm always so jealous of those people, the ones who have small crowds gathered around them at parties. Funny and magnetic, without being at all self conscious. The Major, like everyone else who meets Dahl in this period, is taken with him. And then it happens. The Major tells Dahl that he's looking for smart, well educated young men to go to America to join the British Embassy. This conversation has changed everything, but not how Dahl thinks it has. Dahl thinks he's being recruited for a diplomatic post. What the Major leaves out is what he really has in mind for military intelligence. The head of the Irregulars has tasked the Major with finding brilliant, articulate, charming, morally flexible young men with military backgrounds to join his outfit. The Major seems to have found such a man. The very next week, Dahl is on a plane to Washington. When Dahl first arrives in D.C. he's entranced. It's this big cauldron of power. Ego mixed with ambition, mixed with sex mixed again with power. Yet it all feels as intimate as a college campus. Everybody knows everybody. I grew up in D.C. and in the northwest part of it. Walk into any restaurant, linger in any bookstore, sit at any coffee shop counter, and people are talking politics. It's in the water supply, just like the entertainment industry in la. So every room Dahl enters is an opportunity. Dahl's trickiest endeavor when he first arrives is finding decent housing in the notoriously overcrowded city. He opens the newspaper and looks through the classifieds. He finds a surprisingly nice place that he can actually afford. The reason he can afford it is because there was a bloody murder suicide in it last week. The murder victim, Rosemary Sigley, was a beautiful young researcher for the agency that becomes the CIA. She was also a a wealthy heiress. Her murder was a giant scandal. And two days after, there was a line of people outside waiting to see if the scene of the crime would be rented at a discount. You gotta love the real estate market. But what's important for us is that Dahl is the first man in that line, which tells you so much about who he is. The future author of tales filled with darkly comic violence isn't remotely bothered by the apartment's bloody history. If anything, there's a flicker of fascination as he signs the lease. The apartment's gruesome backstory isn't a deterrent. It's almost an attraction. The man loves gruesome. Here's one of his most beloved books with a little girl torturing her nemesis. It's a snake.

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[Aaron Tracy (Host/Narrator)]

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Matilda. I knew it.

[Aaron Tracy (Host/Narrator)]

So much of Dahl's fiction pulls the reader towards scenes of fear and dread. There's a ton of children in peril and adults with real bad intentions. Danger lurking in what we thought were safe spaces. He's able to conjure these scenes so well because they're part of his fabric. Dahl sees darkness everywhere, which means he barely notices it anymore. When Dahl moves into Rosemary's Place, it takes him two nights before he spots the rusty blood stains still on the carpet and the single bullet hole in the ceiling. Lots of people, me very much included, would immediately move out. Dahl simply makes a mental note of it, another detail in the strange tapestry of his life, and goes to sleep under the same roof where a bullet ended. Someone else's. Now Dahl is ostensibly in D.C. to work for the British Embassy. So that's what he does for a while. He pushes diplomatic papers, attends formal functions, fills out reports, and he's suffocating. Each morning, he sits before stacks of documents, watching the clock move with excruciating slowness. Dahl wants something bigger for his life. He's searching for something with meaning. But what Dahl doesn't realize is that someone is watching his every move.

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[Aaron Tracy (Host/Narrator)]

The big legendary figure you need to know about right now is William Stevenson. Intrepid Stevenson is Winston Churchill's head of espionage in America. He's one of the key inspirations for James Bond, who was created by one of his agents. This gives you a sense of what Stevenson looks like. Impeccably dressed, handsome features and penetrating eyes that catalog everything. He's clean cut, can pose and emanates the confidence of a man who can have you vanished with a single phone call? This is the man whose attention now turns to Roald Dahl to accomplish Britain's mission during this really scary time. Stevenson is the one who assembles that elite spy ring, the Irregulars. Writer and historian Jeanette Conant calls their operation one of the most controversial and almost certainly one of the most successful covert action campaigns in the annals of espionage. Stevenson's eye for talent is wild. Just for starters, there's Roald Dahl, of course, and Ian Fleming, who later creates James Bond, essentially immortalizing his own experiences here. And David Ogilvy, who goes on to invent modern advertising. Three world class creators of fantasy. So picture Roald Dahl, James Bond and Don Draper all hanging out, drinking and seducing their way through a foreign capital during wartime, and you start to have a sense of what it's like. The whole thing feels like the premise of a prestige TV series. Beautiful, rakish young men recruited into a shadow organization far from home because of their smarts, persuasiveness and talent for deception, tasked with doing whatever they have to to save the free world from fascism. The mission of the Irregulars is broad gathering intelligence, sabotaging enemies and creating propaganda that shifts public opinion. Their official history describes them as empowered with the vague task of doing all that was not being done and could not be done by other means. Which, come on, is a license to operate in the gray areas. If I've ever Heard one. Dahl can't believe he's been recruited into this group. A month ago, he was languishing in the English countryside, desperate to figure out his life, hungry for purpose. Now he's found a role filled with subterfuge, deceit, storytelling and roleplay. In other words, all of his natural skills with the highest stakes imaginable. The personal stakes for Dahl are huge too. He can't go home to Buckinghamshire after this and tend to the sheep. This job is about to become his whole identity. You can tell how formative it all is for Dahl by the fact that it echoes through his later fiction like a recurring dream. Willy Wonka with an air of mystery beneath, a playful exterior, constantly testing those who enter his orbit. He's definitely inspired by Stevenson and others Dahl works for in the spy game. Also the secret society and the witches that performs covert missions. All of these stories that are going to captivate millions of children are born in the shadows of wartime espionage. So far, though, the Irregulars are failing at their task of winning America to their side. They're forced to get creative. One of my favorite tactics of theirs is when they hire a Hungarian astrologer, Louis de Waal. The assignment they give him to publicly predict Hitler's demise based on the positions of the stars and therefore make Germany seem less scary to Americans. It's like a PR smear campaign on the fascist dictator. Can't you just picture these young Irregulars around a table at 2am at some smoky Georgetown bar, whiskey flowing, One says, what if we just told Americans they have nothing to lose because the stars have already decided the Third Reich is done for? And instead of laughing it off, there's a long silence. They look at each other intensely and say, that is brilliant. They're so tickled with their idea, they send Louis on a national tour. Stevenson's main tactics, however, involve targeting the upper echelons of the US government. And this is both to bring the US into the war and once that's accomplished, to make sure London maintains significant influence. If Britain can get someone close to the American President, that would be huge. Enter young Roald Dahlia. It turns out one of Dahl's skills in particular makes him especially effective with the Irregulars. It's the same skill he'll later become legendary his storytelling. Dahl has recently begun writing short stories. It's not yet the all consuming passion it will become. Like many young writers, Dahl is trying to find his voice by writing mostly autobiographically. Specifically, he's churning out brief fiction pieces inspired by his childhood and his time in the Royal Air Force. The stories are clever and dark, a little scary and totally original. One story in particular centers on these grotesque little creatures he calls gremlins who sabotage aircraft. A fun gothic story which doubles as a fable for American and British cooperation. One reason Dahl's work continues to be read and seen and performed over a century after his birth is that like Greek myths, his narratives tap directly into our primal fears and desires. They speak to universal human concerns wrapped in the irresistible package of the bizarre and scary and funny. The Gremlins has all of this. And in case you're wondering, as I was, this Gremlins has nothing to do with the Steven Spielberg produced classic. Dahl mails the story out to every magazine excepting unsolicited submissions. And one bites. The Gremlins gets published in a local journal. And the story connects with readers. Those who dig it pass it around to their pals. Of course, in these days, that means literally handing your copy of the physical magazine to someone eventually, because this is just how Dahl's luck works. His story gets passed to a certain very important person you may have heard

[Roald Dahl (Archive or Voice Actor)]

of Eleanor Roosevelt, read it to her grandchildren and loved this book.

[Aaron Tracy (Host/Narrator)]

Here's Dahl years later on a chat show on BBC1, speaking to host Terry Wogan about his stroke of incredible fortune.

[Roald Dahl (Archive or Voice Actor)]

And so I got invited to the White House and we got to know each other a bit, you know, and. And I would go for weekends. FDR had a. His country place was called Hyde Park, a fast place, and used to go there. Got to know him. This. I was only a young chap of 26 in an RAF uniform and had no business around there. Really?

[Aaron Tracy (Host/Narrator)]

Are you kidding me? For a spy, just befriending a staffer or an intern in the Roosevelt administration would be giant. Dahl, in his mid-20s, becomes pals with the first family. And how'd he do it? Through a skill he hasn't yet realized will be his superpower. Making up a clever story, Dahl spends his time at Hyde park swimming, bird watching, barbecuing, and drinking with the President and First Lady. He's making mental notes on everything, desperate to report it all back to Stephenson and prove himself on the job. According to Dahl, he even manages to spend time alone with fdr, mixing martinis before lunch while the tipsy President says things like, I just received an interesting cable from Mr. Churchill, and then proceeds to tell Dahl what Churchill wrote. Surprise, surprise. FDR clearly takes a liking to Dahl, too. He even drives Dahl around the property in his specially made car. It all feels pretty Surreal for a young man not many years out of high school who's been tapped as a spy and is now casually hanging out with the most powerful couple on the planet. At the end of his first weekend with the first family in all those lavish surroundings, Dahl goes back to his tiny apartment with the blood stained carpet and writes up an incredibly thorough 12 page report with journalistic precision. Quote, visit to Hyde Park July 2nd to 4th. Yeah, he got invited there for July 4th. Dahl's report includes everything FDR said about Churchill, his impressions about whether FDR will run for another term, and everything else he thinks could even possibly be relevant. We don't know whether Dahl's report was read by Churchill himself, but it's clear his work helps the British government gain insight into where America stands. There's even a suggestion that Roosevelt may have used Dahl to convey information to the British that was impossible for FDR to state outright for diplomatic reasons. For Dahl, it is such a head trip. Writer Matthew Dennison points out Roald's life had become a double life. He was still ostensibly working for the British Embassy. At the same time he was a gatherer and conduit of information in Britain's best interests. Needless to say, Dahl's handlers are more than a little shocked and beyond thrilled with this kid. And Dahl's early success only makes him more confident. The young man who felt rudderless just months earlier now moves through Washington with the assurance of someone who believes he can't fail.

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[Aaron Tracy (Host/Narrator)]

I'm here with Spinquest where you can play and win from the comfort of your own home with hundreds of slot games and all of the table games you love with real cash prizes. Right now, $30 coin packs are on sale for $10. For new users, it's [e-mail] that's S P I N Q U-E-S-T.com SpinQuest is a free to play social casino void where prohibited. Visit spinquest.com for more details. One of Dahl's more salacious tasks for the Irregulars is seducing powerful women in order to enlist their help. This is a task that young Dahl is very excited about. He's also built for it and he uses this trait for his most important seduction with a woman with the very whimsical, very Dahlian name. Clare Boothe Luce Doll is first sent to Clare because of who she's married to. Clare is one half of one of the most influential power couples of the century. Her husband is Henry Luce, who built a media empire that quite literally shapes what millions of Americans think. He's the founder of Ready for It, Time Magazine, Fortune Magazine, Life magazine and Sports Illustrated. When these publications begin running pieces with distinctly anti British undertones, British intelligence is not happy for a nation fighting for its survival. This isn't just bad press, it's an existential threat. If American public opinion turns against Britain, vital aid could evaporate overnight. The Irregulars have to find a way to change the tenor of Henry's magazines. They're not sure how to reach Henry, who's notoriously stubborn, but maybe they can get to his wife. After all, it's an open secret that the loose marriage is unconventional. For its final 28 years, Henry apparently refuses to sleep with Clare. He says he's in such profound awe of her that he can't get aroused, a truly tragic condition that vanishes whenever he's around, almost literally any other woman. Dahl first meets Claire at the New York premiere of her propaganda film Eagle Squadron. It's about US Airmen who volunteer to fly with the Royal Air Force. The lobby outside the screening room is packed with DC Power players. Cigar smoke hangs in lazy clouds beneath crystal chandeliers. The murmur of hushed conversations about policy and the war intermingles with the clink of cocktail glasses. Dahl's date, Nancy Carroll, is a celebrity once nominated for Best Actress, which tells you everything about Dahl's social currency. There are whispers about the impropriety of Nancy's obvious infatuation with Dahl, who's 12 years younger than her. But Nancy doesn't seem to care, and neither does Dahl. He already draws attention with his height and good looks. He enjoys the gaze of the room but doesn't seek it, and his focus is now pulled elsewhere. Claire Luce is not in a spotlight but in a pocket of conversation where men lean down to hear her. Dahl doesn't approach, not yet. He observes how Claire holds court, teasing some young congressman who said the wrong thing. The house lights begin to flicker. Dahl leads Nancy into the theater, but as they settle in, his eyes remain on Claire. Claire spots his stare, this impossibly handsome, impossibly composed British diplomat. She gets a chill when she realizes he's not looking away. He's telling her. This look is not a passing glance, not an accident. Dahl has already been briefed on Claire by the Irregulars. For Claire's part, there's no flustered, bashful reaction. Doll does not return home that night. Later in the week, when Dahl dutifully writes a letter to his mother, he tells her everything, and I mean everything, even about his awkward exchange with his landlady. After getting home from Claire's, he writes, quote, I got home at 9am the next morning. I had to do a lot of talking to re establish my reputation. Dahl's job, of course, isn't just to have one night stands. If he's going to change Claire's opinion of the Brits and try to get her to influence her husband's magazines, it needs to be a more involved affair. Dahl soon realizes focusing only on the effect Claire might have on time and life is short sighted. Changing Claire's mind about the Brits will also be hugely helpful, because what I haven't mentioned yet is that Claire is incredibly influential in her own right. Claire lives a giant life, almost as noisy as Dahl's. Like Dahl, Claire finds incredible success in a number of completely different fields. She starts out as a short story writer. The New York Times finds her first published volume superficial, but praises its quote, lovely festoons of epigrams and writes, what malice there may be in these pages has a felinity that is the purest Angorian. I have absolutely no idea what that means either, but I guess it's not good because it pushes Claire to pivot away from short stories and to try playwriting. Turns out she's pretty good at it. In 1936, Clare writes the Women, which runs over 600 performances on Broadway. It's a commentary on the pampered lives of wealthy Manhattan socialites which Claire is about to become. The play is adapted twice for the movies, later with Annette Bedding and Meg Ryan, but first with Joan Crawford. Well, girls, looks like it's back to the perfume counter for me. And by the way, there's a name for you ladies, but it isn't used in high society. Outside of a Kennel Lake doll, Claire bores easily. After her success with the Women, Claire decides to move into journalism. She works at Vogue, Vanity Fair, then decides to try war correspondent for Life magazine. Growing restless yet again, Claire takes her varied experiences in creative writing, journalism and in the war and decides to run for Congress. Accomplished, beautiful and wealthy, Claire wins her election and she's seated on the powerful House Military Affairs Committee. Here she is years later on the cartoonishly conservative William F. Buckley show, speaking about the subject of men versus women. Man's brute strength was stronger than woman's strength. It's that simple. After which, in order to get out from under, she developed a thing called guile. Guile was a weapon against tyranny. With Claire's seat in Congress, her powerful committee assignment, and her unique ability to captivate audiences with her writing, plus her husband's little publishing empire, you could argue Clare's about as influential as it gets. Which is bad for the Brits because she also gives a blistering 40 minute speech on the House floor, arguing passionately against cooperation with England. If Dahl can help sway her, he'll be a hero to the Irregulars. Claire is in a very different social stratosphere than 20 something Dahl, who's living off cheese sandwiches in his tiny walk up apartment. But even though Clare is already incredibly successful and married and at 39, 13 years older than Dahl, she falls for him. Here's a tall, handsome ex pilot who can talk literature and theater with her in a way most DC boys cannot. Their relationship is electric, and Dahl is soon complaining to his superiors about Claire's appetite. According to a lawyer who serves in FDR's administration, again with a name that may as well be out of a Dahl story, Creek, Moore Fathom Dahl confides in him that he just can't take another night with Claire. She's completely worn him out over three non stop evenings. He doesn't have anything left. I went to the ambassador this morning, dahl says, and I said, you know, it's a great assignment, but I just can't go on. And according to Dahl, the ambassador replied, roald. Did you ever see the Charles Lawton movie Henry viii? Do you remember the scene of Henry going to the bedroom with Anne of Cleaves? And he turns and says, the things I've done for England. Well, that's what you've got to do. Many years later, Dahl will put the things I've done for England line into Sean Connery's mouth as James Bond. I don't really believe the British ambassador said all that to Dahl. To me, this feels less like a real complaint and more like a humble brag. Dahl is trying to figure out what it means to be a man in this uncertain period. Should he be a macho playboy or a more sensitive man of letters? He's 26. This is when you figure out who you are, which isn't easy when you're lying about your identity to almost everyone you meet. The overall effect of Dahl's relationship with Claire is pretty profound. He reports back on all his intimate, candid conversations with her. He's able to tell his superiors about internal debates regarding the British that are happening in Congress and behind closed doors in influential media circles. He's offering unparalleled insight into American political dynamics. And he helps the British craft proactive ways to engage the Americans for help. And pretty soon, wouldn't you know it, Life magazine is running some pro British stories framing Britain as America's most essential ally. But even more importantly, Dahl is in weekending with the President, carrying on an affair with a congresswoman and mingling with some of the most powerful figures in the country. In espionage, access is everything, and Dahl has it. But he's still far from achieving all his goals. He still has a lot of work left to do and he's going to have to do it with a ton of obstacles in his way. While I've mentioned that pretty much everybody who meets Dahl loves him, the truth is that when anyone is as successful as Dahl is, there are going to be those who don't appreciate it. A charming, arrogant, handsome 26 year old foreigner actively practicing espionage on behalf of MI6 in the US and conducting affairs with some of the most powerful women in the nation. Yeah, that's going to engender some enemies for one the FBI. The Secret World of Roald Dahl is produced by Imagine Audio and Parallax Studios for iHeart Podcasts. Created and written by me, Aaron Tracy produced by Matt Schrader Post production by Wind Hill Studios with editing, scoring and sound design by Mark Henry Phillips Editing by Ryan Seaton Music by APM Executive producers Nathan Klokke, Kara Welker, Brian Grazer, Ron Howard and Aaron Tracy Additional voice performances and recreation by Mark Henry Phillips and 11 Labs if you enjoyed this episode, be sure to rate and review the Secret World of Roald Dahl on Apple Podcasts or wherever you get your podcasts. Copyright 2026, Imagine Entertainment, iHeartMedia and Parallax.

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[Aaron Tracy (Host/Narrator)]

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