The Daily Stoic

BONUS | Ryan Holiday Responds to Daniel Radcliffe

9 min
May 12, 202619 days ago
Listen to Episode
Summary

Ryan Holiday discusses a book on American imperialism and colonialism, exploring how understanding historical colonial expansion helps contextualize modern geopolitical tensions. He emphasizes lessons learned from 20th-century mistakes and how different approaches to global influence—through military bases and alliances rather than territorial control—proved more effective for American power projection.

Insights
  • Understanding historical colonial patterns is essential for interpreting current geopolitical conflicts and policy decisions
  • Territorial control and subjugation proved strategically ineffective compared to maintaining military bases and alliances
  • Post-WWII reconstruction and base-sharing agreements created sustainable power structures at lower long-term cost than colonialism
  • Moral opposition to expansionism existed within American leadership even during peak imperial periods, showing internal resistance to colonial policies
  • Modern isolationist perspectives miss the strategic advantages America gained through international engagement and alliance-building
Trends
Renewed interest in historical analysis of American foreign policy and imperialism among mainstream audiencesGeopolitical saber-rattling echoing 18th-19th century territorial expansion rhetoricGrowing recognition that soft power and alliance structures outperform direct territorial controlEducational gap in understanding America's colonial history and its contemporary implicationsReassessment of post-WWII international agreements as strategic investments rather than charity
Topics
American Imperialism and Colonial HistoryPhilippine-American War and Colonial SubjugationPuerto Rico Medical Experiments and Colonial TreatmentPearl Harbor and American Territorial ClaimsLend-Lease Act and Post-WWII Alliance StrategyVietnam War as Colonial Remnant ConflictMark Twain vs Rudyard Kipling on ColonialismMilitary Base Strategy vs Territorial ControlMexican-American War and Expansionist SlaveryHerbert Hoover's Foreign Policy LegacyCivil Disobedience and Anti-War ResistanceGeopolitical Strategy and Power ProjectionAmerican Exceptionalism and Historical Accountability
Companies
Ramp
Cited as Vantta customer achieving 82% less audit time through compliance automation platform
Ryder
Cited as Vantta customer achieving 82% less audit time through compliance automation platform
People
Daniel Radcliffe
Guest who recommended book on American imperialism and discussed Puerto Rico chapters and Super Bowl attendance
Ryan Holiday
Host responding to Daniel Radcliffe's book recommendation and providing historical analysis and additional book recom...
Mark Twain
Historical figure cited for opposing American colonialism and Philippine annexation, contrasted with Rudyard Kipling
Andrew Carnegie
Historical luminary cited as opposing American annexation of the Philippines
Douglas MacArthur
Grew up in Philippines during American occupation, nearly more Filipino than American in identity
Franklin D. Roosevelt
Gave famous Pearl Harbor speech framing Japanese attack as act of war against America
General Smedley Butler
Most decorated marine in U.S. history who fought in colonial wars and later spoke out against them
Herbert Hoover
Referenced for his love of fishing as meditative practice; wrote book on fishing
Henry David Thoreau
Civil Disobedience essay included in discussed book; resisted Mexican-American War
John Pershing
Quoted regarding conscience about Philippine campaign atrocities
President Truman
Nearly assassinated by Puerto Rican nationalists; shooting incident occurred in Congress
Bad Bunny
Referenced regarding criticism of his nationality and Puerto Rican heritage
Quotes
"The way to understand the present moment is almost always by better understanding the past."
Ryan Holiday
"We abolished them utterly, Mark Twain said, leaving not even a baby alive to cry for his mother."
Ryan Holiday, quoting Mark Twain on Philippines campaign
"I would not have that event on my conscience for the fame of Napoleon."
John Pershing
"What you understand reading this book is we're the ones getting the free ride. We have the great deal."
Ryan Holiday, on post-WWII military base agreements
"Hoover's love of fishing and activity he revered for the quieting of hate, hushing to ambition and a promotion of meekness."
Ryan Holiday, quoting from discussed book
Full Transcript
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Hearing anybody complain about Bad Bunny, like not being American or any of that stuff, like now having, I mean, hearing them complain about it anyway is heinous, but like after having read that book, you're like, no, you guys need to shut up. Get very defensive. I also love the Puerto Rico chapters. It really informed rewatching the Super Bowl. Yes. And I was just like, did you watch that? Sounds like a brag. I can't help it. I was there. Oh my gosh. I picked the right year to do a sports-based comedy with NBC. Yeah. They also had the Super Bowl, so they sent me to that and I got to go. It was awesome. So Daniel Radcliffe, Harry Potter has been raving about this book. I just want to co-sign on this recommendation because it is an incredible book that not only changed how I understood America, but it changed how I understood the world. The way to understand the present moment is almost always by better understanding the past. For instance, did you know that in the 1800s, there was a race to take up islands in the Pacific and all over the oceans that were covered in bird shit because that bird shit, guano, was a critical ingredient in making gunpowder. So many of the wars in the 19th and the early 20th century were a product of colonial wars before that. These empires were fighting over these obscure islands that weren't even inhabited because they wanted to own the bird shit that they could use to make weapons to fight over other more valuable pieces of land. One of the most interesting things I took from this book is at the beginning, he's talking about how when America is attacked at Pearl Harbor. Roosevelt gives this famous speech. He says, you know, this was an act of war. Japan attacked America in Hawaii and also attacked the Philippines, except for from Japan's perspective, the Philippines were also America. It was just attacking America in two places. The American flag was still flying over the Philippines. We've given it back to the Filipinos, but we were still ruling it for like a 10 year interim period before we handed it off. Douglas MacArthur grew up in the Philippines. He was almost more Filipino than he was American. And I think it's worth saying, though, although this book shows some of the horrible things that America did as a colonial power, it also makes it clear that not all Americans were on board with this and that other Americans, Andrew Carnegie, Mark Twain, some luminaries of the time were adamantly opposed to say annexing the Philippines, right? America is saber rattling, threatening its neighbors about overtaking Greenland. This feels like a throwback to the 1700s and the 1800s and the early 1900s. And indeed it is. And so to better understand that, you should understand that period and you should also understand the lessons that were learned from that period, from the mistakes and the injustices and the wars and the disasters that came from it. One of the most powerful things that America learns coming out of World War One and World War Two, two wars that were essentially about colonialism is that actually owning the territory, controlling the land, subjugating the people is a stupid strategy. It's not effective. It's not efficient. It opens you up to not just undermining your values, but it makes enemies of people. We famously didn't learn this lesson so well. Vietnam wouldn't have happened had we fully understood it. We end up backing the French as they attempt to regain possession of Vietnam after the Second World War. And then we replace them and we told ourselves we were fighting communism. Really, we were fighting to preserve the remnants of colonialism. But this is just an amazing book. I think the title is funny. It gives you a peek into what a great job the author does at making a seemingly dry or academic subject really, really interesting. And look, how desperately do more people need to know and read about this book? People claiming that Bad Bunny is not an American. They need to have a better sense of America as an empire. And Daniel rightly highlights the Puerto Rico chapter, which is particularly haunting. There's all these terrible medical experiments that we did on Puerto Ricans as if they were not only not Americans, but somehow not human beings. I just actually had someone grab my copy off the shelf. Let me see some of the stuff I liked in here. I always mark the pages of books that I read and I marked a bunch of them. But to me, the powerful sign about how good a book is, is whether it stays with you. Oh yeah, there's a great chapter in here talking about the difference. Kipling and Twain are both friends. But he points out how they had a very different view of colonialism. And so he obviously talks about the white man's burden, which is interesting. Something that Twain just sort of disputed long before the some of the famous photos coming out of Vietnam, the one with the gun in his head, the napalm photo. There's this famous photo in 1906, a trench filled with bodies in Badajo. We abolished them utterly, Mark Twain said, leaving not even a baby alive to cry for his mother. And then Pershing said famously, I would not have that event on my conscience for the fame of Napoleon. And what we did in the Philippines was horrendous. Those critics were absolutely right to warn about how badly it was going to go. What a moral quagmire it would put us in replacing one colonial power by becoming one ourselves. There's a great chapter in this book in Lend Lease for people now who are sort of like America first, isolationist, not understanding that what America did by coming to Britain's rescue in World War II, the Lend Lease Act, and then what we ended up getting to were rights to bases all over the world, priceless real estate that allows America to project its power in the world by but only controlling small bits of territory, not the whole country, not needing to subjugate people, letting there be free determination and that the act of rebuilding Germany, the act of rebuilding Japan, this wasn't simply an act of charity. This wasn't altruism. The bases that America has there allows it to be a superpower and then the ongoing maintenance of that relationship. Trump sometimes complains that these countries are getting a free ride. What you understand reading this book is we're the ones getting the free ride. We have the great deal. No other country has stuff like that. And certainly to set up those relationships now would cost far more than whatever the terms were in the 1940s and 1950s. And with Puerto Rico, how many people know that President Truman was almost assassinated by Puerto Rican nationalists? There was a shooting in, I think, like in Congress about it. Oh, and it's so funny. I always define a good book by whether I get another book out of it. It wasn't till towards the end of this book that I read this little passage about Hoover loving to fish. It says, Hoover's love of fishing and activity he revered for the quieting of hate, hushing to ambition and a promotion of meekness. I ended up finding a book that Herbert wrote about fishing, which was this lovely, sweet, sort of soul nourishing book. Just to make this a good video, I'll connect you to two other books that I absolutely think you should read. There's this book, War is a Racket by General Smedley Butler, the most decorated marine in U.S. history. He fought in those colonial wars and he came to understand what they really were and what they were really about. And he spoke out about it. And there's another book about him, a biography about him that pairs well with this called Gangsters of Capitalism that I would recommend. But definitely read this book. Henry David Thoreau's Civil Disobedience is included in this one. People forget that Thoreau going to jail and civil disobedience. What was that about? That was in resistance to the Mexican-American War, which Thoreau rightly understood was part of the expansionist slave powers trying to turn America into a slave empire. They had designs not just on Mexico, but Puerto Rico, the Dominican Republic, Cuba, all of Canada. They wanted to expand and expand slavery and they saw America as a future slave empire. Thankfully, that didn't happen. So anyways, couldn't recommend this book highly enough. You should absolutely read it. It helps you understand what's happening in the world. And if more of our leaders in Washington read this book, maybe we wouldn't be making some of the fatal mistakes that we are making right now.