Nate Silver: Libertarians Are the Real Liberals

Journalist Nate Silver burst onto the national scene in 2008, when he correctly predicted 49 out of 50 states in that year’s election, outstripping all other analysts. His former website FiveThirtyEight became a must-visit stop for anyone interested in political forecasting and helped mainstream the concept of “data journalism,” which utilizes the same sort of hard-core modeling and probabilistic thinking that helped Silver succeed as a professional poker player and a staffer at the legendary Baseball Prospectus. Reason’s Nick Gillespie talked to Silver about the 2024 election, why libertarian defenses of free speech are gaining ground among liberals, his take on the “crisis” in legacy media, and his forthcoming book, On The Edge: The Art of Risking Everything.

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Watch the full video here and find a condensed transcript below.

Gillespie: A recent essay in your Substack is called Silver Bulletin. You’ve put a lot of work into that title, didn’t you?

Silver: No, I took about three seconds doing it, and now it has some brand equity, for better or worse. I’m afraid to change it.

Gillespie: You’re like American poet and writer Allen Ginsberg. First thought, best thought?

Silver: It’s hokey and stupid and I like that. It’s unpretentious, right? I’ve workshopped internally better names that some corporate branding consultant would prefer, but I just like the cheesiness of it.

Gillespie: On November 8, you had a fantastic discussion where you used Friedrich Hayek’s libertarian cri de coeur “Why I’m not a conservative” to talk about a crack up on the left side of the political spectrum. Friedrich Hayek wrote “Why I’m Not a Conservative” as a postscript to The Constitution of Liberty. In it, he talked about how in America, the terms conservative and liberal didn’t quite make sense the way they did in a European context. Classical liberals or libertarians over there were often in America coded as conservatives, whereas they were quite liberal in a European context, pretty revolutionary and radical. 

With that as a backdrop, you applied that Hayekian framework to contemporary U.S. politics after the October 7th attacks on Israel to your piece titled “Why Liberalism and Leftism Are Increasingly at Odds: The Progressive Coalition is Splitting Over Israel and Identity Politics.” Can you talk about that?

Silver: There are a lot of dimensions to it. One thing I did internal that helped is that I asked our friend ChatGPT—not the woke one, not Google Gemini—to define liberalism, leftism, progressivism, libertarianism, and “wokeism,” which is a term that is not as commonly used as others. If you break that down, issue by issue, you realize that…liberalism is kind of closer to libertarianism than it is to leftism or to more woke modern variants of that.

Gillespie: Why did it take an event like the October 7th attacks to make that visible? 

Silver: I went to the University of Chicago and London School of Economics, and I took all the European Enlightenment history classes, and read a lot of political philosophy. To me, it’s always been rattling around in the back of my head. I think journalists should take more political philosophy classes. These ideas remain very important and very pertinent to many debates that we’re having today. But if you write a Substack, it might seem off the cuff, but you always have a lot of ideas rattling around in your head. 

I had half-drafted versions of this post, and an event like October 7th—I’m not super polarized on Israel or anything like that—but you have a news hook, you have a moment which is like an emperor has no clothes moment where these university presidents are so clearly out of touch with the American mainstream, and people feel like they have permission to say this now after holding their tongue in a lot of previous events. 

It’s a news peg or a news hook about things I think a lot of people had observed for a long time, which is the kind of Hayek triangle between what I call liberalism—but you can call it classical liberalism or libertarianism—and then what was socialism but might be now more social justice leftism, and then what was conservatism is now more like MAGA-fied, particularly illiberal conservatism.

Gillespie: Is progressivism, or wokeism, or identity politics the same as socialism minus economics? Then you’re left with identity politics, or what’s the defining attribute of that cluster?

Silver: No, I think reorienting the leftist critique around issues having to do with identity, particularly race and gender, as opposed to class, is interesting. I don’t get into every detail of every debate, but when you have The New York Times at the 1619 project, the traditional crusty socialists didn’t like that very much. That was a sign as an anthropologist about how even leftism and the new form of leftism are different in important respects.

Gillespie: Where are conservatives on this? If there’s a crack up on the left between what might have been called liberals—for lack of a better term—and progressives, there’s MAGA on the right. What’s the non-MAGA right? Is that analogous to what’s going on on the left?

Silver: As you pointed out earlier and as Hayek points out, America’s weird in that we were the first country founded in Enlightenment values: the rule of law and free speech and individualism. The market economy is something that comes along right at this time. The Industrial Revolution and the Enlightenment are very closely tied together historically. So if you are appealing to traditional American values, you’re appealing to values that are fairly lowercase libertarian, certainly liberal values. [Sen.] Mitt Romney [R–Utah], a Republican, says he likes liberal democracy and uses that term correctly like people should. It is weird in that they are traditional American values. 

I’m not a fan of almost anything about Donald Trump. I don’t think it’s the most constructive form of conservatism. And I do believe in technological and societal and economic progress. I think it’s very important. It feels like there aren’t very many people who do believe in progress anymore. One of the fundamental factors in all of world history is that for many, many centuries, millennia, human [Gross Domestic Product] GDP grew at 0.1 percent per year. You kept up with population growth, barely, if that. The beginning of the late 18th century, there was a take off toward growth. That coincided with both the Enlightenment and Industrial Revolution. Which came first is a big debate in economic history. But there was progress when there hadn’t been before. People don’t know that basic history.

Gillespie: Every year, our cars get a little bit better, our phones transform from something that was plugged into the wall to something you carry around in your pocket, everything is getting better. Yet, we are in kind of a dank mode right now, where people on the right and the left think we have material progress but everything else is terrible, or we don’t even have that. What’s driving that?

Silver: There are good data driven arguments for secular stagnation.

Gillespie: Can you define that?

Silver: The way it’s used informally is to mean that progress is slowing down or maybe not really happening very much at all, or that there are a lot of headwinds. There’s a more [former U.S. Secretary of the Treasury] Larry Summers technical definition. But GDP in the Western world grows now at 1.5 percent per year, whereas it peaked at 3.5 percent in the 1960s for example. Life expectancy in the U.S. has stagnated. That’s not very good. IQ is a contentious topic, but IQ has stagnated. Mental well-being has declined by various measures. Many European countries have not seen their economy grow substantially in many years. There is lower fertility around the world, which I think is something that the left doesn’t like to talk about, but is certainly an important dimension. Political dysfunction is on the rise. 

That thesis is actually fairly well constructed in some ways. But the constant doomerism on all sides—if you have a political quadrant, everybody has something they’re deeply worried about. A certain type of person thinks that AI is going to destroy the world, which by the way, I take somewhat seriously. That’s a different debate. I had dinner with a group last night and they’re like, why would you bring children into this world because of climate change. I think that view is wrong.

Gillespie: How do you think these intra-ideological issues on the right, the left—and that’s not particularly among libertarians, we don’t want to talk about a right-left spectrum because it tends to leave us out—but how do you think break up on the left and the right is going to play out in the election season coming up?

Silver: In the short term Democrats have going for them is that Trump unites both the liberals and the left. That left-liberal coalition, which partly formed under [Barack] Obama in 2008, in part because people were sick of [George W.] Bush, carried forward unsuccessfully with [Bill] Clinton in 2016 and then [President Joe] Biden successfully in 2020. 

Trump really unites people who would otherwise be at loggerheads over many issues. But this time, I’m not sure. I am not trying to articulate an editorial position on Israel-Gaza stuff. But if you have terms that are being tossed around like genocide, that’s a sign that people [are] very serious. That’s not in the bluffing stage. Maybe I won’t vote for Biden, who by the way is 81 years old.

Gillespie: He presents as like 79 or 80.

Silver: He’s doing above average for an 81 year old. I don’t really want a 78 year old president either.

Gillespie: Are we finally seeing a kind of breakdown—not of the two-party system, because it’s always going to be two parties—of the way Republicans and Democrats talk about the constellation of issues that define them. Is this the end of the road for that iteration?

Silver: When the end comes, it will come more quickly than people think. But I wouldn’t bet on it happening in like the next five or ten years. In some ways, the parties have become more efficient about building their electoral coalition. It’s a remarkable fact that in American politics, each party gets about half the vote. If you get 48 percent versus 52 percent, it’s almost considered a landslide these days.

Gillespie: In 2016, it was about 80,000 votes across three states that changed, and it was about 40,000 votes across three states in 2020.

Silver: In a country of 300 million people. Its remarkable elections are that close. It has to do with the efficiency in some ways of the political system. They do it by enforcing more and more orthodoxy. There’s no a priori reason why your view on taxation, and abortion, and Gaza, and marijuana legalization, and ten other issues needs to be tied together. But you flatten out this multi-dimensional space into two parties. One difference now versus a couple of decades ago is that the public intellectuals, maybe it’s too generous a term, but the pundits are more partisan than the voters. They’re the ones who enforce partisan orthodoxy. I’m basically a good center-left liberal. In some rooms in New York, I feel like I’m the more conservative person in this room, probably one of the most woke. 

Gillespie: You’re practically a stooge of the Soviet Union here.

Silver: Yeah, exactly. But if you break from Orthodoxy, there’s a very efficient policing of people who piss inside the tent and dissent from the coalition, and have the credibility to say that out loud. Because you can influence people if you’re willing to just speak your mind. It helps to be established where you’re not afraid of anything.

Gillespie: A couple of weeks ago, we saw an outpouring of anger that Vice magazine—which up until about two weeks ago had been seen as a charnel house of sexual harassment—suddenly went bankrupt. People were saying, “I can’t believe we lost the last outpost of great journalism.” Similar things have happened before: when Sports Illustrated finally went belly up, the Los Angeles Times, a newspaper that nobody read, is cutting staff. What’s going on with the legacy media? Is that in any way tied to what’s going on in the political identity space?

Silver: In an effort to be nuanced and textured, I think it’s 80 percent secular economic forces where you have this advertising bundle that was very powerful in that probably wasn’t a natural occurrence per se. It was a form of economic rent, more or less, that subsidized the industry. My parents would walk down to the store and buy The New York Times, even growing up in Michigan. I respect traditional journalism, but I think it’s mostly an economic story. It’s hard because I think journalism does create, in theory, social utility. I’m not sure I think that journalism should be funded by governments, though it is in many countries.

Gillespie: When you say you’re not sure, do you mean you know it shouldn’t be?

Silver: Here’s my idea, which I’m stealing for one of my future Substack posts. I think universities should run—maybe it’s a bad idea. I don’t know. It sounds like a bad idea. What if universities bought newspapers? Because newspapers are categorically more useful than academic papers. 

Gillespie: Because they have comic sections.

Silver: But they are producing journalism in real-time. They’re the first draft of history. They’re read much more widely. The writing is much, much, much better. Harvard, you take the fact that members can actually write and communicate with the public and have them write for The Boston Globe instead of for some obscure journal. 

Gillespie: University of Miami or a party school could take over Vice. It’s a brand extension, for God’s sake.

Silver: For once, as the most left-wing person in the room, we could agree probably on the many things I think journalists do wrong. I think it’s not great that local journalism has been hit so badly. I’m a big fan of Substack. I make money from it. You realize your marginal revenue product a little bit more explicitly. There is always an implicit deal where if you go report from the front lines of Ukraine, that’s not actually going to be narrowly profitable. You always had subsidization of enterprise reporting and foreign reporting from cooking and homes. The editorial section, where you pay pretty well. They get lots and lots of clicks, or Wordle or whatever games. If that bundle breaks down, The New York Times has been doing well.

Gillespie: You created FiveThirtyEight. Could you walk through the stages of death that went along with it. When FiveThirtyEight launched, it was a phenomenal resource that was doing things that other sites weren’t doing. You ended up moving to The New York Times with it, and then to ABC and Disney.

Silver: We were under license to The New York Times. We got hired by The Times for three years, and then I sold FiveThirtyEight to Disney/ESPN in 2014, which intercompany transferred to ABC News.

Gillespie: Within a little bit more than ten years, you went from starting something fundamentally new that made a major impact on legacy media into giant news organizations, and now is in its Biden years, let’s say, where it’s taking the afternoons off. 

Is that a tragedy or will something else come up? Is it the fact that you could do that because there’s so much more possibility and capacity for new things? Are you better or worse off being at Substack for the moment?

Silver: The latter question is easier. I feel much better off. I just have like a little extra pep in my step being independent again. You’re probably making the same income, it might be from six different sources of the texts that are more complicated, but it’s very nice to have an incentive. If you write a good Substack post, people will subscribe to your blog and you get money in your bank account. That actually feels good, to have actual incentives to work hard and to develop an audience. 

The problem with ABC News and Disney is that it was basically run like a socialist economy. Obviously, this is a well-run business in some ways, but we were so small relative to their scale that they didn’t care one way or the other. If you make $5 million or lose $5 million, why do they care? It’s like one day of theme park receipts at one theme park somewhere in the world. It’s actually really bad, though. It makes you kind of a client of the regime. Your capacity to stay there depends on the goodwill of people who are able to kind of write off an x million dollar loss a year. 

We had good economics for a subscriber business. We have loyal, high-net-worth readers who have a differentiated willingness to pay, and who have been around FiveThirtyEight for a long time. It could have been a good subscription business, but Disney was literally like, “Well, we are launching Hulu Plus. Therefore this would interfere with that.” No, it wouldn’t. But when you’re in a very large corporation and you’re some subdivision of a subdivision of subdivision, it’s not run very efficiently. Disney is not one of these cultures, like a friend who works for Amazon. Amazon will micromanage everything. It can be good or bad in different ways. 

But Disney is all about scale, scale, scale. You know, the National Football League and theme parks and nine-figure budget movies. If you’re like a little tiny barnacle on the Disney whale, you’ll just get ignored till the politics change, and they have to cut staff and wear this division that no one ever even tried to make a profit with. I think we could have. Of course, at some point, you get cut.

Gillespie: Is it an absolute loss when The LA Times shrinks? Or are you confident that new things will crop up that will perform either the same function or the function as it needs to be done now, rather than what a daily newspaper did in 1970 or 1980?

Silver: Substack is great. Social media has, although complicated, democratized things in a lot of ways. It’s the upper middle class, like a lot of things, it’s gotten quite squeezed. Things like local reporting, the fact that the very obvious and kind of comical, like George Santos story, didn’t get a lot of pick up, for example, like things like that are going by the wayside a bit. I think we can have a few more blind spots: Is it like in my list of ten biggest problems in America right now? No. Top 25? Okay, maybe. I think it’s bad. People have a desire to express themselves. There are some outlets, like The New York Times that are still doing very well. 

Gillespie:  You wrote in a November essay that free speech is in trouble. Young liberals are abandoning it—and other groups are too comfortable with tit-for-tat hypocrisy. Why are young liberals abandoning free speech?

Silver: What I would call Enlightenment liberalism are still relatively new ideas. They’ve been with us for a few centuries and not more than that. In some ways, they’re counterintuitive ideas. The notion is that if we are a little bit more laissez faire, and let people do what they want, the free hand of the market will generate more wealth, and we’ll all be collectively better off. It sounds too good to be true, except it mostly is true, empirically over a long period. 

But, there are a couple of things: One, which is relevant to my book, is that for the first time in history, the younger generation is more risk averse than older people. They’re having less sex. They’re doing fewer drugs. Less can be good or bad, I don’t know.

Gillespie: It’s so bad, they’re having less sex than Joe Biden.

Silver: He apparently is doing quite well. I am not somebody who says that there are never any tangible harms from controversial speech. Look at [novelist] Salman Rushdie, free speech can actually have effects. It’s a powerful thing. But if you’re so risk averse, you just want to maintain harmony. I think that’s part of it. Right. Also, these are not people who grew up with the memory of the Cold War or certainly not of World War II. 

Gillespie: Or mass censorship. When you think back to the idea that books like Lady Chatterley’s Lover, or Tropic of Cancer, or Ulysses really weren’t legally published in America until the late ’50s, early ’60s?

Silver: If you’re like 23 or something, even dumb stuff like the Dixie Chicks in the Bush years. People even forget about that kind of thing.

Gillespie: Why do you think other people—not woke progressives, but conservatives who constantly talk about the Constitution, or perhaps even libertarians in certain circumstances—think “let’s be hypocritical in order to own the libs.” What’s going on there?

Silver: One of the universal truths about everything in life is that if you have a longer time horizon, you almost always benefit from that. People are trying to win the argument to feel satisfaction in that immediate moment or that hour. They think, “If I get into the left on things, not the left actually, it’s kind of more kind of center-left partisan Democrats about Biden’s age,” and they think, “Well, if I can dunk on Nate Silver about Biden’s age, then I’ll win the argument.” But the problem is, it’s not an argument between you or me. Seventy percent of the American electorate thinks Biden is too old, very reasonably so I might add. Eighty is just above the threshold anyone should be commander in chief. But they’re trying to win the argument and not win the war.

Gillespie: This might be an impossible question to answer. It’s kind of a chicken or egg thing, but are we more talking about present short-term things? Because that’s the infrastructure. That’s social media. That’s the way cable news operates now. Or have we conjured those things in order to win quick arguments in the idea that that will transform society?

Silver: It’s three things. It’s partly human nature, partly the nature of modern media, and partly the fact that people are not in politics for truth-seeking reasons. They’re in politics to win partisan arguments and to enforce orthodoxy because you have two parties that are taking this 20-dimensional space and trying to collapse it all down into two coalitions that may not actually have all that much in common if you start to pick apart differences. You need useful idiots to enforce those hierarchies.

Gillespie: Why are you different? Your entire career, going back to your work on Baseball Prospectus and elsewhere, you’ve been more data-driven. Data will tell you whatever you need it to tell you, right? Why aren’t there more journalists like you who are trying to ascertain reality and then tease out trends and meaning, as opposed to those who bulldoze things into what they want it to be.

Silver: It’s funny because now I feel like I’m more of a traditionalist. When I went to The New York Times in 2010, they were very concerned that I said I had voted for Obama in 2008, which I thought was just a matter of basic transparency. I would make the same vote again, to be sure, but that was a big problem that I had been open about my political views at all. It comes full circle now, where if you don’t kind of express your view on every issue, then you’re seen as being suspect potentially. But the world is dynamic, so it’s possible to overcorrect. I think there was or is truth in the left critique of both-sides journalism. The truth is certainly not always, especially for a libertarian, just somewhere in the middle. You people aren’t centrist. It’s a different dimension. 

Gillespie: It’s a very different dimension that some people will claim doesn’t even really exist. You certainly can’t find it on any map. 

Silver: I think even some of the more woke versions of it—at least I think that it’s to some approximation true that white men have a lot of power in the media and, of course, that’s absolutely true. But when you don’t give people credit for being willing to adapt, if you read The New York Times today and compare it to 2013 or something, it’s a vastly different paper now and you have to adjust to that moving target and not to the same standard. Give people credit for being. This is part of why the free market is right: it gives people credit for being intelligent and within their domain, relatively rational. I’m the only smart person in the room. 

[Similar to the] COVID-19 stuff. The early dialogue about masks where [former Chief Medical Advisor Anthony] Fauci [says] “Later on where I tell people masks are worthwhile, but let’s say they don’t really do anything. We need them for essential workers.” People don’t really notice that we’re telling a good, noble lie. That shows contempt for people. 

If you play poker, then you know that, although bluffing is a part of poker, if you’re inconsistent, you’re allowing yourself to be exploited by your opponent. Your opponent’s smart. If you were only playing a certain hand a certain way with a bluff or with a strong hand, then you will be exploited by your opponent, as opposed to treating them as intelligent and adaptable and more sophisticated. You should treat people as being intelligent. It’s a much more robust strategy than to assume that you’re the only worthwhile and smart person in the room.

Gillespie: Can you talk about your book On the Edge, which comes out in August. What’s it about?

Silver: The book is called On the Edge. It’s a book about gambling and risk. It covers a lot of territory. It follows my journey where before we ever covered politics, I played poker online for a period of time in the mid-2000s. It starts out in the poker world.

Gillespie: Why did you stop that?

Silver: Because the government passed a law called the [Unlawful Internet Gambling Enforcement Act], which is what piqued my interest in politics. It was tucked into some unrelated security legislation at the end of 2006. I wanted the bastards who pass legislation, who are mostly Republicans, to lose. And they did. Democrats had a good midterm in 2006. And well, they fucking took away my livelihood. What am I going to do now? I wound up starting to write about politics.

Gillespie: And now you are simping for Trump. What a strange world. To write On The Edge you did a phenomenal amount of interviews and research. Can you talk a little bit about the scope of that?

Silver: It starts out in poker and sports betting but gets into areas like venture capital, gets into crypto—I talked to our friend [FTX founder] Sam Bankman-Fried quite a bit—gets into effective altruism, gets into a lot of the AI stuff. It’s a fundamental book about a certain type of nerd. 

Gillespie: It’s an autobiography. 

Silver: Sort of. But they’re taking over the world in a lot of ways. They’re the ones who run tech and finance. Tech and finance are eating the world. It’s an insider’s tour about how people like that think. There were like 200 interviews. I did a lot of trips to Vegas, which was fun. 

You’re trying to immerse people in the topic and get people a front-row seat. I’m not a big network access guy, but I’m flattering myself here, because I think I am fair. I think people will talk to me that would not talk to other people. I am talking to some of the top Silicon Valley [venture capitalists] VCs on their own terms and unguarded ways because I’m not coming in with an agenda apart from trying to understand them. The book is very critical of some things. But I think it’s fair. It didn’t preconceive what it wanted to say before I actually did the reporting, the interviewing. I think that’ll be reflected in the work.

Gillespie: To go back to Hayek, my favorite work by Hayek is The Counter-Revolution of Science: Studies on the Abuse of Reason. He worried that the French Enlightenment got everything too mathematized, and ultimately, people were just data points in other people’s grand theories and you erased them if they mess up your equation. Are we too quantified in this world? 

Silver: There are a few dimensions of this. One is like the dubious claims to have scientific authority and say, “Oh, we are just doing what the data tells us.” You saw this during like COVID-19 and whatnot. You see this with the concept of misinformation, which is often entirely subjective. That’s one dimension. The book also gets into utilitarianism a little bit and effective altruism, where they try to quantify everything and you run into problems with that. 

First of all, I build models for a living. I build sports models and election models, tried to bet on them myself and in a sense, a game theory of poker strategy is kind of a model. Building a model is pretty hard. There are lots of ways to screw up. There are lots of omitted variable biases. It might be another overcorrection thing where like 20 years ago the world needed to become more data-driven. Now it’s become like a little bit of a, when you have a hammer, everything looks like a nail kind of problem.

This interview has been condensed and edited for style and clarity.

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