Crack-Up Capitalism Chapter 6: Cosplaying the New Middle Ages
Chapter 6 of Crack-Up Capitalism by Quinn Slobodian might be the weirdest chapter in the book. And I mean that in the best way. It is about libertarian thinkers who looked at the Middle Ages and said: “Yes, that. Let’s bring that back.”
Not plagues and mud. Not lords in castles starving peasants. No. They liked the part where there was no single government, no single legal system, just a patchwork of overlapping private jurisdictions. And they tried to make it real, starting with gated communities in Arizona and ending with floating cities at sea.
Sea Ranch: A Modernist Utopia Behind Walls
The chapter opens in 1990 at Sea Ranch, a gorgeous gated community along the Northern California coast. Neoliberal thinkers gathered here to name Hong Kong the freest economy in the world. The New York Times called Sea Ranch a modernist utopia. But Slobodian points out what it really was: a walled settlement with a 56-page rulebook. It told you what color your drapes could be. It banned clothes on visible lines. It limited how tall your trees could grow. And the population was 97 percent white. The original planner called it “a kibbutz without the socialism.”
Sea Ranch was one of the first modern gated communities in America. By the end of the 1990s, these walled neighborhoods were everywhere. People started calling it “a new Middle Ages” where “defensible, walled and gated towns dot the countryside.”
Here’s the thing. Most people saw that comparison and worried. But market radicals saw it and got excited. For them, gated communities were not just a real estate trend. They were laboratories for a new way of organizing society.
David Friedman: The Anarcho-Capitalist Who Lived in the Middle Ages
Milton Friedman, the famous free-market economist, believed government was necessary for some things: law, money, property rights. His son David thought his father did not go far enough.
David Friedman grew up in Hyde Park, Chicago, a small academic enclave surrounded by poorer Black neighborhoods. His father opposed anti-discrimination laws. David pushed even further. In 1973, he published The Machinery of Freedom, calling for full anarcho-capitalism, a system where everything is private. Roads, courts, police, all of it. No public law. No democracy.
But here is what makes this chapter so strange. David Friedman was also a dedicated medieval reenactor. He was a member of the Society for Creative Anachronism and played a character named Duke Cariadoc of the Bow, an early-twelfth-century upper-class Berber. In character, he ate only with his right hand, signed his name in Arabic, and always followed the name of God with an honorific. He launched an annual event called the Pennsic Wars in 1972. The first one drew 150 people. By the late 1990s, it attracted 10,000.
So was this just a hobby? Not at all. His medieval obsession fed directly into his economics. In 1978, he wrote about medieval Iceland as a real-world example of anarcho-capitalism. For three centuries, he argued, Icelandic law was privately enforced. Even murder was just a civil offense where you paid a fine to the victim’s family. And here is the wild part: a crime victim could sell the right to retribution to a third party. You had a property right in your own victimhood. Friedman half-jokingly wrote that “the American legal system is a mere thousand years behind the cutting edge of legal technology.”
Private Justice: From Wergeld to Private Prisons
Other libertarian thinkers built on Friedman’s medieval fantasies. Bruce Benson, another anarcho-capitalist economist, wrote The Enterprise of the Law in 1990. He told a story of legal history where everything went downhill the moment kings got involved. In the early Middle Ages, Benson explained, German tribes had “wergeld” or “man-price.” You committed a crime, you paid money. No prisons. Self-organized groups called “hundreds” handled enforcement. Then kings started appointing sheriffs, taking a cut of fines, and building prisons. By the nineteenth century, public prisons funded by taxes were the norm. For Benson, this was the worst outcome possible.
His solution? Go back. Privatize everything. He pointed to companies like Pinkerton and Guardsmark as the beginning of a return to private justice. He highlighted Behavioral Systems Southwest, which housed detained immigrants for profit. And his biggest argument for privatization was simple: it would crush police unions and slash payroll.
Benson was not some fringe blogger. He was funded by the Pacific Research Institute, the same think tank network connected to the Friedmans. In 1998, his ideas went directly into a report for the State of Kansas on crime reduction. He called privatizing law and order “a return to historical practices rather than something new.”
If you ever wondered why libertarian funders like the Koch Foundation talk about prison abolition, this is the key. They do not want to reform prisons. They want to replace public justice with private restitution. Bounty hunters instead of police. Payback instead of rehabilitation.
Gated Communities as Mini-Governments
The chapter’s second big idea is that gated communities were not just safe neighborhoods. They were models for a new political order.
Gordon Tullock, a trained lawyer who served in Hong Kong and South Korea, became fascinated by the idea. He lived in a gated community of about 250 homes north of Tucson, Arizona. And he used his Sunshine Mountain Ridge Homeowners Association as a template for what he called “sociological federalism.”
Here’s how it works. The HOA owned the streets, hired private guards for night shifts, and had strict rules about how your garden should look and what color you could paint your house. Want to paint your house purple? Sorry, you can be stopped. Votes were allotted by housing unit, not by person. This was not democracy. It was something else.
Tullock was honest about one thing most libertarians avoided: race. His gated community was almost entirely white, while the surrounding county was about a third Mexican-American. He wrote that “people, on the whole, like living with other people who are similar to them.” He defended this voluntary segregation and saw it as good policy. He even proposed applying Ottoman Empire-style “millet” systems to American cities, where ethnic communities would govern themselves.
This was the vision. A checkerboard of racially sorted private territories, each with its own rules, no collective action to address inequality. A clean separation dressed up in the language of choice and freedom.
From Cosplay to Reality
So did any of this actually happen? More than you would think.
David Friedman called the process building “the skeleton of anarcho-capitalism” inside existing society. And it was growing. By 2000, about half of all new housing developments in the American West and South were gated and master-planned. Seven million households lived behind walls or fences. Homeschooling exploded from 20,000 children in the 1970s to 1.8 million by 2016. The University of Chicago’s private police force grew to patrol 65,000 people.
David’s son Patri Friedman took it even further. He grew up attending the Pennsic Wars and later became a fan of Burning Man. But his complaint about Burning Man was telling: there was no commerce allowed. His dream was Burning Man with capitalism. So he co-founded the Seasteading Institute to build floating cities at sea. Gated communities on water. Private law on mobile platforms. As David Friedman explained at the Institute’s second conference, these seasteads could be “legal mobile homes,” plugging into different legal systems depending on which was most convenient.
But Here’s the Problem
Slobodian does not just let these ideas float in the air. He shows where they crash into reality.
Gated communities were supposed to be about freedom and choice. But the actual covenants residents signed were boilerplate documents written by lawyers and insurance companies. They varied almost nothing from community to community. Political signs were banned. A California couple got fined daily for having a wooden swing set instead of a metal one. A Florida woman was taken to court because her dog was over thirty pounds. Economic freedom meant less room for personal expression, not more.
David Friedman himself admitted that anarcho-capitalism would not necessarily create a society where “each person is free to do as he likes.” Privatizing law and order could just as easily mean more restrictions. And America already had proof: the company towns of the twentieth century. In those places, the company built your house, chose its color, owned the only store, and sometimes paid you in scrip you could only spend there. Races were segregated. Unions were banned. Strikes got you evicted. In copper mining towns like Bisbee and Jerome, armed vigilantes rounded up union members and threw them out.
A coal boss from Washington State had a saying that captures the whole anarcho-capitalist dream: “A good kingdom is better than a poor democracy.” But as Slobodian notes, he said nothing about the bad kingdoms. Only in fantasy do people get to live under laws of their own choosing.
This chapter is a strange mix of cosplay, economics, and real politics. People dressing up as medieval characters, writing academic papers about Viking-era justice, then using those ideas to justify gated communities and private police. It would be funny if it was not so influential.
The book is Crack-Up Capitalism by Quinn Slobodian (ISBN: 9781250753908). Worth reading in full if you want to understand how radical these ideas really are.