Taking Down Oligarchy

A lot of people say the democracy is a complete sham. Winters does not. Anybody who has lived in a non-democratic place knows our circumstances are different, and there are important ways in which we are democratic. And yet the system stops responding when serious struggle runs into certain kinds of resistance. Both descriptions hold at once, and the book exists to explain how a society can be structured so that neither one ever wins outright.

Gilens and Page did not claim there is no democracy. On the many issues where the many and the few want the same thing, outcomes look democratic. Their special question was what happens when the interests of the many and the rich few pull apart, and the answer was zero. Never, no matter how big the majority was. The finding does not say the system is unresponsive. It says the system is responsive to a different constituency.

The horizontal axis is how the non-rich treat each other. We exclude, trample, and marginalize people all the time, and over history people have struggled against the rest of the non-rich for representation and voice. It is never perfect and there are setbacks, but struggle on this axis correlates with gains. The vertical axis is the relationship between the non-rich and the rich. Should a democratic society be able to decide how unequal it will be? Most people answer yes. Can we? No, not in a system structured this way.

Wealth pyramids are ancient, and every one of them relied on coercion, violence, or awe to hold itself together, because stratification is inherently unstable and the wealthy always feel threatened. Then 250 years ago the first modern democracy emerged and something new happened. Stratification held through open participation. We take part in the system that produces the inequality, and we feel something like consent while it happens. He gives the arrangement a name, participatory inequality, because nothing before it worked this way.

The War of Independence was funded with debt, and after it came something between a recession and a depression. The financiers wanted repayment with interest, and repayment ran through taxes on small farmers who did not have the money. The many had to pay the debt. The few held the debt and wanted it paid. Winters says the high school version, interstate commerce problems leading sensibly to Philadelphia, is false, and that the real fight of the decade was between debtor majorities and creditor oligarchs.

The United States inherited debtors' prisons from Britain, and they were the first prisons in the country. A farmer who could not pay when the sheriff arrived went to prison with rapists and murderers, along with his family. Tens of thousands of small farmers went in. In some counties 70 percent of the farms had been foreclosed on. The detail that changes the story is that these debtors had votes, which meant the crisis could be fought inside legislatures instead of only in the streets.

Small farmers captured about half the state legislatures and asked for relief from debt and debtors' prisons. They got it in the form of printed paper money, which depreciated, which let a debtor pay off a debt at a discount. The pain of the crisis was shared downward onto creditors by democratic vote. Pennsylvania went furthest: a House of Representatives only, no Senate above it, no governor's veto, because the role of a Senate is for wealthy people to block the House. In the hard-currency states run by creditors, Massachusetts above all, there was no relief at all.

In Massachusetts the begging and marching produced nothing, and thousands kept going into the prisons. So the people marched with fife and drum into town centers, armed, and did exactly two things. They released people from debtors' prisons, and they blocked judges from ordering more foreclosures. They did not attack the creditors, burn their businesses, or destroy their homes. Winters has read what high school students are taught about Shays' Rebellion, and says the anarchist uprising in the textbooks is not what happened. It was the vertical axis of democracy asserting itself.

Washington himself had been unwilling to come out of retirement for a convention. What changed was watching half the states make democratic decisions on behalf of the poor, and watching rebellion in the states where no relief came. The reluctance turned to panic, and they ran to Philadelphia. The Congress had authorized them only to amend the Articles of Confederation. On their own, with no authorization, they decided to scrap the document and write a new one. Their very last decision was to embargo all their notes for a minimum of 30 years so no one could see what they had talked about.

They disagreed about big states and small states, slave states and less slave states. They agreed about the problem. In Elbridge Gerry's words, there was an excess of democracy in America, and they wanted to fix it. These were wealthy men who believed in the consent of the governed and meant it, and who also believed the pyramidal form of society was just. Their word was natural. A flat society would go against human nature. So the diagnosis wrote itself: society is pyramidal, the democracy is too flat, and the democracy must be restructured to match the pyramid.

The House would be the only thing the people were allowed to vote for, and because the House was closest to the people it was dangerous. So a Senate was set over it, constituted exclusively by the wealthy and not by a vote, to check whatever came up. Over both legislative houses, an executive with a veto that takes a supermajority to overturn. And if something got through all of that, a Supreme Court that can block the entire democratic process no matter how legitimate. Winters describes it as a layered wedding cake, each layer a check on the one below. The horizontal checks and balances, protecting us against a king, get taught in every school. The vertical one, protecting the wealthy few against the many, never gets talked about.

The Politics, written 2,300 years before Philadelphia, wrestles with one problem. There are the few and there are the many, the structure is unstable, and the oligarchs will oppress the many while the many will take the oligarchs' money. Aristotle's solution was institutional design that melds oligarchy and democracy at the same time, and his test for getting it right was that on any given day you were not sure which one you were living in. Confusion is the basis of the fusion. Winters says the framers achieved the balance Aristotle laid out, and that it had never been achieved before.

Given who was excluded and enslaved at the founding, the United States is dramatically more democratic than it was. It is also more unequal than it was 250 years ago, and Winters ranks today's liberal democracies among the most unequal societies ever to have existed. The comparison he closes on: the average Roman senator in imperial Rome, a small-farmer enslaved society, held about 16,000 times the wealth of the median Roman. The average of the Forbes 400, roughly the head count of the Roman Senate, holds about 140,000 times the median American's wealth. Eight or nine times the inequality of imperial Rome, sustained with participation, which oligarchs of old could never have dreamed of.

An attendee asked whether the multiple is really the point, since the floor under the average person is so much higher now. Winters' reply reached for the harder case. The American ratio of 140,000 to one becomes 5.6 million to one in India, a country with a comparable billionaire class and a far lower median standard of living. And India is a participatory democracy. He says the Indian case is one of the biggest head-scratchers political scientists have wrestled with for decades: how a society that unequal keeps open, participatory democracy running.

The room's pushback was that life at the bottom is materially better than it was, so maybe the multiple does not matter. His answer: no matter how much additional wealth we generate, the question is whether we allow it to continue to be pyramidally distributed, and whether that is fair. The comparison is not between living standards across centuries. It is between inequality then and inequality now, and on that comparison the present loses to imperial Rome.

Between 1975 and 2025, by his count, 55 trillion dollars shifted upward in American society. A study he cites asked what the median income would be if the inequality of 1975, itself not an equal society, had simply been maintained while the economy grew. Instead of something like 39,000 dollars, the median would be closer to 80,000. He offers the slogan with a straight face: restore the glorious inequality of 1975. That is the size of the loss in the standard of living of the average person, hidden inside a growing economy.

This is a society remarkably tolerant of great material inequality. Lots of people buy lottery tickets wanting to win 100 million dollars, and nobody holds the ticket thinking that winning would make them an oligarch. They think it would be great. At the same time, Bernie Sanders has spent almost two years drawing between 10,000 and 25,000 people to rallies about fighting oligarchy. Winters spent most of his 25 years on the subject being told oligarchs were a Russian phenomenon. The rallies are the evidence that the word has come home.

A student on the first day of his Northwestern seminar blurted out that Russia has oligarchs and the United States has rich people. For a long time the American idea of an oligarch required getting rich in a corrupt way and then engaging in politics. No corruption element, not an oligarch. Winters treats that definition as a detour the word took here. Oligarchs are people empowered by wealth. How the wealth was acquired has nothing to do with it, and the corruption test functioned to exempt every American fortune from the category.

Stealth wealth was the old discipline: in a fused oligarchy and democracy you should not be too visible. After Citizens United, after victory after victory, Winters says the discipline is gone. They are drunk with confidence, brazen, and they feel they legitimately rule. He has a chapter called In Your Face Oligarchy, and he argues the visibility is not an accident or a lapse in taste. It is what winning looks like from inside, and it is also, he argues later, the mistake that restarts the backlash.

People who give blood are donors. People who pump money into the political system to produce outcomes in their favor are investors, and Winters says the accurate sentence is that they are venture capitalists funding outcomes. The euphemism matters because it frames the money as generosity rather than as capital deployed for return. He catches himself mid-talk about to say a shell corporation can donate to a super PAC, stops, and corrects the verb to invest.

The backlash from below against the robber barons ran roughly four decades and delivered real setbacks. Corporations were broken up. In 1894 the first peacetime income tax passed, written so it fell only on the top third of one percent. The Supreme Court struck it down in 1895, the last bulwark doing its job, and reversing the Court took 18 years and a constitutional amendment. The rest of the twentieth century was democracy wanting progressive taxation and oligarchs fighting for regressive, and the oligarchs won. But while they were losing, wealth concentration at the top stagnated and the living standards of the average household tripled in real terms.

The fusion depends on confusion, and confusion is exactly what the oligarchs have squandered. On any given day now, Americans know they are not living in a democracy. Confidence in the institutions is gone, and awareness of what wealth power does is high, which is why the word oligarchy is suddenly everywhere. Wealth taxes, un-American by long habit, are being voted on in California, in play in New York, and under coordinated discussion in Europe, including exit taxes of 40 percent for the wealthy who try to run. It takes awareness, mobilization, and coordination, and all three are in motion.

The number one store of wealth for the average household is the house, and it is taxed annually, reassessed by the county, over and over. Wealthy people pay property tax too, but on a small percentage of their total wealth. The viciousness is in the base: you are taxed on the full value of the house, not your equity. Put 100,000 dollars of equity in a 500,000 dollar house and you are taxed on 500,000. You are taxed on the mortgage. He points at the grandmother who paid off her house over 50 years and has to sell it as the assessments climb, and asks where the boohooing is for her, given how much sympathy attends the oligarch who might not be liquid enough to pay three percent.

The liberal system is designed to stop the definition of democracy at voice and voting. Winters offers a different one: democracy is power, in all of its relevant forms, shared equally. Oligarchs do not mind us having voice and voting, so long as wealth power stays concentrated exclusively in their hands, because the average oligarch holds the equivalent of millions of our voices and votes. The contest is not between the people and the state. It is between wealth power and voting power, and a definition that leaves wealth power out has already conceded it.

After 9/11 the Patriot Act required banks to know their clients and report suspicious activity, because terrorism. Oligarchs and terrorists use the same vehicles, so that law complicated tax evasion and avoidance, and the transactions moved into vehicles with no transparency duties. The ENABLERS Act extended know-your-client rules to about 30 more kinds of entity: law firms doing transactions for oligarchs, family offices, real estate agencies. It was slipped into the defense authorization bill and blocked by a single senator, Toomey of Pennsylvania. It almost passed, which is his point. This is what doable looks like inside the politics of the ordinary.

States like Delaware and Wyoming let a corporation form in complete secrecy, with the beneficial owner never documented, which is what lets a shell invest in a super PAC, buy shares, open bank accounts, move money offshore, and form trusts with only an entity name on record. The Corporate Transparency Act, passed in 2021 inside the defense authorization bill, ordered a national registry of the beneficial owners of some 33 million corporations, six questions each, including name and Social Security number. The registry opened in 2024 and companies began registering. Months after the election, the Treasury Secretary exempted 99.9 percent of corporations by rule, with a stroke of the pen. Winters says nothing was more devastating to oligarchs in the past 30 years, and that they knew it: the act was named in Project 2025. The law is still on the books. A future Treasury can reimpose the requirement the same way it was removed.

C corporations, with one set of owners in a clear structure, turned out to be too easily taxed. The wealth defense industry, his coinage for the lawyers and advisers whose profession is protecting concentrated wealth, built the alternative: large partnerships, a blob of partners in a maze of relationships that the IRS cannot disentangle. The original partnerships had about 100 members. Today a single large partnership can have 500,000, and it is effectively unauditable. The vehicle is legal, growing, and purpose-built to make enforcement arithmetic impossible.

The IRS is required by law to publish the gap between what its own data shows it should collect and what it actually collects. Winters puts the tax gap at about one trillion dollars per year, against a defense budget of about 900 billion. The gap is overwhelmingly oligarchs not paying, serviced by the wealth defense industry, and the mechanics compound: the money not surrendered earns returns, which accelerates the concentration the tax was supposed to slow. Collect what is already owed and the entire military is paid for with change left over, under laws that already exist.

Deep changes proposed today get you called a joker. Winters' answer is not to propose them today. It is to prepare them today. Moments of rupture and crisis are when oligarchs are at their weakest, because the system stops working for them too, and he is not in favor of cataclysms, but the only thing worse than a deep rupture is a wasted one. The politics of preparation means thinking the radical reforms through now, refining them, debating them, testing them at small scale, and being ready for the pushback, because the window is short and you cannot do this work in a politics of the last minute.

His examples of what should be ready. Eliminate the Senate, whose designed function is to block the House. End the absolute executive veto: an executive exists to carry out the legislation of the people, so at most allow a veto that stalls a decision and sends it back down, overridden by a simple majority. And stop talking about expanding the Supreme Court to 13, which just restarts the stacking war. Make it a minimum of 45 members, half appointed through a rotating legislative committee and half by public lottery, open to anyone with a law degree who has served as a judge at any level, on limited terms. Each proposal reverses a specific layer of the vertical wedding cake.

Political science, he says, is largely devoted to explaining how you are not actually represented by the person you voted for. Sortition skips the mechanism that fails. Compose the legislature by national lottery and you get an instant sample of the country: women at half the seats immediately, racial representation immediately, after decades of struggle for both. Oligarchs would do very badly in a lottery. He would not run it at 435 seats but at 3,000, because the odds of a bad sample fall as the number rises. The objection is always whether you can trust an average citizen to legislate, and his students, having invested so much in becoming elites, hate the idea.

Imagine someone campaigning with money to get on a jury. You would immediately call it illegitimate. Yet juries, chosen by lottery, decide guilt and innocence, life and death, and we accept it. Winters has served on two juries, and says he has been consistently blown away by the seriousness of average citizens in positions of real responsibility. You empower people and they get very serious. You disempower people and they are interested in the Kardashians, because why study anything in detail when nothing you conclude can matter? The couch potato, in his argument, is downstream of the disempowerment, not the cause of it.