Second Estate : How the Tax Code Made an American Aristocracy

Named by The New Yorker as one of the Best Books of 2025 and featured on the Armchair Expert podcast with Dax Shepherd.

A revelatory book that lifts the curtain on America’s most consequential public deception: how the rich get richer using tools the government gave them.

Amid conflicting narratives about the drivers of wealth and inequality in the United States, one constant hovers in the background: the US tax code. No political force has been more consequential―or more utterly opaque―than the 7,000-page document that details who pays what in American society and government. Most of us have a sense that it’s an unfair system. But does anyone know exactly how it’s unfair?

Legal scholar Ray D. Madoff knows. In The Second Estate, she offers an unprecedented look behind the scenes of America’s byzantine system of taxation, laying bare not only its capacity to consolidate wealth but also the mechanisms by which it has created two fundamentally separate American societies: the working Americans who pay and the ultra-rich who benefit.

This is not a story of offshore accounts or secret tax havens. In The Second Estate, Madoff shows that the US system itself has, over time, been stripped and reconstituted such that it now offers a series of secret paths, hidden in plain sight, for wealthy people in the know to avoid taxation altogether. Through the strategic avoidance of traditional income, leveraging of investments and debt, and exploitation of rules designed to promote charitable giving, America’s wealthy do more than just pay less than their share; they remove themselves from the tax system entirely. Wealth becomes its own sovereign state, and the living is surprisingly―and maddeningly―cheap.
 

Ray D. Madoff is a professor at Boston College Law School and the cofounder and director of the Boston College Forum on Philanthropy and the Public Good. She is the author of Immortality and the Law: The Rising Power of the American Dead and lead author of The Practical Guide to Estate Planning. Her writing has appeared in The New York Times, The Wall Street Journal,  The Washington Post, and The New York Review of Books, among other outlets.