The Second Estate: Where Billionaires Don’t Pay. You Do. (with Ray D. Madoff)

The Second Estate: Where Billionaires Don’t Pay. You Do. (with Ray D. Madoff)

From Pitchfork Economics with Nick Hanauer by Civic Ventures

April 14, 2026 · 50 min

About this episode

Nick and Goldy discuss the disparities in the tax system with tax law expert Ray D. Madoff.

Would it be a surprise if we told you the rich don’t actually live in the same tax system as everyone else? Tomorrow is Tax Day, when millions of Americans will be filing their taxes or applying for extensions, so Nick and Goldy sit down with Ray D. Madoff, Professor of Tax Law at Boston College, and author of The Second Estate, to pull back the curtain on how wealth really moves—and why so much of it never gets taxed at all. Because here’s the twist: The system wasn’t supposed to work this way. But over time, something changed. Now, the people who live off paychecks carry the tax burden… while the people living off wealth often don’t have to play the game at all. Professor Madoff explains what happened and what it would take to fix it. Ray D. Madoff is a professor at Boston College Law School and director of the Forum on Philanthropy and the Public Good. She is a leading expert on tax policy, wealth, and philanthropy, and author of The Second Estate: How the Tax Code Made an American Aristocracy. Social Media: @raymadoff Further reading: The Second Estate: How the Tax Code Made an American Aristocracy. The Atlantic - How to Tax Billionaires CNBC - Lawsuit over $21 million…

People in this episode

Host: Nick Hanauer

Guest: Ray D. Madoff

Topics covered

  • tax policy
  • wealth inequality
  • billionaires
  • tax system
  • philanthropy

Keywords

  • taxes
  • wealth
  • billionaires
  • tax law
  • American aristocracy

Mentioned in this episode

Organizations: Boston College, Civic Ventures, The Atlantic, CNBC, Washington Post, New York Times

Books & works: The Second Estate

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