The Second Estate: Where Billionaires Don’t Pay. You Do. (with 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 donor-advised fund highlights risks of DAF giving Washington Post - A Signature GOP Issue Is Omitted From Trump’s ‘Big’ Tax Bill. Weird New York Times - America Builds an Aristocracy Website: Facebook: Pitchfork Economics Podcast Bluesky: @pitchforkeconomics.bsky.social Instagram: @pitchforkeconomics Threads: pitchforkeconomics TikTok: @pitchfork_econ YouTube: @pitchforkeconomics LinkedIn: Pitchfork Economics Twitter: @PitchforkEcon, @NickHanauer Substack: ⁠The Pitch⁠

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The Second Estate: Where Billionaires Don’t Pay. You Do. (with Ray D. Madoff) is an episode from Pitchfork Economics with Nick Hanauer by Civic Ventures.

This episode is 50:11 long.

This episode was published on Apr 14, 2026.

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