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

Pitchfork Economics with Nick Hanauer

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: http://pitchforkeconomics.com

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

More description

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: http://pitchforkeconomics.com

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

2026-04-14 50 min
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