Ray Madoff (on how billionaires avoid taxes & threaten capitalism)

2. september 2026 · 2h 26m

Ray Madoff (The Second Estate, Immortality and the Law, Practical Guide to Estate Planning) is a Boston College law professor, author, and tax-policy expert. Ray joins Armchair Expert to discuss being a proudly mediocre high school student, reluctantly trading philosophy for law school, and becoming a terrible Wall Street tax lawyer who loved teaching. Ray and Dax talk about America’s return to a pre-revolutionary aristocracy, how “salaries are for suckers” among the ultrawealthy, and why $50 trillion in wealth yielded only $28 billion in estate tax. Ray explains why high earners and wealth holders aren’t the same, how fair taxation could rescue capitalism, and why the problem is the system and not billionaires themselves.

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Armchair Expert with Dax Shepard

Ray Madoff (on how billionaires avoid taxes & threaten capitalism)

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