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

Armchair Expert with Dax Shepard · Sep 2, 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…