Ray Madoff: "The Tax System No Longer Taxes Investments And Inheritances" episode artwork

EPISODE · Jul 6, 2026 · 51 MIN

Ray Madoff: "The Tax System No Longer Taxes Investments And Inheritances"

from The Gist · host Mike Pesca

Today on The Gist, the media misinformation surrounding historical focus groups and billionaire tax histories. Then, Boston College Law School professor Ray Madoff joins the show to discuss her new book, The Second Estate: How the Tax Code Made an American Aristocracy. Madoff unpacks the modern "buy, borrow, die" strategy, detailing how the top tier of wealth utilizes the "step-up in basis" loophole to wash away billions in capital gains upon death. She challenges the legal and rhetorical definitions that prioritize taxing working-class wages over massive generational asset transfers and explains how the estate tax was systemically defanged into a multi-billion-dollar cover for dynastic wealth. Produced by Corey Wara Video and Social Media by Geoff Craig Do you have questions or comments, or just want to say hello? Email us at ⁠⁠⁠⁠[email protected] For full Pesca content and updates, check out our website at https://www.mikepesca.com/⁠ For ad-free content or to become a Pesca Plus subscriber, check out ⁠⁠⁠⁠https://subscribe.mikepesca.com/ For Mike's daily takes on Substack, subscribe to The Gist List https://mikepesca.substack.com/ Follow us on Social Media:⁠⁠⁠⁠ YouTube https://www.youtube.com/channel/UC4_bh0wHgk2YfpKf4rg40_g⁠⁠⁠⁠ Instagram https://www.instagram.com/pescagist/ X https://x.com/pescami TikTok https://www.tiktok.com/@pescagist To advertise on the show, contact ⁠⁠⁠⁠[email protected] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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Ray Madoff: "The Tax System No Longer Taxes Investments And Inheritances"

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