The leaked tapes that show how the rich avoid taxes
May 27, 2026
Summary
Planet Money investigates a controversial tax loophole allowing wealthy Americans to shelter assets in Maltese retirement accounts. Former IRS lawyer Carolyn Shank details the agency’s initial crackdown, which was halted after Kenneth Keyes, a lobbyist for the scheme, joined the Trump administration. The episode explores the blurred line between legal avoidance and evasion, revealing how political shifts can stall enforcement efforts.
Topics discussed
Intro: IRS investigations and whistleblower stories
Episode overview: The life cycle of a tax loophole
Tax avoidance vs. evasion and the Malta connection
Origin of the loophole: US-Malta tax treaty and Roth IRAs
Pitching the loophole to the ultra-wealthy
IRS crackdown: The Dirty Dozen list and economic substance
Closing the loophole via treaty clarification
Industry pushback: Secret recordings and lobbying strategies
The 'Come Clean' rule and IRS enforcement under Biden
Political shift: Trump administration and stalled regulations
Conclusion: The malleable line between legal and illegal
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