Planet Money Planet Money

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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