Why's it so hard to tax billionaires?

A Search Engine two-parter

Oct 22, 2024

Happy Tuesday!

We have not one, but two new episodes for you this week. (Wow, no wonder the newsletter is so late (and short!))

Episode 1: A rogue IRS contractor leaks the private tax returns of the country’s wealthiest citizens to a reporter. That reporter, ProPublica’s Jesse Eisinger, learns that some of our billionaires are paying as little as zero dollars in federal income taxes. The story of how this country came up with an income tax in the first place, and how the wealthiest discovered an opt-out strategy.

Episode 2: We reveal the one weird trick some billionaires use to pay less in federal income taxes than you do. And we explain the consequences faced by the person who leaked the tax returns of billionaires like Jeff Bezos and Taylor Swift, thereby enraging some of the most powerful people in our country.

Follow Pro Publica’s reporting

The Secret IRS Files: Inside the Tax Records of the .001%

Gutting the IRS: Who Wins When a Crucial Agency Is Defunded

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Should we tax billionaire borrowings?

This was a question we got from a few listeners who heard the episode, and which Search Engine producer Garrott Graham was asking a lot during our work on the story.

Here’s what we know about that idea. The academics who conducted the research on taxing billionaire borrowings estimated that it would raise $100 billion in revenue over 10 years, which is, in the grand scheme of things ... not very much. On the other hand, reporter Jesse Eisinger thinks those estimates are probably on the conservative side. And either way, it's a solution aimed directly at closing the Buy, Borrow, Die loophole discussed in the episodes.

So, it’s a policy solution worth keeping an eye on that just didn't find its way into the episode, even though Garrott happened to be very charmed by the idea.

You can read a bit more about taxing billionaire borrowings here and even more here.

Another idea that I’m personally curious about is Georgeism, which, frankly, I barely understand right now. I know it begins with the idea of taxing land and then gets somewhat weirder. My old boss Alex Blumberg says we should do an episode on it. Depending on how these somewhat wonky episodes go over, perhaps we’ll consider.

OK, that’s it from us until Friday.

Thank you for allowing us into the sanctity of your email inbox. We’ll have a new episode of the show for you at the end of this week with one of our favorite recurring guests.

Talk to you soon,