Prediction markets are a multi-billion dollar industry, led by companies like Kalshi and Polymarket. They are also controversial. Some want them banned and believe they are operating illegally, while others see them as invaluable truth-seeking markets.

This podcast is a multi-hour deep dive on prediction markets, starting from conclave betting in 15th century Rome to the CFTC's proposed rulemaking on Rule 40.11 earlier this month.

My goal: The internet's most comprehensive explainer on prediction markets.

By the end of this episode, I promise you'll be in the top percentile for understanding prediction markets, regardless of where you're starting from. (You just might need to listen twice. There's a lot here.)

Timestamps:

0:00 Intro

1:40 16th century papal betting (Koleman Strumpf)

11:13 Insider trading rules on prediction markets (Bobby DeNault)

16:20 The Google search insider case and Rule 180.1 (Sam Enzer)

27:38 Why prediction markets matter (Chris Giancarlo)

33:20 Election betting in America38:35 Iowa Electronic Markets and the 1992 no-action letter

45:56 Dodd-Frank, swaps and the Special Rule

48:08 Senator Lincoln on Super Bowl and Derby contracts

55:49 Parlays as swaps (Josh Sterling)

1:01:23 CFTC's exclusive jurisdiction (Thania Charmani)

1:07:30 Perspective on the CFTC's NPRM (Michael Passalacqua)

1:14:55 Exceptions that swallow the rule (Paul Grewal)

1:27:25 How prediction markets actually work

1:36:05 Kalshi's probability-weighted fee structure

1:38:18 Cardi B and the resolution problem (Dustin Gouker)

1:45:05 Oracles, UMA and decentralized resolution (Jeff Amico)

1:51:55 Inside the Ninth Circuit case

2:07:49 The CFTC's June 2026 proposed rulemaking (Brad Bourque, Stefan Schropp)

2:19:06 Kalshi's landmark 2024 win

2:23:05 PASPA, Murphy v. NCAA (Daniel Wallach)

2:45:14 The case against banning prediction markets (Bobby DeNault)

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Sponsors: This episode is sponsored by Cahill Gordon & Reindel, the Hyperliquid Policy Center, and the Solana Policy Institute. To get in touch with the Cahill team about how the issues discussed in this episode apply to your situation, email mtomsky@cahill.com. Subscribe to Cahill's free client alerts on digital assets and emerging technology at https://www.cahill.com/news/index?search=1&practice=litigation-digital-assets-and-emerging-technology.

In this episode, you'll hear from the world's leading experts on the legal layer of prediction markets:

Josh Sterling, partner at Millbank
Bobby DeNault, Head of Enforcement at Kalshi
Chris Giancarlo, former Chairman of the CFTC
Daniel Wallach, founder of Wallach Legal LLC
Stefan Schropp, Senior Regulatory Counsel at Paradigm
Sam Enzer, partner at Cahill Gordon & Reindel and co-chair of CahillNXT
Paul Grewal, Chief Legal Officer at Coinbase
Koleman Strumpf, economics professor at Wake Forest
Brad Bourque, Policy Counsel at Hyperliquid Policy Center
Thania Charmani, partner at Winston & Taylor
Michael Passalacqua, Senior Advisor to CFTC Chairman Selig
Jeff Amico, Chief Operating Officer at Gensyn
Matt Kalish, co-founder of DraftKings and CEO of Hardscope
Dustin Gouker, author of the Event Horizons newsletter

Disclaimer: This podcast is for informational and educational purposes only and does not constitute legal or investment advice. Views expressed by guests are their own and do not necessarily reflect those of their employers. Listening to this podcast does not create an attorney-client relationship.