Prediction markets are a (poorly understood) multi-billion dollar industry. Polymarket, Kalshi and others processed over $20 billion in April of 2026 alone, while ongoing litigation is now playing out in courts across the country. 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. In this episode, you'll hear from the world's leading experts on the legal layer of prediction markets: Josh Sterling, partner at MillbankBobby DeNault, Head of Enforcement at KalshiChris Giancarlo, former Chairman of the CFTCDaniel Wallach, founder of Wallach Legal LLCStefan Schropp, Senior Regulatory Counsel at ParadigmSam Enzer, partner at Cahill Gordon & Reindel and co-chair of CahillNXTPaul Grewal, Chief Legal Officer at CoinbaseKoleman Strumpf, economics professor at Wake ForestBrad Bourque, Policy Counsel at Hyperliquid Policy CenterThania Charmani, partner at Winston & TaylorMichael Passalacqua, Senior Advisor to CFTC Chairman SeligJeff Amico, Chief Operating Officer at GensynMatt Kalish, co-founder of DraftKings and CEO of HardscopeDustin Gouker, author of the Event Horizons newsletterBy 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 America 44:50 Iowa Electronic Markets and the 1992 no-action letter 52:11 Dodd-Frank, swaps and the Special Rule 54:23 Senator Lincoln on Super Bowl and Derby contracts 1:02:04 Parlays as swaps (Josh Sterling) 1:07:38 CFTC's exclusive jurisdiction (Thania Charmani) 1:13:45 Perspective on the CFTC's NPRM (Michael Passalacqua) 1:21:10 Exceptions that swallow the rule (Paul Grewal) 1:33:40 How prediction markets actually work 1:42:20 Kalshi's probability-weighted fee structure 1:44:33 Cardi B and the resolution problem (Dustin Gouker) 1:51:20 Oracles, UMA and decentralized resolution (Jeff Amico) 1:58:10 Inside the Ninth Circuit case 2:14:04 The CFTC's June 2026 proposed rulemaking (Brad Bourque, Stefan Schropp) 2:25:21 Kalshi's landmark 2024 win 2:29:20 PASPA, Murphy v. NCAA (Daniel Wallach) 2:51:29 The case against banning prediction markets (Bobby DeNault) Newsletter: Stay updated on emerging tech law for free at lawofcode.fm. https://www.lawofcode.fm/ Any feedback on this episode? Or how to improve the podcast? Click here. https://forms.gle/W4d2a5aHuLJjuNdn7 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. 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.
