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On July 28, U.S. District Judge Denise Cote of the Southern District of New York entered a judgment against Papaya Gaming Ltd. in Skillz Platform Inc. v. Papaya Gaming Ltd., No. 1:24-cv-01646. The ruling followed an April jury verdict of $420 million in damages; the court separately awarded $719 million in disgorgement—an alternative remedy the plaintiff may elect in lieu of damages—along with $10.1 million in attorneys’ fees. The lawsuit stemmed from Papaya’s alleged misrepresentation that its mobile cash tournament games rewarded player skill, when the outcomes were instead shaped by undisclosed bots designed to replicate a house advantage.

In this crossover episode of Payments Pros and Regulatory Oversight, Stephen Piepgrass and Keith Barnett provide an update on the fast-developing prediction markets landscape. They discuss how federal and state regulators are responding to the growth of event contracts and the legal questions surrounding this emerging market. The conversation highlights the CFTC’s continued focus on oversight, market integrity, and the need for platforms to maintain strong controls to detect and prevent manipulation or other improper trading activity.

This article was originally published in Dow Jones Risk Journal and is republished here with permission as it originally appeared on May 4, 2026.

Prediction markets allow users to trade event contracts on real-world events, such as election outcomes, sporting events and even the highest temperature in New York City today. Seemingly overnight, they have achieved mainstream prominence. Since 2025, Kalshi’s user base alone has grown from approximately 600,000 to more than 5,000,000.

On March 11, Kalshi filed a lawsuit in the U.S. District Court for the Southern District of Iowa against Attorney General (AG) Brenna Bird and members of the Iowa Racing and Gaming Commission. Kalshi’s complaint asks the court to declare that the Commodity Exchange Act (CEA) and the Commodity Futures Trading Commission’s (CFTC) “exclusive jurisdiction” over trading on designated contract markets preempt Iowa’s gambling and election‑wagering provisions as applied to Kalshi’s event contracts.

On March 12, 2026, the Commodity Futures Trading Commission’s (CFTC) Division of Market Oversight issued Staff Advisory Letter No. 26-08 to all designated contract markets (DCMs), signaling a supportive stance toward prediction markets and other event-based derivatives, including contracts based on the outcome of sporting events. While reiterating existing compliance obligations, the advisory emphasizes the agency’s interest in fostering innovation and growth in these markets within the framework of the Commodity Exchange Act. At the same time, the CFTC released an advance notice of proposed rulemaking seeking broad public comment on whether and how to further regulate event contracts.

A recent decision from the U.S. District Court for the Middle District of Tennessee marks a significant development in the ongoing dispute over whether sports event contracts offered on prediction market platforms are properly regulated by the Commodity Futures Trading Commission (CFTC) or whether such contracts should be regulated by the states as sports betting. Tennessee officials had issued a cease‑and‑desist order contending that certain sports‑linked event contracts were akin to unlicensed sports wagering under state law. Prediction contract platform provider, Kalshi, responded by filing suit in federal court, arguing that these contracts were “swaps” governed exclusively by the Commodity Exchange Act and subject to the CFTC’s jurisdiction, not Tennessee’s sports‑betting framework.

In this crossover episode, Regulatory Oversight host Stephen Piepgrass teams up with Payments Pros host Keith Barnett to unpack how prediction markets, gaming, and payments intersect in a rapidly evolving and legally uncertain landscape. Drawing on Keith’s extensive regulatory experience, they explain what prediction markets are, why these contracts are treated as swaps rather than securities, and how that distinction affects insider trading issues. Stephen and Keith then address the growing tension between federal regulators and state attorneys general over whether these products are trading or unlicensed sports betting, the CFTC chair’s recent criticism of “regulation by enforcement,” and the NCAA’s push to pause college sports contracts. They close by examining what this means for banks, payment processors, and other service providers navigating know-your-customer and “lawful transaction” obligations while the law remains in flux.

Stephen Piepgrass, a partner in Troutman Pepper Locke’s Regulatory Investigations, Strategy, and Enforcement Practice Group, was quoted in the January 30, 2026 Corporate Compliance Insights article, “CFTC Withdraws Proposed Rule on Prediction Markets.”

“Taken together, these statements leave observers unclear about what position the CFTC may ultimately take on insider trading-type behaviors,” Stephen…

State attorneys general (AGs) are among the most active and influential regulators in the U.S., using broad statutory authority, political visibility, and growing technical knowledge to shape policy and enforcement across sectors. In 2025, they asserted their authority to shape the legal and regulatory environment across the U.S. through aggressive and coordinated action. Despite changing…