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From Vegas to Venezuela: High-Stakes Predictive Markets

By Stephen C. Piepgrass & Lu Reyes on January 9, 2026
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In this episode of Regulatory Oversight, host Stephen Piepgrass, who leads Troutman Pepper Locke’s Regulatory Investigation Strategy and Enforcement (RISE) practice, is joined by partner Lu Reyes for a deep dive into the national security and enforcement implications of predictive markets. The discussion centers on a headline‑grabbing Polymarket trade that appeared to anticipate former Venezuelan President Nicolás Maduro’s capture and yielded roughly $400,000 in profit, raising questions about insider trading and classified information leaks.

Stephen and Lu discuss how current regulatory frameworks and enforcement tools struggle to keep pace with emerging predictive markets, particularly where anonymity and digital assets can make it difficult to identify traders or trace funds. Drawing on Lu’s experience as a senior national security official in the Bush administration, they explore how markets that allow betting on geopolitical and military outcomes could place a cash bounty on secrets, potentially encouraging espionage, recruitment of insiders, and even attempts to influence events rather than merely predict them.

The episode also highlights key differences between predictive markets and traditional gambling, including post hoc event definitions and asymmetric access to information, and considers how regulators, Congress, and market operators might respond.


Transcript: From Vegas to Venezuela: High-Stakes Predictive Markets (PDF)

Photo of Stephen C. Piepgrass Stephen C. Piepgrass

Stephen leads the firm’s Regulatory Investigations, Strategy + Enforcement (RISE) Practice Group. He focuses his practice on enforcement actions, investigations, and litigation. Stephen primarily represents clients engaging with, or being investigated by, state attorneys general and other state or local governmental enforcement bodies,

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Stephen leads the firm’s Regulatory Investigations, Strategy + Enforcement (RISE) Practice Group. He focuses his practice on enforcement actions, investigations, and litigation. Stephen primarily represents clients engaging with, or being investigated by, state attorneys general and other state or local governmental enforcement bodies, including the CFPB and FTC, as well as clients involved with litigation, with a particular focus on heavily regulated industries. He also has experience advising clients on data and privacy issues, including handling complex investigations into data incidents by state attorneys general other state and federal regulators. Additionally, Stephen provides strategic counsel to Troutman Pepper’s Strategies clients who need assistance with public policy, advocacy, and government relations strategies.

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Photo of Lu Reyes Lu Reyes
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  • Posted in:
    Administrative and Regulatory, Banking, Finance and Securities, Government and Public Policy
  • Blog:
    Regulatory Oversight
  • Organization:
    Troutman Pepper Locke
  • Article: View Original Source

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