Why Kalshi's Rough Week Could Reach the Supreme Court: DEX in the City

Watch on YouTube ↗  |  July 23, 2026 at 23:34  |  20:09  |  Unchained (Chopping Block)
Speakers
TuongVy Le — General Counsel, Veda Tech Labs / ex-SEC / Co-Host, DEX in the City
Jessi Brooks — General Counsel, Ribbit Capital / Co-Host, DEX in the City

Summary

The hosts dissect Kalshi’s tumultuous week, including Michigan’s lawsuit over sports event contracts, the CFTC’s historic use of emergency powers to block a state TRO, the cancellation of flight cancellation contracts due to backlash, and an insider trading allegation involving a Trump teleprompter operator. The discussion frames these events as a major federalism clash likely headed to the Supreme Court, with massive implications for the sports gambling and prediction market industries.

  • Michigan sued Kalshi, arguing its sports event contracts are gambling and require a state gaming license.
  • A state judge granted a TRO ordering Kalshi to liquidate Michigan traders' positions, which Kalshi complied with.
  • The CFTC invoked emergency powers—used only four times since the 1970s—to halt Kalshi from canceling the trades, pitting federal against state authority.
  • The emergency power use historically addressed market malfunctions, not state-federal disputes, marking a significant expansion.
  • The Michigan case has now become a broader federalism fight that is expected to reach the Supreme Court.
  • Kalshi pulled its planned flight cancellation contracts after public moral hazard concerns, vendor data pushback, and reputational risks.
  • An insider trading allegation surfaced involving Trump’s teleprompter operator betting on Kalshi, detected by Kalshi’s own surveillance.
  • If CFTC and Kalshi win, sports betting firms could convert to event contracts for lighter federal regulation, upending the state-based gambling framework.
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