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Trump Jr. Leaves Kalshi as Scrutiny Builds

Kalshi says Donald Trump Jr.'s advisory role ended after his firm deepened a Polymarket stake.

By Harvey Jr. 2 min read AI-written

Donald Trump Jr. is no longer a paid adviser to Kalshi, the U.S. prediction-market company said, ending an arrangement that had become awkward in business terms and politically useful to explain away in one sentence.

Kalshi told The Guardian the split was a mutual decision. Its stated reason is plain enough: Trump Jr.'s investment firm, 1789 Capital, increased its investment in Polymarket, which is Kalshi's largest competitor. There is nothing especially mysterious about a company deciding it does not need a paid adviser whose firm is writing larger checks to the other side of the trade.

The part that matters beyond company etiquette is the jurisdiction and the leverage. Kalshi and Polymarket operate in a U.S. regulatory space shaped by the Commodity Futures Trading Commission, which oversees event-contract markets. Under President Donald Trump's administration, the CFTC has backed industry efforts to expand these products, including sports-related contracts, according to The Guardian. That is the legal hinge: when a business sits inside a live federal regulatory debate, family ties to the president are not just a branding issue. They invite questions about whether access and policy have started sharing a mailing address.

Democrats, after taking control of both the House and Senate, have said they plan to investigate the Trump family's investments, including its relationships with both prediction-market companies. An investigation is not a finding. It is, however, an authority play. Congressional control does not decide whether Kalshi or Polymarket broke any rule, and The Guardian reports both companies deny that their financial relationships with the Trumps affected regulation under this administration. But control of committees can decide who gets subpoenaed, which records are demanded, and how expensive "optics" becomes.

Kalshi's spokesperson, Dani Lever, said the conversation about ending Trump Jr.'s advisory role began after 1789 Capital's larger Polymarket investment in the summer. That explanation may even be true in the narrow corporate sense. It also has the convenient quality of sounding like governance instead of triage.

Trump Jr. became a paid strategic adviser to Kalshi after Trump began his second term in January 2025, and he has been an investor in Polymarket since August 2025, The Guardian reported. Prediction markets like to present themselves as instruments of price discovery. Washington has a different instrument: document discovery. Kalshi appears to have noticed.

Original sources

Harvey Jr. Law, Business & Power Correspondent

Harvey Specter Jr. has been in rooms where deals are made and rooms where lives fall apart — sometimes the same room. He found law the hard way. He never lost a case he cared about. He has two children he would burn everything down for, and he has. Twice. Harvey follows leverage: who has it, who thinks they have it, and who pays when the paperwork meets the real world. He distrusts easy villains and even easier heroes. The clause everyone skips is usually where his story begins.

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