Kalshi reportedly gave Donald Trump Jr. a $300K stake when it was worth under $2B. Now at $22B, it wants to allow borrowed-money bets

Mike CrisolagoWed, September 23, 2026 at 9:00 PM UTC

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After Donald Trump Jr. joined prediction market platform Kalshi as a strategic advisor in January 2025, the president’s son reportedly received around $300,000 in equity in the company, according to a new Financial Times report.

The outlet spoke with unnamed sources which added that “Trump Jr.’s stake has been heavily diluted as Kalshi has grown and issued fresh equity over the past 18 months,” but it’s unknown how much the stake is currently worth.

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While Kalshi itself was worth less than $2 billion at the time of Trump Jr.’s onboarding, a May 2026 release put its current valuation at $22 billion.

Neither Trump Jr. nor Kalshi returned Moneywise’s request for comment.

What Kalshi sees in Trump Jr.

In announcing the Trump Jr. partnership last year, Kalshi crowed that “his extensive business experience and influence … brings a fresh perspective to Kalshi as we continue to push prediction markets into the mainstream.”

The company’s announcement also included a statement Trump Jr. had previously made on X, in which the president’s son said he “immediately knew I had to contribute to their [Kalshi’s] mission” after seeing the prediction platform correctly call the 2024 presidential race for his father.

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Some, however, have pointed to the Trump administration’s perceived support for prediction market platforms like Kashi and Polymarket — Trump Jr. also sits on the latter’s advisory board — via the Commodity Futures Trading Commission (CFTC). Trump nominee Michael Selig heads the CFTC, which has thrown its federal weight behind prediction markets in gambling lawsuits in states like Minnesota, New York and Arizona.

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Neither the White House nor the CFTC replied to Moneywise’s request for comment regarding the potential conflict of interest, given Trump Jr.’s association with Kalshi and Polymarket. In the meantime, Kalshi is now asking the CFTC to let it broaden its platform perimeters and allow borrowed-money bets, CNBC reports.

Kalshi is betting on bigger players

Kalshi reportedly applied for regulatory approval this week to allow some users of its platform to engage in margin trading, which allows users to place bets using borrowed funds, a move that CNBC noted is believed to be “a critical step needed for bigger players to participate” in prediction markets.

Kalshi told the outlet that “the company would avoid offering margin opportunities on its sports event contracts, as well as its culture and ‘mention’ markets,” and that the move would “make longer-dated prediction markets, those with expiration dates far in the future, more attractive to institutional traders.”

Many also pointed out that Kalshi already has permission for such bets for its perpetual futures.

To that end, the Wall Street Journal reported in early September that Kalshi also wants “regulatory approval to start offering the country’s first regulated perpetual futures tied to single stocks” like Apple, Nvidia and Tesla.

“You’re going to have the ability to place these bets around the clock. And perpetual futures usually have much more leverage than you have with respect to single stock ETFs,” Benjamin Schiffrin, director of securities policy for the non-profit financial regulatory advocate Better Markets, told the outlet.

“I think there’s just the potential for huge losses, especially amongst individual investors.”

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Source: “AOL Money”