Donald Trump Jr. is reportedly sitting on a sizable paper gain after prediction market platform Kalshi handed him equity worth roughly $300,000 when he joined as a strategic adviser in early 2025.
Trump Jr. did not invest his own money. Kalshi granted him the stake when the company was valued at under $2 billion — less than a tenth of its $22 billion valuation in a funding round last month, the Financial Times reported on Friday, citing people familiar with the matter.
The company is also reportedly in talks to raise fresh capital at a valuation of around $40 billion as soon as the third quarter of this year.
The Regulatory Tailwind
Kalshi has been a direct beneficiary of the Trump administration’s light-touch approach to prediction markets. The Commodity Futures Trading Commission (CFTC), which had previously tried to halt Kalshi’s event contracts on congressional elections, dropped its appeal against the company in May 2025.
Two months later, the DOJ ended a separate probe into rival platform Polymarket over whether it had illegally accepted bets from American traders.
Trump Jr. announced his Kalshi role in January 2025 on X, writing that his family had used the platform on election night to know they had won “hours ahead of the fake news media.”
A Pattern Of Strategic Bets
The Kalshi stake is part of a broader pattern. Trump Jr. also sits on Polymarket’s advisory board, holds a small stake in online weapons retailer GrabAGun, and joined cage-fighting group MMA as a strategic adviser last September.
Together with his brother Eric, he has contributed to a $1 billion war chest invested in drone manufacturers and crypto companies.
Kalshi and Polymarket now attract billions in monthly trading volume, though sports betting on both platforms has triggered lawsuits from several U.S. states.
Kalshi and spokespeople for Trump Jr. did not immediately respond to Benzinga‘s requests for comment.
Disclaimer: Kalshi and Benzinga have an existing data collaboration agreement.
Image via Shutterstock
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