Kalshi stake gives Trump Jr paper windfall as prediction market valuation climbs

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Trump Jr stake in Kalshi rises

Highlights

Donald Trump Jr received about $300,000 in Kalshi equity when the company was valued below $2 billion, now reaching a $22 billion valuation in last month's funding round.
Kalshi is in talks to raise funding at a $40 billion valuation in Q3 2025, amid soaring monthly trading volumes and rapid expansion in prediction markets.
Regulatory agencies have softened their stance on Kalshi and Polymarket after the 2024 election, with the CFTC dropping legal challenges in May 2025 and substantial legal scrutiny shifting to state-level lawsuits over sports contracts.

Equity award and valuation surge

As first reported by Financial Times, Donald Trump Jr received about $300,000 worth of Kalshi equity when he joined the privately held platform as a strategic adviser in early 2025, according to people familiar with the matter. The share grant gave him a stake when the company was valued at less than $2 billion, well below the $22 billion valuation reached in a funding round last month.

Trump Jr did not invest his own money in Kalshi at the time, one of the people said. Although his holding has been diluted as the company issued fresh equity over the past 18 months, the rise in Kalshi's valuation has still left him with a substantial paper gain.

Kalshi is also in talks to raise new funding at a valuation of about $40 billion as soon as the third quarter of this year. The platform allows users to trade on binary outcomes, including political and sports events.

Regulatory tailwinds and wider Trump ties

U.S. regulatory bodies led by the president's appointees are taking a hands-off approach to Kalshi and rival Polymarket after prediction markets moved into the mainstream during the 2024 election cycle. Both platforms have grown rapidly since then and are attracting billions of dollars in monthly trading volume, with sports betting accounting for much of the activity.

That growth is also drawing legal scrutiny from several U.S. states, which have filed lawsuits over sports-related contracts. Last month, President Trump called several prominent critics of the platforms "scum" in a social media post.

Trump Jr joined Kalshi two months after his father returned to the presidency and said in a January 2025 post on X that prediction markets had signalled the election result before traditional media outlets. He also joined Polymarket's advisory board last August, when 1789 Capital, an investment group where he is a partner, made a strategic investment of undisclosed size.

Before Trump's election victory, the Commodity Futures Trading Commission had tried to block Kalshi's event contracts tied to congressional elections, but the company won its case shortly before election day. The CFTC dropped its appeal in May 2025, and two months later the CFTC and the Department of Justice ended a probe into whether Polymarket had illegally accepted bets from Americans while officially serving overseas traders. Kalshi began offering crypto perpetuals in late May, and CME Group last week sued the CFTC over its approval of similar perpetual futures contracts tied to cryptocurrency prices.

Our earlier coverage of the legal battles over President Trump’s second-term executive actions described how U.S. courts have repeatedly moved to block or slow parts of his domestic agenda, particularly around immigration enforcement and National Guard deployments. It also noted that the Supreme Court’s June 2025 stance on lower-court stays, along with public backlash and the prospect of midterm shifts in Congress, could materially affect how far the administration can push policy despite ongoing judicial resistance.

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