Key Takeaways:
Prediction market Kalshi gave Donald Trump Jr. about $300,000 in shares after he became a strategic adviser early last year, a stake now poised to multiply in value as the startup's valuation surges toward $40 billion.
Kalshi handed the president's eldest son the shares shortly after he joined as a strategic adviser in January 2025, when the prediction market platform was valued at less than $2 billion, the Financial Times reported, citing unnamed sources familiar with the matter.
"While biased outlets called the race a coin toss, my family and close friends used prediction market @Kalshi to know we had won hours ahead of the fake news media," Trump Jr. wrote on X in January 2025, announcing his advisory role.
The stake came as Kalshi was valued at under $2 billion, a fraction of the $22 billion price tag in its most recent financing round last month. The startup is now in talks to raise funds at a valuation of about $40 billion, which could happen as soon as the third quarter of this year, the FT reported. Trump Jr.'s shares have been diluted as Kalshi grew, making their exact current value difficult to determine.
The arrangement raises questions about regulatory capture as Kalshi has benefited from a lighter touch under US agencies now led by Trump appointees. The CFTC abandoned its appeal against Kalshi's election contracts in May 2025 after the startup secured a court victory, and the agency — alongside the Department of Justice — closed an investigation into rival Polymarket last summer.
A Regulatory Landscape Transformed
Kalshi's legal victory came shortly before Election Day 2024, when a federal court ruled the CFTC could not block the platform from offering event contracts tied to congressional elections. The agency dropped its appeal in May 2025, effectively clearing the path for prediction markets to operate in the US without the threat of federal enforcement.
Trump Jr.'s ties to the sector extend beyond Kalshi. He joined Polymarket's advisory board in August 2025, coinciding with a strategic investment in the company by 1789 Capital, the investment firm where he is a partner. The CFTC and DOJ closed their investigation into Polymarket in summer 2025, which had examined whether the platform illegally accepted wagers from US customers.
Kalshi declined to comment to the FT, and Trump Jr. did not respond to the paper's requests for comment.
What's at Stake
The convergence of political connections, regulatory forbearance, and surging valuations creates a dynamic that critics say blurs the line between legitimate business growth and preferential treatment. For Kalshi, the path to a $40 billion valuation depends not only on user adoption but on maintaining the regulatory tailwinds that have emerged since the change in administration. The startup's next fundraising round, expected as soon as the third quarter, will test whether investors see the current environment as sustainable or contingent on political alignment.
This article is for informational purposes only and does not constitute investment advice.
