The son of the U.S. president has turned the competition between two giants of the event betting market into his own risk-free strategy. Donald Trump Jr.'s venture fund, 1789 Capital, invested $300 million in Polymarket, while he himself holds a paid advisory position at Kalshi and owns a stake in this competitor. The result: no matter the outcome, he comes out ahead.
Financial symmetry: how the deal works
My analysis shows that we are witnessing a unique precedent. 1789 Capital entered Polymarket's round at a $1 billion valuation, after which the platform was valued at $21 billion—a more than 20-fold increase. Trump Jr. acquired his stake in Kalshi back in 2025, when the company was valued at a modest $300,000. Since then, Kalshi's market capitalization has soared to $22 billion. This is not just investment—it is a strategic alliance that spans both sides of the market standoff.
An advisor with a double bottom
In January 2025, Trump Jr. took a paid position as a strategic advisor at Kalshi. Just seven months later, he joined the advisory board of Polymarket, simultaneously with the first tranche from 1789 Capital. Formally, Kalshi states that his role is limited to marketing strategy and does not touch regulatory matters. However, as industry insiders emphasize, such a combination is a direct conflict of interest, especially when it comes to fighting for the same users and the rules of the game.
Industry advocate and regulatory wars
Against this backdrop, Trump Jr. is actively lobbying for the sector's interests. According to my data, he personally urged Republican attorneys general not to pressure the platforms, arguing that the campaign against them was launched by traditional gambling companies to protect their business. The situation has reached a boiling point: the CFTC filed lawsuits against nine states, trying to block their attempts to regulate markets at the local level. Eight of these states are led by Democratic attorneys general, and in Arizona, criminal charges were even filed against Kalshi for illegal gambling services.
It is telling that President Trump himself in May called betting markets a new financial product, insisting on maintaining CFTC oversight. Thus, his son's interests in leading platforms have become part of a broader regulatory battle. Any defeat of one of the companies in a state court will hit both—and therefore Trump Jr.'s portfolio. But it is precisely this diversification that makes his position invulnerable.
My verdict: This is a brilliant, albeit cynical, example of how political capital is converted into financial capital. However, for the market, this is an alarming signal—when a key industry player simultaneously sits on both sides of the barricades, questions of ethics and transparency become critical for long-term investor trust.