US President's son Donald Trump Jr. has become a central figure in the standoff between two giants of the event betting market — Kalshi and Polymarket. And tellingly, his position looks like a perfect hedge: he has invested in both sides of the conflict, securing financial gain for himself regardless of who emerges victorious from this legal and business battle.
Trump Jr.'s venture fund, 1789 Capital, invested $300 million in a Polymarket funding round, after which the platform was valued at $21 billion. Meanwhile, he acquired a stake in the competing Kalshi back in 2025, when the company was valued at a modest $300 thousand. Since then, Kalshi's market capitalization has soared to $22 billion — a multiple-fold growth that makes any early investment in the project extremely profitable.
An advisor sitting on two chairs
The story began in January 2025, when Trump Jr. took a paid position as a strategic advisor at Kalshi. Just seven months later, he joined the advisory board of Polymarket, and his fund became an investor in the project. Thus, he is simultaneously tied by both capital and consulting obligations to two direct competitors that are fighting for the same users and the same regulatory framework.
The ethical question here begs itself. However, Kalshi emphasizes that Trump Jr. is exclusively involved in marketing strategy and does not participate in regulatory engagement matters. In practice, though, his dual role has landed at the epicenter of the dispute over the future of the entire industry.
Political lobbying and regulatory war
According to my information, Trump Jr. personally persuaded Republican attorneys general to stop pressuring betting platforms. He claimed that the campaign against such platforms was launched by traditional gambling companies seeking to protect their business from new digital competitors. These negotiations took place at closed-door meetings, including in New Orleans.
The situation escalated to the limit after the CFTC filed lawsuits against nine states, attempting to block their efforts to regulate betting markets at the local level. Eight of these states are led by Democratic attorneys general. The conflict was particularly acute in Arizona, where criminal proceedings were initiated against Kalshi in March for illegal gambling services.
Trump Jr.'s position is unique: if Kalshi or Polymarket lose in any state, it will hit both of his businesses simultaneously. But if the industry as a whole holds up and receives federal protection, his investments in both companies will yield enormous profits. The US President has also supported the industry, calling betting markets a new financial product and speaking in favor of maintaining CFTC oversight.
My expert assessment: This situation is a vivid example of how political capital and financial interests intertwine in the crypto industry. Trump Jr. is not simply diversifying risks — he is insuring himself against any outcome of the regulatory battle. However, such a conflict of interest creates a serious reputational risk for both platforms, which in the eyes of regulators may appear not as independent market players, but as pawns in a political game.