The son of the U.S. president is demonstrating a rare example of financial diversification that raises questions among regulators but guarantees him profit regardless of the outcome of the market battle. Donald Trump Jr. finds himself in a unique position: his venture fund, 1789 Capital, invested $300 million in Polymarket, while he himself holds a paid advisory role at the competing platform Kalshi. This strategy allows him to come out ahead no matter how events unfold.
Double Bottom: How the Investment Position Works
The financial structure looks as follows. In January 2025, Trump Jr. became a paid strategic advisor to Kalshi, and seven months later, his fund entered Polymarket's capital as part of a round valued at $1 billion. Subsequently, 1789 Capital's $300 million investment helped revalue the platform to $21 billion. The businessman acquired his stake in Kalshi even earlier, when the company was valued at a modest $300,000—today, that figure has grown to $22 billion.
In essence, Trump Jr. is tied to both of the largest U.S. event-betting platforms both financially and through advisory obligations. At the same time, both companies are fiercely competing for the same users and for unified regulatory rules.
Political Weight and Regulatory Risks
The situation is compounded by the fact that the president's son is using his political capital to protect the industry's interests. At a closed meeting in New Orleans in March, he personally urged Republican attorneys general to stop pressuring the platforms, arguing that the campaign against them was initiated by traditional gambling companies to protect their own businesses.
The conflict of interest is obvious: if Kalshi or Polymarket lose in any state, the blow would hit both businesses simultaneously. This year, the CFTC filed lawsuits against nine states, attempting to block their local-level regulation. The situation is most acute in Arizona, where a criminal case was opened against Kalshi over illegal gambling services.
President Trump himself in May called betting markets a new financial product and emphasized the need to maintain CFTC control over them. Thus, his son's interests have become part of a broader regulatory discussion.
My take: This ownership structure is not just a business move but effectively a lobbying mechanism embedded in both competing companies. For the market, this creates a serious reputational risk, as the platforms' independence from political influence becomes illusory. In the long term, this could lead to increased regulation rather than the deregulation the industry seeks.