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 and a stake in competing platform Kalshi. Essentially, he comes out ahead no matter who wins this battle of giants.
1789 Capital's investment in Polymarket's $1 billion round was a landmark: afterward, the platform was valued at $21 billion. Trump Jr. acquired his stake in Kalshi back in 2025, when the company was valued at a modest $300,000. Since then, Kalshi has grown to $22 billion—growth that is hard to describe as anything other than phenomenal.
Advisor on both sides
In January 2025, Trump Jr. took on the role of paid strategic advisor at Kalshi. Just seven months later, he joined the ranks of advisors at Polymarket—that was when 1789 Capital first invested in the project. Now the president's son is tied to the two largest event-betting platforms in the U.S. through both money and job responsibilities. Both companies are waging a fierce battle for the same users and the same rules of the game.
Such a dual role inevitably raises questions of ethics and conflicts of interest. Kalshi responds that Trump Jr. is exclusively involved in marketing strategy and does not advise on regulatory matters. However, how true that is remains a big question.
Direct contact with regulators
According to my information, Trump Jr. personally urged Republican attorneys general to stop pressuring betting platforms. He made this case at a closed meeting in New Orleans in March, arguing that the campaign against such platforms was initiated by traditional gambling companies to protect their own business.
This year, the CFTC filed lawsuits against nine states to prevent them from regulating betting markets at their own level. Eight of those states are led by Democratic attorneys general. The situation became especially acute in Arizona, where criminal charges were filed against Kalshi in March for illegal gambling services.
Trump Jr.'s dual role has landed at the very center of this struggle. Should Kalshi or Polymarket lose in any state, the blow would hit both businesses he is connected to at once.
Separately, the U.S. president himself supported the industry. In May, he called betting markets a new financial product and stated that CFTC oversight over them should be maintained. Thus, his son's interests in leading platforms became part of the dispute over market regulation.
My analysis: the situation is unprecedented. Trump Jr. has not simply invested in two competing platforms—he has become a bridge between them and regulators. This creates systemic risk for the entire sector: if his influence is perceived as excessive, it could trigger stricter regulation that would hit both companies simultaneously. Investors should closely monitor developments in Arizona and other states.