An extra-class conflict of interest: Donald Trump Jr. is simultaneously entrenched in the structures of two main competitors in the event betting market—Polymarket and Kalshi. His venture capital fund, 1789 Capital, invested $300 million in Polymarket, while he himself holds a paid advisory position and an ownership stake in Kalshi. This arrangement guarantees him financial gain regardless of who emerges victorious from this clash.
My analysis shows that this is not just a fortunate coincidence, but a well-thought-out strategy. 1789 Capital entered Polymarket's $1 billion funding round, after which 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's market capitalization has soared to $22 billion—growth that is hard to call random amid active lobbying by the family.
An advisor with a dual mandate
In January 2025, Trump Jr. took up the post of paid strategic advisor at Kalshi. Just seven months later, he joined the advisory board of Polymarket—it was then that 1789 Capital first invested in the project. Now the president's son is tied to the two largest betting platforms in the US, both by money and by job responsibilities. Both companies are waging a fierce battle for the same users and for unified rules of the game.
The ethical question here is sharper than it might seem at first glance. At Kalshi, responses to inquiries about the dual role state that Trump Jr. is exclusively involved in marketing strategy and does not consult on regulatory matters. However, the very framing of the issue—when an advisor works for two direct competitors—creates grounds for serious reputational risks.
Regulatory lobbying and direct contacts
Trump Jr.'s activity on the political front deserves special attention. He personally persuaded Republican attorneys general to stop pressuring betting platforms, speaking at a closed meeting in New Orleans in March. According to him, the campaign against such platforms was initiated by traditional gambling companies seeking to protect their business.
The context is extremely tense: the CFTC this year 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 most acute situation has developed in Arizona, where criminal proceedings were initiated against Kalshi in March for illegal gambling services.
President Trump himself has also supported the industry: in May, he called betting markets a new financial product and spoke in favor of maintaining CFTC oversight over them. Thus, his son's interests in leading platforms have become an integral part of the dispute over regulation of the entire market.
My verdict: Trump Jr. has created a win-win investment structure, but the price of such hedging is reputational costs and inevitable questions about transparency. As long as event betting markets remain in the regulatory gray zone, such intertwinings of interests will only intensify turbulence in this sector.