Donald Trump Jr.'s strategic position in the U.S. prediction market is unique: he is linked to both main competitors — Polymarket and Kalshi. His venture fund, 1789 Capital, invested $300 million in Polymarket as part of a round that valued the platform at $21 billion. Meanwhile, he acquired a stake in Kalshi back in 2025, when the company was valued at a modest $300,000. Today, Kalshi's market capitalization has grown to $22 billion. Thus, the president's son is hedged against any outcome of the competitive battle: regardless of who wins, his investments will yield a profit.
An advisor sitting on two chairs
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 major injection from 1789 Capital. Such a dual role is rare even for such a niche industry. This is not only about money, but also about direct access to the management processes of both platforms, which are fighting for the same audience and the same set of rules in the U.S. market.
The question of ethics and conflict of interest here is obvious. At Kalshi, however, they were quick to assure that Trump Jr. is exclusively involved in marketing strategy and does not advise on regulatory matters. In practice, however, his influence appears to extend far beyond PR.
Regulatory lobbying and direct contacts
His activity on the political track is of particular interest. Trump Jr. personally persuaded Republican attorneys general to stop pressuring event-betting platforms. In March, at a closed meeting in New Orleans, he claimed that the campaign against such platforms was allegedly initiated by traditional gambling companies to protect their own business.
The conflict reached its peak this year when the CFTC filed lawsuits against nine states, trying to block their attempts to regulate prediction markets at the local level. Eight of these states are led by Democratic attorneys general. The situation became most acute in Arizona, where in March a criminal case was opened against Kalshi for illegal gambling services.
Trump Jr.'s position found itself at the epicenter of this struggle. If Kalshi or Polymarket lose in any state, the blow will land on both businesses he is connected to. Notably, the U.S. president himself has supported the industry: in May, he called betting markets a new financial product and spoke in favor of keeping CFTC oversight over them. Thus, his son's interests in the leading platforms have become an integral part of the broader dispute over regulating this rapidly growing sector.
My take: such an intertwining of political capital and market positions creates a precedent that could cost the entire industry dearly. When regulators see that key players in the prediction market are using administrative resources for lobbying, trust in them as independent "oracles" will be undermined. For long-term growth, the sector needs transparency, not family symbioses with power.