1789 Capital, the venture firm linked to Donald Trump Jr., is contributing about $300 million to Polymarket’s roughly $1 billion funding round, valuing the prediction-market platform at $21 billion and deepening the firm’s stake after an earlier position of about $200 million. Trump Jr. is a partner at 1789 Capital and sits on Polymarket’s advisory board; he separately became a paid strategic adviser to rival Kalshi in January 2025 and received an equity stake then valued at $300,000, before Kalshi raised capital at a $22 billion valuation. Kalshi has said his work there concerns marketing strategy rather than regulatory matters, while Front Office Sports has flagged the dual advisory roles at direct competitors. The New York Times reported that in March he privately urged Republican attorneys general at a closed-door gathering in New Orleans to stop pursuing prediction markets, arguing traditional gambling companies were driving the pushback. The dual ties sit atop a federal-state fight in which the Commodity Futures Trading Commission has sued nine states to block state regulation, Arizona has filed criminal charges against Kalshi over unlicensed gambling, and President Trump has backed prediction markets as a new class of financial product under intact CFTC authority.