Donald Trump Jr. is deepening his ties to Polymarket through a new $300 million investment from 1789 Capital, his venture firm. He also holds a paid advisory role, and equity, at rival Kalshi, giving him a stake in whichever platform wins.

1789 Capital is contributing $300 million to Polymarket’s $1 billion round, valuing the platform at $21 billion. Trump Jr. separately holds a Kalshi stake, granted in 2025 and worth $300,000 at the time, before Kalshi’s valuation climbed to $22 billion.

Advisor to Both Sides

Trump Jr. became a paid strategic advisor to Kalshi in January 2025. He joined Polymarket’s advisory board seven months later, alongside 1789 Capital’s initial investment in the platform.

The arrangement gives the president’s son financial or advisory ties to the two largest prediction market platforms in the country. Both compete for the same users and the same regulatory outcomes.

Front Office Sports flagged the dual role at the time, noting that advising two direct rivals raises its own conflict-of-interest questions. Kalshi has told CNBC that Trump Jr.’s advisory work concerns marketing strategy, not regulatory matters.

A Direct Line to Regulators

The New York Times reported that Trump Jr. privately urged Republican attorneys general to stop pursuing prediction markets. The remarks came in March, at a closed-door gathering in New Orleans. He argued that traditional gambling companies were driving the pushback to protect their own market position. The Times cited people familiar with the matter.

The Commodity Futures Trading Commission has sued nine states this year to block state regulation of prediction markets. Eight of those states have Democratic attorneys general. Arizona has gone further than most, filing criminal charges against Kalshi in March over unlicensed gambling.

Trump Jr.’s dual advisory roles sit inside that fight. Any state loss for Kalshi or Polymarket touches a business he is tied to twice over.

President Trump has separately backed the industry. He called prediction markets a new class of financial product in May. He also argued that the CFTC’s authority over them should stay intact. His son’s financial interests in both leading platforms now sit atop that same policy debate.

Source: BeInCrypto