Donald Trump Jr. Profits from Both Kalshi and Polymarket

Donald Trump Jr., through his venture firm 1789 Capital, is increasing his involvement with Polymarket via a $300 million investment. He also serves as a paid advisor and holds equity in Kalshi, a competitor, meaning he benefits from the success of either platform.

The $300 million from 1789 Capital is part of Polymarket's $1 billion funding round, which values the prediction market at $21 billion. Trump Jr. also holds a separate stake in Kalshi, awarded in 2025 and then valued at $300,000, before Kalshi's valuation rose to $22 billion.

Advisor to Both Sides

In January 2025, Trump Jr. started as a paid strategic advisor at Kalshi. Seven months after that, he took a seat on Polymarket's advisory board, coinciding with 1789 Capital's first investment in that platform.

Trump Jr's firm led a $1 billion Polymarket raise while he also advises Kalshi

"1789 Capital is putting in about $300 million, adding to a roughly $200 million stake, as the prediction market's valuation rises from $15 billion to $21 billion."

"Interestingly, Polymarket is not… https://t.co/7DNyvHDDAo

— The Wolf Of All Streets (@scottmelker) September 1, 2026

As a result, the president's son has financial or advisory connections to the nation's two biggest prediction market platforms. These two platforms vie for the same customers and face the same regulatory environment.

Front Office Sports highlighted the dual role when it was announced, pointing out that advising two direct competitors creates inherent conflict-of-interest issues. Kalshi has informed CNBC that Trump Jr.'s advisory responsibilities are limited to marketing strategy, not regulatory issues.

A Direct Line to Regulators

According to a New York Times report, Trump Jr. privately encouraged Republican attorneys general to cease their pursuit of prediction markets. The comments were made in March during a private meeting in New Orleans. He contended that traditional gambling firms were behind the opposition, seeking to safeguard their own market share. The Times based its report on individuals with knowledge of the discussions.

This year, the Commodity Futures Trading Commission has taken legal action against nine states to prevent them from regulating prediction markets. Eight of those states have Democratic attorneys general. Arizona has taken the most aggressive stance, bringing criminal charges against Kalshi in March for operating unlicensed gambling.

Trump Jr.'s dual advisory positions are directly within this conflict. Any legal defeat for Kalshi or Polymarket affects a business with which he has ties on both fronts.

President Trump has also supported the industry independently. In May, he described prediction markets as a new category of financial product. He further stated that the CFTC should retain its authority over them. His son's financial involvement in the two major platforms now sits at the center of that same policy discussion.