Donald Trump Jr.'s investment firm, 1789 Capital, made an early investment in Polymarket, a prediction market betting site, when the company was valued at $300 million. Following a series of regulatory changes and licensing approvals during the second Trump administration, Polymarket's valuation soared to $15 billion, resulting in a roughly 50-fold paper gain for 1789 Capital. This substantial return contributed to 1789 Capital's main fund achieving approximately 200% returns as of June 30, significantly outperforming the average 21% return for venture firms started in 2023.

Polymarket's trajectory dramatically shifted after facing a $1.4 million fine from the Commodity Futures Trading Commission (CFTC) in January 2022 and being banned from accepting monetary wagers from U.S. residents. The turnaround began in July 2025 when Polymarket acquired QCEX, a derivatives exchange with a CFTC license for $112 million, and a CFTC investigation against it was dropped. By November 25, the CFTC, led by a Trump appointee, cleared Polymarket to operate as a fully regulated U.S. platform. This regulatory approval reopened the U.S. market, its largest potential customer base, to Polymarket.

Following its regulatory approvals, Polymarket attracted significant investments, including up to $2 billion from Intercontinental Exchange (parent company of the NYSE), with a $600 million tranche completed in March. By April, Polymarket was reportedly seeking an additional $400 million at its $15 billion valuation. 1789 Capital's investment in Polymarket was made before these regulatory changes and before the platform became widely available in the U.S. Donald Trump Jr. also serves as a strategic adviser to Polymarket's rival, Kalshi, and has stated that he does not rely on inside information for his investments. The firm, co-run by Donald Trump Jr. and Omeed Malik, now manages about $3.5 billion, with approximately 40% from foreign investors.