Trump’s Complicated Stance On Prediction Markets

Trump’s administration actively supports prediction markets in spite of his complicated gambling legacy that includes Atlantic City casino bankruptcies in the 1980s. Trump owned numerous casinos during that era and boasted about their success before they eventually collapsed financially. The former casino mogul publicly supported online gaming legislation in 2011, stating the U.S. was missing out while other countries embraced digital betting. His second-term administration has taken several steps to help online betting markets, including ending restrictions on Polymarket’s U.S. operations. Trump Media announced plans in October to offer prediction markets on Truth Social through Crypto.com. The CFTC now battles state regulators over exclusive authority to oversee these markets.

Trump Denounces Prediction Markets Despite Administration’s Pro-Gambling Stance

Following the Department of Justice indictment of U.S. Army soldier Gannon Ken Van Dyke, Trump expressed discontent with prediction markets during an Oval Office exchange with reporters. “The whole world, unfortunately, has become somewhat of a casino,” Trump stated. He added that he was “never much in favor” of betting in financial markets and declared himself “not happy with any of this”.

Van Dyke faces charges for using classified information about Operation Absolute Resolve to profit more than £317,664.05 on Polymarket. The soldier placed 13 bets between December 27, 2025, and January 2, 2026, wagering on outcomes related to Maduro’s capture and U.S. military action in Venezuela.

Trump compared the case to Pete Rose, the baseball manager banned for betting on his team, stating, “Now, if he bet against his team, that would be no good, but he bet on his own team”.

Despite Trump’s criticism, his administration defends prediction markets aggressively. CFTC Chair Michael Selig called them “valuable to society” and withdrew Biden-era proposals banning prediction markets on sports and elections. The CFTC sued states attempting to regulate these platforms, arguing only federal jurisdiction applies.

White House staff received an email on March 24 prohibiting the use of non-public information for prediction market bets.

How Trump Family Profits from the Prediction Markets Boom

Donald Trump Jr. secured a financial stake in the prediction markets industry through multiple channels that raise questions about conflicts of interest. His venture capital firm 1789 Capital invested double-digit millions of dollars in Polymarket, with Trump Jr. joining the platform’s advisory board as part of the arrangement. The investment positions him to benefit directly from Polymarket’s expansion, which recorded £4.76 billion in trading volume during the first half of the year.

Trump Jr. simultaneously maintains a paid strategic advisor role with Kalshi, Polymarket’s direct competitor in prediction markets. Both platforms recently raised substantial funding rounds, with Kalshi securing £146.92 million led by Paradigm while Polymarket attracted over £158.83 million from Peter Thiel’s Founders Fund. A spokesman for Trump Jr. stated the dual roles don’t create conflicts, claiming he remains “committed to supporting the prediction market industry as a whole”.

Trump Media deepened the family’s financial exposure through a partnership with Crypto.com. The company purchased £83.39 million in Cronos tokens for its balance sheet, while Crypto.com acquired £39.71 million in Trump Media stock. According to the mutual cooperation agreement, Trump Media will integrate the CRO token across Truth Social and Truth+ platforms, creating a rewards system anchored by Crypto.com’s digital wallet infrastructure.

Federal Regulators Launch Aggressive Campaign to Control Prediction Markets

The CFTC filed lawsuits in early April against Arizona, Connecticut, Illinois, and New York, demanding federal courts declare states lack authority to regulate prediction markets. Chairman Michael Selig stated the agency would defend its exclusive jurisdiction against what he termed “overzealous state regulators”. Hours after New York Attorney General Letitia James joined 37 other attorneys general in supporting Massachusetts’ case against Kalshi, the CFTC sued New York in Manhattan federal court.

The bipartisan coalition of 38 state attorneys general argued Kalshi’s sports betting violated state gambling laws. Kalshi users wagered more than £0.79 billion monthly on the platform in 2025, with sports betting accounting for roughly 90% of volume in certain months. The coalition rejected Kalshi’s claim that its contracts qualify as financial “swaps” under the Dodd-Frank Act, stating Congress designed that legislation to address instruments causing the 2008 recession, not legalize sports gambling nationwide.

Court rulings split sharply. The Third Circuit sided with Kalshi against New Jersey, while judges in Nevada, Maryland, Ohio, and Massachusetts ruled against the platform. Arizona filed the first criminal charges against Kalshi in March for operating unlicensed gambling and election wagering. A federal judge granted a temporary restraining order blocking Arizona’s prosecution on April 10. Analysts expect the dispute to reach the Supreme Court by 2028.