Being Donald Trump’s eldest son has opened some interesting business doors for Donald Trump Jr. His connections to the prediction market industry have put him in positions at two companies competing for a share of a booming business. But with Democrats preparing to scrutinize the Trump family’s financial interests, one of those relationships has now ended.
Kalshi confirmed on Thursday that it had mutually agreed to end Don Jr.’s paid advisory role. The company pointed to his investment firm’s growing stake in Polymarket, one of its biggest competitors, as the reason for the split.
“We have mutually agreed to end Don’s advisory role after his firm’s significant investment in a competitor this past summer,” a Kalshi spokesperson told Reuters. The company added: “We are grateful for his contributions in helping us market Kalshi to more customers.”
Kalshi also said talks about ending Don Jr.’s contract started in August, after 1789 Capital increased its investment in Polymarket. The company says the decision was strictly business, although Reuters reported that some employees were worried his role could bring unwanted congressional scrutiny.
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The arrangement had been financially attractive for Trump Jr. When Kalshi hired him as a strategic adviser in January 2025, he reportedly received company shares worth approximately $300,000, according to the Financial Times. That was before the prediction market’s valuation climbed dramatically, reaching a reported $40 billion.
But Kalshi was not the only prediction market interested in having the president’s son on its side.
Trump Jr. joined Polymarket’s advisory board in August 2025, around the time his investment firm first backed the company. 1789 Capital subsequently led a $1 billion funding round for Polymarket, making the competing business relationship increasingly difficult for Kalshi to ignore.
The political situation has also changed considerably since he first joined Kalshi.
Democrats have won control of both chambers of Congress in the midterms and are preparing to investigate the Trump family’s business interests, including its connections to prediction markets.
California Democrat Robert Garcia, who is set to take over the House Oversight Committee, has already put the Trump family on notice.
“Democrats are ready to take on all of it; to take on the crime family that is sitting in the White House, to take on the large corporations ripping off the American taxpayer,” Garcia said in a video posted on X.
Oversight Democrats are ready to take on the crooks, the con men, and the Trump crime family. Lawyer up. https://t.co/Bat1pWfoEB
— Congressman Robert Garcia (@RepRobertGarcia) November 6, 2026
Sen. Elizabeth Warren has also been looking into the prediction market business. In a letter to Kalshi boss Tarek Mansour and Polymarket CEO Shayne Coplan, she questioned the “legitimacy and regulation” of election betting. Republican Sen. John Curtis also signed the letter.
Oregon Sen. Jeff Merkley has also called for tighter restrictions, telling Politico: “Folks are rightfully concerned about dangerous bets on elections, war, assassinations, terrorism, and government actions that go against the public interest.”
He added: “We need to rein in this gambling, and with Democrats taking back control of Congress, now is the time for long-overdue legislative action.”
Kalshi’s business took off during the 2024 election, when Americans began placing bets on political outcomes on an unprecedented scale. The Trump administration has since given prediction markets room to expand, but members of Congress are now asking whether wagers involving wars, elections and government decisions have gone too far.
Featured image via Political Tribune Gallery
