As US-Iran bets mint millions for prediction market users, questions over Donald Trump Jr’s involvement remain: Report

The largely unregulated ecosystem of prediction markets allows users to place direct bets on world events (e.g. Donald Trump’s re-election). More recently, users have made huge profits by placing correct bets on when the United States will attack Iran ($529 million in transactions on Polymarket, according to Bloomberg) and regime change in Iran after Supreme Leader Ali Khamenei (Kalshi reported $36 million).

However, with only one wallet and the need for complete anonymity, analysts have raised concerns about potential insider trading. According to a Bloomberg report, the betting contract dated February 27 (just a day ago) gained over $25 million in volume, and a $26,513 bet for Saturday (the account’s largest bet yet) netted its owner more than $1,74,000.

Analysts from Bubblemaps SA found that six accounts made a profit of $1 million by betting on February 28 (Saturday), the exact date of the attack. While analytics firm Polysights found that bets on the ouster of Iran’s religious leader had a 40 percent probability, it said its data showed 90 percent of accounts with alleged insider trading and supported the convention.

Trump’s connection to prediction markets

In the midst of all this, we look at the big guns, how much the markets as a whole are benefiting from, and who owns these prediction markets.

According to a report by the New York Times, Donald Trump Junior, the US President’s eldest son, is one of the key figures in Polymarket and Kalshi, two of the largest prediction markets.

The report stated that Trump Jr. was both an investor and unpaid consultant of Polymarket, while Kalshi was a paid consultant. He added that Truth Social, owned by the Trump family, has also announced plans to launch its own Truth Forecast.

Ethical questions loom amid loose regulations, no action

The report also noted that critics have long raised questions about the ethical boundaries crossed by the Trump family’s initiatives during Donald Trump’s second term as US President. He also noted that despite breaches of regulations, the Commodity Futures Trading Commission (CTFC) did not take enforcement action against Polymarket or Kalshi last year.

Citing Ann Skeet, senior director of leadership ethics at the Markkula Center for Applied Ethics, who told the NYT that Trump Jr.’s involvement was “problematic,” the report said Trump Jr.’s closeness to power and the fact that the city’s newest businesses are banking on information only a few people would know also raise suspicion.

How did Trump Jr respond to the allegations?

Andrew Surabian, a spokesman for Trump Jr., told the publication that the entrepreneur was limited to an advisory role at Polymarket and Kalshi, did not trade on the platform and never interacted with the federal government on behalf of any company in which he invested or advised.

“He works like any other businessman. The idea that Don, who has never worked in government in his life, would stop working in the private sector and providing for his five children just because his father was elected president is a ridiculous claim. The only conflict of interest that exists here is between the network of left-wing activists and their ideological allies in the media, who continue to use lies and unfounded insinuations to smear Don,” Surabian said.

However, the report also stated that Trump Jr.’s participation in the companies was seen as a benefit by the companies. Case in point: They appoint him as a consultant to their rivals Polymarket and Kalshi. Since Trump’s re-election, at least seven companies have approached his eldest son to join them as a board member, advisor or director, the report said.

Polymarket and Kalshi, Trump Jr. Did he benefit from the partnership?

The cases of the CEOs of Polymarket and Kalshi, who were under regulatory scrutiny, were dropped after the CFTC chose not to pursue the issues. Both have now joined the commission’s innovation council, which was created to help shape policy for cryptocurrency and prediction markets.

NYT reported a pattern in the decline in cases. Kalshi was banned in 2023, sued in federal court and won in 2024, hired Trump Jr. a week before Trump’s inauguration, and saw CFTC charges dropped four months later in 2025. In a statement to the NYT, the company denied that the connections to the president’s son worked. They said: “Donald Trump Jr. is not meeting with government officials on Kalshi’s behalf. We never asked him, and he has not intervened in cases on our behalf.”

Kalshi was founded in 2018 by financial analysts Tarek Mansour and Luana Lopes Lara and has received funding from venture capital (VC) firms Sequoia, Andreessen Horowitz and Y Combinator.

Polymarket agreed to pay a $1.4 million fine for failing to register as an online trading platform in 2022 and was ordered to block US users. CEO Shayne Coplan’s apartment was raided at a time when bets on the 2024 US presidential election are increasing. In July 2025, the CFTC and Department of Justice charges were dropped, and in August 2025, Trump Jr. invested in the company through his venture capital firm 1789 Capital. A week later, Polymarket was given permission to restart services in the US.

Polymarket was founded by Coplan and receives investment from a number of VC funds, including Intercontinental Exchange (ICE), the parent company of the New York Stock Exchange (NYSE), and Trump Jr’s 1789 Capital.

What is Accuracy Estimation?

The report stated that the Trump family’s company, Trump Media & Technology Group (TMTG), is close to joining the industry with Truth Predict.

According to NYT’s news, based on a statement from TTMTG, Truth Predict will use Crypto.com as its partner in crypto initiatives, and Truth Social users will be allowed to trade on topics such as sports, inflation, interest rates, gold and oil prices.

Spokesperson Surabian told NYT Trump Jr. was not involved in the decision to create Truth Predict and is not part of the company’s day-to-day operations.

Trump Jr. is also the sole trustee of his father’s trust and controls the president’s majority stake in the company. TMTG spokeswoman Shannon Devine said last year that Trump Jr. was “extremely engaged in operations and strategy as well as the work of the board.”

Citing US Securities and Exchange Commission (SEC) filings, the report stated that he earned $8,13,000 (largely in stock) as a director of TMTG in 2024; This accounts for approximately 25% of the company’s annual revenue.