The largely unregulated prediction markets ecosystem allows for users to place direct bets on world events (Donald Trump’s re-election for example). More recently, users made big gains by correctly placing bets on when the United States would strike Iran ($529 million in trades on Polymarket as per Bloomberg), and regime change in Iran following Supreme Leader Ali Khamenei (reportedly $36 million on Kalshi).
However, with need for only a wallet and complete anonymity, analysts have raised concerns over potential insider trading. One contract with bet for 27 February (just a day earlier), gained over $25 million in volume and a $26,513 bet for Saturday (this account’s largest bet ever), pocketed for its owner over $1,74,000, the Bloomberg report said.
Analysts from Bubblemaps SA found that six accounts minted $1 million in profits by betting the exact date of the attack — 28 February (Saturday), it added. While analytics company Polysights found bets placed on the overthrow of the Iranian supreme leader at 40% likelihood, but said its data showed 90% of alleged insider trading accounts, supported the contract.
The Trump connection to prediction markets
Amid all this, we take a look at the big guns — how much the markets as a whole benefitted, and who own these prediction markets.
According to a New York Times report, the US President’s eldest son, Donald Trump Junior, is a key figure in two of the biggest prediction markets — Polymarket and Kalshi.
Trump Jr is both investor and unpaid advisor to Polymarket, and a paid advisor to Kalshi, the report said. It added that the Trump family’s Truth Social has also announced plans to start its own Truth Predict.
Ethical questions loom amid loose regulations, no action
The report further noted that critics have long raised questions over ethical lines crossed by the Trump family ventures amid Donald Trump‘s second term as US President. It further noted that despite breaching regulations, the Commodity Futures Trading Commission (CTFC) did not pursue enforcement against Polymarket or Kalshi last year.
Trump Jr’s proximity to power and the newest businesses in town making bank on information that only few would know has also raised eyebrows, the report said, citing Ann Skeet, senior director of leadership ethics at the Markkula Center for Applied Ethics, who told NYT that Trump Jr’s involvement is “problematic”.
How has Trump Jr responded to allegations?
Andrew Surabian, a spokesman for Trump Jr., told the publication the entrepreneur is limited to an advisory role in Polymarket and Kalshi, does not conduct trades on the platform, and never interacts with the federal government on behalf of any company he has invested in or advises.
“He operates like any other businessman. The idea that Don, who has never worked in the government in his life, should cease working in the private sector and providing for his five children, just because his dad was elected president, is an absurd premise. The only conflict of interest that exists here is between the network of left-wing activists and their ideological allies in the media who keep using lies and baseless innuendo to smear Don,” Surabian said.
However, the report further noted that Trump Jr’s involvement in companies is viewed as a benefit by companies. Case-in-point: Both Polymarket and Kalshi — rivals — have him as an advisor. It added that since Trump’s re-election, at least seven other companies have approached his eldest son to join as either a board member, advisor or director.
Did Polymarket, Kalshi benefit from Trump Jr association?
CEOs of Polymarket and Kalshi, which were under regulatory scrutiny, had their cases dropped after the CFTC chose to not pursue the issues. Both have now joined the commission’s innovation council created to help shape policy for cryptocurrency and prediction markets.
NYT reported a pattern to the drop 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 four months later saw the CFTC charges dropped in 2025. In a statement to NYT, the company denied that links to the president’s son helped. They said: “Donald Trump Jr. does not engage with government officials on Kalshi’s behalf. We have never asked him, nor has he ever intervened in court cases for us.”
Kalshi was established by financial analysts Tarek Mansour and Luana Lopes Lara in 2018 and has received funding from venture capital (VC) firms Sequoia, Andreessen Horowitz, and Y Combinator among others.
For Polymarket, it agreed in 2022 to pay $1.4 million fine for failing to register as an online trading platform, and was ordered to block US users. CEO Shayne Coplan‘s apartment was raided in 2024 amid surge in bets about the US presidential election. In July 2025, the CFTC and Justice Department’s 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 cleared to restart services in the US.
Polymarket was founded by Coplan and has 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 Truth Predict?
The report noted that Trump family’s company Trump Media & Technology Group (TMTG) is close to joining the sector with Truth Predict.
Truth Predict will have Crypto.com as its partner in crypto ventures and Truth Social users would be allowed to trade on topics including sports, inflation, interest rates, and gold and oil prices, NYT reported citing a statement from TMTG.
Spokesperson Surabian told NYT Trump Jr was not involved in the decision to create Truth Predict and is not a part of the company’s day-to-day operations.
Trump Jr is also the sole trustee of his father’s trust, overseeing the president’s majority stake in the company. TMTG spokesperson Shannon Devine last year said Trump Jr is “highly engaged in the board’s work, as well as operations and strategy”.
In 2024, he earned $8,13,000 (largely stock) as a director of TMTG — around 25% of the company’s annual revenue, the report said citing US Securities and Exchange Commission (SEC) filings.