Trump opposed prediction markets for a full two days

Original Author: TechFlow

At a White House press conference, Trump said with a disheartened expression: "You know, the entire world has unfortunately become a casino to some extent."

When he said this, his son, Donald Trump Jr., was simultaneously serving as a paid advisor for Kalshi, one of the two largest prediction market platforms, and an investor and board member for Polymarket, the other.

48 hours later, Trump did an about-face and expressed support for prediction markets.

This is arguably the most brilliant piece of political performance art of 2026.

He Changed His Answer in 48 Hours

The story begins with a U.S. Army Special Forces soldier.

Earlier this year, this soldier participated in a military operation to capture Venezuelan President Nicolás Maduro. During the operation, he placed bets on Polymarket, wagering that Maduro would be ousted by the end of the month and that the U.S. would use military force against Venezuela. In total, he made 13 bets with a principal of about $33,000, ultimately profiting over $400,000.

Afterwards, he tried to delete his account and obscure the money trail using cryptocurrencies. It didn't work. Federal prosecutors arrested him on charges of abusing classified government information, wire fraud, and commodity fraud.

Reporters took this case to Trump and asked: What do you think of prediction markets?

Trump's first answer was: "I've never really been in favor of this industry." He said gambling had turned the whole world into a casino, his tone carrying a hint of moral concern.

48 hours later, he changed his tune.

Trump shifted his position, claiming that "very smart" people he knows believe the industry is worth supporting, and stated that the U.S. should not fall behind in this field.

Two answers, from the same person, less than two days apart.

The Person Who Convinced Him Was His Son

Observers generally credit Donald Trump Jr. for this shift by Trump.

Donald Trump Jr. simultaneously serves as an advisor for both Kalshi and Polymarket. He has long been an advocate for prediction markets, particularly in election coverage, arguing that they can reflect election results more accurately than traditional media.

But his vested interests go far beyond just being an "advisor." His advisory role at Kalshi is a paid position. Additionally, through his venture capital firm 1789 Capital, he invested "several million dollars" in Polymarket and joined its advisory board.

One person simultaneously taking money from two competitors is odd enough in itself. What's even odder is that his father is the highest executive officer of the U.S. federal government, and the agency responsible for regulating this industry is the federal body, the CFTC.

Donald Jr.'s spokesperson said he "does not interact with the federal government on behalf of any company."

That statement is about as reassuring as a referee announcing he won't influence the game on behalf of a team.

The Regulatory Agency Is Shrinking

To understand this story, you need to know another thread.

The Commodity Futures Trading Commission (CFTC), which oversees prediction markets, has cut 24% of its staff since Trump returned to the White House, reducing its workforce to a 15-year low.

Meanwhile, Trump's social media company announced plans to launch its own prediction platform. Donald Trump Jr. is a paid advisor for Kalshi and an investor in Polymarket.

On one hand, family members are counting money in the industry; on the other, the agency regulating that industry is laying off staff. CFTC Chairman Selig explained this by saying that artificial intelligence is filling the personnel gap: "Our operational efficiency is higher than ever."

Former high-ranking CFTC officials disagree with this assessment. They worry that regulatory capacity has declined: "Some of the layoffs don't make logical sense. Some things will be put on hold. They won't be able to pursue as many cases as they could when fully staffed."

The Maduro case is just the tip of the iceberg. Researchers have already identified multiple potential insider trading cases, including precise bets on oil futures before major U.S. policy changes towards Iran were announced.

Who Is Responsible for Turning the World into a Casino?

Let's go back to Trump's statement: "The entire world has unfortunately become a casino to some extent."

He probably forgot when he said this that he himself built a real casino empire in the 1980s, which later went bankrupt following a series of Chapter 11 filings. He also probably forgot that his own Memecoin is, in essence, a casino chip.

Today, the monthly trading volume of prediction markets has skyrocketed from about $1.2 billion at the start of 2025 to over $20 billion in January 2026, with more than 800,000 monthly active wallets.

This casino is doing very good business.

And the arrested soldier? He was just an ordinary player who used confidential information to win $400,000 in this casino. He broke the law. But he simply did something that many people close to power might consider doing, but he did it too conspicuously.

As one analyst noted: How many of Trump's direct subordinates have already tried the same thing? No one knows. Has the Justice Department investigated? We haven't heard anything about it.

Trump changed his tune 48 hours later, saying that "very smart" people he knows support prediction markets.

Everyone knows who he is talking about.