Trump opposes prediction markets, lasting for a full two days

Author: Deep Tide TechFlow

At the White House press conference, Trump looked distressed and said, “You know, unfortunately, the whole world has become a kind of casino.”

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

48 hours later, Trump dramatically changed his stance and expressed support for prediction markets.

This is probably the most exciting political performance art of 2026.

Within 48 hours, he changed his answer.

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 Maduro. During the operation, he placed bets on Polymarket, betting that Maduro would step down before the end of the month and that the U.S. would take military action against Venezuela. A total of 13 bets, with about $33k in principal, ultimately earning over $400k in profit.

Afterward, he tried to delete his account and obfuscate the flow of funds through cryptocurrency. No use. Federal prosecutors arrested him on charges of misuse of classified government information, telecommunications fraud, and commodities fraud.

A reporter took this case to ask Trump: What do you think of prediction markets?

Trump’s first answer was: “I’ve never been very supportive of this industry.” He said gambling turns the whole world into a casino, with a tone tinged with moral concern.

48 hours later, he changed his tune.

Trump shifted his position, claiming that “very smart” people he knows think this 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 responsible for persuading him was his son.

Many observers generally attribute this turnaround to Donald Trump Jr.

Donald Trump Jr. serves as an advisor to both Kalshi and Polymarket, has long spoken out in favor of prediction markets, especially in election coverage, where he believes prediction markets can more accurately reflect election outcomes than traditional media.

But his interests go far beyond just “adviser.” His paid advisory role at Kalshi, along with injecting “multi-million dollar” investments into Polymarket through his venture capital firm 1789 Capital, and sitting on Polymarket’s advisory board, make his involvement quite complex.

Someone holding stakes in two competing platforms is already unusual enough. Even more so because his father is the highest executive of the U.S. federal government, responsible for regulating this industry through the CFTC.

Donald Trump Jr.’s spokesperson said he “does not interact with the federal government on behalf of any company.”

This statement offers reassurance roughly equivalent to a referee announcing they will not influence calls in the name of their team.

Regulators are shrinking.

To understand this story, another clue must be considered.

The Commodity Futures Trading Commission (CFTC), responsible for regulating prediction markets, has cut 24% of its staff since Trump returned to the White House, bringing its total to the lowest in 15 years.

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

On one side, family members are profiting from the industry; on the other, the agency responsible for regulation is downsizing. CFTC Chair Selig explained that AI is filling the staffing gap, saying, “Our operational efficiency is higher than ever.”

Former CFTC officials disagree, worried that regulatory capacity has declined: “Some layoffs don’t make sense. Some matters will be left pending, and they won’t be able to investigate as many cases as when fully staffed.”

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

Who’s to blame for turning the world into a casino?

Let’s return to Trump’s statement: “The whole world has unfortunately become a kind of casino.”

He probably forgot that in the 1980s, he built a real casino empire, which later shut down after a series of bankruptcies. He also likely forgot that the Memecoin he issued is essentially casino chips.

Today, the monthly trading volume of prediction markets skyrocketed from about $1.2 billion in early 2025 to over $20 billion in January 2026, with more than 800k active wallets each month.

This casino business is thriving.

And that soldier who was arrested is just an ordinary player who won $400k using confidential information. He broke the law. But he only did what many close to power might do—just made it too obvious.

As one analyst said: How many of Trump’s direct subordinates have tried the same? No one knows. Has the Justice Department investigated? We haven’t heard anything.

48 hours later, Trump changed his tune, saying he knows “very smart” people who support prediction markets.

Everyone knows who he’s talking about.