A year ago, Wall Street’s new wizards faced the full force of the federal government.
Now, under President Donald Trump, Shayne Coplan and Tarek Mansour — the two disheveled 20-something billionaires behind betting platforms Polymarket and Kalshi — are in the spotlight.
Copeland’s Polymarket is returning to the United States, a year after federal agents raided his apartment to investigate whether the company was operating illegally in the country. Mansour’s Karsi defeated its main regulator, the Commodity Futures Trading Commission, in a battle over electoral gambling. Both companies are now expanding further into politics and sports, while attracting big-name backers such as Donald Trump Jr. and the parent company of the New York Stock Exchange.
These companies, known as prediction markets, place online bets on everything from elections to details of Taylor Swift’s wedding to the return of Jesus Christ. This trading then produces odds that show the likelihood of a specific event happening, such as who will win the 2028 presidential election. (VP J.D. Vance’s current odds are around 30%, the highest of any contender on Polymarket and Kalshi.)
Mansour said prediction markets, once a fringe corner of finance, could eventually become a multi-trillion dollar industry, making online betting commonplace in everyday life. This raises questions about the possibility of insider trading and other risks that come with all things gambling. As the largest players, Polymarket and Kalshi will benefit the most from this.
The stories behind the two companies’ comebacks offer a window into what it takes to succeed in Trump’s Washington, where few have seen their stars rise so quickly.
In 2022, federal regulators under then-President Joe Biden claimed that Polymarket was operating an unregistered exchange in the United States, leading the company to agree to block U.S. traders. But the Justice Department and the U.S. Commodity Futures Trading Commission subsequently investigated whether U.S. traders were still active on Polymarket and hiding their locations online, leading to an early morning raid on Copeland’s apartment. Biden’s Commodity Futures Trading Commission also blocked Calshe from placing bets on the election, which the company successfully challenged in court.
Fast forward a year, and Trump’s Department of Justice and the U.S. Commodity Futures Trading Commission (CFTC) dropped their investigations into Polymarket, setting the stage for the company’s comeback. The CFTC also dropped its appeal of the Kalshi ruling, opening the door to billions of dollars in new bets. The appeal was withdrawn after a bipartisan vote “after it became clear that the CFTC was likely to fail,” the agency wrote in a statement.
Over the past year and a half, Polymarket and Kalshi hired high-profile Trump allies and sought meetings with the president and his circle. They also benefit from the Trump family’s interest in non-traditional finance such as cryptocurrencies. They were quick to seize on the friendlier regulatory environment.
Result: Polymarket is currently valued at $9 billion and Kalshi is valued at $11 billion. Both companies list Trump Jr. as a consultant. Polymarket also counts the younger Trump as an investor. Both companies have signed new deals with CNN, CNBC, the National Hockey League and the Ultimate Fighting Championship, among others.
If prediction markets have their way, pollsters and media outlets will face new competition from gamblers and traders for insights into election predictions, as the companies say their platforms provide more accurate odds. On Polymarket’s international platform alone, the trading volume of the 2028 election market has exceeded $150 million. Analysts at Citizens Financial Group recently estimated that revenue from the prediction markets industry could grow from $2 billion today to more than $10 billion by 2030.
“They did take a gamble and it paid off with a Trump victory,” said Pratik Chogul, a political market trader who knows Copeland and Mansoor. “We’re in a very, very light regulatory environment.”
Mansour called it a “seminal moment” for prediction markets in a recent interview. “This is going to be bigger than the stock market.”
Neal Kumar, chief legal officer at Polymarket, said the regulatory environment is not one of “do whatever you want.” Instead, he said, “it gives the opportunity to predict market growth.”
The companies and their backers argue that they are well-regulated financial exchanges operating under strict consumer and investor protections, and they see this as a significant upgrade from casinos and sports betting. But skeptics say the market may also make gambling and the risks that come with it — from addiction to rigged incidents — more commonplace in everyday life. Dorothy DeWitt, a former official at the U.S. Commodity Futures Trading Commission (CFTC), likened it to an episode of “Black Mirror,” referring to TV series like “The Twilight Zone.”
“Is Congress ready for this? No, no more than they were ready for cryptocurrencies and social media a decade ago,” she said.
Copeland, wearing a dark T-shirt, first met with Trump Jr. and financier Omid Malik at last summer’s Republican National Convention in Milwaukee, according to a person with direct knowledge of the meeting. That person, like several others for this article, requested anonymity to discuss the companies candidly.
They were introduced through co-investors in Polymarket and 1789 Capital, the person said. 1789 Capital is the venture capital firm run by Malik, where Trump Jr. is a partner. (Photos from the meeting were widely shared on social media.)
In his first television interview shortly after the election, Copeland teased Polymarket’s return to the United States. Mansour met with the president-elect at the Ultimate Fighting Championship in New York City the next week. In January, Kalshey began to get involved in sports.
These companies are also starting to recruit employees. Polymarket hired former Trump campaign adviser David Urban and former CFTC official Keaghan Ames as its first lobbyists. Kalshey appointed Trump Jr. as adviser. Polymarket later did the same and announced that 1789 Capital had invested in the company.
The companies also have bipartisan connections: Democratic megadonor Ron Conway, for example, invested in Polymarket, and former Arkansas Democratic Sen. Blanche Lincoln registered as a lobbyist for Kalshi.
“This is how things work in Washington,” said Dennis Kelleher, director of Better Markets, a Wall Street watchdog group. “It’s a scrambling, growing race that puts your tentacles into all parts of Washington and makes it very difficult to dislodge them.”
Kalshi spokesperson Elisabeth Diana said the company relies on “open channels with governments to navigate the changing regulatory environment.” She added that the election betting decision in favor of Calshe came from a Biden-appointed judge and that the company operated as a regulated exchange under both Democratic and Republican administrations. Diana declined to comment on personal interactions between Calshe executives and elected officials.
“If someone believes in what I’m doing and understands how politics works and can help me… there’s nothing wrong with that,” Copeland said when asked about Trump Jr. in a recent “60 Minutes” interview. Polymarket declined to comment on the RNC meeting.
In a January social media post, Trump Jr. explained the companies’ appeal. The pair not only battled Biden regulators, but also went ahead of established prognosticators in predicting a Trump victory. He said in the post that he and his family tracked Kalsi on election night “knowing we were winning hours ahead of the Fake News Media.”
Trump Jr. and Malik declined to comment. A person close to Trump Jr. said he would not interact with the government as part of his role with the company.
Urban, Ames and Conway did not respond to requests for comment. Lincoln said in an emailed statement that the CFTC “guarantees fair and orderly trading and prevents fraud and abuse while allowing the market to carry out its function of determining contract value.”
Mansour and Kalsi have long been lobbying the U.S. Commodity Futures Trading Commission (CFTC) on a raft of new market plans, lawsuits over election betting decisions and, more recently, a series of pending applications from new rivals, according to six people familiar with the matter.
One person familiar with the matter said they have become bolder under Trump. The person said that while Kalshey has always been able to get in touch with CFTC commissioners, lately, “they’ve just been calling them.”
“They were very, very aggressive,” a former CFTC official said of Kalshey. “They’re all on everybody’s face.”
Asked for comment, Kalsh spokesperson Diana said, “If by positivity you mean a successful push to legalize election contracts on behalf of the industry as a whole, then yes.” The CFTC declined to comment.
Regulators that once went after these companies are now rolling out the red carpet. In September, Copeland and Mansour appeared on a panel co-sponsored by the U.S. Commodity Futures Trading Commission (CFTC), along with Wall Street titans including CME Group CEO Terry Duffy and Intercontinental Exchange CEO Jeff Sprecher.
Next week, Polymarket announced a deal that had been months in the making: Sprecher’s company, owner of the New York Stock Exchange, would invest up to $2 billion.
Chris Giancarlo, a former chairman of the U.S. Commodity Futures Trading Commission and a consultant to Polymarket, said both Mansour and Copeland were “poster children” for their nascent industry. “They are the Terry Duffy and Jeff Sprecher of 30 years ago,” he said.
Spokespersons for CME Group and ICE declined to comment.
But trouble is brewing outside Washington. Polymarket and Kalshi face new competition from Robinhood, Duffy’s CME and even Trump’s Truth Social parent company. State officials also question the legality of sports prediction markets, which they say violates state gambling regulations.
The companies argue that they answer only to the Commodity Futures Trading Commission and that their platforms are not sportsbooks but federally regulated financial exchanges. The fight is being watched closely inside the Beltway: Sen. Catherine Cortez Masto, D-Nev., told POLITICO that sports prediction markets are “nothing less than illegal gambling.”
So far, neither seems worried. Mansour’s Karhi continues to make money from investors. In November, Copeland posted a photo of a cake with white frosting and powdered sugar on social media to mark the anniversary of the attack on his apartment.
The headline read: “A toast to the free market, the American dream, and $3,000-an-hour lawyers.”