The 20-something billionaires ushering in a betting bonanza in Trump’s Washington
Declan Harty
Sun, December 21, 2025 at 10:00 AM EST
9 min read
Wall Street’s newest whiz kids were up against the full force of the federal government a year ago.
Now, with President Donald Trump in charge, Shayne Coplan and Tarek Mansour — the messy-haired, 20-something billionaires behind the betting platforms Polymarket and Kalshi — are riding high.
Coplan’s Polymarket is returning to the U.S., one year after federal agents raided his apartment as part of a probe into whether the company was illegally operating domestically. And Mansour’s Kalshi has beaten back the Commodity Futures Trading Commission, its chief regulator, in a fight over election betting. Both are now expanding further into politics and sports while drawing big-name backers like Donald Trump Jr. and the New York Stock Exchange’s parent company.
The companies, known as prediction markets, take online bets on everything from elections to details of Taylor Swift’s wedding to the return of Jesus Christ. That trading then generates odds showing the likelihood of a particular event happening, such as who will win the 2028 presidential election. (Vice President JD Vance’s odds are currently at around 30 percent, the highest of any contender on Polymarket and Kalshi.)
Once a fringe corner of finance, prediction markets could eventually become a trillion-dollar industry, according to Mansour, making online bets pervasive in everyday life. This raises questions about the potential for insider trading and other risks that come with gambling on everything and anything. As the biggest players, Polymarket and Kalshi stand to benefit the most.
The story behind the comeback of these two companies offers a window into what it takes to get ahead in Trump’s Washington, where few have seen their stars rise so far so fast.
Federal regulators under then-President Joe Biden alleged in 2022 that Polymarket was operating an unregistered exchange in the U.S., leading the company to agree to wall off American traders. But both the Justice Department and the CFTC later investigated whether U.S.-based traders were still active on Polymarket by concealing their locations online — resulting in the early-morning raid on Coplan’s apartment. Biden’s CFTC also blocked Kalshi from taking bets on elections, which the company successfully challenged in court.
Fast forward one year, and Trump’s Justice Department and CFTC have dropped their investigations into Polymarket, setting the stage for the company’s return. The CFTC also abandoned its appeal of the decision in the Kalshi case, opening the door for billions of dollars in new bets. The agency wrote in a statement the appeal was dropped following a bipartisan vote “after it became clear that the CFTC was likely to lose.”
Story Continues
Over the past year and a half, Polymarket and Kalshi have hired high-profile Trump allies and elbowed their way into face time with the president and his circle. They’ve also benefited from the Trump family’s interest in less traditional finance, such as cryptocurrencies. And they’ve been quick to seize on the friendlier regulatory landscape.
The result: Polymarket is now valued at $9 billion and Kalshi at $11 billion. Both companies list Trump Jr. as an adviser. Polymarket also counts the younger Trump as an investor. And both are inking new deals with the likes of CNN, CNBC, the National Hockey League and the Ultimate Fighting Championship.
If the prediction markets get their way, pollsters and the media will have new competition from gamblers and traders for insights into election forecasting, as the companies say their platforms offer more accurate odds. On Polymarket’s international platform alone, the 2028 election market has already hit more than $150 million in volume. Analysts at Citizens Financial Group recently estimated that revenues within the prediction market industry could grow from $2 billion now to north of $10 billion by 2030.
“They really took a gamble, and it paid off with Trump’s victory,” said Pratik Chougule, a political market trader who knows Coplan and Mansour. “We’re in a very, very permissive regulatory environment.”
Mansour, in a recent interview, called it a “seminal moment” for prediction markets. “This is going to be bigger than the stock market.”
Polymarket Chief Legal Officer Neal Kumar said the regulatory environment is not “do whatever you want.” Rather, he said, “it’s giving prediction markets the opportunity to grow.”
The companies and their backers argue they are well-regulated financial exchanges operating under strict consumer and investor protections, a marked upgrade from casinos and sportsbooks, in their eyes. But skeptics say the markets could also make betting and the risks that come with it — from addiction to rigged events — more ubiquitous in daily life. Dorothy DeWitt, a former CFTC official, likened it to an episode of “Black Mirror,” referring to the “Twilight Zone”-like television series.
“Is Congress ready for this? No, no more so than they were ready for crypto and social media a decade ago,” she said.
‘Be first and grow big’
At the Republican National Convention in Milwaukee last summer, Coplan, wearing a dark T-shirt, met Trump Jr. and financier Omeed Malik for the first time, according to a person with direct knowledge of the meeting, who, like several others for this article, was granted anonymity to candidly discuss the companies.
The person said they were introduced through a mutual investor in Polymarket and 1789 Capital, the venture capital firm run by Malik and where Trump Jr. is a partner. (A photo of the meeting was widely shared on social media.)
Shortly after the election, during his first-ever TV interview, Coplan teased Polymarket’s return to the U.S. The next week, Mansour met the president-elect at an Ultimate Fighting Championship event in New York City. In January, Kalshi began pushing into sports.
The companies began staffing up, too. Polymarket hired David Urban, Trump’s former campaign adviser, and Keaghan Ames, a one-time CFTC official, as its first lobbyists. Kalshi added Trump Jr. as an adviser. Polymarket later did the same while announcing 1789 Capital had invested in the company.
Both companies also have bipartisan ties: Democratic megadonor Ron Conway, for instance, has invested in Polymarket, and former Democratic Sen. Blanche Lincoln of Arkansas is registered to work for Kalshi as a lobbyist.
“This is the way Washington works,” said Dennis Kelleher, who leads the Wall Street watchdog group Better Markets. “There’s a race to be first and grow big and get your tentacles into the various parts of Washington to make it difficult to dislodge them.”
Elisabeth Diana, a Kalshi spokesperson, said the company relies “on open channels with the government to navigate the ever-changing regulatory environment.” She added that the election-betting decision in favor of Kalshi came from a Biden-appointed judge and that the company has operated as a regulated exchange under both Democratic and Republican administrations. Diana declined to comment on personal interactions between Kalshi’s executives and elected officials.
Coplan, when asked about Trump Jr. during a recent “60 Minutes” interview, said, “if I have people who believe in what I do, who understand how politics works and can help me … there’s nothing wrong about that.” Polymarket declined to comment on the RNC meeting.
In a January social media post, Trump Jr. explained the companies’ appeal. Not only did both battle Biden regulators, they also called Trump’s victory ahead of established prognosticators. He said in the post that he and his family tracked Kalshi on election night “to know we won hours ahead of the fake news media.”
Trump Jr. and Malik declined to comment. A person close to Trump Jr. said he doesn’t interact with the government as part of his roles with the companies.
Urban, Ames and Conway did not respond to requests for comment. In an emailed statement, Lincoln said the CFTC “safeguards fair and orderly trading, preventing fraud and abuse while allowing the market to fulfill its function of determining the values of contracts.”
Between flooding the CFTC with new market plans, suing over the election-betting decision and, more recently, lobbying around a series of pending applications from new competitors, Mansour and Kalshi have long been aggressive with the agency, according to a half dozen people familiar with their interactions.
They’ve grown bolder under Trump, said one of the people. While Kalshi has always been able to connect with CFTC commissioners, more recently, “they would just cold call” them, the person said.
“They’re extremely, extremely aggressive,” a former CFTC official said of Kalshi. “They are all up in everybody’s face.”
When asked for comment, Diana, the Kalshi spokesperson, said “if by aggressive you mean pushing — successfully — for the legalization of election contracts on behalf of the entire industry, then yes.” The CFTC declined to comment.
Slowly then suddenly
Regulators who once went after the companies are now rolling out the red carpet. In September, Coplan and Mansour appeared on a panel co-hosted by the CFTC alongside Wall Street titans, including CME Group CEO Terry Duffy and Intercontinental Exchange CEO Jeff Sprecher.
The next week, Polymarket announced a deal months in the making: Sprecher’s company — owner of the NYSE — would invest up to $2 billion.
Former CFTC Chair Chris Giancarlo, a Polymarket adviser, said Mansour and Coplan are each the “poster child” of their rising industry. “They’re the Terry Duffy and Jeff Sprecher of 30 years ago,” he said.
Spokespeople for CME and Intercontinental Exchange declined to comment.
But trouble is brewing outside Washington. Polymarket and Kalshi face new competition from Robinhood, Duffy’s CME and even the parent company of Trump’s Truth Social. State officials are also challenging the legality of sports prediction markets, which they say violate state gambling regulations.
The companies argue they only answer to the CFTC, and that their platforms are not sportsbooks but federally regulated financial exchanges. The fight is attracting scrutiny inside the Beltway: Sen. Catherine Cortez Masto (D-Nev.) told POLITICO sports prediction markets are “tantamount to illegal gambling.”
For now, neither seem worried. Mansour’s Kalshi continues to rake in money from investors. And in November, Coplan commemorated the anniversary of the raid on his apartment, posting a photo on social media of a cake with white frosting and sprinkles.
The caption: “cheers to free markets, the American dream, and $3000/hr lawyers.”
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