Photo: Dina Litovsky
At 6 a.m. on Wednesday, November 13, eight FBI agents in black windbreakers burst through the door of Shayne Coplan’s Soho apartment with a battering ram, surprising him and his girlfriend in bed. They seized his phone from the bedside table but wouldn’t let him touch it, not even to unlock it, lest he destroy evidence that might criminally implicate him or his company, Polymarket, the popular betting platform that over a week before had set off celebrations at Mar-a-Lago when it showed Donald Trump winning the presidential election well before the networks did. After grabbing both his and his girlfriend’s devices, the FBI spent hours sifting through his belongings and eclectic art collection. Coplan popped up on X later that day to write, “new phone, who dis?”
His irreverence can be partly explained by the fact that the raid was not his first run-in with the government, which Coplan has been fighting almost since he started Polymarket in his “bathroom office” on the Lower East Side five years ago, when he was just 21 years old. Polymarket is unlike other gambling forums in that it’s not a bookie and it doesn’t set the odds of its markets. Each market is simply structured as a question on which you can bet “yes” or “no.” Will Volodymyr Zelenskyy apologize to Trump? Will Fyre Festival 2 sell out? Will TikTok be banned again before May? The question that first catapulted Coplan, a New York University dropout, into being an unlikely main character of the 2024 election was whether Joe Biden would quit the race, which Polymarket’s predictions, based on thousands of bets, got right. Bettors on the site were so persistent in calling a Trump victory, despite reputable pollsters showing a tight contest, that Trump’s campaign included a Polymarket slide as the first page of its daily briefings. “These are a lot more accurate than the polls, you know,” Trump told aides.
Polymarket became the most-downloaded free news app from Apple in the fall and processed bets of more than $3 billion on the election alone — even though the site itself, which is still in world-eating expansionary mode, does not collect fees and doesn’t actually make any money. “It was just outrageously beyond anyone’s expectations, other than Shayne’s,” says Rob Hadick, a venture capitalist at Dragonfly who invested in Polymarket. The statistician Nate Silver, who once represented the gold standard of election forecasting, joined Polymarket as an adviser despite public reservations. And Elon Musk struck up a rapport with Coplan, quipping in late October, “Polyamorousmarket?” Coplan replied by likening Polymarket to X: “Sounding like porn sites but actually solving misinformation.”
“A lot of what I do is manifestations of longtime dreams,” Coplan told me a few months later. Polymarket has become the first prediction market to achieve truly mainstream scale with trading volumes well ahead of competitors like Kalshi and predecessors like PredictIt and a valuation approaching $1 billion. And since Polymarket runs on the blockchain and accepts bets only in crypto, it is the first killer blockchain app for consumers that can be used for something other than trading digital coins. Polymarket’s odds have become such an accurate glimpse into the future — effectively a crowdsourced crystal ball — that they can even move the stock market as Wall Street behemoths from Apollo to Goldman Sachs factor them into their analyses. Shervin Pishevar, the longtime tech investor, in November recalled a conversation with Travis Kalanick in which the Uber founder claimed “the truth doesn’t have a business model,” a maxim Pishevar declared turned on its head by Polymarket. Added Pishevar, “Going to call it: Shayne and Polymarket will be a decacorn within 24 months,” a term for a privately held company with a valuation exceeding $10 billion.
This is all despite the fact that Polymarket is not, strictly speaking, legal to use in New York or anywhere else in this country. Since the election, France, Singapore, Thailand, and Belgium have banned Polymarket too. Prediction markets are event contracts under U.S. law, regulated by the Commodity Futures Trading Commission, which means companies wishing to offer such bets must apply for permission to do so — something Polymarket apparently had neglected to do. Even then, betting on U.S. elections is expressly forbidden, or at least was until this past fall, when a court ruling lifted such restrictions on registered prediction markets like Kalshi. But that verdict did not apply to Polymarket, which in 2022 paid a $1.4 million penalty and promised to ban Americans from trading on its site as long as it remained unregistered. “It’s surprising to me that someone would try to start a platform like this in the United States,” Timothy Massad, a former CFTC chairman, says with a slight chuckle, “and not understand that they’re supposed to register with the CFTC. Very surprising. I mean, the law is pretty clear on that.”
And yet, as is obvious to anyone with eyes and an internet connection, many of the degens (as the site’s bettors are often known) gambling on Polymarket are American, putting money on everything from March Madness to how much DOGE will cut from the federal budget to when Taylor Swift will get engaged and logging on via a virtual private network that disguises a user’s location. Martin Shkreli, the New York–based convicted fraudster known for hiking drug prices, has posted about betting on Polymarket, screenshotting his balance. The lack of a barrier strong enough to keep out American traders is what felled other top crypto entrepreneurs, from Arthur Hayes of BitMEX to Changpeng Zhao of Binance. Andrew Tate, whose recent return from Romania was predicted by Polymarket, replied to Coplan’s “new phone” post with “See you in jail friend,” accompanied by a salute emoji.
Americans trading on Polymarket is the alleged crime the FBI and the Southern District of New York are now investigating, according to multiple sources. And the fact that Polymarket has already been reprimanded once by the CFTC for this, and settled, could be a further strike against it. “They are bound by their own hands,” says a former regulator. “You know, or a reasonable person would know, that you are breaking the law.”
But that may have been true only in a prior era, when notions like the law and justice were taken more seriously. Now Trump is back in the White House touting meme coins and adopting a decidedly forgiving stance on crypto crime. On day two of his second term, Trump let Ross Ulbricht — who was serving an even longer sentence than Sam Bankman-Fried for running the illicit crypto-based drug bazaar Silk Road — out of jail. On day four, he signed an executive order aimed at ending a yearslong crypto crackdown. Federal securities investigations or lawsuits against crypto exchanges Binance, Coinbase, and Gemini were put on ice.
Washington is now undergoing a sea change when it comes to prediction markets. Musk recently had breakfast with Robin Hanson, the economist and longtime evangelist of them. Donald Trump Jr. joined Kalshi as an adviser in January, and Brian Quintenz, who sits on the board of Kalshi and works for Andreessen Horowitz’s crypto fund, is Trump’s pick to lead the CFTC.
Coplan may have correctly wagered that the law would change in his favor before he got in real trouble. “I mean, the plan is to build something that didn’t exist yet that needed to exist, that I cared more about than anyone else,” he said, acknowledging that he started Polymarket without consulting lawyers on the regulatory prohibitions. He sounds a lot like Kalanick, who launched Uber as a basically illegal taxi service, then fought bans around the world to win the right to operate. As Trump and Musk have shown in their ongoing campaign against the bureaucracy and the separation of powers, the rules don’t necessarily apply to those bold enough to disregard them, which might make the 26-year-old Coplan the emblematic entrepreneur of this new era. At Crypto Ball, the black-tie party held in Washington during Trump’s inauguration weekend, Coplan ran into Mark Pincus, the founder of the video-game developer Zynga, who was stuck in line. Coplan told Pincus, a billionaire decades his senior, to “just follow me” to the VIP section, Pincus recounted on a podcast: “He said, ‘Just have the confidence,’ and he just walked us in.”
That Coplan didn’t ask permission before starting his website may speak as much to the way the world has changed as it does to his personal mind-set. In a country where legal gambling is ubiquitous and day-trading has spread to anyone with a smartphone, and where the old divisions are crumbling and rules are created as much as they are destroyed, the idea that betting on an election is inherently bad might strike a Gen-Z up-and-comer as pretty odd. Coplan’s cavalier approach is kind of like a bet on his site: Either he is right about the way the world works or he isn’t.
Photo: Dina Litovsky
On a mild evening in late February, I met Coplan at a five-star Soho hotel that is a favorite see-and-be-seen spot for the city’s tech and crypto elite. He had reserved the back corner table of the restaurant for privacy but still had a full view of the dining room, his eyes darting constantly, scanning the crowd. Dressed all in black, he kept his wool chevron scarf coiled around his neck the whole time, unwrapping it only to eat a few bites of steak, ignoring the frites and salad. As he talked, he twirled his long fusilli-like curls; after the meal, as we wandered around the neighborhood, he rubbed a charm necklace between his fingers like a rosary.
The only child of South African college professors, Coplan grew up living with just his mother. He describes his father as a “mad scientist” who has studied panic disorder and depression. His mom taught in the film departments at NYU and Columbia and cast young Shayne in her own work. In one of her short films, a 9-year-old Shayne stars as the smart-mouthed son of a single mom, asking her, “Have you had sex with anyone since you and my dad split up?” Then he follows up, grinning mischievously: “You have! I knew it! Who are they? I’ll find out!”
Coplan was surrounded by wealth but didn’t grow up wealthy, and he was conscious of his middle-class status even as an adolescent. “It’s different growing up in New York, where, you know, it’s all relative,” he said. He developed, he said, a “major itch” to find ways to make money. He was sucked into a variety of “shadow economies,” downloading music on file-sharing sites like BitTorrent (which generally ignored the copyright status of the material being exchanged) and trading fingerboards — the miniature-skateboard fidget toys — with YouTubers, though sometimes counterparties would ghost him without fulfilling their end of the deal. “So that’s a lesson in trust and markets,” he said.
In middle school, he began using Uber to get rides to school, which is around the time he remembers wanting to be an entrepreneur. Coplan then attended the Beacon School, a selective public high school that eschews testing and exempts students from the statewide Regents Exams, where friends say he fit in with both the nerds and the popular kids. He was smart — a friend remembers him being the first to solve assignments in his tech class — but he struggled to pay attention in school, his grades suffered, and he was placed in a special-ed program for students with learning disabilities. “I could tell a lot of times he was bored because nothing was a challenge for him, nothing stimulated or excited him,” the friend says.
Photo: Shayne Coplan/Facebook
“I was not a good student at all,” Coplan said. “I would just sit in class and think and daydream — about this!” He gestured at the life he’s built and the neighborhood he said he “fantasized about” living in when he was younger. “I think having a background that was so uncredentialed, it was very clear to me I was a goner if I was gonna go the path everyone else was going and just try and compete there,” he added. “I just never got picked. That was never me. It was always like, I’m gonna have to go stake out my own way and take the side roads to go find my own destination. That was something that I internalized when I was very young.”
Coplan had a dim view of schoolwork (“i’d like to thank sparknotes, caffeine, and Wikipedia,” he captioned a Facebook photo from that era), preferring to spend his time online, vacuuming up facts about architecture and geography and music and practicing coding. “I was always someone who would hyperfixate and learn an enormous amount of different topics, one after the other,” he said. He added earnestly, “You can call me a polymath.” (He got near-perfect scores on the ACT, which he posted on his LinkedIn.)
A regular at the school stock-market club, Coplan won its paper-trading competition. As minors, none of the club’s members could actually invest in stocks, but Coplan began dabbling in crypto around this time, which would ultimately give him spending power on the internet that he did not possess in real life. When ethereum first went on presale in 2014, Coplan took the equivalent of about $150 and bought coins that would be worth more than $1 million at today’s prices, if he’d held on to them.
Coplan was becoming obsessed with the tech founders who’d gone on to become billionaires and set his sights on interning at what was then one of the city’s hottest startups, the lyric and web-annotation company Genius. After his pleas to the founders were rejected, an anxious 16-year-old Coplan took the subway to Williamsburg and knocked on the door of the Genius offices. “Within minutes I learned that Shayne possessed near-encyclopedic knowledge of major tech entrepreneurs, and he eagerly volunteered to add annotations to the Wikipedia pages of Mark Zuckerberg and Travis Kalanick,” Christopher Glazek, who would become Coplan’s boss, recalled in a college recommendation letter he wrote for his intern. Coplan wrote hundreds of annotations, becoming the site’s top expert on the Facebook founder. (Describing Coplan’s “seemingly infinite reservoir of energy and obsessive passion,” Glazek added, “if he chooses to become a tech entrepreneur, which seems likely, I have no doubt that we’ll be seeing his name again in the press before long.”)
Genius, like other venture-capital-funded endeavors of the era, is now a shell of its former self, the company’s ambitions to annotate the entire web long ago eclipsed by other platforms and its aura of cool all but incomprehensible to anyone who wasn’t there to witness a group of know-it-all whiz kids swimming in lakes of cash. But Coplan received an infusion of confidence that has yet to wear off. “I remember thinking, If I get it this way — if I get it from just showing up — I’m gonna get what I want in life,” he said. “I almost think that I’m living off a blueprint from when I was a child.”
Coplan gained admission to NYU as a computer-science major in the fall of 2016, but just a few months in he was already telling friends school wasn’t for him, and he dropped out after the first semester. Crypto was on a historic tear, and friends remember Coplan, who had also mined litecoin and traded meme coins like DOGE, keeping a balance in the hundreds of thousands. He spent the next few years going out with crypto bros and other aspiring entrepreneurs and developed a reputation as someone who could will his way in anywhere, even a club with a long line. “He’d just talk to the bouncer and we’d get in. He could always smooth-talk his way through things,” says David Spiegel, a college friend. Coplan didn’t drink, but he went out enough that Spiegel randomly ran into him on the Lower East Side in the middle of the night on four separate occasions.
Coplan quickly grew disillusioned with the tech scene, unimpressed with what he calls the “Build-A-Bear” lineup of copycat start-ups and crypto “scams.” At the time, there was an explosion of “initial coin offerings,” or ICOs, in which teams raised enormous sums for legally dubious token projects they often never fully built; he’d worked on one project that had promised to pay him $160,000 but then tried to back out of paying the second half. “I realized these are not role models for me. These guys are grifters, and they half-ass things,” he said. He reached out to Joey Krug, the founder of an early blockchain-based prediction market called Augur, to complain that its user experience was wonky and its fees too high.
He bought the domain union.market because he was a devotee of Union Market, the Lower East Side (and Brooklyn) grocery store where Coplan bought the mushrooms and brioche buns that sustained him. (“That place is fire,” he said.) He’d stumbled across a famous paper by Robin Hanson, the George Mason University economist who breakfasted with Musk, titled “Shall We Vote on Values, But Bet on Beliefs?,” which proposes a form of governance-by-market that Hanson called futarchy. In early 2019, Coplan wrote to Hanson, proclaiming in a verbose email with multiple block paragraphs that he wanted “to be the person to bring prediction markets to life.” Hanson brushed him off — in the decades since he first began writing about them, many companies had tried without achieving a critical mass.
Coplan had been living off the funds the crypto project had eventually paid him and a small amount of venture capital, building union.market into a marketplace for yield-generating digital assets, but money was running out. At one point, he made a Google Sheet and appraised all of his belongings because he needed to pay rent; he sold musical instruments, tech gadgets, and other sentimental items. “I think that being broke is a virtue,” he said. “I’m very glad that I’ve spent, you know, large swaths of my time as an adult, since I dropped out, broke, or at least borderline, to feel that strain, to feel that anxiety.”
When COVID struck in 2020, Coplan saw his opening. With the whole world trying to guess whether a pandemic would be declared, how long it would last, and the timeline of everything from lockdowns to mask mandates to vaccines, Coplan holed up in his bathroom and began building a site with real-time “information markets” where people could essentially buy shares of the outcome they believed most likely. Coplan had no co-founders — “In my mind, it would be like, Who would want to work with me? I got nothing,” he said — and he launched poly.market in June, referring union.market’s traffic there.
As the 2020 election approached, Coplan desperately tried to drum up interest in his site. He was manning Polymarket’s social-media accounts himself, and he would personally DM his posts to each of his investors and anyone else he could think of, asking them to “like” it or if they wanted to bet. “Every single tweet he would send us — I mean, like, every one,” says an early investor. “That happened pretty much every day.”
Polymarket correctly predicted Biden’s win. In a podcast around that time, Coplan described his site as part of the “Napsterization of finance,” referring to the controversial music-sharing site that had influenced Polymarket’s peer-to-peer format and that had been forced by the courts to shut down owing to copyright infringement when Coplan was just 3 years old. Napster was a conduit for people sharing mp3s and other content that the site itself never actually owned, and Coplan saw Polymarket similarly: Its users took either side of a bet by putting wagers on a blockchain without Polymarket ever having to hold their money. “At no point are we intermediating anything, or custodying anything, or even taking fees — it’s basically nonprofit,” Coplan said on a different podcast at the time. “What we really focus on is the information.”
As we strolled the streets of Soho after dinner, I asked Coplan if he still sees Polymarket as a technological descendant of Napster. “I think there are parallels,” he said. “There were probably a lot of implementation details that if they’d done differently, it would have had more longevity. But nonetheless, it’s a complete, you know, generational product.”
As Coplan entered a frenzied period of fundraising, he seemed undaunted by anyone older or ostensibly more powerful than him. “He always treated everybody as a peer, which is pretty rare — he kind of weaponized it, in a way. He was like, ‘I have growth,’” says the early investor. Coplan didn’t mind debating with those more experienced than him, either. “Shayne definitely triggers people. I would bring Shayne to parties, and people would be like, ‘I don’t fucking like that guy.’ He just says what he wants, he says what he thinks, and he doesn’t really care if he hurts people’s feelings,” says Meltem Demirors, who invested in Polymarket after Coplan “violently argued” with her for two hours during their first meeting. “He’s been in rooms that would intimidate most people, and 100 percent I can guarantee you he’s just sitting there, yapping about Polymarket. It just doesn’t faze him. He doesn’t care who you are.”
Others who encountered Coplan in social situations were struck by his nerve. At a bar, Coplan once tried to flirt with a waitress at least a decade older than him, “chatting her up,” says the early investor. On another occasion, he recognized a woman on the street from afar and DM’d her his address in case she wanted “to come over later,” despite not having spoken with her in years.
At the time, Coplan was in the midst of amassing what Sotheby’s would later call “one of the largest collections of NFT art in the world.” Under the name ethsquiat, Coplan collected 318 NFTs beginning in 2020, buying them for as much as $19,000 apiece, before selling some for as much as $250,000 each in 2023. Indeed, much of the NFT craze of that period can be attributed to Coplan, who personally discovered at least three of the industry’s biggest artists. One of them was FEWOCiOUS, a transgender teen who had been selling his work for as little as $5. Coplan told FEWOCiOUS he would buy more pieces but wanted them to be digital and fronted the artist money to start minting his work on the blockchain. FEWOCiOUS went on to become one of the most successful NFT artists, with Christie’s selling one of his works for about $2.2 million the next year.
Coplan said the best feedback he’s gotten was that in 2021, he was “overselling” himself: “I would just come in really hot.” After a party at Art Basel, Coplan got in a car with Dan Loeb, the hedge-fund billionaire, and used the ride to pitch his company. “This kid is crazy,” remarked a bemused Loeb, who now calls Coplan a friend. He also gave the impression of being fast and loose to investors, several of whom described him as immature. He’d be seen at parties “partaking in whatever people were partaking in,” according to one venture capitalist who passed on Polymarket. “There’s a vibe in which he sort of seemed like he was playing a game.” Combined with his dismissive answers to questions about regulatory restrictions, Coplan’s swagger struck some as a red flag. “We’re used to dealing in gray area, right, where the laws aren’t clear yet,” said the investor, “but I think for Polymarket it was more ‘Who cares about that?’ — like the whole point is to kind of be averse to the law.”
“The culture at the time was kind of like, ‘We’re rebels, we’re mavericks, and we’re just gonna build this thing and figure out the regulatory stuff later,’” says a former employee. Coplan liked to quote Steve Jobs and sometimes joined company meetings wearing a bathing suit in Miami or while getting ready to go out. He was an in-your-face kind of CEO, often FaceTiming people cold, with the camera on, to ask them questions or favors. Once, Orlando Bloom called Coplan during a team meeting, and Coplan added him to the Google Meet, introducing him as a potential investor.
Polymarket was less than a year old and had only a dozen or so employees when the CFTC first came knocking, forcing the company in January 2022 to pay $1.4 million to settle charges of failing to get proper regulatory approval. “Like, What are they gonna do — they’re gonna go after me for building this?” Spiegel says of Coplan’s mind-set. “I don’t think he ever thought he would be raided. I don’t think he actively thought he was doing something that was wrong.”
As part of the CFTC order, Coplan agreed to keep U.S. traders off Polymarket and instituted a geoblock, a virtual fence for anyone logging on with an American IP address. On paper, the company would now be based in Panama, but its office headquarters would stay in lower Manhattan. When I asked Coplan about this ordeal, he still seemed mystified that he was targeted at all. “We built something that everyone’s been happy with, that’s worked as intended,” he said. “Seems like the type of thing that, you know, especially when you think about its importance as an information source, should be fostered and cultivated and welcomed.”
From the moment he signed the settlement, Coplan had to contend with a three-letter problem: VPN, which allows users to make it look like they are logging on from a different country and which Polymarket now prohibits in its terms of service. Late one evening in February, at home in Manhattan, I signed up for a free trial of a service called ExpressVPN, and a couple of minutes later I was in Spain, at least virtually. Then I was using my work email to log into Polymarket, checking a box to “attest” that I am “not a U.S. person,” nor located here or in any other restricted zone. From there, I tried to use my credit card to buy stablecoins, the only currency Polymarket accepts, but got an error message when I put in my billing address. No matter — option B was to connect my Coinbase account, from which I sent a minuscule fraction of ethereum, the equivalent of $20. Before I could trade, I had one more chance to be honest when a window popped up that made me additionally swear I was not using a VPN. I hesitated for about half a breath, then clicked “I accept.” I was in.
I put a few bucks on Adrien Brody winning Best Actor at the Oscars and a couple more on egg prices topping $6. With each clicked wager, a burst of confetti erupted on my screen. When I checked back a month later, I had made a profit of 43 cents. The whole thing felt about as thrillingly illicit as running a red light while riding a bicycle.
But my actions alone could be grounds enough to investigate Coplan, former enforcement officials told me. All the government needs to prove is that Polymarket broke its word from its 2022 settlement with the CFTC. And there is ample evidence that the problem is widespread: This winter, Polymarket traders bet more than $1 billion on the Super Bowl, at least some of which likely came from the U.S. “I’m sorry, I don’t think there’s that much offshore interest in our Super Bowl,” says Michael Bucella, who invested in Polymarket’s seed round. Before we went to press, I fessed up to Polymarket that I had broken its rules, and a spokesperson informed me that I would be blocked from trading. But Polymarket was only able to find my account and boot me after I handed over my username (jenw) and blockchain address.
When the government seized Coplan’s phone this past fall, it would have been looking for evidence that he was aware of the circumventions and either turned a blind eye or willfully encouraged it. “I think he knew,” says the venture capitalist who passed on Polymarket. “There was a bit of a wink-wink, like, ‘We geoblocked the U.S., and hopefully regulation will change at some point.’ It was sort of at that level of not really taking it seriously and hoping it just gets fixed for them but, in the meantime, being open to violating it, which made us uncomfortable.”
Other investors were willing to take the risk. Krug, the founder of the short-lived blockchain-based prediction market Augur, which Coplan had criticized, initially rebuffed Coplan’s repeated investment pitches. “What I told him was prediction markets are one of the hardest types of start-ups to build. There have been dozens of them, and none of them hit escape velocity,” says Krug. He made up a random target volume of $5 million a week and told Coplan he would invest if he reached it. In late 2023, Coplan called Krug to tell him he had done it. The ouster of Sam Altman at OpenAI had inspired a bet on Polymarket on whether he would return as CEO, and wagers poured in. Krug, who by then had joined Peter Thiel’s venture firm Founders Fund, led a $45 million investment round in Polymarket, announced in 2024. Coplan had proved his ability to persevere through some of the most difficult challenges a start-up can face. “It’s sort of like the slowness of the takeoff of Airbnb but combined with the legal frustrations of Uber,” says Krug.
In 2024, Polymarket delivered a powerful proof of concept when it predicted Joe Biden would drop out of the race almost immediately after the debate — a moment when many pundits, and Biden himself, were still denying the possibility. “There’s just this really interesting shift that started to happen as people started understanding that the traditional people you’d relied on to tell you what was going to happen were so wrong,” says Demirors. “And all of these random, anonymous people from all over the world are betting on Polymarket, and they’re getting it right. And it made a lot of people question, What else is wrong?”
Now, about 90 percent of all prediction-market activity happens on Polymarket, making it the winner among its peers. It boasts about 200,000 active traders who together bet an average of $12.5 million each day. And Polymarket has become at least as important for people who aren’t betting on it at all but who use it as an oracle to predict the future — a contingent that makes up some 94 percent of the site’s traffic. At Crypto Ball, Pincus’s daughter told Coplan that her school had given her an assignment to call the result of the election, so she “just looked at Polymarket and I got 100 percent.”
Coplan said he did not know Trump was going to win until the night of the election. A couple of weeks earlier, in fact, he attended a fundraiser with Tim Walz and contributed nearly $100,000 to Kamala Harris’s campaign. Of course, it’s possible to read Coplan’s donations as a hedge against his bigger bet that Democrats, who had pledged to crack down on prediction markets, would lose. “To the extent he had any look into the future — I don’t know if it was by luck or by accurate foresight, but he ended up with a business that was catapulted and catalyzed by the election that now allows his company to develop,” says Bucella, now the managing partner of Neoclassic Capital, who thinks Polymarket would not have survived another Democratic administration. “He took a big swing and a relatively big risk, and it paid off.”
What People Are Betting on Polymarket Right Now
Photo:
Photo:
Photo:
Photo:
Photo:
Photo:
One of the questions looming over Polymarket is whether it’s all that different from a stock-trading app or a gambling website. It has a disreputable air that makes it a magnet for buttoned-up regulators, a roguish atmosphere with its own coarse lingo. A “rules cuck,” for example, describes a disagreement on the definition of a betting outcome. Certain prediction markets, such as “assassination markets” or deadpools, can also incentivize people to do bad things, which sounds less far-fetched after an election cycle with multiple attempts on Trump’s life. A current market on whether there will be a new pope this year could be included in this category.
“I don’t think anybody’s gonna assassinate anybody for 100 bucks, but if it was, you know, $10,000 or a million? Okay, maybe. All these things about whether Trump will do anything- — obviously you could win in those markets by killing Trump because then Trump’s not going to do any of those things,” says Hanson. “But if we’re talking about things in Polymarket, almost all these things are not things that any one person could do much about.”
Polymarket drew criticism this winter when, as the Palisades fire still raged, it listed what might be called arson markets, which asked how many acres would burn and when the L.A. wildfires would be contained. The viral outrage over this choice only helped drive more people to bet on Polymarket. For his part, Coplan views the questions on his site — all of which Polymarket currently writes in-house — as merely a faithful reflection of what is happening in the world, akin to what the media does. “I don’t want us to be known as a site that’s like, ‘Oh, it’s these crazy things,’” said Coplan. “But it’s the same way that if you’re running a news station, you’re gonna want to cover whatever is going on.”
Election betting comes with its own stigmas. “It just feels a little unseemly to me,” says Massad, the former CFTC chairman. “I think there’s just a risk of a corrupting influence, if you will, and I think it degrades the democratic process.” A large trader who became known as the “French whale” after betting some $70 million on a Trump win ahead of the election caused much public hand-wringing about potential manipulation of Polymarket odds and therefore the election itself: If voters think the outcome is predetermined, that could create a self-fulfilling prophecy. But so far it appears that the guy just correctly read the room. “It turns out that this particular institution happens to be much more resistant to those attempts to influence it,” says Hanson of betting markets. “It’s a fact that we’ve shown in lab experiments and in mathematical theory and in the field.”
“Polymarket creates an environment where being right is financially rewarded,” Pishevar tells me. Which is not to say outcomes judged by Polymarket bettors to be highly likely always pan out. Last August, a market on the platform predicted a 98 percent chance of Beyoncé performing at the Democratic National Convention, but the pop star never showed up.
There are also questions of how and when Polymarket will begin making money. Several investors and many of the site’s traders expect the company to launch its own cryptocurrency, or token, though Coplan said he’s not clamoring to do so. “If we were just rushing to do a token, we would have done one by now,” he said. (The anticipation of a token, which could reward active bettors on the site, may partly explain a phenomenon called wash trading, in which bettors artificially inflate volume by taking both sides of a wager.) Or Polymarket could simply begin taking a cut of the billions of dollars of bets it is facilitating or charging others — say, hedge funds — to list their own betting markets. As with most existential questions about the business, Coplan’s not worried about it: “Look, when you’re a financial platform and there’s money in the mix, historically those are not really businesses that have a tough time monetizing.”
But the continued existence of Polymarket will likely depend on the extent to which Coplan can convince the government and the world at large that what he is doing is essentially within the bounds of current social mores surrounding trading and gambling and prognosticating. Some see the government’s case against the company as open and shut. In this view, Polymarket’s weak geofence and self-certifying box-checking are insufficient guardrails and a brazen abdication of the company’s duty. “I think that’s wrong,” says Massad. “If you were to say, ‘Oh, we don’t care if people are going around that geofencing,’ that would be a bad precedent vis-à-vis our markets generally.” A more diligent approach would be to verify customers’ identities the way that banks do, critics say. But among the dozen or so lawyers and regulatory sources I spoke with, several shrugged at what they described as a ticky-tacky sort of case against companies essentially playing a game of Whac-A-Mole with their law-evading customers.
Pishevar likens Coplan to Kalanick in that both “are geniuses and radical thinkers.” But comparing Polymarket to Uber may understate the magnitude of the legal challenges Coplan faces, since offering people rides isn’t quite as legally fraught as launching what could be described as an online casino. “Travis had to deal with cities, taxi medallions, and entrenched unions,” Pishevar says. “Shayne is dealing with the CFTC, gambling laws, and a financial system resistant to disruptive transparency.” Says a source close to Polymarket, “One of Polymarket’s top priorities for 2025 is to reenter the U.S. market in a legally compliant manner.”
“I think the most important thing is that we can sit here and say the world is a better place because Polymarket exists,” said Coplan. Certainly, Polymarket’s competitors seem ready to fill the void should Coplan go down. After the FBI raid, a slew of social-media influencers began posting on X about him. An account called Clown World compared Coplan to a certain other curly-haired professors’ son and crypto entrepreneur, posting, with side-by-side photos, “SBF LOOK ALIKE RAIDED BY FBI IN ILLEGAL BETTING SCHEME. If only there were signs.” Others piled on, including Antonio Brown, the former football player, who reposted a photo of Coplan with Tim Walz with the comment, “This [N-word] seem guilty …” Brown came clean and shared damning screenshots of direct messages from two members of Kalshi’s growth team, one of whom fed him the text, adding, “yo AB are you down to QT this,” while the other wrote, “let’s hit it.” Soon, others came forward with similar stories, including Elijah Schaffer, a conservative podcaster and TV personality, who said Kalshi offered him $3,500 to post about the raid proving Polymarket is “corrupt.” (He declined.) Tarek Mansour, the CEO of Kalshi, who is nicknamed “Tiny T” internally at Polymarket, did not provide comment. But in a now-deleted segment of a podcast following the dustup, reported by TechCrunch, Mansour admitted, “Some of our team got pretty heated. They didn’t pay anyone; they just asked some of our long-standing affiliates to post some of the memes.”
But Kalshi was doing more than just smearing Polymarket on social media; it may have put the fledgling start-up on the CFTC’s radar in the first place. When Polymarket launched in 2020, Kalshi was meeting frequently with the CFTC in pursuit of its own registration and requested the regulators investigate it, according to people familiar with those discussions. In Washington, Kalshi had a reputation for such tactics and is also believed to be at least partly responsible for the CFTC seeking in 2022 to suddenly shut down PredictIt, a U.S.-only prediction market it had previously allowed. John Aristotle Phillips, PredictIt’s CEO, says the only reason he was given for the shutdown was that the CFTC was “tired of having to tell” would-be competitors that they couldn’t do the same thing. “We got mugged,” Phillips says.
For now, Polymarket’s future is in the hands of the Trump administration. Trump’s nominee to lead the CFTC, Brian Quintenz, is a former commissioner who has expressed an open-mindedness toward prediction markets but who also sits on the board of Kalshi. While normally he might have had to recuse himself from Polymarket matters, this is the Trump administration, where officials wear their conflicts of interest like cuff links. If Coplan is undone by a Kalshi ally taking advantage of his regulatory power to punish a Kalshi rival, it would be an ironic reminder that ethical norms exist for a reason.
It will perhaps come as no surprise that several people I spoke with ventured to bet on Polymarket’s future. Krug tells me he’d give it a 60 percent chance of being legal sometime next year. (Coplan is “never someone I would bet against,” he adds.) “If I was putting my money on it, I think by the 2028 election, people are sure as hell going to bet on Polymarket in the U.S. I’m 99.9 percent sure that that would be legal by then,” says Jason Levin, a Polymarket fan who runs a marketing company called Memelord Technologies. Phillips says, “I’d give Polymarket better than 50-50 odds of surviving.”
Coplan himself resists betting on it. “People love Polymarket. We’ve run a tight and honest ship,” he said. “I’m optimistic.”
Related
