The Secret History of Polymarket - Part 1

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Investigative Series

The Secret History of Polymarket – Part 1

Part I of a two-part series exposing the truth behind the world’s most popular prediction market and its dark ambitions to alter both markets and representative government forever

byMark GoodwinandbyWhitney Webb<br>June 30, 2026<br>55 minute read

Shayne Coplan, now the world’s youngest “self-made” billionaire, is the public face of what purports to be the world’s largest crypto-powered prediction market – Polymarket. Coplan and his alleged arch-rival, Tarek Mansour of the competing prediction market platform Kalshi, recently buried the hatchet to create a new venture capital firm called 5c(c) Capital, a reference to the section of the Commodity Exchange Act which is currently used to regulate prediction markets. The fund is aimed at bulking up the infrastructure for what has rapidly become an insurgent digital industry.

Since the early days of Donald Trump’s 2nd term, prediction markets like Polymarket and Kalshi have largely been told to police themselves. This comes courtesy of the current head of the (CFTC), Michael Selig, who was previously a lawyer representing major cryptocurrency industry clients. Selig became the CFTC chair only after the Trump administration rescinded the nomination of Brain Quintenz, who then sat on Kalshi’s board and worked for the crypto venture team at Marc Andreessen’s firm Andreessen Horowitz. Andreessen Horowitz has notably backed Coplan’s new prediction market VC firm 5c(c) Capital and is also heavily invested in Kalshi.

During the past couple of years, Polymarket and Kalshi have become important components of reporting on global finance and politics. This is partially due to their extensive cultivation of wide-ranging media partnerships. For instance, in the case of Polymarket, the company now boast partnerships with the Wall Street Journal and its parent company Dow Jones, as well as Yahoo! Finance, Substack and the live-streaming platform Parti. While these partnerships have been framed as an effort to further legitimize prediction markets, concerns have been raised that these media partnerships could be used to intentionally manipulate these very markets via the implantation of false and misleading stories.

Concerns like these have dogged these new prediction markets just as their star has risen. Insider trading allegations, including from the platforms themselves, have shown how prediction markets can be abused by traders with insider access to market movers and policy makers. Now with Congress trying to get involved, both Polymarket and Kalshi have announced new efforts to work to improve “market integrity” without the need for government intervention. However, the effects of their efforts remain to be seen, as several of the new measures are based on traders self-reporting their conflicts of interests.

Concerns about widespread insider trading have only been exacerbated by both the White House’s open dismissal of those concerns as well as the Trump family’s close ties to both Polymarket and Kalshi. For instance, Trump’s son, Donald Trump Jr., is both a strategic advisor to Kalshi and also advises Polymarket. Trump Jr. is also a major investor in Polymarket via his venture capital firm 1789 Capital. The evidence of insider trading on these platforms, particularly in cases where it is directly related to Trump’s “most consequential decisions,” is now widely acknowledged by mainstream media.

While the ascendance, and arguably the normalization, of insider trading are being treated as unintended “flukes” of these markets, there is an argument to be made that they are operating just as intended. Some of the evidence for that argument can be found in what appears to be Polymarket’s true origins.

Despite being nominally founded in 2020, Coplan –– in founding his company –– was admittedly following the model of the Big Tech billionaires he had admired as a teen, particularly those who created their flagship companies by rebranding and privatizing controversial military programs from the George W. Bush era for maximum profit and, seemingly, to advance even darker ambitions.

Previous reports from Unlimited Hangout have explored how Mark Zuckerberg’s Facebook gave new life to the Pentagon’s LifeLog program the day it...