Prediction betting sites that rode to prominence on Trump-world connections are now flooding Democratic circles with cash and hires before Democrats take both chambers of Congress.
Kalshi and Polymarket built their brands under the Trump administration's hands-off regulatory approach. Donald Trump Jr. holds financial stakes in both competitors. But with Democrats about to control the Hill and promising investigations, the platforms are buying bipartisan insurance — and the money trail tells the story.
Since the start of the year, Kalshi has hired two former Biden White House officials — one as a policy adviser, another as a top lobbyist, according to The Intercept. The company's co-founders have dropped nearly $1 million on federal candidates, with more than a third — $377,000 — flowing to Democrats including Sen. Kirsten Gillibrand of New York. Kalshi's hires tilt toward establishment Democrats, including Stephanie Cutter, a strategist who worked across the Obama and Biden administrations and on Kamala Harris's campaign.
Polymarket, for its part, hired a Republican former top official at the Commodity Futures Trading Commission as a lobbyist. The CFTC under Trump has sued states that tried to regulate sports betting as gambling.
The spending spree comes as prediction markets face mounting scrutiny over election betting and a spate of suspicious Washington trades tied to policy moves and even military action. Democrats on Capitol Hill have already called for Trump to bar White House staffers from using the sites, and with a Democratic Congress incoming, investigations are widely expected.
Ella Fanger, corporate power policy adviser for the progressive group Demand Progress, predicted the companies will keep courting allies on both sides. "They've been hopeful that they can have Democratic champions for their policy agenda," she said, "and not just have Trump's cronies sticking out their necks for them."
Kalshi's head of government relations, John Bivona — himself a former Democratic congressional staffer and Biden White House official — said the company is willing to work "across the ideological spectrum." In a statement, Bivona said Kalshi has backed "legislation that protects consumers, keeps minors off our platform, makes insider trading bans standard across the industry, and ensures the CFTC has the resources they need."
The Demand Progress report details Trump Jr.'s industry ties but also shines a light on the revolving door of former Democratic staffers now carrying water for the betting platforms. The bipartisan hiring and donation blitz is a textbook play: when the power shifts, the lobbying dollars follow.
The question is whether Democrats — who spent years railing against prediction markets as a threat to election integrity — will cash the checks or crack down. History says the revolving door usually wins.
