Kalshi Names Obama Campaign Veteran as Policy Advisor

Kalshi continues to focus on the future by bringing in yet another high-profile Washington insider to assist it with paving its operations amid growing pressure and legal troubles.

After tapping into former Biden-era staffer John Bivona at the end of January 2026 and naming Donald Trump Jr. as a strategic advisor in 2025, the prediction market company has now brought in another prominent political strategist, this time one who previously worked on campaigns for Barack Obama and Bill Clinton.

“I Want to Help Kalshi Own That Story”

Stephanie Cutter, a longtime advisor to Democratic leaders, has joined Kalshi’s team as a policy advisor. Cutter previously served as a senior advisor during Obama’s 2008 run, later becoming chief of staff to Michelle Obama.

From her new position, Cutter will assist the company with deepening its relationships in Washington, D.C., at a time when prediction markets are facing both growing interest and political pressure.

“I’ve spent my career at the intersection of media, politics, and business, where noise and polarization often obscure the truth. Data cuts through that,” Cutter said.

“Kalshi gives millions of Americans a data-driven alternative to opinion and guesswork, and they do it responsibly. In a world drowning in opinion, prediction markets are one of the few places where the data has real skin in the game, and I want to help Kalshi own that story,” she added.

Kalshi co-founder and CEO Tarek Mansour welcomed the move:

“Stephanie Cutter is the person you want on your team. She understands better than most how to cut through the noise and get your message to the right people,” Mansour said. “I’m excited to learn from her.”

Beyond her political work, Cutter is also a managing partner at Precision Strategies, a Washington-based consulting firm.

Complex Landscape

Kalshi has drawn attention over the past year for expanding into sports-related event contracts, as well as political outcome trading. Despite the company arguing that its platform offers regulated, data-driven forecasting tools, critics are concerned about the implications of trading on real-world events.

The regulatory landscape has also greatly shifted in the last few years. Under the current administration, the Commodity Futures Trading Commission has taken steps toward providing clearer oversight for both sports and election-related contracts. 

Still, some lawmakers continue to push for tighter restrictions, including proposals to limit political and sports event trading on regulated exchanges. Kalshi, together with competitors like Polymarket, keeps promoting prediction markets as a tool that can complement polling by aggregating what it calls the “wisdom of the crowd.” Whether that argument holds as regulation evolves, it remains to be seen.