Business · Prediction Markets
Kalshi Investigates Well-Timed Bets on Trump’s Press Secretary Pick
Three small wagers placed before Katie Zacharia’s selection became public stand to pay out nearly $10,000, renewing questions about insider trading on event-betting platforms.

The prediction market Kalshi is investigating a cluster of small bets that correctly forecast President Trump’s choice of Katie Zacharia as White House press secretary before the news became public, according to The Wall Street Journal, which first reported the review. A Kalshi spokesperson confirmed the investigation to the Journal and declined to say more, Reuters and The Block reported.
The wagers were modest in size but extraordinary in their returns. A $19 bet placed around 10:40 p.m. Eastern time on Thursday is set to pay $1,896. Two more, of about $74 and $80, were placed around 1:41 p.m. on Friday and are expected to pay $3,689 and $4,023. Together the three stakes came to about $173, with a combined expected payout of roughly $9,600, according to The Block’s account of the Journal’s reporting.
Those prices reflected long odds. Before her selection was reported, traders on Kalshi gave Zacharia about a 1% chance of getting the job. News of the pick broke around 2 p.m. Friday, and Trump confirmed it on social media that afternoon. Zacharia, a conservative commentator who briefly worked at the Department of Homeland Security, succeeds Karoline Leavitt.
The investigation itself does not establish wrongdoing, and the traders have not been publicly identified. Bets on Kalshi appear anonymous to other users, but the company keeps records of who places them. The White House did not respond to the Journal’s request for comment. It had earlier warned staff in a memo against using nonpublic information for private gain, after well-timed bets tied to the war with Iran drew scrutiny. The Commodity Futures Trading Commission, which regulates Kalshi, also did not respond before the Journal published.
The case is the latest in a series that has put event-betting platforms under pressure. In July, a former White House teleprompter operator came under investigation by the commission over bets on what Trump would say in public, and in August he agreed to repay about $107,500 in profits and pay a $65,000 civil penalty, according to The Block. In May, House Oversight Committee Chairman James Comer opened an inquiry into insider trading on Kalshi and its rival Polymarket.
Kalshi has said it is tightening its own controls. In June it began requiring some traders to disclose their employers before betting on markets it considers at high risk of insider trading, and it reported more than 20 referrals to law enforcement and over 150 internal investigations in the first quarter of the year.
Defenders of regulated prediction markets argue that cases like this show the system working: because a federally supervised exchange knows who its customers are, suspicious trades can be traced and punished in a way that is impossible on offshore sites. Critics counter that markets on government personnel decisions invite exactly the kind of leak-driven betting that erodes public trust, however small the dollar amounts.
Sources
- Reuters (via The Star), Oct. 9, 2026: Wall Street Journal report, Kalshi confirmation, bet sizes and payouts, Zacharia’s roughly 1% odds and background, CFTC investigation of a former teleprompter operator in July
- The Block, Oct. 10, 2026: exact timing of the three bets, total stake and expected payout, timing of the announcement, Kalshi’s record keeping, White House memo and lack of comment, CFTC settlement terms in August, Comer inquiry, Kalshi’s disclosure rules and first-quarter referral and investigation figures
This article was drafted with automated tools from the sources listed, checked by a review pass, and published by Daniel Varrone. Corrections: editor@monochromechronicles.com