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Anna Kelly Climbs to 26% for Press Secretary Despite Trump's Reported

Kelly gained 8 percentage points in three days. The rise came while NOTUS reported Trump is specifically seeking a male replacement for Leavitt.

August 31, 20264 min readJoseph Francia, Market Analyst
Where the market standsUpdated September 28, 2026
20%−6 pp since publishedvia Polymarket

Bottom line

Traders are backing Anna Kelly at 26%, up from 18% in three days, betting her deputy role outweighs Trump's reported preference for a male pick.

Market average
21% YES
Best listed price
21¢ · Kalshi
KalshiTrade YES at 21¢
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Anna Kelly Is Rising in Press Secretary Odds Despite a Reported Gender Filter

Anna Kelly, the White House Deputy Press Secretary, has risen to 26% in the "Who will be Trump's next Press Secretary?" market on both Kalshi and Polymarket, up from 18% three days ago, even as NOTUS reports that President Trump is specifically seeking a male successor to Karoline Leavitt. That 8-percentage-point gain came during the exact window when the male-preference reporting circulated. Traders moved her price up, not down.

The signal is hard to ignore. Kelly already briefs reporters and understands the internal rhythm of the communications shop. Proximity to the podium, in prediction market pricing, often functions as a gravitational pull that overrides stated preferences from principals. Traders appear to be betting that institutional positioning beats a president's reported mood.


Who Is Replacing Karoline Leavitt? The Full Candidate Field

Leavitt's departure sent the White House into a scramble. The Daily Beast reported that nearly a dozen staffers have left in recent weeks, including Deputy Press Secretary Abigail Jackson, Deputy National Security Adviser Andy Baker, and Director of Media Affairs Sonny Joy Nelson. The incoming press secretary will inherit a depleted communications operation.

Scott Jennings, the conservative CNN commentator, has been the most prominent male name floated. Oddschecker noted Jennings surging in some market snapshots. His profile fits the reported criterion: male, media-savvy, and publicly loyal to Trump. If Trump's stated preference holds, Jennings is the logical beneficiary.

Yet Kelly's 26% tells a different story. The market is pricing her as a serious contender despite the gender filter. One explanation: Trump's reported preferences often shift. A second: Kelly is already inside the building, already cleared, already briefing. Outside hires require vetting, relocation, and trust-building with a president who prizes familiarity. Jennings has never held a government communications role.


Anna Kelly Press Secretary Prediction Market Odds: Live Tracker

The current snapshot captures a market in tension. Kelly's 26% implied probability reflects traders who believe proximity outweighs stated preference. The price is synchronized across Kalshi and Polymarket, leaving no platform arbitrage and reinforcing that the move reflects genuine consensus rather than thin-market noise on a single exchange.

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For context, 26% translates to roughly a one-in-four chance. That is not a frontrunner position, but it is strong enough to represent a serious market bet that Trump's male-preference filter either does not hold or does not apply with enough force to disqualify the deputy already doing the job.


The Case Against Kelly

The strongest argument against a Kelly appointment is straightforward: the president reportedly does not want her profile for the role. According to NOTUS, Trump is weighing a male candidate specifically to create visual and stylistic distance from Leavitt. If that preference is firm, Kelly's insider positioning is irrelevant.

There is a second risk. The White House staff exodus, as The Daily Beast documented, is broad enough that Kelly herself could choose to leave rather than compete for the top job. Lisa Camooso Miller, a former RNC communications director, told Bloomberg that hiring into this administration during its second two years will be exceptionally difficult. That same dynamic could accelerate departures among those already there. If Kelly exits, her contract goes to zero.

Traders buying at 26% need to believe that either Trump's stated preference is soft, that no viable male candidate emerges quickly, or that Kelly's daily presence at the podium creates a fait accompli. All three are plausible. None is certain.


How Anna Kelly's Odds Have Moved Over Three Days

The trajectory from 18% to 26% is the core data point. What matters is when the price moved relative to the NOTUS report. If the gain accelerated after that story dropped, traders are actively disagreeing with the reported preference. If it preceded the report, the move may simply reflect organic positioning based on Leavitt's departure.

This market resolves by December 31, 2026, giving it roughly four months of trading life. That timeline matters because Trump could announce a pick within days or let the deputy role function as an interim arrangement for weeks. Every day Kelly holds the podium without a named replacement, her implied probability should structurally increase. The full field and live prices are on the Who will be Trump's next Press Secretary? odds page.

The bottom line: Anna Kelly is trading like an insider whose physical proximity to the job outweighs a presidential preference that may or may not survive contact with the actual hiring process. At 26%, the market is pricing real doubt about whether Trump follows through on the male-candidate filter, while also acknowledging she is far from a lock.

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The story so far: Who will be Trump's next Press Secretary?

7 updates · Aug 19 – Sep 13

Anna Kelly Leads the Press Secretary Race at 15%, Down 9 Points in ThreeSep 13Kelly dropped from 24% to 15% in three days. Trump's silence is redistributing speculative money to outside names, not any rival's strength.Anna Kelly's Press Secretary Odds Fall 8 Points Amid White House ChaosSep 5Kelly dropped from 26% to 18% in three days. A Pentagon resignation, policy infighting, and an insider-trading scandal are rattling the entire appointment field.Scott Jennings Drops 9 Points as Trump Reportedly Has DoubtsAug 28Jennings fell from 29% to 20% in three days after Mediaite reported Trump is 'not quite sold,' even as Chief of Staff Susie Wiles backs the CNN commentator.