Anna Kelly Press Secretary Odds Slip to 17% as Scott Jennings Leads Kalshi at 39%. A Kalshi contract asking whether Anna Kelly will be the next White House press secretary swung to an 18% implied chance of yes as of August 13, 2026, up roughly 18 points in a single day, after President Donald Trump’s August 12 announcement that Karoline Leavitt would leave the podium at the end of the month, with no successor named. Nearly all of the market’s all-time volume traded on the day the news broke. The market has kept moving since: by August 20, 2026, Kelly’s contract stood at 17% while Republican strategist Scott Jennings surged to a market-leading 39%, a shift that changes how this succession race should be read — the internal-continuity favorite from the first 24 hours is now running second. The volatility has not settled even a week later: a Covers market update on August 24, 2026 put Kelly’s implied probability back up to 22%, per Covers, and the rally kept building from there — PredictionHunt tracked Kelly climbing to 26% within three days of that update, with Kalshi’s best available price hitting $0.23 and market consensus reading 25% YES, while Action Network’s September 2026 tally had her outright leading the Kalshi board again at 26%, with Alina Habba now the closest tracked challenger in third at 7.4%, a reminder that this contract keeps repricing right up to the moment Trump actually names someone.
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Current Odds at a Glance
The frontrunner has changed more than once since the story first broke. Based on the most recent Kalshi figures from the August 20, 2026 update, also reported that day by odds aggregator Oddschecker, here is how the top names compared at that point — though by September 2026 Action Network had Kelly back on top of the Kalshi board at 26%, with Alina Habba emerging as her closest tracked rival at 7.4%:
- Scott Jennings: 39% — up from an unquoted outside pick in the original August 13 field reporting, to 30% on August 19 and 39% on August 20.
- Anna Kelly: 17% — down from her 18% peak on August 13, after dipping to 13% on August 19 and then recovering four points on August 20.
- Natalie Harp: 6% — individually quoted for the first time in Oddschecker’s August 20 report, confirming her in third place.
- Everyone else: 38% combined — split among Steven Cheung, Roma Daravi, Alina Habba, Matthew Boyle, and other names not individually quoted.
No appointment has been confirmed. The figures above reflect Kalshi pricing, not a White House announcement, and the market can keep moving until Trump names his pick.
What the Kalshi market is asking
How the contract resolves
The contract is narrow and specific: Will Anna Kelly be the next White House Press Secretary of the United States? It trades on Kalshi, the US derivatives exchange regulated by the Commodity Futures Trading Commission. A “yes” pays out only if Kelly is the person who formally succeeds Leavitt. If Trump picks anyone else, the contract settles at zero.
Why the binary structure matters
That structure matters. This is not a market on whether Kelly is qualified, popular, or well positioned. It is a binary bet on one appointment decision that rests with one person. For readers new to how these instruments price events, our explainer on how prediction markets work walks through the mechanics of contracts that resolve to yes or no.
The odds as of August 13, 2026, and what they imply
A dormant contract turned active
As of August 13, 2026, the Kelly contract sat at an 18% implied probability of yes on Kalshi. In plain terms, traders collectively put a bit less than one-in-five odds on Kelly getting the job. The number climbed about 18 points over the prior 24 hours, and roughly 99% of the market’s all-time volume changed hands on that same day, a sign that the contract was effectively dormant until the Leavitt news gave traders something to price. Pricing was not uniform even within that single day: Action Network’s tracking of the live Kalshi market showed Kelly’s implied odds briefly surging past 40% intraday before settling back down, while a separate recap from Kalshi News pegged her chances at 23% for the month of August 2026, a spread that shows how much a single contract can swing within hours and across different recaps of the same feed.
How to read the 18% figure
Implied probability is just the contract price read as a percentage. An 18-cent “yes” contract that pays one dollar corresponds to an 18% chance in the eyes of the market. Our primer on implied probability covers why that translation is not the same thing as a forecast from a polling model or a betting tipster. On August 13, 18% said Kelly was a live contender, not a favorite, leaving 82% spread across every other possible pick. That gap between contender and favorite is exactly what widened over the following week.
The field shifts: Scott Jennings overtakes Kelly
The August 19 update: Kelly slips to 13% as Jennings climbs to 30%
Later Kalshi market updates show the August 13 spike did not hold. By August 19, 2026, Kelly’s contract had cooled to 13%, down five points from her peak. Over the same window, Scott Jennings, the Republican strategist and commentator listed in the original field reporting only as an outside pick with no percentage attached, had climbed to 30%, already more than double Kelly’s number. That is the first sign the “leading internal continuity pick” framing from August 13 was incomplete: reporters and traders had a second name to price once the initial burst of attention on Kelly settled.
The August 20 update: Kelly recovers to 17% as Jennings extends the lead to 39%
One day later, the picture shifted again. Kelly’s contract recovered four points to 17%, nearly back to her August 13 level, while Jennings kept climbing, rising nine points to a market-leading 39%. Both names gaining ground in the same 24-hour window points to money moving out of the longer tail of the field, the Cheung, Daravi, Habba, and Boyle names from the original reporting, and concentrating on the candidates traders now see as most likely to actually get the nod. Together, Jennings and Kelly accounted for 56% of the field market’s implied weight by August 20, leaving 44% spread across the remaining names and other possibilities. Oddschecker’s August 20, 2026 report breaks that 44% down further: Natalie Harp, a close presidential aide and former OAN anchor, was individually quoted at 6%, putting her in a clear third place for the first time in this market’s tracked history. That leaves roughly 38 percentage points spread across Cheung, Daravi, Habba, Boyle, and any name not yet prominently listed.
The gap between first and second place is widening faster than either candidate’s own number suggests. On August 19, Jennings led Kelly by 17 points, 30% to 13%. By August 20, that gap had grown to 22 points, 39% to 17%, even though Kelly herself gained four points in the same window. The only way a leader’s advantage grows while the runner-up is also gaining ground is if new money entering the market favors the leader more heavily, which is exactly what a nine-point Jennings gain against a four-point Kelly gain shows. Harp’s 6% now sits 11 points behind Kelly and 33 points behind Jennings, a wide enough spread that the race reads as a two-name contest with a distant third rather than a genuine three-way race.
What the shift signals about the field
The net move for Kelly from August 13 to August 20 looks small on its own, down one point overall from 18% to 17%, but the underlying story is not “nothing happened.” She lost the outright frontrunner status she held on August 13, and by August 20 she was running about 22 points behind Jennings rather than leading the field. For a market that resolves winner-take-all on a single appointment, second place still pays zero, so that gap matters more to traders than the raw one-point net change in Kelly’s own number suggests. Whether the numbers keep moving from here depends on the same kind of catalyst that started the whole event on August 12: a credible signal of Trump’s actual preference, not trading momentum on its own.
What moved the market: Leavitt’s exit
Trump’s August 12 announcement
The catalyst was concrete. On August 12, 2026, Trump announced that Karoline Leavitt would step down as White House press secretary at the end of August. Trump said she was leaving to spend more time with her young children and family and would continue to serve as an outside adviser. The departure was reported across mainstream outlets including CNN, CNBC, The Washington Post, NBC News, and Axios.
Why the lack of a named successor mattered
Crucially, neither Trump nor Leavitt named a replacement in their statements. That single gap is what turned a slow contract into an active one. Before August 12, the market had almost nothing to price because the seat was not open. Once the vacancy became a near-term certainty, the question flipped from “will there be a change” to “who gets picked,” and money flowed toward the names already inside the press operation, and, within a week, toward Jennings as an outside name as well. Kelly, as the sitting principal deputy press secretary, was the most obvious internal continuity candidate on day one, which is why she moved first and fastest.
Who is Anna Kelly
Career background and credentials
Anna Kelly is the White House principal deputy press secretary. She joined the administration in January 2025 after serving as a national press secretary at the Republican National Committee and in communications roles tied to the House of Representatives. Reporting describes her as being in her late twenties, with a political science degree from Auburn University and a master’s in political management from George Washington University.
Her podium experience during Leavitt’s leave
Her most relevant credential for this market is practical: Kelly helped cover press secretary duties while Leavitt was on maternity leave in spring 2026, following the White House Correspondents’ Dinner in late April. That stint gave her documented fill-in experience at the podium, and outlets covering her debut noted a mix of praise and criticism about her polish. For traders, prior time in the role is a reason to price her above communications staff who have never briefed the press corps under the lights, and it is likely why she still holds the second-highest reported number even after Jennings overtook her.
The rest of the field
Kelly is not the only name in circulation, and the crowded field is exactly why her contract sits well under a majority. Multiple outlets have floated a long list of internal and external candidates. The table below summarizes the names most frequently reported, along with their described roles and the most recent odds where individually quoted. Odds across outlets varied and shifted through the period, so the figures below are directional rather than settled.
| Reported candidate | Current role or background | Positioning in reporting | Odds, Aug 20 update |
|---|---|---|---|
| Scott Jennings | Republican strategist and commentator | Market-leading frontrunner as of Aug 20 | 39% |
| Anna Kelly | Principal deputy press secretary | Leading internal continuity pick, now second | 17% |
| Natalie Harp | Close presidential aide, former OAN anchor | Confirmed third place as of Aug 20 | 6% |
| Steven Cheung | White House communications director | Named as a leading contender | Not separately quoted |
| Roma Daravi | Kennedy Center VP of public relations | Cited as a top name on Kalshi’s field market | Not separately quoted |
| Alina Habba | Trump attorney, former acting US attorney | Early frontrunner who reportedly slipped | Not separately quoted |
| Matthew Boyle | Breitbart Washington bureau chief | Named among external options | Not separately quoted |
Scott Jennings’ climb from outside pick to frontrunner
Jennings is the field’s clearest mover. He entered the reporting as an outside pick with no individual percentage attached in the original field-market breakdown, then was individually quoted at 30% on August 19 and 39% on August 20, a nine-point jump in a single day. That trajectory, rising fast once he was broken out as his own line in the market rather than folded into “the rest of the field,” is the main reason the race now reads as a two-name contest rather than a Kelly-led field.
Natalie Harp’s confirmed third place
Harp is the field’s other notable mover, though for a different reason than Jennings. She had circulated in outlet reporting from the start as a close presidential aide and former OAN anchor with a plausible path to the podium, but no outlet had attached her a specific number through the August 19 update. That changed on August 20, 2026, when Oddschecker individually quoted her at 6%, the first hard figure tied to her name in this market. Six percent is a modest number in isolation, but it is meaningful in context: it puts her ahead of Cheung, Daravi, Habba, and Boyle, none of whom carry an individually quoted figure at all. Being the third name to break out of the unquoted pack, rather than the fourth, fifth, or sixth, is itself informative for traders trying to gauge which names the market treats as live possibilities versus which are along for the ride in outlet reporting.
Where the rest of the field stands
Cheung, Daravi, Habba, and Boyle remain in circulation in outlet reporting, and none were individually quoted with a specific percentage in the August 19 or August 20 updates referenced above, though a separate Kalshi market note from later in August 2026 broke out a fourth name, GOP operative Martin, at 11%, alongside Jennings at 30% and Kelly at 17% in that same snapshot. With Jennings, Kelly, and now Harp together accounting for 62% of the field market’s implied weight by August 20, the remaining 38% is what is left to divide among these four names and any late entrant, a shrinking share compared with where the field stood on August 13. Separately, Federal News Network reported that roughly 23% of prediction-market participants were backing Kelly for the role across August 2026, broadly in line with where Kalshi itself had her that month. Sportsbooks were pricing the same question in a different format that same week: a BetOnline sheet dated August 13, 2026, reported by journalist Jim Rosica, listed Kelly at 4/1 to be named the next press secretary, a traditional odds format that converts to roughly a 20% implied chance and lines up closely with where Kalshi itself had her that day.
Because Kalshi runs a separate “field” market listing many candidates against one another, no single name dominated as of August 13, with several clustered in the high teens to low twenties depending on the outlet and the hour. That fragmentation was the mathematical reason a strong internal candidate could still read at only 18% that day. By August 20, the fragmentation had narrowed considerably: Jennings’ 39% was more than double Kelly’s 17%, which was itself nearly triple Harp’s 6%, and the top three names had pulled away from the rest of the reported field by a wide margin.
Why traders are cautious about calling Kelly a lock
Trump’s pattern with combative communicators
The core uncertainty is that the decision is unresolved and personal. There is no confirmed appointment and no official White House statement naming Kelly, or Jennings for that matter. Trump has a documented pattern of choosing communications figures who match a combative media style, and several names on the list, including Cheung, fit that profile as well as Kelly does. A continuity pick is the low-disruption option, but this White House has not always taken the low-disruption path.
Settlement risk in a single-name contract
There is also settlement risk baked into any single-name contract. Even a candidate widely described as the internal favorite loses the entire bet if Trump reaches outside the press shop. That asymmetry keeps disciplined traders from bidding a lone name much above the point where the reward stops compensating for the chance of an outside pick. It is the same dynamic that shows up in other event contracts we have tracked, from the Fed rate cut odds to binary political and technology markets.
That caution proved warranted. Six days after peaking at 18% on August 13, Kelly’s contract had already fallen to 13%, and even after a partial recovery to 17% on August 20 she was running well behind Jennings’ 39%. The swing is a live example of why traders discount a single name even when the early reporting narrative favors that person: the field can reprice faster than a “leading candidate” label can catch up. The volatility did not stop there either — a Covers update dated August 24, 2026 had Kelly’s implied probability back up at 22%, yet another double-digit move in under two weeks that underscores just how unsettled this single-name bet remains.
What this means for a tech and finance audience
Dormant-to-explosive volume patterns
Personnel markets like this one are a useful case study in how regulated event exchanges behave when a discrete, high-attention catalyst hits. Volume was effectively nonexistent until the vacancy became real, then spiked to nearly all of the contract’s lifetime turnover in hours. That pattern, dormant then explosive, is characteristic of markets tied to a single announcement with a known trigger and an unknown outcome.
Why regulated exchanges price on news flow, not fundamentals
It also underlines a structural point about the venues themselves. Kalshi operates as a CFTC-regulated exchange available to US persons, which is why a Washington personnel question can trade openly on it. Traders weighing where these contracts live can compare the platforms in our Kalshi versus Polymarket comparison and our detailed Kalshi review. The takeaway for a finance reader is that liquidity and price discovery here are driven by news flow, not fundamentals, so a headline can reprice a contract faster than any model would. The Kelly-Jennings swing between August 19 and August 20 adds a second data point to that pattern: a nine-point, one-day move in Jennings’ number and a four-point rebound in Kelly’s show that the volatility did not end once the initial news cycle passed. For a market structured around a single yes-or-no resolution, that is a reminder that repricing can continue for as long as the underlying decision stays open.
What to watch next
Signals that would move Kelly’s number
The market resolves on a single event: Trump naming a new press secretary before or around Leavitt’s end-of-August departure. Watch for an official White House announcement, since that is the only thing that settles the contract. Short of that, expect Kelly’s odds to move on reporting about who is interviewing, who is inside the building, and whether Trump signals a preference for continuity over a fresh public face. If a name other than Kelly keeps consolidating support in credible reporting the way Jennings did between August 13 and August 20, her contract should keep drifting lower, because the field market is close to zero-sum.
Signals that would move Jennings’ number
Jennings enters this next stretch as the reported frontrunner, so his number is now more exposed to reversal than Kelly’s was in mid-August. A signal that Trump wants an internal continuity pick after all, a credible report naming a different outsider, or simply a quiet news cycle could all cut into his 39%. Because the field market is close to zero-sum, any losses for Jennings have to show up as gains somewhere else, whether that is Kelly or a name not yet prominently listed.
Signals that would move Harp’s number
Harp’s move into the individually quoted tier changes what counts as a signal worth watching for her specifically. At 6%, she needs a specific, credible catalyst, not just continued attention, to close the 11-point gap to Kelly or the 33-point gap to Jennings. The kind of news that moved Jennings from an unquoted outside pick to a 39% frontrunner in about a week is the template: a report naming her as an active interview candidate, or a signal that Trump favors a media-facing profile similar to hers, is the type of catalyst that could push her past Kelly the way Jennings already has. Absent that, her 6% is more likely to hold as a marker of “plausible but not favored” than to keep climbing on its own.
A second thing to monitor is volume. If turnover stays concentrated and thin, sharp swings like the August 13 jump to 18% or Jennings’ nine-point rise on August 20 can reverse just as fast on a single well-sourced story. Thin markets move more per dollar traded, which cuts both ways.
Frequently asked questions
Is Anna Kelly confirmed as the next press secretary?
No. As of September 2026, there is still no confirmed appointment and no official White House statement naming her. She was the leading reported candidate on August 13 at 18%, then slipped to 13% on August 19 and only partly recovered to 17% on August 20 while running behind Scott Jennings — but the picture flipped again after that: PredictionHunt had her climbing to 26% within days of an August 24 Covers update, and by September 2026 Action Network had her back on top of the Kalshi board at 26%, with Alina Habba running second in that tracked field at 7.4%.
Why did the odds jump 18 points in a day?
Trump announced on August 12, 2026, that Karoline Leavitt would leave at the end of August. That opened the seat and turned a dormant contract into an active succession market, with nearly all of its lifetime volume trading that day.
What does an 18% implied probability mean?
On August 13, 2026, it meant the market priced roughly a one-in-five chance that Kelly would get the job. It is a market-implied estimate, not a forecast or a guarantee, and it has already moved: by August 20 Kelly’s contract was at 17% and no longer the field’s highest.
Who is leading the race now?
As of the August 20, 2026 update, Republican strategist and commentator Scott Jennings led the Kalshi field market at 39%, ahead of Kelly at 17%. Jennings was listed only as an outside pick with no individual percentage in the original August 13 reporting.
Who is in third place behind Jennings and Kelly?
Natalie Harp, a close presidential aide and former OAN anchor, was individually quoted at 6% in Oddschecker’s August 20, 2026 report, the first time she has carried a specific number in this market. That puts her a clear third, 11 points behind Kelly and 33 points behind Jennings.
Who else could replace Leavitt?
Reported candidates include Scott Jennings, communications director Steven Cheung, Roma Daravi, Alina Habba, Natalie Harp, and Matthew Boyle, among others. By the August 20 update, Jennings, Kelly, and Harp accounted for 62% of the field market’s implied weight, with Cheung, Daravi, Habba, and Boyle among the names splitting the remaining 38% and not separately quoted.
When will the market resolve?
It resolves when Trump names a new press secretary, expected around Leavitt’s end-of-August 2026 exit.
The Bottom Line
Sources
- CNN — White House press secretary Karoline Leavitt leaving role, Trump announces
- CNBC — Trump says Karoline Leavitt resigning as White House press secretary
- NBC News — Karoline Leavitt to step down as White House press secretary at end of month
- Axios — Karoline Leavitt stepping down as White House press secretary
- Newsweek — Karoline Leavitt Departing: Who Could Replace Her?
- Kalshi — Next White House Press Secretary market
Prediction markets carry financial risk and are not investment, legal, or betting advice. Availability is restricted by jurisdiction: Kalshi is a CFTC-regulated US exchange, while Polymarket is not available to US persons. Participation is limited to those of legal age, generally 18 or 21 depending on your location. Odds cited reflect Kalshi and Oddschecker market data through August 20, 2026, and change constantly. If gambling is a problem for you or someone you know, call 1-800-GAMBLER for confidential help.
