Scott Jennings Doubles to 32% After Wiles Meetings and Trump Endorsement

---

Why Is Scott Jennings Surging to 32% as Trump's Next Press Secretary?

Scott Jennings has jumped from 16% to 32% in the "Who will be Trump's next Press Secretary?" market after a cluster of reporting revealed he held secret dinners with White House Chief of Staff Susie Wiles and publicly defended Trump aide Natalie Harp on air. Multiple White House staffers now believe Wiles is backing him for the job. That combination of moves, along with Trump saying "Scott Jennings is good," has reshaped the race to replace the departing Karoline Leavitt.

Prediction markets on Kalshi and Polymarket now price Jennings at 32% implied probability, up 15 percentage points in three days and 24 points from his period low of 8%. He is currently the highest-priced candidate in the field. The move coincides with reporting that Wiles met Jennings at Mastro's Steakhouse in Washington at the White House's request, according to CNN's account published by The Daily Beast. A senior White House official told CNN: "He's competent and good on TV."

The timing matters. Former Trump attorney Alina Habba, once a strong contender, has publicly ruled herself out. That narrowed the field and redirected attention toward Jennings, who has been sending clips of his media appearances directly to senior White House staff, according to Politico's Playbook as reported by The Daily Beast.

With the market reacting this sharply, understanding where Jennings stands relative to other candidates is essential.

---

Scott Jennings vs. the Field: Where the Press Secretary Market Stands Now

Jennings sits at 32%, but this is not a coronation. At Kalshi, he prices at 36%. At Polymarket, 27%. That nine-point spread between platforms reflects genuine uncertainty about whether Wiles' reported backing will translate into a Trump decision.

The remaining candidates illustrate how open this race remains. Natalie Harp, Trump's 35-year-old executive assistant and former One America News host, is reportedly in the mix after Trump joked to advisers that he might tap her for the role. Ari Fleischer, George W. Bush's former communications director, has also been floated. Trump has reportedly told aides he wants a male replacement to avoid direct comparisons with Leavitt, which would theoretically favor Jennings and Fleischer over Harp.

Prediction-market view

Live prices, venue by venue

Compare the latest YES price at each venue. Check market rules, liquidity, and fees before trading.

Scott Jennings

Consensus YES price across 3 venues

15%average

PolymarketBest YES price14.7¢Kalshi16¢Predict.fun16.7¢

Danielle Alvarez

Consensus YES price across 1 venues

8%average

KalshiBest YES price9¢

No new person

Consensus YES price across 1 venues

5%average

KalshiBest YES price8.1¢

Steven Cheung

Consensus YES price across 1 venues

1%average

KalshiBest YES price1.7¢

Current new-user offer · Kalshi

Get a $35 trading bonusCode PRED35

New users only. Eligibility restrictions and terms apply.

View current offer

Even at 32%, there is a 68% implied probability that someone other than Jennings gets the job. The market is pricing him as the frontrunner, not the presumptive pick.

---

Scott Jennings Price History: Tracking the Move from 16% to 32%

The chart below captures one of the sharpest three-day moves in this market's history. Jennings sat near 16% at the start of the week. By August 24, he had doubled.

The acceleration appears to track a cluster of reporting between August 18 and August 20. On August 18, The Daily Beast published details of Jennings criticizing Senator Jon Ossoff for attacking Harp. By August 19, the outlet reported on Jennings' secret meetings with Susie Wiles. On August 20, CNN reported Wiles considers him her preferred candidate. Each data point compounded the previous one, creating a staircase of repricing.

The period low of 8% puts the total swing at 24 points. That kind of move in an appointment market typically requires at least one principal (in this case, Wiles or Trump) to signal a preference on or near the record.

---

Are There Polls for Who Will Be Trump's Next Press Secretary?

No traditional polling exists for this question. White House staff appointments are not elected positions, so Gallup, Quinnipiac, and similar organizations do not survey them. There are no primary ballots, no exit polls, no approval ratings specific to press secretary candidates.

Prediction markets are the only continuously updated, quantified probability signal available. The 32% figure for Jennings represents the aggregated beliefs of traders on Kalshi and Polymarket who are putting real money behind their assessments. Unlike a poll, these prices adjust in real time as new information emerges. When The Daily Beast reported the Wiles dinner, the price moved within hours.

This makes the market uniquely valuable but also uniquely susceptible to information cascades. A single well-sourced report can move the price dramatically because there is no polling baseline to anchor expectations. The 15-point swing this week is a feature of thin-information markets, not a flaw.

---

The Case Against Scott Jennings as Press Secretary

The strongest bear case against Jennings is simple: Trump has not decided, and Trump's decisions are notoriously unpredictable. Wiles may favor Jennings, but the president has a documented pattern of overriding staff recommendations, especially for high-visibility positions. Multiple sources told NOTUS that while Trump is "interested" in Jennings, he is "not sold," per The Daily Beast.

There is also the CNN problem. Jennings has spent years as the network's designated Republican voice, which gives him media fluency but also associates him with an outlet Trump has repeatedly labeled "fake news." Whether Trump sees a CNN contributor as an asset (someone who can handle hostile press) or a liability (someone who legitimized the enemy) remains genuinely unclear. His Bush administration background could cut both ways for the same reason.

Then there is the Natalie Harp wildcard. Trump reportedly joked about promoting her, but Trump's jokes have a way of becoming policy. Harp travels with the president constantly, has on-camera experience from OAN, and would generate the kind of media spectacle Trump gravitates toward. At 32%, Jennings is priced as though Wiles' backing is close to decisive. If Trump decides on gut instinct rather than staff process, that 32% could deflate rapidly.

For those tracking the full field and live prices, the Who will be Trump's next Press Secretary? odds page has continuously updated standings across all candidates. The market resolves December 31, 2026, giving Trump months to make or delay this decision.