Trump 'Not Quite Sold' on Jennings, Who Falls to 27% for Press Secretary

---

Scott Jennings' Chances for White House Press Secretary Are Falling. Here's Why.

Scott Jennings has dropped to 27% on Kalshi and Polymarket to become Trump's next Press Secretary, down from 35% three days ago, after a NOTUS report revealed Trump is "not quite sold" on him as Karoline Leavitt's successor. The 8-point drop came despite Jennings meeting with Chief of Staff Susie Wiles and actively circulating pro-Trump TV clips to senior West Wing staff.

Scott Jennings has been doing everything a candidate for White House Press Secretary is supposed to do: meeting with the chief of staff, defending Trump allies on national television, and circulating clips of his performances to senior West Wing staff. None of it appears to be working on the one person whose opinion actually matters.

The gap between platforms tells its own story. Kalshi holds Jennings at 31%, while Polymarket prices him at 23%. That 8-point spread suggests genuine disagreement among traders about how to interpret Trump's hesitation: is it a soft rejection or a negotiating posture?

---

Scott Jennings Has Been Openly Auditioning for Press Secretary, and Washington Has Noticed

The lobbying effort has been anything but subtle. White House Chief of Staff Susie Wiles met Jennings at Mastro's Steakhouse in Washington, a sit-down reported by The Wrap that signaled Jennings had at least cleared the first gate. His background checks the conventional boxes: former Bush White House staffer, longtime Republican strategist, senior adviser to Mitch McConnell, and a CNN contributor whose combative pro-Trump segments have made him a favorite among MAGA viewers.

Then came the Natalie Harp episode. After Democratic Senator Jon Ossoff criticized Harp, Trump's special assistant, Jennings went on air and called Ossoff a "sucker punching coward." He then reportedly sent clips of the exchange directly to senior White House staffers, per Politico's Playbook, treating it as an informal audition tape. The move attracted attention. The Daily Beast described it as "desperate." Whether or not that framing is fair, the act of distributing your own highlight reel to the West Wing is not the behavior of someone who has already been told the job is his.

---

Why Trump Being "Not Quite Sold" Is the Only Signal That Matters for This Race

Trump's press secretary selection process has never resembled a standard hiring funnel. There is no search committee, no shortlist vetted by HR. It is a single-decision-maker race in which personal chemistry, television presence, and loyalty instinct outweigh credentials. Trump has cycled through Sean Spicer, Sarah Huckabee Sanders, Stephanie Grisham, Kayleigh McEnany, and Leavitt across two terms. Each choice reflected a specific mood and strategic need, not a resume competition.

That history makes the "not quite sold" report from NOTUS especially damaging for Jennings' implied probability. When Trump likes a candidate, the process moves fast. Leavitt herself was named within days of the transition. Hesitation at the presidential level, especially hesitation that leaks, typically means one of two things: either Trump is using the delay to extract concessions, or the candidate is being kept warm while the real pick materializes. Sources have also told reporters that Trump is eager to select a man for the role to avoid direct comparisons with Leavitt, which should theoretically help Jennings. The fact that it hasn't closed the deal reinforces how personal Trump's reservations appear to be.

---

Where Scott Jennings Sits in the Press Secretary Market Right Now

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

Jennings at 27% means the market assigns roughly a one-in-four chance he gets the job. That is a clear downgrade from where he stood when the Wiles meeting became public. The competitive field remains in flux. Alina Habba, who briefly led the market at over 41%, publicly denied she is seeking the position and crashed to 7%. Other names floated include Harp and former Bush communications director Ari Fleischer, though neither has drawn the kind of sustained market interest Jennings initially attracted.

The broader context adds uncertainty. Leavitt's resignation is effective at the end of August, giving Trump days rather than weeks to make a final call. The departure of James Braid, Trump's top congressional liaison, adds to a broader exodus that may be consuming West Wing bandwidth. The market resolves December 31, 2026, meaning a prolonged vacancy with rotating senior officials handling briefings is itself a plausible outcome.

---

The Case for Jennings: Why 27% Could Be Too Low

The strongest argument for Jennings is structural. He is the most publicly visible candidate. He has already sat down with the chief of staff. He has a built-in audience from CNN that would generate the kind of media coverage Trump values in a press secretary. And his willingness to go to war on air, unprompted, on behalf of a mid-level Trump aide demonstrates exactly the kind of loyalty instinct that has historically won these auditions.

There is also a reading of the "not quite sold" report that works in Jennings' favor. Trump frequently expresses ambivalence about candidates he ultimately selects. The leak itself may have come from rivals hoping to tank Jennings' momentum. And with Habba out, Fleischer untested in the market, and Harp lacking the public profile Trump typically demands, the field may simply be too thin for Trump to pass on the most obvious option.

Traders considering a position at 27% need to weigh that thinning field against one uncomfortable fact: when Trump is enthusiastic about a hire, everyone knows it. Silence from the principal, especially with a deadline looming, is not a negotiating tactic. It is data. You can track the full field and live pricing on the Who will be Trump's next Press Secretary? odds page.