Trump’s Next Press Secretary Prediction Redux: Turning the Page After Zacharia’s Chapter Abruptly Ends

David Huber
Published: Mon 2nd November, 07:01 2026
Reviewed By Paul Skidmore
press secretary Katie Zacharia

Just 24 hours before the 2026 midterm elections, a revamped “new market” for who will become President Trump’s next press secretary has emerged on prediction market apps. Kalshi traders have already placed $5.3 million in trades on which individual will follow in the footsteps of Katie Zacharia, the shortest-term press secretary in US history.

Will the 45th and 47th POTUS opt to go with the “next in line” personality this time? Or will he decide to give the position to longshot Scott Jennings? Let’s take a look at what prediction market forecasters are saying via real money trading activity!

Our two main picks for Trump’s next press secretary

The lineup for potential candidates includes a “who’s who” of MAGA Republican talent: from former TV host Kari Lake and presidential confidant Laura Loomer to family prodigy Lara Trump. Yet the two frontrunners are Deputy Press Secretary Anna Kelly and Republican strategist Scott Jennings.

At 21¢ per contract, we believe Anna Kelly’s contracts possess plenty of value, especially now that Trump’s “3D chess” appointment of Katie Zacharia backfired. Kelly has both the knowledge and experience necessary to bring White House press conferences back to the standard that her former boss Karoline Leavitt set.

Kelly is 29 years old and female; Jennings is 49 years old and male. The “central casting” advantage obviously goes to Anna Kelly, if previous trends set by President Trump are anything to go on. We’re also picking up the 35¢ contracts on the appointment being announced before November 20th of this year.

Favorite Picks: Who will become Trump’s next press secretary? – Anna Kelly, When will Trump announce the appointment? – Before November 20th, 2026

Examining the underdog picks for Trump’s next press secretary

There are several contracts currently available on Kalshi’s political prediction markets that may be severely undervalued. If the Democrats win control of both the House and Senate, the probability that the president will pursue prosecutorial avenues or invoke emergency powers increases. Such actions would cause the contract prices of Trump “loyalists” to surge.

Massive longshot contracts for Laura Loomer and Lara Trump could increase from less than a penny all the way up to 5¢ between now and November 20th if the Democrats sweep congressional control. Look for these two to provide loads of value if the perception of a January 2021 repeat of the “rigged” narrative begins to fester within the current administration following the November 3rd midterms.

Separately, the contract prices for “The Huddle” host Sean Spicer and Fox personality Peter Doocy could gain momentum if POTUS chooses to accept the election results without much of a legal challenge. Either way, we don’t believe a new press secretary will be named this week, at least not until congressional control has been “called” by several major media outlets.

Anna Kelly remains the “sensible” choice

Kalshi forecasters seem to place Anna Kelly as the most “sensible” choice for Trump’s next press secretary. The only question is whether Kelly will be a strong enough ally if the president goes into full “rampage mode” following the midterms.

The Texas Senate race, specifically, could prove to be the most accurate indicator of which party will control the upper chamber once new members are sworn into office this coming January.

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