Anna Kelly Leads US Press Secretary Prediction Market as Katie Zacharia Leaves

Written By Jon Young | Published at October 20, 2026
Past US press secretaries - next US press secretary prediction market
Past US press secretaries - who will succeed Katie Zacharia in the White House? IMAGE: USA TODAY Network via Reuters Connect

Another week, another ‘Trump’s Next Press Secretary’ prediction market opens. After Katie Zacharia’s disastrous term as the White House spokesperson, Kalshi has opened a new market on who will take the job.

Zacharia was a surprise choice to begin with, surprising Kalshi traders as she leapt from $0.01 obscurity to settle at $1.00. Backers of long-term favorites Anna Kelly and Scott Jennings were left scratching their heads and counting their losses.

Then came Katie Zacharia’s first day on the job, when she managed to mangle at least one press conference and fail to answer at least half a dozen questions.

The prediction markets continue, however, and it’s business as usual. Well, kinda…

Next US Press Secretary Prediction Market: Frontrunners (for now)

It seems like literally days ago that we were predicting an early exit for Katie Zacharia from her White House position.

We correctly predicted Zacharia would be out before Jan 1, 2027. At $0.40, that was the smart play as it factored in both her inexperience and some inevitably bad midterms to explain away.

After a few days in the job, Donald Trump took pity on his pick and let her go. It didn’t help, of course, that Zacharia had perhaps been economical with the truth about her legal career.

Anna Kelly: ‘Yes’ @ $0.15

So, it’s as you were before Zacharia’s surprise appointment, with Anna Kelly back heading the Kalshi market.

Traders are a little more cautious this time around. The experienced deputy press secretary was trading at $0.23 in the original ‘Next Press Secretary’ market.

Kelly still heads the new market, but at $0.15 there’s a little more value to be had.

Kelly has the experience and will be able to answer tricky questions from the press. With a midterms slaughter expected this month, wise heads will be needed.

Our pick: Kelly the rightful favorite – Kalshi, $0.15

Scott Jennings: ‘Yes’ @ $0.14

Scott Jennings may not be a former beauty queen, but that hasn’t stopped traders thinking the media man has a real chance of getting the job long-term.

Jennings is a conservative strategist (although he’s spoken out against Trump in the past) and has worked on several presidential campaigns in the past.

Jennings has also worked as a senior contributor to CNN, writes newspaper columns, and hosts his own podcast: ‘Flyover Country with Scott Jennings’. That sounds like the complete package if Trump can steel away from beauty queens.

Our pick: Jennings the media cool head – Kalshi, $0.14

Elizabeth Pipko: ‘No’ @ $0.95

There is one model in the list of favorites to become the next U.S. press secretary: Elizabeth Pipko.

Pipko has the right-wing credentials to succeed Zacharia. She started out as a volunteer on Donald Trump’s 2016 presidential campaign and has worked as a spokesperson for right-wing Jewish group, The Exodus Movement.

However, as with Zacharia, Pipko’s education history may come under scrutiny. She’s claimed to have studied at Harvard but was actually a student at Harvard Extension School.

Despite some appearances on FOX, Pipko ultimately lacks the experience to take on what will be a tough gig over the next two years. The ‘No’ is the only play here.

Our pick: A safe ‘No’ for Pipko – Kalshi, $0.95

The ‘Next U.S. Press Secretary’ prediction market is turning out to be one of the most volatile of 2026. Check back tomorrow to discover another hot trending market.