WILD CARD

New Long-Shot Pick Emerges for Trump’s Next Press Secretary

Kalshi bettors are weighing the contenders to replace Katie Zacharia, whose five-day tenure ended after a rocky debut.

Kalshi bettors are predicting who will replace Katie Zacharia as President Donald Trump’s new press secretary and one relatively unknown name is cropping up.

Prediction markets on Tuesday have White House deputy press secretary Anna Kelly as the frontrunner, at 15 percent. CNN’s MAGA pundit Scott Jennings follows at 13 percent, while former model and Republican Party spokesperson Elizabeth Pipko is the third favorite at 6 percent.

All three candidates were floated as possible successors to Karoline Leavitt in August, with Jennings the early favorite and believed to be the preferred candidate of Trump’s Chief of Staff Susie Wiles.

Kelly, 29, is the natural successor, having joined the press team in January 2025 as Leavitt’s deputy and later being promoted to principal deputy. However, she has already been passed over for the top job in favor of Katie Zacharia, who only lasted five days in the role.

She’s a former beauty queen and regularly appears on Fox News, both of which are basically qualifications for the job under the image-obsessed Trump.

Kelly has not commented publicly on whether she wants the role.

Jennings, 48, is known for defending Trump on CNN.

His own network reported that he had an “elevator pitch” meeting with Wiles where he discussed the job and made his case. Jennings has previously worked as communications director for George W. Bush and Sen. Mitch McConnell.

In August, Trump told reporters, “Scott Jennings is good,” when asked whether the political contributor was being considered for the position.

The wildcard is 31-year-old Pipko.

She was signed by Wilhelmina Models at 17 and then worked on Trump’s 2016 presidential campaign.

The former swimsuit model’s family is also closely connected to Trump world. Her husband, Darren Centinello, was a former staffer for Trump’s 2016 and 2020 campaigns. Her father, Roman Pipko, is U.S. ambassador to Estonia.

Her Russian-Jewish parents emigrated to the U.S. from the former Soviet Union, and she published a book in 2020 entitled Finding My Place: Making My Parents’ American Dream Come True. She also appears regularly on Fox News.

“She’s a beautiful woman inside and out,” Trump said of Pipko during a 2025 Hanukkah celebration at the White House.

At the same event, Pipko called Trump “the greatest president this world has ever seen” and said she is “grateful” to him for “so many things.”

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Zacharia was fired last week after a number of missteps.

Her sole press briefing was disastrous, lasting just 14 minutes and only taking questions from three conservative-leaning outlets. She followed that up by a Fox News interview where she blundered through explaining her qualifications and finally admitted she had never passed the bar exam, despite identifying herself as a lawyer.

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Her TV struggles ultimately proved her undoing to the TV-obsessed president, who initially hailed his new spokesperson as “terrific” before changing his tune Friday.

After getting canned, Zacharia described Trump as “kind, wonderful, gracious, thoughtful, enthusiastic, and the most hardworking man.”

Her five-day tenure broke the record for the shortest modern White House stint, previously held by Anthony Scaramucci, who lasted just 11 days as White House communications director in the president’s first term.

Trump can be quick to let people go, especially if they make him look bad. U.S. Ambassador to Greece Kimberly Guilfoyle, who was once engaged to Donald Trump Jr., got the boot last week after reports that she tried to get a donor to pay off her $100,000 Amex bill in return for access to the president. Attorney General Pam Bondi and Homeland Security Secretary Kristi Noem have also been ousted in the last year.

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Lauren HartleyBreaking News Intern

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