On Wednesday, President Trump announced that Karoline Leavitt would be leaving her post as White House Press Secretary at the end of August 2026. Leavitt has served as White House Press Secretary since President Trump started his second term in January of 2025. Leavitt followed President Trump's announcement with a statement of her own, citing her children as a primary factor for departing the role.
In July, Leavitt returned from maternity leave following the birth of her second child in May. President Trump added in his statement that she will remain a close advisor. Her departure leaves one of the most forward-facing roles in the Trump administration vacant with a plethora of options for President Trump to pick as Leavitt's successor.
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Alina Habba was the early frontrunner for the vacancy, but the market has shifted since the announcement. Habba served as President Trump's legal counsel for a number of different cases during Trump's four years out of office between terms.
Since the Trump administration retook office, Habba has held a string of roles throughout the Trump administration. Habba's role as advisor to Pam Bondi linked her as a possible Attorney General nominee after Bondi's departure. However, Trump opted towards Todd Blanche to fill Bondi's shoes. Habba currently sits at 13% on Kalshi markets.
The candidate who has gained the most ground is already within the West Wing. Anna Kelly, the White House Principal Deputy Press Secretary, now leads the Kalshi market at 23% and could be a viable option for promotion from within.
Another candidate within the West Wing is White House Communications Director Steven Cheung. Cheung has served in an array of roles for President Trump in both administrations as well as in between President Trump's terms, including leading communications for President Trump's PAC, MAGA Inc. He currently has a 10% chance.
Jason Miller, a senior Trump communications aide who held a prominent role in both the 2016 and 2020 campaigns, is another West Wing-adjacent name in the mix. Kalshi markets give him a 9% chance at the role.
Beyond the West Wing, a number of GOP political operatives could also receive the call. Roma Daravi is a candidate who has been tied to the Trump administration since 2016 who could vie for the position. She currently works as the Vice President of Public Relations at The John F. Kennedy Center for the Performing Arts and has a 14% chance.
Natalie Harp, a former One America News anchor and vocal Trump supporter, is also in the mix at 13%. Elizabeth Pipko, a model who started her career in politics on the Trump campaign in 2016, has served as the national spokeswoman for the Republican National Committee since 2024. She has a 4% chance.
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