President Trump faces an unexpected challenge as White House Press Secretary Karoline Leavitt announced her departure at the end of August 2026, leaving the administration just two weeks to find her replacement. The 28-year-old, citing her desire to spend more time with her two young children following maternity leave, triggered an immediate search for the next face of the White House press briefing room.

The Leading Contenders Emerge

Conservative political commentator Scott Jennings currently leads the race to replace Leavitt, according to prediction markets. The CNN contributor and former aide to President George W. Bush was considered for the role when Trump retook office in 2024. Trump has publicly praised Jennings as a patriot who gets it and promoted his recent book. Anna Kelly, the principal deputy press secretary who filled in during Leavitt’s maternity leave, ranks second among potential candidates despite never taking the podium for an official briefing.

Alina Habba, who previously declined the press secretary position to serve in other capacities, now ranks third. After a controversial stint as interim attorney for the District of New Jersey that ended when her appointment was ruled unconstitutional, Habba currently serves as senior advisor to the attorney general for United States Attorneys. Other names circulating include White House communications director Stephen Cheung, senior advisor Stephen Miller’s wife Katie Miller, Breitbart Washington Bureau Chief Matthew Boyle, and former deputy chief of staff Taylor Budowich.

Rotating Briefers Likely

Former Trump press secretary Sean Spicer predicts the next press secretary will be someone with a strong existing relationship with the president. Spicer withdrew his name from consideration, emphasizing Trump understands the importance of this role in communicating positions on policy, personnel and key issues. Some administration observers expect a rotating line of Trump officials to brief the press corps temporarily, similar to what occurred during Leavitt’s maternity leave this summer, rather than an immediate permanent replacement.

Historical Context

Leavitt served 19 months as press secretary, making her Trump’s second-longest-serving spokesperson in the role. Only Arkansas Governor Sarah Huckabee Sanders, who held the position for 23 months during Trump’s first term, served longer. The turnover in this critical position has been notable throughout Trump’s presidencies. Stephanie Grisham famously held the role for nine months without conducting a single press briefing before Kayleigh McEnany took over through the end of Trump’s first term. The scramble to find Leavitt’s successor highlights the demanding nature of one of the most visible and scrutinized positions in the White House.