Karoline Leavitt’s abrupt departure reportedly blindsided Donald Trump’s White House—and new details suggest the president tried to persuade one of his most trusted aides not to leave.

CNN White House correspondent Alayna Treene reported that Leavitt’s decision “came as a surprise to many people” inside the administration. Her exit leaves Trump without his chief public messenger only three months before the pivotal midterm elections.

Leavitt announced Wednesday that she will step down as White House press secretary at the end of August. She attributed the decision to the difficulty of caring for two young children while handling one of the most demanding communications jobs in American politics.

She gave birth to a daughter on May 1 and returned to work after taking only about a month of maternity leave, according to CNN.

Trump publicly praised Leavitt and said she would continue as one of his top outside advisers. But Treene reported that the president had asked her to remain in her White House position.

“This came as a surprise to many people,” Treene said, adding that the press secretary’s role has been particularly difficult to fill under Trump.

Leavitt was reportedly far more than the administration’s podium spokesperson. Treene described her as one of Trump’s closest advisers and part of the small circle of loyalists who traveled with him during the 2024 campaign.

Her relationship with Trump extends back to his first administration, when she worked in the White House press operation. Years of service reportedly allowed her to gain access and trust that exceeded what many press secretaries ordinarily enjoy.

“She’s part of that very small group of really loyal people who have been with the president on the 2024 campaign trail,” Treene said.

Leavitt was also reportedly among the relatively few officials admitted to sensitive West Wing meetings, giving her direct knowledge of major administration decisions. Her departure therefore removes not only a highly visible defender but also an insider deeply embedded in Trump’s decision-making process.

“She has continued to be one of those people that goes into sensitive meetings as one of the few people that actually knows what is going on at high levels in the West Wing,” Treene explained. “So it’s a loss for the president.”

The timing compounds the disruption.

With the November elections approaching, the White House must now find someone capable of defending Trump, coordinating the administration’s message and responding to controversies under intense scrutiny. A new press secretary would need to earn the president’s confidence almost immediately.

“The White House is losing their chief messenger just three months before the midterm elections,” Treene said.

Trump’s frequent contact with Leavitt during her brief maternity leave also underscored why she may have concluded that the position was incompatible with family life.

Treene said sources told her that Trump continued calling Leavitt while she was away and sometimes asked when she planned to return. That account does not establish that the president forced her to cut her leave short, but it illustrates the persistent pressure surrounding her role.

“When she was on maternity leave, the president, even then, was still frequently calling her and at times was asking when she was going to come back,” Treene reported.

Leavitt described her resignation as a painful but necessary choice. She said she could not provide her children with the time, attention and energy they deserved while fulfilling the constant responsibilities of press secretary.

Trump said he understood and respected the decision. He also made clear that the political relationship would continue, calling Leavitt a trusted aide and predicting that she would become an influential Republican voice outside the government.

That arrangement could allow Leavitt to campaign for Trump and defend his agenda without maintaining the relentless schedule of an official White House spokesperson.

It does not, however, solve the administration’s immediate communications problem.

Replacing Leavitt requires more than hiring an experienced media professional. Trump has historically demanded fierce loyalty from his spokespeople and expects them to defend his statements aggressively, often with little preparation. The successful candidate must also be someone he trusts enough to include in private deliberations.

Leavitt’s unusual combination of loyalty, institutional knowledge and television combativeness made her especially valuable to the president. Her successor may inherit the title without immediately inheriting that influence.

The White House has not publicly named a replacement. Until it does, questions will persist about whether the administration had any succession plan—or whether Leavitt’s announcement truly left officials scrambling.

Her departure may be driven entirely by the family considerations she described. But the reported surprise inside the West Wing demonstrates how little prepared Trump’s team appeared to be for losing her.

The president will retain Leavitt as an outside ally. What he loses is the person who stood at the podium, entered the sensitive meetings and translated his wishes into the administration’s daily message.

And she is walking away at precisely the moment the political battle is about to become most punishing.