A single guest list from a New Jersey estate has thrown Washington’s rumor mill into overdrive.
President Donald Trump hosted dozens of allies at his Bedminster property over the weekend, and one attendee in particular has political observers buzzing.
Alina Habba, the president’s former personal lawyer, appeared in a social media video taken at the gathering, placing her squarely inside the circle of candidates being weighed for one of the administration’s most visible jobs.
That job belongs, for now, to Karoline Leavitt.
The 28-year-old press secretary announced this week she will leave her post, pointing to the strain of raising two young children while running the White House press operation.
Her second child, Viviana, was born May 1, and the return to work afterward proved increasingly difficult to manage alongside her duties.
Habba’s name has circulated for weeks as a possible replacement. Her attendance at the Bedminster gathering has now added fresh fuel to that speculation.
Long before her name entered the succession conversation, Habba built her reputation in the courtroom.
She defended Trump during the New York civil fraud trial brought by state Attorney General Letitia James, a case centered on allegations that Trump and his company misrepresented the value of financial assets.
Judge Arthur Engoron ruled against Trump in 2024, ordering him to pay a judgment exceeding $460 million. That outcome did not stand.
A New York appellate court reversed the decision in August 2025, handing Trump a major legal win and vindicating the defense Habba helped mount.
Habba’s professional path includes founding her own firm. She launched Habba, Madaio and Associates LLP in 2020, opening offices in Bedminster and New York, her home state.
Her role expanded further in March 2025 when she was named acting U.S. Attorney for New Jersey, a position overseeing federal criminal and civil prosecutions throughout the state.
That chapter closed in December 2025, when an appeals court found her appointment did not satisfy federal requirements and ordered her removal from the post.
She did not go quietly.
“But do not mistake compliance for surrender,” Habba wrote in a statement posted to X. “This decision will not weaken the Justice Department, and it will not weaken me.”
Habba is one name among several. Monica Crowley, Trump’s chief of protocol, has been floated as a contender, as has CNN commentator Scott Jennings.
Jason Miller, a former adviser to Trump’s campaign, appears on the list as well.
So does Anna Kelly, Leavitt’s own deputy, along with Katie Miller, a former administration official turned conservative podcaster who is married to White House Deputy Chief of Staff Stephen Miller.
Internal deliberations over the pick remain unsettled, according to people familiar with the discussions.
One source characterized Leavitt’s departure as “unplanned” but stressed the position she is vacating is “a super important job” for the president.
No immediate timeline has been set for naming a successor. “There is probably time before he makes a decision,” the source told the UK’s Mirror.
Leavitt’s plan to leave first became public last week, setting the current round of speculation into motion.
Signs of transition had already been building for months. Leavitt began maternity leave in April, a stretch that forced the administration to adjust how it managed press briefings in her temporary absence.
Kelly’s name surfaced as a top internal contender even during that earlier period.
Reports in March described her as widely viewed within the White House as the leading in-house candidate for the job, well before Leavitt’s resignation became official.
Kelly’s background includes senior communications roles at the Republican National Committee and in the House of Representatives before she joined the White House in January.
She also holds the title of special assistant to the president, a position noted on her social media profile that places her near the center of top-level administration decisions.
The pressure to settle the question is expected to grow.
With November’s midterm elections approaching and control of both chambers of Congress on the line, Republicans are likely to push for a faster resolution to the search for Leavitt’s replacement.
