By Katie Rogers, Annie Karni and Maggie Haberman
If a White House official wanted to talk to President Donald Trump, it helped to have a good relationship with Madeleine Westerhout, his 28-year-old assistant. She was known for brusquely deflecting officials senior to her both in title and age who wanted a few minutes of face time with the president with one withering question: “Why are you here?”
But it was not what some administration officials saw as Westerhout’s overprotectiveness of the president that led to her abrupt and unceremonious departure from the White House on Thursday. Instead, it was an act of disloyalty.
At an off-the-record dinner and several rounds of drinks with reporters two weeks ago during the president’s working vacation in Bedminster, New Jersey, she shared personal details about the president and his family.
Westerhout attended the dinner with Hogan Gidley, a White House spokesman. After he left, she began to tell reporters about Trump’s eating habits, his youngest son, Barron Trump, and his thoughts about the weight and appearance of his daughter Tiffany Trump, according to a group of current and former administration officials who were told what happened.
Accounts of the dinner, which reporters from The New York Times did not attend, began circulating at the White House within a couple of days. But it took over a week for the information to reach the president. It was delivered to him by Mick Mulvaney, the president’s acting chief of staff, who said Westerhout had indiscreetly discussed details of his family to reporters.
An ambivalent Trump had to be persuaded throughout the day Thursday that Westerhout, who was on vacation in California, needed to resign, which she did that night.
In interviews, over a dozen current and former Trump administration officials said that the episode was emblematic of a White House where constant turnover has allowed inexperienced staff members to rise to positions of power — or, at least, to pursue them.
Westerhout, a 2013 graduate of the College of Charleston in South Carolina, came to the White House on the recommendation of Trump’s first chief of staff, Reince Priebus, the former head of the Republican National Committee, where she has been an assistant. Her previous experience included time as an intern in the 2012 Romney campaign and a job as a fitness instructor.
As he departed Washington for Camp David on Friday afternoon, Trump said Westerhout had been drinking when she “said things about my children” to reporters. He praised Westerhout’s work in the White House and admonished reporters for breaking an off-the-record agreement.
“But still, you don’t say things like she said,” Trump added of Westerhout, “which were just a little bit hurtful to some people.”
Trump also said that he loved his daughter: “Tiffany is great,” the president said.
Even for a White House besieged with leaks from the beginning, Westerhout’s behavior was considered a stunning breach of protocol for an aide who Trump this year had promoted to special assistant and director of Oval Office operations.
“He was expressing confidence in her,” Martha Joynt Kumar, a political science professor at Towson University who has studied the presidency and the culture of the White House. “As president, you need to be confident that that person is going to respect your wishes and your privacy and also the privacy of the family.”
After two years in the White House, one former senior official said, “she thought she was a senior adviser” and who tried recently to weigh in on crafting Trump’s tweets rather than an aide in a secretarial role. In recent months, Westerhout had become more interested in traveling with the president and in Bedminster it was noticed that she was seated closer to the president than his chief of staff at a campaign briefing.
Westerhout’s main responsibilities were answering the phone and providing clerical help to the president. But her role was tailored to Trump’s particular eccentricities. Whenever the president held an event at the White House, it fell to Westerhout to make sure that it was well attended, according to one White House official.
“How’s the room looking?” she would email to dozens of White House staffers in different departments. If there was any question that the room appeared full, Westerhout would make sure to find staff members or interns to send to it to avoid Trump’s anger at lackluster attendance.
Westerhout became an expert at reading his moods and translating them for other aides, according to those officials. She also became good at monitoring whom he was speaking with and, in some cases, alerting other White House officials if someone had called to try to rile the president up, as some of his outside advisers have been known to do.
Trump did not immediately trust her when she was hired at the White House. She had no prior relationship with the president, and according to “American Carnage,” a recent book by Tim Alberta, the chief political correspondent for Politico Magazine, she wept on election night at the fact that he won — an account confirmed by White House officials.
But she was immediately installed outside the president’s office. Trump, who was whipsawed and overwhelmed by his own surprise victory, has historically cared a great deal about who guards access to him; at Trump Tower, it was a role of considerable influence. With so much to learn and so many jobs to fill, Trump had little choice but to go along with the staff that was provided to him, according to current and former officials. He was told by Priebus that she could be trusted.
Priebus eventually left the White House but Westerhout developed her own relationship with her perennially suspicious boss. The president appeared happy to see her when she would pop her head into the Oval Office to try to interrupt a meeting that had dragged on too long, even if he shooed her away, according to White House aides.
The president had grown to trust her and grew fond of her. According to Alberta’s book, he would refer to her as “my beautiful beauty.” She was often at his side on trips to Mar-a-Lago, his Palm Beach, Florida, resort, where she would accept gifts on behalf of Trump and trade business cards with his supporters. Some of them knew that if they wanted to reach the president by phone, they could bypass his other gatekeepers and go directly to her.
But she also had a fairly large coterie of enemies, including some in the East Wing, the purview of the first lady, Melania Trump, which viewed her with suspicion. Some of the president’s friends counseled him over the last two years that she was, in the words of one, “immature,” and was blocking access to him from some people he’d known for years.
She had also raised suspicion with her indiscreet comments about the president, including openly complaining to aides that Trump had disrupted his own schedule because he had been late leaving the White House residence after his daily executive time sessions, according to one former official.
Inside the faction-split White House, Trump loyalists cheered Westerhout’s departure as a move that was long overdue, and said they hoped it served as something of a wake-up call for Trump to bring in more loyalists into the West Wing. But current and former officials also expressed alarm about what information Westerhout could share down the road, not just about the president, but her colleagues.
Adding to the concern was the fact that, unlike most other officials, Westerhout was not thought to have signed a nondisclosure agreement, a document that Trump has frequently used in effort to tamp down on leaks.
At least one publishing house on Friday had discussions about trying to approach Westerhout for a book, according to one person familiar with the discussions.
Chris Whipple, who has written a book about White House chiefs of staff, said that Westerhout had broken a cardinal rule in discussing the president’s family.
“This is a unique presidency,” Whipple said in an interview. “But the idea that the first family is off limits is certainly not unique and that’s certainly something that White House staffers in the past have done at their peril.”