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Over the course of 11 interviews, Wiles offered pungent assessments of the president and his team: Trump “has an alcoholic’s personality.” Vice President JD Vance has “been a conspiracy theorist for a decade,” and his conversion from Trump critic to ally was based not on principle but was “sort of political” because he was running for Senate.
Elon Musk is “an avowed ketamine” user and “an odd, odd duck,” whose actions were not always “rational” and left her “aghast.” Russell T. Vought, the budget director, is “a right-wing absolute zealot.” And Attorney General Pam Bondi “completely whiffed” in handling the Epstein files.
Wiles described her own reservations about certain policies in real time to Whipple, author of a well-regarded book on White House chiefs of staff, even as debates raged inside the administration. She said she urged Trump not to pardon the most violent rioters from Jan. 6, 2021, which he did anyway. She unsuccessfully tried to get him to delay his major tariffs because of a “huge disagreement” among his advisers. And she said the administration needed to “look harder” at deportations to prevent mistakes.
But she did not complain about being overruled and at various points said she “got on board” with the eventual decisions. “There have been a couple of times where I’ve been outvoted,” she said. “And if there’s a tie, he wins.”
The off-script comments felt reminiscent of a similar episode in President Ronald Reagan’s first term when his budget director, David A. Stockman, likewise gave a series of interviews to what was then called The Atlantic Monthly with candid observations that caused a huge stir.
While Stockman kept his interviews secret from the White House (and nearly got fired), the broader Trump team cooperated with Vanity Fair. Vance and Secretary of State Marco Rubio gave interviews and along with top aides such as Stephen Miller and Karoline Leavitt posed for glamour photographs by Christopher Anderson.
Wiles, a low-key Florida political strategist who ran Trump’s successful comeback campaign last year, has been the president’s most important aide this term, credited with running a more disciplined operation than he had in his chaotic first term. He has embraced her so much that he referred to her during a rally last week as “Susie Trump.”
But the White House under Wiles is chaotic, too, just in a different way. Unlike John F. Kelly, the president’s longest-serving chief of staff in his first term, who saw his job as trying to prevent what he considered radical, unwise, or even illegal actions, Wiles does not view her role as constraining Trump. Instead, she makes clear that her mission is to facilitate his desires even if she sometimes thinks he is going too far.
She attributes her ability to work for Trump to growing up with an alcoholic father, sportscaster Pat Summerall.
“High-functioning alcoholics or alcoholics in general, their personalities are exaggerated when they drink,” she said. “And so I’m a little bit of an expert in big personalities.” While Trump does not drink, she said he has “an alcoholic’s personality” and operates with “a view that there’s nothing he can’t do. Nothing, zero, nothing.”
In a sign of how much her job revolves around the president’s big-personality, stream-of-consciousness public comments, she keeps a free-standing video monitor next to the fireplace in her West Wing office with a live feed of Trump’s social media posts.
The president’s fixation on payback against his enemies offers a case study. Wiles confided in Whipple in March that she had told Trump that his presidency was not supposed to be a retribution tour.
“We have a loose agreement that the score settling will end before the first 90 days are over,” she said then. When that did not happen by August, she told Whipple that “I don’t think he’s on a retribution tour” but said that he was aiming at people who did “bad things” in coming after him. “In some cases, it may look like retribution,” she said. “And there may be an element of that from time to time. Who would blame him? Not me.”
Among the targets, she acknowledged, was New York Attorney General Letitia James, who won a civil court verdict against Trump for business fraud with a penalty of nearly $500 million. “Well, that might be the one retribution,” Wiles said. Did she advise Trump to back off? “Not on her. She had a half a billion dollars of his money.” (An appeals court later threw out the penalty as excessive but left the verdict intact.)
As for James Comey, the FBI director who was fired by Trump while leading an investigation into Russian interference in the 2016 election, Wiles said, “I mean, people could think it does look vindictive. I can’t tell you why you shouldn’t think that.” She added: “I don’t think he wakes up thinking about retribution. But when there’s an opportunity, he will go for it.”
The Trump administration has brought indictments against James and Comey, but both were dismissed by a federal judge. The administration has vowed to keep trying, but two grand juries have since refused to re-indict James and another judge issued a ruling that will make it harder to pursue Comey.
Reached for comment Monday evening, Wiles played down Trump’s personal motivations in the actions against his enemies. “It’s not that he thinks they wronged him, although they did,” she told The New York Times. “He thinks that they wronged, and they should not be able to do to somebody else what they did to him and the way that you could cure that, at least potentially, is to expose what was done.”
She added that she wanted to get that over with early in the term. “You don’t want it to get in the way of the real agenda,” she said. “And so, loosely, let’s get it all going within 90 days. Which we did. Now, the justice system works slowly and so even if it was initiated in 90 days, it could be a long time before it’s done.”
In the interviews published by Vanity Fair, Wiles faulted Bondi, one of her closest friends in the administration, for her early handling of the Epstein files, an issue that has been a cause célèbre for Trump’s right-wing base.
“I think she completely whiffed on appreciating that that was the very targeted group that cared about this,” Wiles said. “First, she gave them binders full of nothingness. And then she said that the witness list, or the client list, was on her desk. There is no client list, and it sure as hell wasn’t on her desk.” Vance, by contrast, understood the sensitivity because he himself was “a conspiracy theorist,” she said.
Wiles said she has read the Epstein documents and acknowledged that Trump’s name is in them. “We know he’s in the file,” she said. “And he’s not in the file doing anything awful.”
But neither, apparently, is Clinton. Asked about Trump’s claims going back years that Clinton had visited the Epstein island, Wiles said, “There is no evidence.” Asked if there was anything incriminating about Clinton in the files, as Trump has suggested, she said, “The president was wrong about that.”
Wiles described frustration with Musk, the billionaire who early in the year was empowered to eviscerate federal agencies and fire employees en masse with almost no process. “He’s an odd, odd duck, as I think geniuses are. You know, it’s not helpful, but he is his own person.” When he shared a post saying that Stalin, Mao and Hitler didn’t murder millions, their public sector workers did, Wiles said, “I think that’s when he’s microdosing.” Asked what she meant, she said, “he’s an avowed ketamine” user.
