That said, there's nothing here that tells me I've been wrong about any part of my deeply held opinion that Trump and Company are fucking us all with our pants on pretty much every fucking day.
By the end of this piece, I'm convince Wiles was just pretending to make nice while lying her ass off, just like every other douche nozzle in the Trump administration.
Susie Wiles, JD Vance, and the “Junkyard Dogs”: The White House Chief of Staff On Trump’s Second Term
Throughout the first year of Donald Trump’s second administration, Vanity Fair writer Chris Whipple has interviewed Wiles amid each moment of crisis. This insider’s account joins a portfolio of portraits for an unflinching, up-close look at power—and peril.
On the morning of November 4, 2025, an off-year Election Day, White House chief of staff Susie Wiles was meeting in the Oval Office with the president and his top advisers, men she calls her “core team”: Vice President JD Vance, Secretary of State Marco Rubio, and Stephen Miller, deputy chief of staff. The agenda was twofold: ending the congressional filibuster and forcing Venezuelan president Nicolás Maduro from power. As she related it later, President Donald Trump was holding forth on the filibuster when Wiles stood up and started for the door. Trump eyed her. “Is this an emergency, that you have to leave?” he demanded. It was nothing of the sort—but Wiles left Trump guessing. She replied: “It’s an emergency. It doesn’t involve you.” With that, according to Wiles, she departed the Oval.
Wiles, wearing dark pants and a plain black leather top, met me in her office with a smile and a handshake. Over sandwiches from the White House Mess, we talked about the challenges Trump faces. Throughout the past year, Wiles and I have spoken regularly about almost everything: the contents, and consequences, of the Epstein files; ICE’s brutal mass deportations; Elon Musk’s evisceration of USAID; the controversial deployment of the National Guard to US cities; the demolition of the East Wing; the lethal strikes on boats allegedly being piloted by drug smugglers—acts many have called war crimes; Trump’s physical and mental health; and whether he will defy the 22nd Amendment and try to stay on for a third term.
Most senior White House officials parse their words and speak only on background. But over many on-the-record conversations, Wiles answered almost every question I put to her.
We often spoke on Sundays after church. Wiles, an Episcopalian, calls herself “Catholic lite.” One time we spoke while she was doing her laundry in her Washington, DC, rental. Trump, she told me, “has an alcoholic’s personality.” Vance’s conversion from Never Trumper to MAGA acolyte, she said, has been “sort of political.” The vice president, she added, has been “a conspiracy theorist for a decade.” Russell Vought, architect of the notorious Project 2025 and head of the Office of Management and Budget, is “a right-wing absolute zealot.” When I asked her what she thought of Musk reposting a tweet about public sector workers killing millions under Hitler, Stalin, and Mao, she replied: “I think that’s when he’s microdosing.” (She says she doesn't have first-hand knowledge.)
Wiles is the most powerful person in Trump’s White House other than the president himself; unlike any chief of staff before her, she is a woman.
“So many decisions of great consequence are being made on the whim of the president. And as far as I can tell, the only force that can direct or channel that whim is Susie,” a former Republican chief told me. “In most White Houses, the chief of staff is first among a bunch of equals. She may be first with no equals.”
“I don’t think there’s anybody in the world right now that could do the job that she’s doing,” Rubio told me. He called her bond with Trump “an earned trust.” Vance described Wiles’s approach to the chief’s job. “There is this idea that people have that I think was very common in the first administration,” he told me, “that their objective was to control the president or influence the president, or even manipulate the president because they had to in order to serve the national interest. Susie just takes the diametrically opposite viewpoint, which is that she’s a facilitator, that the American people have elected Donald Trump. And her job is to actually facilitate his vision and to make his vision come to life.”
It’s been a busy year. Trump and his team have expanded the limits of presidential power, unilaterally declared war on drug cartels, imposed tariffs according to whim, sealed the southern border, achieved a ceasefire and hostage release in Gaza, and pressured NATO allies into increasing their defense spending.
At the same time, Trump has waged war on his political enemies; pardoned the January 6 rioters, firing nearly everyone involved in their investigation and prosecution; sued media companies into multimillion-dollar settlements; indicted multiple government officials he perceives as his foes; and pressured universities to toe his line. He’s redefined the way presidents behave—verbally abusing women, minorities, and almost anyone who offends him. Charlie Kirk’s assassination in September turbocharged Trump’s campaign of revenge and retribution. Critics have compared this moment to a Reichstag fire, a modern version of Hitler’s exploitation of the torching of Berlin’s parliament.
Historically, the White House chief of staff is the president’s gatekeeper, confidant, and executor of his agenda. That often means telling the president hard truths. Upon taking office, Ronald Reagan was hell-bent on reforming Social Security. James A. Baker III explained to him that cutting Social Security benefits was the third rail of American politics. Reagan pivoted to tax cuts—and was ultimately reelected in a landslide. Donald Rumsfeld, Gerald Ford’s chief, explained: “The White House chief of staff is the one person besides his wife…who can look him right in the eye and say, ‘This is not right. You simply can’t go down that road.’ ”
Just how far will Trump veer off the guardrails of democracy?
The question around Wiles’s tenure under Trump has been whether she will do anything to restrain him. A better question: Does she want to?
T-MINUS 9 DAYS
January 11, 2025
“Our job is lethality and readiness and war fighting.” —Pete Hegseth on his first day at the Pentagon, days after Vance cast the tiebreaking vote in his Senate confirmation
For Trump, Wiles has helped pick a Cabinet of MAGA hard-liners: Pete Hegseth, secretary of war (formerly defense); Kash Patel, FBI director; John Ratcliffe, CIA director; Pam Bondi, attorney general; Tulsi Gabbard, director of national intelligence; and Kristi Noem, head of Homeland Security. Wiles calls them “a world-class Cabinet, better than anything I could have conceived of.” Trump’s Cabinet members are either one of the least qualified presidential teams in history or, to hear Wiles tell it, disrupters—the only people with the balls to take on an entrenched deep state.
“It was a horrific hour-plus at midnight,” Wiles said of an interaction with Trump in 2016. “And I don’t think I’ve seen him that angry since. He was ranting and raving. And I didn’t know whether to argue back or whether to be stoic. What I really wanted to do was cry.”
“People talk about the deep state being at the State Department,” Wiles said. “It’s not. It’s the military-industrial complex.” Hegseth, in her view, is just the guy to take on the powers that be. She referred to Health and Human Services secretary Robert F. Kennedy Jr., another world-class disrupter, as “my Bobby” and “quirky Bobby.” In Wiles’s view, RFK Jr.’s shock treatment of HHS is warranted. “He pushes the envelope—some would say too far. But I say in order to get back to the middle, you have to push it too far.” (In December, Kennedy’s federal vaccine panel voted to end the decades-long recommendation for newborn vaccinations against hepatitis B, which is highly infectious and causes liver failure.)
DAY 56
March 16, 2025
“US deports hundreds of Venezuelans to El Salvador, despite court order.” —NPR
In mid-March, after Trump invoked the Alien Enemies Act, Immigration and Customs Enforcement agents (ICE) shackled and herded 238 immigrants onto transport planes and flew them to a notoriously brutal Salvadoran prison. According to Trump, the men were members of Tren de Aragua, a violent Venezuelan gang, but the evidence was sketchy (often based on tattoos alone). Most had committed no serious crimes; one, Kilmar Abrego Garcia, was deported by mistake, the Trump administration admitted.
“I will concede that we’ve got to look harder at our process for deportation,” Wiles told me at the time.
When we spoke again in April, in cities across the country, masked ICE agents were snatching people off the street, throwing them in vans, and zip-tying and frog-marching them into makeshift deportation camps. Many were US citizens or entitled to be here. (ProPublica documented 170 cases in the first nine months of 2025 of US citizens being caught up in ICE’s dragnet.)
“I’m a little bit of an expert in big personalities.” Wiles said Trump has “an alcoholic’s personality.”
“If somebody is a known gang member who has a criminal past, and you’re sure, and you can demonstrate it, it’s probably fine to send them to El Salvador or whatever,” Wiles told me. “But if there is a question, I think our process has to lean toward a double-check.” But as the usa.gov site itself notes, “In some cases, a noncitizen is subject to expedited removal without being able to attend a hearing in immigration court.” Not long after the El Salvador deportation fiasco, in Louisiana, ICE agents arrested and deported two mothers, along with their children, ages seven, four, and two, to Honduras. The children were US citizens and the four-year-old was being treated for stage 4 cancer. Wiles couldn’t explain it.
“It could be an overzealous Border Patrol agent, I don’t know,” she said of the case, in which both mothers had reportedly been arrested after voluntarily attending routine immigration meetings. “I can’t understand how you make that mistake, but somebody did.”
DAY 74
April 3, 2025
“Long-threatened tariffs from U.S. President Donald Trump have plunged the country into trade wars abroad….” —PBS News
The president declared April 2 “Liberation Day,” bragging about billions of dollars that would flow into US coffers from tariffs, refusing to acknowledge that the levies were a tax on consumers.
The question around Wiles’s tenure under Trump has been whether she will do anything to restrain him. A better question: Does she want to?
“So much thinking out loud is what I would call it,” said Wiles of Trump’s chaotic tariff rollout. “There was a huge disagreement over whether [tariffs were] a good idea.” Trump’s advisers were sharply divided, some believing tariffs were a panacea and others predicting disaster. Wiles told them to get with Trump’s program. “I said, ‘This is where we’re going to end up. So figure out how you can work into what he’s already thinking.’ Well, they couldn’t get there.”
Wiles recruited Vance to help tap the brakes. “We told Donald Trump, ‘Hey, let’s not talk about tariffs today. Let’s wait until we have the team in complete unity and then we’ll do it,’ ” she said. But Trump barreled ahead, announcing sweeping “reciprocal” tariffs, from 10 to 100 percent—which triggered panic in the bond market and a sell-off of stocks. Trump paused his policy for 90 days, but by that time the president’s helter-skelter levies had given rise to the TACO chant: “Trump Always Chickens Out.”
Wiles believed a middle ground on tariffs would ultimately succeed, she said, “but it’s been more painful than I expected.”
At the time this article went to press, shortly before the December holidays, a Harvard poll showed 56 percent of voters think Trump’s tariff policies have harmed the economy.
DAY 207
August 14, 2025
“National Guard mobilizes 800 troops in DC to Support Federal, Local Law Enforcement—Trump declared a crime emergency in the nation’s capital.” —US Department of War
During the summer, Trump ordered the National Guard into four Democratic-led cities, claiming the troops were needed to crack down on crime and protect federal immigration facilities. In June the president deployed some 4,000 guard troops to Los Angeles; later he sent them to Washington, describing the city’s crime rate as “out of control.” “This was like a vitamin boost of ICE, of the [National] Guard, of the Park Service police, who actually have more authority than the DC Metro Police,” Wiles said. “And the idea was to right the ship and then slowly back off. And that’s what we’re doing.”
Critics denounced the deployments as unconstitutional, performative, and ineffective, and many feared Trump had another, more sinister plan up his sleeve.
Will the president use the military to suppress or even prevent voting during the midterms and beyond?
“I say it is categorically false, will not happen, it’s just wrongheaded,” she snapped.
“Do you understand where people who think that are coming from?” I asked.
“I do a little bit, but not fully. I mean, I think they hate the president. They think he’s too wrapped up in what happened in 2020.”
The president and his team were pushing almost every legal and constitutional boundary and defying courts to stop them. But would Trump obey the Supreme Court? “Do you think he will adhere to whatever the courts decide in the end?” I asked Wiles. “I do,” she replied. But Wiles made a prediction: “The smart lawyers around us think that we will be slowed down, as we already have been, but we will ultimately prevail.”
DAY 289
November 4, 2025
The day I met Wiles at the White House was a watershed for Trump: Voters would choose governors in New Jersey and Virginia and a new mayor in New York City; they would also vote on Proposition 50, California governor Gavin Newsom’s proposal to counter a brazen Republican gerrymander in Texas. Collectively, the contests were a referendum on Trump’s second presidency.
Over lunch in her West Wing corner office, Wiles recounted the morning. Escorting Trump from the White House residence to the Oval Office, she gave the president her election predictions: “I’m on the hook because he thinks I’m a clairvoyant.” Wiles thought the GOP had a chance of electing the governor in New Jersey, but she knew they were in for a tough night. (It would prove to be a Republican disaster, with Democrats running the table on the marquee races, passing Proposition 50, and winning downballot elections in Pennsylvania, Georgia, and Mississippi.)
Given voters’ anxiety about the cost of living, Wiles told me she thought Trump should pivot more often from world affairs to kitchen-table issues. “More talks about the domestic economy and less about Saudi Arabia is probably called for,” said Wiles. “They like peace in the world. But that’s not why he was elected.”
Not far from where we sat was a gaping hole where the East Wing had been until just days before. I asked her about the fierce criticism that followed its demolition to make way for Trump’s 90,000-square-foot ballroom. “Were you surprised by it?”
“No,” Wiles replied. “Oh, no. And I think you’ll have to judge it by its totality because you only know a little bit of what he’s planning.”
Was she saying that Trump was planning more, as yet undisclosed renovations?
“I’m not telling.”
T-MINUS 232 DAYS
June 2, 2024
“Would you declassify the Epstein files?” —Fox News’s Rachel Campos-Duffy
“Yeah....I think I would.” —Trump
For many of Trump’s followers, it’s an article of faith that the US government has long been run by an elite cabal of pedophiles. Less conspiratorially but no less seriously, others question whether politicians and powerful people either participated in or knew about Jeffrey Epstein’s sex trafficking of young women, from his posh Manhattan townhouse to his private Caribbean islands. Perhaps most critical to Trump followers, though, is the fact that Trump indicated a willingness to release the files—and didn’t. As this article went to press, grand jury material from the Epstein records was due to be released in December.
Wiles told me she underestimated the potency of the scandal: “Whether he was an American CIA asset, a Mossad asset, whether all these rich, important men went to that nasty island and did unforgivable things to young girls,” she said, “I mean, I kind of knew it, but it’s never anything I paid a bit of attention to.”
In February, Bondi gave binders labeled “The Epstein Files: Phase 1” to a group of conservative social media influencers who were visiting the White House, including Liz Wheeler, Jessica Reed Kraus, Rogan O’Handley, and Chaya Raichik. The binders turned out to contain nothing but old information. “I think she completely whiffed on appreciating that that was the very targeted group that cared about this,” Wiles said of Bondi. “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.”
As Noah Shachtman reported in Vanity Fair, “dozens and dozens” of FBI agents at the New York field office were tasked with combing through the Epstein files. Many observers assumed they were looking for (and possibly redacting) Trump’s name. “I don’t know how many agents looked through things, but it was a lot,” said Wiles. “They were looking for 25 things, not one thing.”
Wiles told me she’d read what she calls “the Epstein file.” And, she said, “[Trump] is in the file. And we know he’s in the file. And he’s not in the file doing anything awful.” Wiles said that Trump “was on [Epstein’s] plane…he’s on the manifest. They were, you know, sort of young, single, whatever—I know it’s a passé word but sort of young, single playboys together.” (Trump started dating Melania Knauss, whom he married in 2005, sometime in 1998. Virginia Giuffre, Epstein’s most prominent accuser, who died by suicide earlier this year, first met Epstein while she was a Mar-a-Lago spa worker in 2000. Trump and Epstein reportedly had a falling out in 2004.)
Trump has claimed, without evidence, that Bill Clinton visited Epstein’s infamous private island, Little St. James, “supposedly 28 times.” “There is no evidence” those visits happened, according to Wiles; as for whether there was anything incriminating about Clinton in the files, “The president was wrong about that.”
The people that really appreciated what a big deal this is are Kash [Patel] and [FBI deputy director] Dan Bongino,” she said. “Because they lived in that world. And the vice president, who’s been a conspiracy theorist for a decade…. For years, Kash has been saying, ‘Got to release the files, got to release the files.’ And he’s been saying that with a view of what he thought was in these files that turns out not to be right.”
In July, Todd Blanche, the deputy attorney general and Trump’s former lawyer, traveled to a Tallahassee, Florida, courthouse to interview Epstein’s longtime associate, Ghislaine Maxwell. Convicted on sex trafficking charges in 2021, she received a 20-year prison sentence. “It’s not typical, is it,” I asked Wiles, “to send the number two guy in the DOJ and the president’s former defense lawyer to interview a convicted sex trafficker?” According to Wiles, “It was [Blanche’s] suggestion.”
Wiles said that neither she nor Trump had been consulted about Maxwell’s transfer to a less restrictive facility after Blanche’s visit. “The president was ticked,” according to Wiles. “The president was mighty unhappy. I don’t know why they moved her. Neither does the president.” But, she said, “if that’s an important point, I can find out.” (At press time, Wiles said she still had not found out.)
What about the birthday greeting featuring a sketch of a nude woman, which, according to The Wall Street Journal, bore Trump’s name and was sent to Epstein for his 50th birthday? “That letter is not his,” Wiles said. “And nothing about it rings true to me, nor does it to people that have known the president a lot longer than I have. I can’t explain The Wall Street Journal, but we’re going to get some discovery because we sued them. So we’re going to find out.” Trump’s lawyers filed a $20 billion defamation lawsuit against Dow Jones & Company, publisher of The Wall Street Journal, which the defendants have asked a federal judge in Florida to dismiss.
So will the president sit for a deposition in that process?
“I mean, if he had to,” she said.
The Epstein files debacle poses a dire political threat to Trump and the future of the GOP. “The people that are inordinately interested in Epstein are the new members of the Trump coalition, the people that I think about all the time—because I want to make sure that they are not Trump voters, they’re Republican voters,” Wiles said. “It’s the Joe Rogan listeners. It’s the people that are sort of new to our world. It’s not the MAGA base.”
A senior White House official described the mindset of an overlapping bloc of voters who are angered by both Trump’s handling of the Epstein files and the war in Gaza. It’s as much as 5 percent of the vote and includes “union members, the podcast crowd, the young people, the young Black males. They are interested in Epstein. And they are the people that are disturbed that we are as cozy with Israel as we are.”
Vance keeps his eye on the voters. “It’s Epstein, Gaza, and the coziness with Israel,” said this White House source. “If you dive deeply into the internet, you’ll find things that say, ‘Well, why don’t we just put Bibi at the Resolute Desk?’ ” the source said, referring to Israeli prime minister Benjamin Netanyahu.
Across our year of conversations, Wiles wanted to put an end to what she believes is a persistent myth, that Trump is a warmonger. To the contrary, Wiles says, the president genuinely cares about ending wars and saving human lives. “I cannot overstate how much his ongoing motivation is to stop the killing, which is not, I don’t think, where he was in his last term,” she said. “Not that he wanted to kill people necessarily, but stopping the killing wasn’t his first thought. It’s his first and last thought now.” Whether that thought is genuine or driven by his desire for a Nobel Peace Prize is, of course, open to debate.
Susie Wiles, JD Vance, and the “Junkyard Dogs”: The White House Chief of Staff On Trump’s Second Term
Throughout the first year of Donald Trump’s second administration, Vanity Fair writer Chris Whipple has interviewed Wiles amid each moment of crisis. This insider’s account joins a portfolio of portraits for an unflinching, up-close look at power—and peril.
On the morning of November 4, 2025, an off-year Election Day, White House chief of staff Susie Wiles was meeting in the Oval Office with the president and his top advisers, men she calls her “core team”: Vice President JD Vance, Secretary of State Marco Rubio, and Stephen Miller, deputy chief of staff. The agenda was twofold: ending the congressional filibuster and forcing Venezuelan president Nicolás Maduro from power. As she related it later, President Donald Trump was holding forth on the filibuster when Wiles stood up and started for the door. Trump eyed her. “Is this an emergency, that you have to leave?” he demanded. It was nothing of the sort—but Wiles left Trump guessing. She replied: “It’s an emergency. It doesn’t involve you.” With that, according to Wiles, she departed the Oval.
Wiles, wearing dark pants and a plain black leather top, met me in her office with a smile and a handshake. Over sandwiches from the White House Mess, we talked about the challenges Trump faces. Throughout the past year, Wiles and I have spoken regularly about almost everything: the contents, and consequences, of the Epstein files; ICE’s brutal mass deportations; Elon Musk’s evisceration of USAID; the controversial deployment of the National Guard to US cities; the demolition of the East Wing; the lethal strikes on boats allegedly being piloted by drug smugglers—acts many have called war crimes; Trump’s physical and mental health; and whether he will defy the 22nd Amendment and try to stay on for a third term.
Most senior White House officials parse their words and speak only on background. But over many on-the-record conversations, Wiles answered almost every question I put to her.
We often spoke on Sundays after church. Wiles, an Episcopalian, calls herself “Catholic lite.” One time we spoke while she was doing her laundry in her Washington, DC, rental. Trump, she told me, “has an alcoholic’s personality.” Vance’s conversion from Never Trumper to MAGA acolyte, she said, has been “sort of political.” The vice president, she added, has been “a conspiracy theorist for a decade.” Russell Vought, architect of the notorious Project 2025 and head of the Office of Management and Budget, is “a right-wing absolute zealot.” When I asked her what she thought of Musk reposting a tweet about public sector workers killing millions under Hitler, Stalin, and Mao, she replied: “I think that’s when he’s microdosing.” (She says she doesn't have first-hand knowledge.)
Wiles is the most powerful person in Trump’s White House other than the president himself; unlike any chief of staff before her, she is a woman.
“So many decisions of great consequence are being made on the whim of the president. And as far as I can tell, the only force that can direct or channel that whim is Susie,” a former Republican chief told me. “In most White Houses, the chief of staff is first among a bunch of equals. She may be first with no equals.”
“I don’t think there’s anybody in the world right now that could do the job that she’s doing,” Rubio told me. He called her bond with Trump “an earned trust.” Vance described Wiles’s approach to the chief’s job. “There is this idea that people have that I think was very common in the first administration,” he told me, “that their objective was to control the president or influence the president, or even manipulate the president because they had to in order to serve the national interest. Susie just takes the diametrically opposite viewpoint, which is that she’s a facilitator, that the American people have elected Donald Trump. And her job is to actually facilitate his vision and to make his vision come to life.”
It’s been a busy year. Trump and his team have expanded the limits of presidential power, unilaterally declared war on drug cartels, imposed tariffs according to whim, sealed the southern border, achieved a ceasefire and hostage release in Gaza, and pressured NATO allies into increasing their defense spending.
At the same time, Trump has waged war on his political enemies; pardoned the January 6 rioters, firing nearly everyone involved in their investigation and prosecution; sued media companies into multimillion-dollar settlements; indicted multiple government officials he perceives as his foes; and pressured universities to toe his line. He’s redefined the way presidents behave—verbally abusing women, minorities, and almost anyone who offends him. Charlie Kirk’s assassination in September turbocharged Trump’s campaign of revenge and retribution. Critics have compared this moment to a Reichstag fire, a modern version of Hitler’s exploitation of the torching of Berlin’s parliament.
Historically, the White House chief of staff is the president’s gatekeeper, confidant, and executor of his agenda. That often means telling the president hard truths. Upon taking office, Ronald Reagan was hell-bent on reforming Social Security. James A. Baker III explained to him that cutting Social Security benefits was the third rail of American politics. Reagan pivoted to tax cuts—and was ultimately reelected in a landslide. Donald Rumsfeld, Gerald Ford’s chief, explained: “The White House chief of staff is the one person besides his wife…who can look him right in the eye and say, ‘This is not right. You simply can’t go down that road.’ ”
Just how far will Trump veer off the guardrails of democracy?
The question around Wiles’s tenure under Trump has been whether she will do anything to restrain him. A better question: Does she want to?
T-MINUS 9 DAYS
January 11, 2025
Our first conversation took place little more than a week before the inauguration. Wiles called from the road, en route from Mar-a-Lago to her home in Ponte Vedra, Florida, in her BMW 530. She was in high spirits, basking in Trump’s victory. Not that she’d ever doubted the outcome. “At no point did I think we would not win,” she said. “Not in my core, not in my sleep, not in my rational mind.”
But on that January day, as his second inauguration approached, Wiles was determined to show the world a new Trump. “I told Hakeem Jeffries, ‘You will see a different Donald Trump when he gets there,’ ’’ she recounted to me. “I’ve not seen him throw anything, I’ve not seen him scream. I didn’t see that really horrible behavior that people talk about and that I actually experienced years ago.”
Wiles’s childhood had prepared her for difficult men. She was raised in Stamford, Connecticut, and Saddle River, New Jersey, the only daughter and eldest of three siblings. It was her famous father, Pat Summerall, who put Wiles on a path to the pinnacle of political power. Summerall had been a kicker for the New York Giants and afterward parlayed his knowledge and mellifluous baritone into fame and fortune as the “voice of the NFL.”
At her father’s knee, Susie Summerall became a football aficionado, rattling off win-loss records and player stats like a miniature John Madden—an ability she says Trump shares. “The president, it turns out, is a junkie of that and is like a statistical savant,” she said. “And I remember a lot of it.” As a child, Susie also absorbed the zeitgeist of her father’s 1970s Manhattan. “Much of what Donald Trump remembers about the New York of the ’70s I lived through with my dad,” she said. “So when he talks about Frank Sinatra’s bodyguard, I know that name.” Steve Witkoff, Trump’s real estate friend turned special envoy, says Wiles and Trump are creatures of that same bygone era: “That whole world of the Copacabana and Sammy Davis Jr. and all, those are things that he wants to talk about.”
The most valuable gift Susie got from her dad was hard-earned. Summerall was an absentee father and an alcoholic, and Wiles helped her mother stage interventions to get him into treatment. (Summerall was sober for 21 years before his death in 2013.) “Alcoholism does bad things to relationships, and so it was with my dad and me,” Wiles said.
“Some clinical psychologist that knows one million times more than I do will dispute what I’m going to say. But high-functioning alcoholics or alcoholics in general, their personalities are exaggerated when they drink. And so I’m a little bit of an expert in big personalities.” Wiles said Trump has “an alcoholic’s personality.” He “operates [with] a view that there’s nothing he can’t do. Nothing, zero, nothing.”
Susie Summerall got her first taste of politics in the late 1970s, interning as a college student in the Capitol Hill office of Jack Kemp, the New York congressman, who’d been a Giant with her father. Then, at 23, she landed a job in the Reagan White House as a scheduler, where she watched his chief of staff Baker in action. She married a GOP advance man, Lanny Wiles, and in 1984 they moved to Ponte Vedra. Wiles wanted to “start a family and a life outside politics.” But in 1988, Baker lured Wiles back to work with Dan Quayle, George H.W. Bush’s running mate. The couple had two daughters, Katie and Caroline. Wiles plunged into state politics—and over the next two decades became a formidable political strategist, serving as chief of staff to the mayor of Jacksonville, Florida, running Rick Scott’s gubernatorial campaign, and, briefly, leading Jon Huntsman’s campaign for president.
In 2015, Wiles was invited to Trump Tower to meet the real estate tycoon turned presidential candidate. The star of The Apprentice couldn’t believe he was talking to the daughter of the great Pat Summerall. “He’s said it a million times,” Wiles said. “ ‘I judge people by their genes.’ ” Wiles thought Trump was interesting and smart. “And they called me one night and said, ‘We’re serious about Florida now. Would you like to co-chair our leadership team?’ And I said, ‘Yeah, I would.’ ”
“I had become disenchanted with what we now call traditional Republicans,” she recalled.
Wiles’s relationship with Trump almost ended at his Miami golf club one night in the fall of 2016. Unhappy with a poll showing him doing worse than expected in Florida, Trump berated her in front of a gaggle of cronies. “It was a horrific hour-plus at midnight,” Wiles told me. “And I don’t think I’ve seen him that angry since. He was ranting and raving. And I didn’t know whether to argue back or whether to be stoic. What I really wanted to do was cry.”
Wiles steeled herself. “I finally said, ‘You know Mr. Trump, if you want somebody to set their hair on fire and be crazy, I’m not your girl. But if you want to win this state, I am. It’s your choice.’ ” Wiles walked out. Trump turned on a dime. “Lo and behold, he called me every day.” Wiles never looked back. Trump carried Florida, the first big prize in his stunning 2016 upset over Hillary Clinton.
Then, in a fateful turn of events, Wiles went to work in 2018 for an ambitious gubernatorial candidate named Ron DeSantis. (Trump urged DeSantis, then his protégé, to hire her.) She led the underdog candidate to victory. But afterward, DeSantis turned on her, denouncing Wiles publicly and bad-mouthing her privately. To this day, Wiles doesn’t know what triggered the governor’s vendetta. “I think he thought I was getting too much attention, which is ironic,” she told me. “I don’t ever seek attention.”
George W. Bush himself had gotten wind of the gutting of PEPFAR. He called Rubio to express alarm, according to a former aide close to Bush. “He’s been appalled by Trump from the beginning.”
Wiles landed on her feet, organizing Florida for Trump’s 2020 reelection bid. Trump had rescued Wiles, recently divorced, at a dark moment in her life. (Wiles and her husband divorced in 2017—due, she has said, to his bad financial decisions.) Looking back on DeSantis’s behavior, Wiles reflected: “Had he said, ‘Look, thank you. I appreciate your help. We’re done here.’ I believe the course of his history would have been different. I might or might not have gone to work for Donald Trump.”
DAY 1
January 20, 2025
But on that January day, as his second inauguration approached, Wiles was determined to show the world a new Trump. “I told Hakeem Jeffries, ‘You will see a different Donald Trump when he gets there,’ ’’ she recounted to me. “I’ve not seen him throw anything, I’ve not seen him scream. I didn’t see that really horrible behavior that people talk about and that I actually experienced years ago.”
Wiles’s childhood had prepared her for difficult men. She was raised in Stamford, Connecticut, and Saddle River, New Jersey, the only daughter and eldest of three siblings. It was her famous father, Pat Summerall, who put Wiles on a path to the pinnacle of political power. Summerall had been a kicker for the New York Giants and afterward parlayed his knowledge and mellifluous baritone into fame and fortune as the “voice of the NFL.”
At her father’s knee, Susie Summerall became a football aficionado, rattling off win-loss records and player stats like a miniature John Madden—an ability she says Trump shares. “The president, it turns out, is a junkie of that and is like a statistical savant,” she said. “And I remember a lot of it.” As a child, Susie also absorbed the zeitgeist of her father’s 1970s Manhattan. “Much of what Donald Trump remembers about the New York of the ’70s I lived through with my dad,” she said. “So when he talks about Frank Sinatra’s bodyguard, I know that name.” Steve Witkoff, Trump’s real estate friend turned special envoy, says Wiles and Trump are creatures of that same bygone era: “That whole world of the Copacabana and Sammy Davis Jr. and all, those are things that he wants to talk about.”
The most valuable gift Susie got from her dad was hard-earned. Summerall was an absentee father and an alcoholic, and Wiles helped her mother stage interventions to get him into treatment. (Summerall was sober for 21 years before his death in 2013.) “Alcoholism does bad things to relationships, and so it was with my dad and me,” Wiles said.
“Some clinical psychologist that knows one million times more than I do will dispute what I’m going to say. But high-functioning alcoholics or alcoholics in general, their personalities are exaggerated when they drink. And so I’m a little bit of an expert in big personalities.” Wiles said Trump has “an alcoholic’s personality.” He “operates [with] a view that there’s nothing he can’t do. Nothing, zero, nothing.”
Susie Summerall got her first taste of politics in the late 1970s, interning as a college student in the Capitol Hill office of Jack Kemp, the New York congressman, who’d been a Giant with her father. Then, at 23, she landed a job in the Reagan White House as a scheduler, where she watched his chief of staff Baker in action. She married a GOP advance man, Lanny Wiles, and in 1984 they moved to Ponte Vedra. Wiles wanted to “start a family and a life outside politics.” But in 1988, Baker lured Wiles back to work with Dan Quayle, George H.W. Bush’s running mate. The couple had two daughters, Katie and Caroline. Wiles plunged into state politics—and over the next two decades became a formidable political strategist, serving as chief of staff to the mayor of Jacksonville, Florida, running Rick Scott’s gubernatorial campaign, and, briefly, leading Jon Huntsman’s campaign for president.
In 2015, Wiles was invited to Trump Tower to meet the real estate tycoon turned presidential candidate. The star of The Apprentice couldn’t believe he was talking to the daughter of the great Pat Summerall. “He’s said it a million times,” Wiles said. “ ‘I judge people by their genes.’ ” Wiles thought Trump was interesting and smart. “And they called me one night and said, ‘We’re serious about Florida now. Would you like to co-chair our leadership team?’ And I said, ‘Yeah, I would.’ ”
“I had become disenchanted with what we now call traditional Republicans,” she recalled.
Wiles’s relationship with Trump almost ended at his Miami golf club one night in the fall of 2016. Unhappy with a poll showing him doing worse than expected in Florida, Trump berated her in front of a gaggle of cronies. “It was a horrific hour-plus at midnight,” Wiles told me. “And I don’t think I’ve seen him that angry since. He was ranting and raving. And I didn’t know whether to argue back or whether to be stoic. What I really wanted to do was cry.”
Wiles steeled herself. “I finally said, ‘You know Mr. Trump, if you want somebody to set their hair on fire and be crazy, I’m not your girl. But if you want to win this state, I am. It’s your choice.’ ” Wiles walked out. Trump turned on a dime. “Lo and behold, he called me every day.” Wiles never looked back. Trump carried Florida, the first big prize in his stunning 2016 upset over Hillary Clinton.
Then, in a fateful turn of events, Wiles went to work in 2018 for an ambitious gubernatorial candidate named Ron DeSantis. (Trump urged DeSantis, then his protégé, to hire her.) She led the underdog candidate to victory. But afterward, DeSantis turned on her, denouncing Wiles publicly and bad-mouthing her privately. To this day, Wiles doesn’t know what triggered the governor’s vendetta. “I think he thought I was getting too much attention, which is ironic,” she told me. “I don’t ever seek attention.”
George W. Bush himself had gotten wind of the gutting of PEPFAR. He called Rubio to express alarm, according to a former aide close to Bush. “He’s been appalled by Trump from the beginning.”
Wiles landed on her feet, organizing Florida for Trump’s 2020 reelection bid. Trump had rescued Wiles, recently divorced, at a dark moment in her life. (Wiles and her husband divorced in 2017—due, she has said, to his bad financial decisions.) Looking back on DeSantis’s behavior, Wiles reflected: “Had he said, ‘Look, thank you. I appreciate your help. We’re done here.’ I believe the course of his history would have been different. I might or might not have gone to work for Donald Trump.”
DAY 1
January 20, 2025
On Trump’s first day in office, the president signed a flurry of executive orders, 26 in all, withdrawing the US from the World Health Organization and the Paris climate agreement, rescinding birthright citizenship, sending troops to the southern border, freezing foreign aid, and stopping federal hiring. Then Trump issued pardons to almost everyone convicted in the bloody January 6, 2021, assault on the Capitol, in which nine people ultimately died and 150 were injured. Even rioters who’d beaten cops within an inch of their lives were set free. (Fourteen people convicted of seditious conspiracy had their sentences commuted.)
Did she ever ask the president, “ ‘Wait a minute, do you really want to pardon all 1,500 January 6 convicts, or should we be more selective?’ ”
“I did exactly that,” Wiles replied. “I said, ‘I am on board with the people that were happenstancers or didn’t do anything violent. And we certainly know what everybody did because the FBI has done such an incredible job.’ ” (Trump has said his FBI investigators were “corrupt” and part of a “deep state.”) But Trump argued that even the violent offenders had been unfairly treated. Wiles explained: “In every case, of the ones he was looking at, in every case, they had already served more time than the sentencing guidelines would have suggested. So given that, I sort of got on board.” (According to court records, many of the January 6 rioters pardoned by Trump had received sentences that were lighter than the guidelines.) “There have been a couple of times where I’ve been outvoted,” Wiles said. “And if there’s a tie, he wins.”
In the West Wing, Wiles is surrounded by young MAGA men. “She is a ‘go to church every Sunday, uses a swear word very, very rarely’ ” person, said James Blair, Wiles’s 36-year-old deputy chief of staff. “She doesn’t raise her voice. But she likes being around junkyard dogs.” Indeed, Wiles has seemed content to let her pit bulls—deputy chiefs of staff Miller, Blair, and Dan Scavino—run loose as she watches.
During Oval Office events, Wiles almost always sits just off camera. “There’s the president and then there’s whoever the three high-ranking people are on the sofa,” she said. “And then there’s a chair at the corner of the sofa, which is my chair, which means I’m the one that gets hit in the head with the boom mic.”
For all the chaos in the Cabinet, Wiles has kept palace intrigue and shivving to a minimum in the White House. Trump has empowered her; when Wiles weighs in, everyone knows she is speaking for him. She has in turn empowered her team: Blair, Miller, Scavino, and Taylor Budowich, who departed in September.
“First and foremost, she brings no ego,” says Blair. “And that is the starting point from which just an immense amount of power flows. There’s so much ego and testosterone around her, there wouldn’t be any room for hers anyway.”
From day one, Wiles had to grapple with another power center: Elon Musk.
“He is a complete solo actor,” said Wiles of Trump’s billionaire pal who led the scorched-earth blitz known as the Department of Government Efficiency. Wiles described Musk as something akin to a jacked-up Nosferatu. “The challenge with Elon is keeping up with him,” she told me. “He’s an avowed ketamine [user]. And he sleeps in a sleeping bag in the EOB [Executive Office Building] in the daytime. And he’s an odd, odd duck, as I think geniuses are. You know, it’s not helpful, but he is his own person.”
Musk triggered the first true crisis of the Trump presidency and an early test for Wiles. Trump’s chief was shocked when the SpaceX founder eviscerated USAID, the United States Agency for International Development. “I was initially aghast,” Wiles told me. “Because I think anybody that pays attention to government and has ever paid attention to USAID believed, as I did, that they do very good work.”
In his executive order freezing foreign aid, Trump had decreed that lifesaving programs should be spared. Instead, they were shuttered. “When Elon said, ‘We’re doing this,’ he was already into it,” said Wiles. “And that’s probably because he knew it would be horrifying to others. But he decided that it was a better approach to shut it down, fire everybody, shut them out, and then go rebuild. Not the way I would do it.”
Wiles knew that fixing this was on her. “The president doesn’t know and never will,” she told me. “He doesn’t know the details of these smallish agencies.”
Wiles says she called Musk on the carpet. “You can’t just lock people out of their offices,” she recalls telling him. At first, Wiles didn’t grasp the effect that slashing USAID programs would have on humanitarian aid. “I didn’t know a lot about the extent of their grant making.” But with immunizations halted in Africa, lives would be lost. Soon she was getting frantic calls from relief agency heads and former government officials with a dire message: Thousands of lives were in the balance.
Wiles continued: “So Marco is on his way to Panama. We call him and say, ‘You’re Senate-confirmed. You’re going to have to be the custodian, essentially, of [USAID].’ ‘Okay,’ he says.” But Musk forged ahead—all throttle, no brake. “Elon’s attitude is you have to get it done fast. If you’re an incrementalist, you just won’t get your rocket to the moon,” Wiles said. “And so with that attitude, you’re going to break some china. But no rational person could think the USAID process was a good one. Nobody.”
The shuttering of USAID crippled the President’s Emergency Plan for AIDS Relief (PEPFAR). The antiretroviral program, launched with $15 billion by George W. Bush in 2003, was credited with preventing millions of deaths. It depended on USAID grants. In an interview with The Financial Times, Bill Gates remarked: “The picture of the world’s richest man killing the world’s poorest children is not a pretty one.”
Privately, another drama was playing out.
Bush himself had gotten wind of the gutting of PEPFAR. He called Rubio to express alarm, according to a former aide close to Bush. “He’s been appalled by Trump from the beginning and he’s determined not to weigh in,” the aide said. But Musk’s attack on one of his legacy achievements was too much. Bush, said that person, “cares deeply about the PEPFAR program. That and Wounded Warriors are the two things where he will weigh in, not publicly, but with intention.”
Did Rubio have any regrets about the untold number of lives that PEPFAR’s evisceration might cost? “No. First of all, whoever says that, it’s just not being accurate,” he told me. “We are not eviscerating PEPFAR. PEPFAR has been rearranged and reorganized in such a way where we’re now going to be able to deliver aid in a way that has a goal. The goal is to help countries become self-sustaining.” With a note of “America First,” he added: “Let’s begin with the premise: Is it the United States’ fault? Why isn’t China paying for more immunizations? Why isn’t the UK or Canada or any of the G7 countries?” (The UK, following in the footsteps of the US, slashed foreign aid in 2025. In November, China, which funded the Africa CDC, pledged $3.5 million in AIDS prevention in South Africa alone.)
When I repeated Rubio’s comment to a former GOP White House chief of staff, he remarked: “I find that immoral.”
DAY 8
January 27, 2025
Did she ever ask the president, “ ‘Wait a minute, do you really want to pardon all 1,500 January 6 convicts, or should we be more selective?’ ”
“I did exactly that,” Wiles replied. “I said, ‘I am on board with the people that were happenstancers or didn’t do anything violent. And we certainly know what everybody did because the FBI has done such an incredible job.’ ” (Trump has said his FBI investigators were “corrupt” and part of a “deep state.”) But Trump argued that even the violent offenders had been unfairly treated. Wiles explained: “In every case, of the ones he was looking at, in every case, they had already served more time than the sentencing guidelines would have suggested. So given that, I sort of got on board.” (According to court records, many of the January 6 rioters pardoned by Trump had received sentences that were lighter than the guidelines.) “There have been a couple of times where I’ve been outvoted,” Wiles said. “And if there’s a tie, he wins.”
In the West Wing, Wiles is surrounded by young MAGA men. “She is a ‘go to church every Sunday, uses a swear word very, very rarely’ ” person, said James Blair, Wiles’s 36-year-old deputy chief of staff. “She doesn’t raise her voice. But she likes being around junkyard dogs.” Indeed, Wiles has seemed content to let her pit bulls—deputy chiefs of staff Miller, Blair, and Dan Scavino—run loose as she watches.
During Oval Office events, Wiles almost always sits just off camera. “There’s the president and then there’s whoever the three high-ranking people are on the sofa,” she said. “And then there’s a chair at the corner of the sofa, which is my chair, which means I’m the one that gets hit in the head with the boom mic.”
For all the chaos in the Cabinet, Wiles has kept palace intrigue and shivving to a minimum in the White House. Trump has empowered her; when Wiles weighs in, everyone knows she is speaking for him. She has in turn empowered her team: Blair, Miller, Scavino, and Taylor Budowich, who departed in September.
“First and foremost, she brings no ego,” says Blair. “And that is the starting point from which just an immense amount of power flows. There’s so much ego and testosterone around her, there wouldn’t be any room for hers anyway.”
From day one, Wiles had to grapple with another power center: Elon Musk.
“He is a complete solo actor,” said Wiles of Trump’s billionaire pal who led the scorched-earth blitz known as the Department of Government Efficiency. Wiles described Musk as something akin to a jacked-up Nosferatu. “The challenge with Elon is keeping up with him,” she told me. “He’s an avowed ketamine [user]. And he sleeps in a sleeping bag in the EOB [Executive Office Building] in the daytime. And he’s an odd, odd duck, as I think geniuses are. You know, it’s not helpful, but he is his own person.”
Musk triggered the first true crisis of the Trump presidency and an early test for Wiles. Trump’s chief was shocked when the SpaceX founder eviscerated USAID, the United States Agency for International Development. “I was initially aghast,” Wiles told me. “Because I think anybody that pays attention to government and has ever paid attention to USAID believed, as I did, that they do very good work.”
In his executive order freezing foreign aid, Trump had decreed that lifesaving programs should be spared. Instead, they were shuttered. “When Elon said, ‘We’re doing this,’ he was already into it,” said Wiles. “And that’s probably because he knew it would be horrifying to others. But he decided that it was a better approach to shut it down, fire everybody, shut them out, and then go rebuild. Not the way I would do it.”
Wiles knew that fixing this was on her. “The president doesn’t know and never will,” she told me. “He doesn’t know the details of these smallish agencies.”
Wiles says she called Musk on the carpet. “You can’t just lock people out of their offices,” she recalls telling him. At first, Wiles didn’t grasp the effect that slashing USAID programs would have on humanitarian aid. “I didn’t know a lot about the extent of their grant making.” But with immunizations halted in Africa, lives would be lost. Soon she was getting frantic calls from relief agency heads and former government officials with a dire message: Thousands of lives were in the balance.
Wiles continued: “So Marco is on his way to Panama. We call him and say, ‘You’re Senate-confirmed. You’re going to have to be the custodian, essentially, of [USAID].’ ‘Okay,’ he says.” But Musk forged ahead—all throttle, no brake. “Elon’s attitude is you have to get it done fast. If you’re an incrementalist, you just won’t get your rocket to the moon,” Wiles said. “And so with that attitude, you’re going to break some china. But no rational person could think the USAID process was a good one. Nobody.”
The shuttering of USAID crippled the President’s Emergency Plan for AIDS Relief (PEPFAR). The antiretroviral program, launched with $15 billion by George W. Bush in 2003, was credited with preventing millions of deaths. It depended on USAID grants. In an interview with The Financial Times, Bill Gates remarked: “The picture of the world’s richest man killing the world’s poorest children is not a pretty one.”
Privately, another drama was playing out.
Bush himself had gotten wind of the gutting of PEPFAR. He called Rubio to express alarm, according to a former aide close to Bush. “He’s been appalled by Trump from the beginning and he’s determined not to weigh in,” the aide said. But Musk’s attack on one of his legacy achievements was too much. Bush, said that person, “cares deeply about the PEPFAR program. That and Wounded Warriors are the two things where he will weigh in, not publicly, but with intention.”
Did Rubio have any regrets about the untold number of lives that PEPFAR’s evisceration might cost? “No. First of all, whoever says that, it’s just not being accurate,” he told me. “We are not eviscerating PEPFAR. PEPFAR has been rearranged and reorganized in such a way where we’re now going to be able to deliver aid in a way that has a goal. The goal is to help countries become self-sustaining.” With a note of “America First,” he added: “Let’s begin with the premise: Is it the United States’ fault? Why isn’t China paying for more immunizations? Why isn’t the UK or Canada or any of the G7 countries?” (The UK, following in the footsteps of the US, slashed foreign aid in 2025. In November, China, which funded the Africa CDC, pledged $3.5 million in AIDS prevention in South Africa alone.)
When I repeated Rubio’s comment to a former GOP White House chief of staff, he remarked: “I find that immoral.”
DAY 8
January 27, 2025
“Our job is lethality and readiness and war fighting.” —Pete Hegseth on his first day at the Pentagon, days after Vance cast the tiebreaking vote in his Senate confirmation
For Trump, Wiles has helped pick a Cabinet of MAGA hard-liners: Pete Hegseth, secretary of war (formerly defense); Kash Patel, FBI director; John Ratcliffe, CIA director; Pam Bondi, attorney general; Tulsi Gabbard, director of national intelligence; and Kristi Noem, head of Homeland Security. Wiles calls them “a world-class Cabinet, better than anything I could have conceived of.” Trump’s Cabinet members are either one of the least qualified presidential teams in history or, to hear Wiles tell it, disrupters—the only people with the balls to take on an entrenched deep state.
“It was a horrific hour-plus at midnight,” Wiles said of an interaction with Trump in 2016. “And I don’t think I’ve seen him that angry since. He was ranting and raving. And I didn’t know whether to argue back or whether to be stoic. What I really wanted to do was cry.”
“People talk about the deep state being at the State Department,” Wiles said. “It’s not. It’s the military-industrial complex.” Hegseth, in her view, is just the guy to take on the powers that be. She referred to Health and Human Services secretary Robert F. Kennedy Jr., another world-class disrupter, as “my Bobby” and “quirky Bobby.” In Wiles’s view, RFK Jr.’s shock treatment of HHS is warranted. “He pushes the envelope—some would say too far. But I say in order to get back to the middle, you have to push it too far.” (In December, Kennedy’s federal vaccine panel voted to end the decades-long recommendation for newborn vaccinations against hepatitis B, which is highly infectious and causes liver failure.)
DAY 56
March 16, 2025
“US deports hundreds of Venezuelans to El Salvador, despite court order.” —NPR
In mid-March, after Trump invoked the Alien Enemies Act, Immigration and Customs Enforcement agents (ICE) shackled and herded 238 immigrants onto transport planes and flew them to a notoriously brutal Salvadoran prison. According to Trump, the men were members of Tren de Aragua, a violent Venezuelan gang, but the evidence was sketchy (often based on tattoos alone). Most had committed no serious crimes; one, Kilmar Abrego Garcia, was deported by mistake, the Trump administration admitted.
“I will concede that we’ve got to look harder at our process for deportation,” Wiles told me at the time.
When we spoke again in April, in cities across the country, masked ICE agents were snatching people off the street, throwing them in vans, and zip-tying and frog-marching them into makeshift deportation camps. Many were US citizens or entitled to be here. (ProPublica documented 170 cases in the first nine months of 2025 of US citizens being caught up in ICE’s dragnet.)
“I’m a little bit of an expert in big personalities.” Wiles said Trump has “an alcoholic’s personality.”
“If somebody is a known gang member who has a criminal past, and you’re sure, and you can demonstrate it, it’s probably fine to send them to El Salvador or whatever,” Wiles told me. “But if there is a question, I think our process has to lean toward a double-check.” But as the usa.gov site itself notes, “In some cases, a noncitizen is subject to expedited removal without being able to attend a hearing in immigration court.” Not long after the El Salvador deportation fiasco, in Louisiana, ICE agents arrested and deported two mothers, along with their children, ages seven, four, and two, to Honduras. The children were US citizens and the four-year-old was being treated for stage 4 cancer. Wiles couldn’t explain it.
“It could be an overzealous Border Patrol agent, I don’t know,” she said of the case, in which both mothers had reportedly been arrested after voluntarily attending routine immigration meetings. “I can’t understand how you make that mistake, but somebody did.”
DAY 74
April 3, 2025
“Long-threatened tariffs from U.S. President Donald Trump have plunged the country into trade wars abroad….” —PBS News
The president declared April 2 “Liberation Day,” bragging about billions of dollars that would flow into US coffers from tariffs, refusing to acknowledge that the levies were a tax on consumers.
The question around Wiles’s tenure under Trump has been whether she will do anything to restrain him. A better question: Does she want to?
“So much thinking out loud is what I would call it,” said Wiles of Trump’s chaotic tariff rollout. “There was a huge disagreement over whether [tariffs were] a good idea.” Trump’s advisers were sharply divided, some believing tariffs were a panacea and others predicting disaster. Wiles told them to get with Trump’s program. “I said, ‘This is where we’re going to end up. So figure out how you can work into what he’s already thinking.’ Well, they couldn’t get there.”
Wiles recruited Vance to help tap the brakes. “We told Donald Trump, ‘Hey, let’s not talk about tariffs today. Let’s wait until we have the team in complete unity and then we’ll do it,’ ” she said. But Trump barreled ahead, announcing sweeping “reciprocal” tariffs, from 10 to 100 percent—which triggered panic in the bond market and a sell-off of stocks. Trump paused his policy for 90 days, but by that time the president’s helter-skelter levies had given rise to the TACO chant: “Trump Always Chickens Out.”
Wiles believed a middle ground on tariffs would ultimately succeed, she said, “but it’s been more painful than I expected.”
At the time this article went to press, shortly before the December holidays, a Harvard poll showed 56 percent of voters think Trump’s tariff policies have harmed the economy.
DAY 207
August 14, 2025
“National Guard mobilizes 800 troops in DC to Support Federal, Local Law Enforcement—Trump declared a crime emergency in the nation’s capital.” —US Department of War
During the summer, Trump ordered the National Guard into four Democratic-led cities, claiming the troops were needed to crack down on crime and protect federal immigration facilities. In June the president deployed some 4,000 guard troops to Los Angeles; later he sent them to Washington, describing the city’s crime rate as “out of control.” “This was like a vitamin boost of ICE, of the [National] Guard, of the Park Service police, who actually have more authority than the DC Metro Police,” Wiles said. “And the idea was to right the ship and then slowly back off. And that’s what we’re doing.”
Critics denounced the deployments as unconstitutional, performative, and ineffective, and many feared Trump had another, more sinister plan up his sleeve.
Will the president use the military to suppress or even prevent voting during the midterms and beyond?
“I say it is categorically false, will not happen, it’s just wrongheaded,” she snapped.
“Do you understand where people who think that are coming from?” I asked.
“I do a little bit, but not fully. I mean, I think they hate the president. They think he’s too wrapped up in what happened in 2020.”
The president and his team were pushing almost every legal and constitutional boundary and defying courts to stop them. But would Trump obey the Supreme Court? “Do you think he will adhere to whatever the courts decide in the end?” I asked Wiles. “I do,” she replied. But Wiles made a prediction: “The smart lawyers around us think that we will be slowed down, as we already have been, but we will ultimately prevail.”
DAY 289
November 4, 2025
The day I met Wiles at the White House was a watershed for Trump: Voters would choose governors in New Jersey and Virginia and a new mayor in New York City; they would also vote on Proposition 50, California governor Gavin Newsom’s proposal to counter a brazen Republican gerrymander in Texas. Collectively, the contests were a referendum on Trump’s second presidency.
Over lunch in her West Wing corner office, Wiles recounted the morning. Escorting Trump from the White House residence to the Oval Office, she gave the president her election predictions: “I’m on the hook because he thinks I’m a clairvoyant.” Wiles thought the GOP had a chance of electing the governor in New Jersey, but she knew they were in for a tough night. (It would prove to be a Republican disaster, with Democrats running the table on the marquee races, passing Proposition 50, and winning downballot elections in Pennsylvania, Georgia, and Mississippi.)
Given voters’ anxiety about the cost of living, Wiles told me she thought Trump should pivot more often from world affairs to kitchen-table issues. “More talks about the domestic economy and less about Saudi Arabia is probably called for,” said Wiles. “They like peace in the world. But that’s not why he was elected.”
Not far from where we sat was a gaping hole where the East Wing had been until just days before. I asked her about the fierce criticism that followed its demolition to make way for Trump’s 90,000-square-foot ballroom. “Were you surprised by it?”
“No,” Wiles replied. “Oh, no. And I think you’ll have to judge it by its totality because you only know a little bit of what he’s planning.”
Was she saying that Trump was planning more, as yet undisclosed renovations?
“I’m not telling.”
T-MINUS 232 DAYS
June 2, 2024
“Would you declassify the Epstein files?” —Fox News’s Rachel Campos-Duffy
“Yeah....I think I would.” —Trump
For many of Trump’s followers, it’s an article of faith that the US government has long been run by an elite cabal of pedophiles. Less conspiratorially but no less seriously, others question whether politicians and powerful people either participated in or knew about Jeffrey Epstein’s sex trafficking of young women, from his posh Manhattan townhouse to his private Caribbean islands. Perhaps most critical to Trump followers, though, is the fact that Trump indicated a willingness to release the files—and didn’t. As this article went to press, grand jury material from the Epstein records was due to be released in December.
Wiles told me she underestimated the potency of the scandal: “Whether he was an American CIA asset, a Mossad asset, whether all these rich, important men went to that nasty island and did unforgivable things to young girls,” she said, “I mean, I kind of knew it, but it’s never anything I paid a bit of attention to.”
In February, Bondi gave binders labeled “The Epstein Files: Phase 1” to a group of conservative social media influencers who were visiting the White House, including Liz Wheeler, Jessica Reed Kraus, Rogan O’Handley, and Chaya Raichik. The binders turned out to contain nothing but old information. “I think she completely whiffed on appreciating that that was the very targeted group that cared about this,” Wiles said of Bondi. “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.”
As Noah Shachtman reported in Vanity Fair, “dozens and dozens” of FBI agents at the New York field office were tasked with combing through the Epstein files. Many observers assumed they were looking for (and possibly redacting) Trump’s name. “I don’t know how many agents looked through things, but it was a lot,” said Wiles. “They were looking for 25 things, not one thing.”
Wiles told me she’d read what she calls “the Epstein file.” And, she said, “[Trump] is in the file. And we know he’s in the file. And he’s not in the file doing anything awful.” Wiles said that Trump “was on [Epstein’s] plane…he’s on the manifest. They were, you know, sort of young, single, whatever—I know it’s a passé word but sort of young, single playboys together.” (Trump started dating Melania Knauss, whom he married in 2005, sometime in 1998. Virginia Giuffre, Epstein’s most prominent accuser, who died by suicide earlier this year, first met Epstein while she was a Mar-a-Lago spa worker in 2000. Trump and Epstein reportedly had a falling out in 2004.)
Trump has claimed, without evidence, that Bill Clinton visited Epstein’s infamous private island, Little St. James, “supposedly 28 times.” “There is no evidence” those visits happened, according to Wiles; as for whether there was anything incriminating about Clinton in the files, “The president was wrong about that.”
The people that really appreciated what a big deal this is are Kash [Patel] and [FBI deputy director] Dan Bongino,” she said. “Because they lived in that world. And the vice president, who’s been a conspiracy theorist for a decade…. For years, Kash has been saying, ‘Got to release the files, got to release the files.’ And he’s been saying that with a view of what he thought was in these files that turns out not to be right.”
In July, Todd Blanche, the deputy attorney general and Trump’s former lawyer, traveled to a Tallahassee, Florida, courthouse to interview Epstein’s longtime associate, Ghislaine Maxwell. Convicted on sex trafficking charges in 2021, she received a 20-year prison sentence. “It’s not typical, is it,” I asked Wiles, “to send the number two guy in the DOJ and the president’s former defense lawyer to interview a convicted sex trafficker?” According to Wiles, “It was [Blanche’s] suggestion.”
Wiles said that neither she nor Trump had been consulted about Maxwell’s transfer to a less restrictive facility after Blanche’s visit. “The president was ticked,” according to Wiles. “The president was mighty unhappy. I don’t know why they moved her. Neither does the president.” But, she said, “if that’s an important point, I can find out.” (At press time, Wiles said she still had not found out.)
What about the birthday greeting featuring a sketch of a nude woman, which, according to The Wall Street Journal, bore Trump’s name and was sent to Epstein for his 50th birthday? “That letter is not his,” Wiles said. “And nothing about it rings true to me, nor does it to people that have known the president a lot longer than I have. I can’t explain The Wall Street Journal, but we’re going to get some discovery because we sued them. So we’re going to find out.” Trump’s lawyers filed a $20 billion defamation lawsuit against Dow Jones & Company, publisher of The Wall Street Journal, which the defendants have asked a federal judge in Florida to dismiss.
So will the president sit for a deposition in that process?
“I mean, if he had to,” she said.
The Epstein files debacle poses a dire political threat to Trump and the future of the GOP. “The people that are inordinately interested in Epstein are the new members of the Trump coalition, the people that I think about all the time—because I want to make sure that they are not Trump voters, they’re Republican voters,” Wiles said. “It’s the Joe Rogan listeners. It’s the people that are sort of new to our world. It’s not the MAGA base.”
A senior White House official described the mindset of an overlapping bloc of voters who are angered by both Trump’s handling of the Epstein files and the war in Gaza. It’s as much as 5 percent of the vote and includes “union members, the podcast crowd, the young people, the young Black males. They are interested in Epstein. And they are the people that are disturbed that we are as cozy with Israel as we are.”
Vance keeps his eye on the voters. “It’s Epstein, Gaza, and the coziness with Israel,” said this White House source. “If you dive deeply into the internet, you’ll find things that say, ‘Well, why don’t we just put Bibi at the Resolute Desk?’ ” the source said, referring to Israeli prime minister Benjamin Netanyahu.
Across our year of conversations, Wiles wanted to put an end to what she believes is a persistent myth, that Trump is a warmonger. To the contrary, Wiles says, the president genuinely cares about ending wars and saving human lives. “I cannot overstate how much his ongoing motivation is to stop the killing, which is not, I don’t think, where he was in his last term,” she said. “Not that he wanted to kill people necessarily, but stopping the killing wasn’t his first thought. It’s his first and last thought now.” Whether that thought is genuine or driven by his desire for a Nobel Peace Prize is, of course, open to debate.
That is bullshit. IMO, Trump loves the thought of making life-or-death decisions, and his fucked up ego demands that he find out what it's like to kill somebody.
DAY 213
August 20, 2025
“Israel says it has taken first steps of military operation in Gaza City.” —Reuters
In early October, Trump announced that his envoys had brokered a deal with mediators from Qatar, Egypt, and Turkey to end two years of bloodshed in Gaza. The 20-point plan, calling for the disarmament of Hamas and the administering of Gaza by a multinational force, was far from a sure thing. But the ceasefire and the release of almost all the hostages (the remains of one are still missing) was a considerable achievement. During his triumphant appearance at Israel’s Knesset, Trump struck a bellicose tone, praising Netanyahu and the Israeli armed forces with no mention of the Palestinian civilian casualties. Trump had previously lauded Bibi’s efforts in another action by calling him a “war hero”—a remark partially aimed at Israelis. Talking about it then, Wiles winced. “I’m not sure he fully realizes,” she said, “that there’s an audience here that doesn’t love it.”
When I asked her last fall what she thought Trump’s greatest achievement had been in 2025, Wiles was upbeat: “I think the country is beginning to see that he’s proud to be an agent of peace. I think that surprises people. Doesn’t surprise me, but it doesn’t fit with the Donald Trump people think they know. I think this legislation [the so-called One Big Beautiful Bill], which funded the entire domestic agenda, is a huge accomplishment. And even though it isn’t popular in total, the component parts of it are. And that will be a very big deal in the midterms.”
Dream on, dumbass.
DAY 287
November 2, 2025
“Three killed in latest US strike on alleged drug boat in Caribbean.” —BBC News
During my first visit with Wiles at the White House in November, Trump’s revenge tour against his domestic enemies was in full swing. So was his lethal campaign against Venezuelan president Nicolás Maduro, who, Trump was convinced, headed a powerful drug cartel. Over lunch, Wiles told me about Trump’s Venezuela strategy: “He wants to keep on blowing boats up until Maduro cries uncle. And people way smarter than me on that say that he will.” (Wiles’s statement appears to contradict the administration’s official stance that blowing up boats is about drug interdiction, not regime change.)
I’d already pressed Wiles on Trump’s practice of blowing boats out of the water. The casualties almost certainly include unsuspecting fishermen. In 2016, Trump had famously mused that he could shoot someone on Fifth Avenue and not lose any supporters. Now he seemed to be testing that idea on the global stage. When a critic on X denounced these killings as “war crimes,” Vance posted: “I don’t give a shit what you call it.” Pressed at an October press conference on why he didn’t just ask Congress for a declaration of war, Trump swatted the question away: “I think we’re just going to kill people that are bringing drugs into our country. Okay?” I asked Wiles: “What do you say to people who ask, doesn’t anybody in this administration have a heart?”
Wiles didn’t mince words: “The president believes in harsh penalties for drug dealers, as he’s said many, many times…. These are not fishing boats, as some would like to allege.” The boats, she argued, carried drugs; eliminating them saves lives. “The president says 25,000. I don’t know what the number is. But he views those as lives saved, not people killed.”
As of this article’s publication, at least 87 people had been killed in US strikes on boats in the Caribbean and eastern Pacific. The Washington Post reported that Hegseth had directed the US military to “kill everybody” in a strike on a boat; this was followed by a second strike that killed two survivors—a possible war crime. Hegseth said an admiral was responsible for the second strike. Congressional Democrats and even some Republicans were talking about calling hearings to investigate the matter.
“Drug smuggling,” I pointed out to Wiles, “is not a death penalty offense, even if the president wishes it were.”
“No, it’s not. I’m not saying that it is. I’m saying that this is a war on drugs. [It’s] unlike another one that we’ve seen. But that’s what this is.”
“Obviously it’s a war declared only by the president and without any congressional approval,” I said.
“Don’t need it yet,” Wiles replied.
“We’re very sure we know who we’re blowing up,” she’d told me during lunch in November. “One of the great untold stories of the US government is the talents of the CIA. And there may be an interest in going inside territorial waters, which we have permission [to do] because they’re skirting the coastline to avoid getting [caught].” But Wiles conceded that attacking targets on Venezuela’s mainland would force Trump to get congressional approval. “If he were to authorize some activity on land, then it’s war, then [we’d need] Congress. But Marco and JD, to some extent, are up on the Hill every day, briefing.”
In December, when asked about Trump falling asleep in Cabinet meetings, Wiles said, “He’s not asleep. He’s got his eyes closed and his head leaned back…and, you know, he’s fine.”
In October I asked Rubio what legal authority the administration had to conduct its lethal strikes. “Obviously, that’s a DOD [Department of Defense] operation,” he replied. “So I’m not in any way disavowing it. I agree with it 100 percent. I think we’re on very strong, firm footing, but I don’t want to be giving legal answers on behalf of the White House or the Department of War.” The secretary of state was unequivocal about the targets of the US strikes. “These are not alleged drug dealers,” he said. “These are drug dealers. Where are the YouTube videos of the family saying my poor innocent fisherman son, you know, was killed?”
DAY 40
February 28, 2025
“Trump, Vance and Zelenskyy get into heated exchange during Oval Office meeting.” —Face the Nation
I asked Wiles what she makes of the president’s affinity for Russian president Vladimir Putin, who seems to have cast a spell over Trump since he first ran for president. In 2018 the leaders met in Finland, where Trump appeared to side with Putin when asked whether he believed him about Moscow’s noninterference in the 2016 election. “Watching it at a distance in Helsinki,” she recalled, “I thought there was a real sort of friendship there, or at least an admiration. But on the phone calls that we’ve had with Putin, it’s been very mixed. Some of them have been friendly and some of them not.”
Vance, Rubio, and Steve Witkoff, Trump’s all-purpose special envoy, and Trump’s son-in-law, Jared Kushner, an informal adviser, have been running Trump’s foreign policy since the departure of National Security Advisor Mike Waltz, who was moved to UN ambassador after Signalgate. “I’m not horrified by it,” Wiles said of the infamous unsecured chat about US attack plans against the Houthis to which The Atlantic editor Jeffrey Goldberg was mistakenly admitted. She noted, with an edge, “The burden’s on us to make sure that [national security] conversations are preserved. In this case, Jeff Goldberg did it for us.”
Wiles said she saw trouble brewing before Trump’s infamous Oval Office scrum with Volodymyr Zelenskyy last February, when the president and Vance berated Ukraine’s leader on worldwide television. “If we had it to do over,” Wiles said, “I wouldn’t have cameras, because it was going to end that way.”
Wiles claims the ugly spectacle was the culmination of churlish behind-the-scenes behavior by Zelenskyy and his entourage. It began with Zelenskyy failing to show up for a meeting with Treasury Secretary Scott Bessent when he visited Kyiv to make a deal on mineral rights—and escalated. “It just was a bad sort of sentiment all the way around. And I wouldn’t say JD snapped, because he’s too controlled for that. But I think he’d just had enough.”
The Trump-Putin relationship has zigged and zagged. In the walk-up to the August summit with Putin in Alaska, Trump had publicly sought a ceasefire in Ukraine. It seemed he was finally getting tough with Putin. But in fact, Trump gave up on a ceasefire before the Anchorage meeting began.
Trump’s team was divided on whether Putin’s goal was anything less than a complete Russian takeover of Ukraine. “The experts think that if he could get the rest of Donetsk, then he would be happy,” Wiles told me in August. But privately, Trump wasn’t buying it—he didn’t believe Putin wanted peace. “Donald Trump thinks he wants the whole country,” Wiles told me.
In October I asked Rubio if that was true. “There are offers on the table right now to basically stop this war at its current lines of contact, okay?” he said. “Which include substantial parts of Ukrainian territory, including Crimea, which they’ve controlled since 2014. And the Russians continue to turn it down. And so…you do start to wonder, well, maybe what this guy wants is the entire country.” (In Wiles’s office is a photograph of Trump and Putin standing together, signed by Trump: “TO SUSIE YOU ARE THE GREATEST! DONALD.”)
Will Marco Rubio challenge Vance for the top spot on the 2028 GOP presidential ticket? His answer: “If JD Vance runs for president, he’s going to be our nominee, and I’ll be one of the first people to support him.”
I asked Wiles about the remarkable 180-degree conversion of the secretary of state and the vice president from fierce Trump critics to high-ranking acolytes—and heirs apparent. Trump has floated a Vance-Rubio GOP presidential ticket in 2028. Rubio’s transformation was ideological and principled, she said: “Marco was not the sort of person that would violate his principles. He just won’t. And so he had to get there.” By contrast, she suggested, Vance had other motivations. “His conversion came when he was running for the Senate. And I think his conversion was a little bit more, sort of political.” During another visit to the White House on November 13, when I asked Vance about his conversion to Trump loyalist, he said: “I realized that I actually liked him, I thought he was doing a lot of good things. And I thought that he was fundamentally the right person to save the country.”
Will Rubio challenge Vance for the top spot on the 2028 GOP presidential ticket? His answer: “If JD Vance runs for president, he’s going to be our nominee, and I’ll be one of the first people to support him.”
Wiles is known for having an open-door policy. Trump sometimes comes in unannounced (“he apparently never did in the first administration”). During lunch, no one interrupted us, and Wiles checked her phone only once. She was enjoying a rare moment of downtime. “They don’t know what I’m doing,” she said, motioning toward the Oval, and laughed out loud. After an hour, as I got up to go, I told her about how President Barack Obama’s chief Rahm Emanuel used to complain to visitors about how thankless his job was: “This is nice,” he said, pointing to the wood-burning fireplace, “and this is nice,” gesturing toward the outdoor patio. “And everything in between sucks.” Wiles replied: “I don’t feel that way at all.”
To the left of the fireplace was a freestanding video monitor: a live feed of Trump’s Truth Social posts.
The average tenure for a modern White House chief of staff is a year and a half. George W. Bush’s Andrew Card holds the record at five years and three months. Wiles may yet eclipse Trump’s so-far longest-lasting chief, John Kelly, at 17 months. If she chose to quit, Wiles could make a fortune running the campaign of any number of would-be GOP nominees; though Wiles says she earned around $350,000 for her role managing Trump’s 2024 campaign, she was reported to have made millions more through her consulting firm (Wiles had not replied when asked about this by the time this article went to print). When reports emerged that Biden aide Mike Donilon stood to make $8 million if his boss had stayed in the race and won, Wiles said her co–campaign chair Chris LaCivita sent her a note that said, “Boy, am I stupid. Why was [I] so cheap?
Wiles says she’d originally planned to serve as chief for six months. “I have not had a day I would describe as overwhelming, though there’s plenty of frustration here. But you go to bed at night, you say your prayers, and you get up and do it again.” I asked her about her health and the president’s. “Mine is good,” she said. “His is great. My kids are grown. I’m divorced. This is what I do if I stay four years.”
In December, when asked about Trump falling asleep in Cabinet meetings, Wiles said, “He’s not asleep. He’s got his eyes closed and his head leaned back…and, you know, he’s fine.”
What about Trump’s increasingly frequent verbal attacks on women, as when, in November, he snapped “Quiet, Piggy!” at a female reporter from Bloomberg? Wiles replied: “He’s a counterpuncher. And increasingly, in our society, the punchers are women.”
Is Wiles really irreplaceable, as Rubio said? “Not patting myself on the back, but just recognizing the reality of this president at this time,” she said, “I’m just not [sure] who else could do this.”
In August I’d asked her if she felt she would outlast her Trump predecessors. “As long as I still feel honored to do it, and I feel like things are going well, we’re moving the country forward positively,” she’d said. “It’s two steps forward, one step back. I get that. But it’s two steps nobody else could make.”
“Will the president run for a third term?” I asked in November.
“No,” she said and then added, “But he sure is having fun with it.” Wiles said he knows it’s “driving people crazy.”
“So that’s why he talks about it,” I said.
“Yeah, 100 percent.”
“Would you say categorically no, and that the 22nd Amendment rules out [a third term]?”
“I do. Yeah. And I’m not a lawyer, but based on my reading of it, it’s pretty unequivocal.”
“And has he told you that in so many words?”
“Yes. Oh, a couple times, yeah.”
And then she went on. “Sometimes he laments, ‘You know, gosh, I feel like we’re doing really well. I wish I could run again.’ And then he immediately says, ‘Not really. I will have served two terms and I will have gotten done what I need to get done, and it’s time to give somebody else a chance.’ So, you know, any given day, right? But he knows he can’t run again.”
Months earlier she’d mused on the future of the party and the need for it to turn Trump voters into Republican voters. “Donald Trump will be an ex-president,” she said, looking ahead. And “I’ll be gone to do whatever I do next, which hopefully will be nothing.”
The 2026 midterm elections may determine the fate of Trump’s presidency. Vance told me that he hopes to minimize GOP losses in 2026. “I think a good midterm election for an incumbent presidency would be to lose a dozen seats in Congress and two or three seats in the Senate,” he said. “I think it will be better than that.” I asked Wiles for her prediction. “We’re going to win the midterms,” she said crisply.
DAY 15
February 3, 2025
A couple weeks into his presidency, Trump found himself taking stock. “How is it that you’re doing this so well?” he asked Wiles. “Sir,” Wiles replied, “remember that I am the chief of staff, not the chief of you.” She was paraphrasing one of James Baker’s favorite maxims.
Wiles said that neither she nor Trump had been consulted about Ghislaine Maxwell’s transfer to a less restrictive facility after Blanche’s visit. “The president was ticked.”
But executing the president’s agenda requires telling him the truth. This is especially important when the president is surrounded by acolytes reading almost entirely from the same playbook. An effective chief steers the president clear of land mines. An ineffective one, by ducking tough conversations, lets him blunder into harm’s way. Four years into Reagan’s presidency, Baker, who understood the job, was replaced as White House chief by Treasury Secretary Donald Regan, who didn’t. Soon after, an ill-fated scheme to trade arms to Iran for hostages was born. Richard Nixon overreacted to the leak of the Pentagon Papers by authorizing a special investigative unit in the White House nicknamed the “plumbers”; the result was the Watergate scandal.
Bill Daley, Obama’s former chief of staff, believes Trump and his team could fall victim to overreach. “There’s no doubt the Charlie Kirk assassination gives them an opportunity to put the left on its heels,” he told me. “They believe they are in an incredibly strong position to do whatever the hell they want,” said Daley. “And usually that’s when [people] make mistakes. They go too far.”
DAY 309
November 24, 2025
“US judge throws out criminal cases against James Comey and Letitia James.” —The Guardian
In late September, in a message to “Pam,” his attorney general, Trump wrote (apparently inadvertently) on Truth Social that he’d been seeing posts online saying “same old story as last time, all talk, no action. Nothing is being done. What about Comey, Adam ‘Shifty’ Schiff, Leticia [sic]??? They’re all guilty as hell, but nothing is going to be done.” He told her, “We can’t delay any longer, it’s killing our reputation and credibility.”
Five days later, a federal grand jury indicted James Comey, the ex-FBI director, for making a false statement and obstructing a congressional investigation. Then, on October 9, 2025, a Virginia grand jury indicted Letitia James, the New York attorney general, on one count of bank fraud and one count of making false statements to a financial institution.
Back in March, on the 56th day of Trump’s presidency, I’d asked Wiles: “Do you ever go in to Trump and say, ‘Look, this is not supposed to be a retribution tour? ’”
“Yes, I do,” she’d replied. “We have a loose agreement that the score settling will end before the first 90 days are over.”
In late August, I asked Wiles: “Remember when you said to me months ago that Trump promised to end the revenge and retribution tour after 90 days?”
“I don’t think he’s on a retribution tour,” she said. “A governing principle for him is, ‘I don’t want what happened to me to happen to somebody else.’ And so people that have done bad things need to get out of the government. In some cases, it may look like retribution. And there may be an element of that from time to time. Who would blame him? Not me.”
“So all of this talk,” I said, “about accusing Letitia James of mortgage fraud….”
“Well, that might be the one retribution,” Wiles replied.
“So you haven’t called him [out] on that, or said, ‘Hey, wait a minute.’ ”
“No, no, not on her,” Wiles said. “Not on her. She had a half a billion dollars of his money!” Wiles laughed. (The massive civil fraud penalty won by the New York attorney general’s office in a case against Trump had just been thrown out by an appeals court.)
Wiles said that Trump “was on [Epstein’s] plane…he’s on the manifest. They were, you know, sort of young, single, whatever—I know it’s a passé word but sort of young, single playboys together.”
“Do you really think that Merrick Garland went after the president, persecuted him?” I’d asked her in March, referring to Biden’s buttoned-down, by-the-book attorney general.
“I do,” she replied, “and I think history will prove it to be so.”
That right there - that's the true Trump Derangement Syndrome
In November, it was Comey’s turn in the dock. “So tell me why the Comey prosecution doesn’t just look like the fix is in,” I asked her.
“I mean, people could think it does look vindictive. I can’t tell you why you shouldn’t think that.” Wiles said of Trump: “I don’t think he wakes up thinking about retribution. But when there’s an opportunity, he will go for it.”
On November 24, a federal judge dismissed the Comey and James indictments, finding that prosecutor Lindsey Halligan had been appointed unlawfully. Bondi vowed to appeal both decisions—in the Comey case, the statute of limitations may prevent it. Still, Trump’s retribution campaign continued.
Leon Panetta, Bill Clinton’s formidable White House chief, has never met Wiles but observes, “A good chief of staff is willing to stand up and look the president in the eye and say no,” Panetta told me. “I’m not sure whether she’s an enabler,” he said, “or whether she’s somebody who’s a disciplinarian and wants to try to make sure that he does the right thing.”
Wiles told me in March that she had difficult conversations with Trump every day. “They’re over little things, not big,” she said. “I hear stories from my predecessors about these seminal moments where you have to go in and tell the president what he wants to do is unconstitutional or will cost lives. I don’t have that.”
Wiles said Trump has been clear-eyed about what he wanted to do, “having not been there for four years and [having] had time to think about it.” And therefore she can pick her battles.
“So no, I’m not an enabler. I’m also not a bitch. I try to be thoughtful about what I even engage in. I guess time will tell whether I’ve been effective.”
As the 2026 midterm elections approach, the stakes for Trump and his chief of staff couldn’t be higher. Trump’s second term has been more consequential than his first. He could leave office as a transformational president who sealed the southern border, passed major tax cuts, brought peace to Gaza, and re-created the GOP in his image. Or he could pursue reckless vendettas, shred democratic guardrails, and end up in the crosshairs of Democrat-led investigations. Either way, Wiles may be the thin line between the president and disaster. As one former GOP chief put it, “She may be more consequential than any of us.”
“I think what he meant by that,” I told Wiles, “is that we’ve never had a president who governs so much by whim and who depends so much on one person: you.”
“Oh, good Lord,” Wiles said. “Trump doesn’t depend on anybody.”
