Donald Trump was a builder at heart. That was the business he grew up in, the business his father taught him. That was how he made, and remade, his fortune. Building, renovating, haggling over designs and costs, rebuilding—that was the world he knew best. So I guess it was no surprise that he fixated on his physical surroundings sometimes in minute detail. I found this intriguing, considering his general lack of interest in the minutiae of—well, pretty much everything else.
Among the first times he visited the campaign war room in Trump Tower, he became preoccupied with the renovations that had taken place since he’d last visited the fourteenth floor. No detail seemed to escape his discerning eye. He patted his black dress shoes on the new carpet. “This is quality stuff, very nice,” he said admiringly. He ran his hands along the doorframes and inspected the trim.
His fascination with architecture and design came out in random conversations. From day one, the J. Edgar Hoover Building, the FBI’s aging headquarters on Pennsylvania Avenue, was a particular focus of his ire. “Honestly, I think it’s the ugliest building in the city,” he said of the massive concrete structure. The building was like a giant tan blob—the size of a city block—with hundreds of tiny square portals for windows. It was built in an architectural style known as “brutalism,” and the name was entirely fitting. You’d be hard-pressed to find anyone in D.C. who disagreed with Trump’s assessment on this one.
Later, a Disney production team would come to the White House to record the President’s voice and mannerisms for the animatronic Trump that would go in Disney World’s Hall of Presidents. This was a presidential duty that filled the President with unusual boyish excitement. He was going to be up there onstage next to Lincoln, Reagan, FDR. An animatronic Trump would literally walk among giants.
I read through the draft script for him, which included Trump discussing “achievements of the American spirit,” like inventing the lightbulb, the internet … “And the skyscraper,” he interjected. “It should have the skyscraper in there.” He smiled. “Then I could add a little, ‘Which, of course, I know a thing or two about,’ right?”
The Disney executives, unfortunately, didn’t like that idea. “How can the President claim Americans invented the skyscraper?” one asked. “That’s just a taller building.” Americans didn’t invent the concept of buildings—fine. So I agreed to keep that line out of the script and Trump never mentioned it. (For the record, the first steel-structured skyscraper appeared in Chicago.) The point is that building is never far from Trump’s mind.
So, presented with the opportunity to remodel the most famous office in the world, the Oval one, it came as no surprise that Trump led the effort himself.
The President received a lot of criticism for press reports that he called the White House a dump—a charge he later denied. In this instance, both Trump and the media were telling the truth. He never denigrated the actual White House residence, the way most of the news reports were presented. But he did use that term, with some justification, about the working offices of the West Wing. He’d occasionally express disgust that, in his view, the Obamas had allowed the place to fall into disrepair.
When we arrived in the West Wing, the carpet was light brown and worn, and the walls were a dingy, yellowish color. There was no rhyme or reason to the decor. Sometimes a vase from the 1920s was placed next to a lamp from the 1970s, on top of a table from the late 1800s, next to a couch from the 1980s. It wasn’t all from a lack of style or taste; in some instances it was simply the fact that the most highly trafficked workspace on earth hadn’t been freshened up in eight years. Flies swooped down from the recessed lighting tucked along the walls, targeting my daily club sandwich like hawks attacking prey. Beside my desk, the light blue bulb of an “inside insect killer”—or “bug zapper” where I come from—buzzed 24/7.
Cosmetic updates happen with the transition of each new administration, of course, but I doubt any president has ever been as hands-on as The Donald.
Traditionally every new president, usually with the help of the First Lady, makes cosmetic changes to the Oval Office. In Trump’s case, he personally selected the rug (Reagan era), curtains (gold, of course), couches (Bush 43 era), and wallpaper. He moved the most famous Thomas Jefferson portrait from the Blue Room in the residence to the Oval. He added a painting of Andrew Jackson, a fellow populist icon. One shift in artwork seemed to please him more than any other. Always looking to buck any precedent set by Obama, Trump moved Winston Churchill’s bust back to the Oval after his predecessor exiled it to a hallway outside the Treaty Room.
“Did you see who we brought back?” he’d ask when guests would visit for the first time. “Churchill’s back. We brought him back. Obama had sent him away—a disgrace. He’s back now.”
But then he went far beyond what a traditional President and First Lady would do, personally supervising, or even micromanaging, a redo of the rest of his Oval Office suite as well as the larger West Wing.
Trump never uses a computer himself, so instead he hovered over his executive assistant, Madeleine Westerhout, as she sat at her desk outside the Oval Office scrolling through decor options on her computer, while he pointed at items he liked. No item of decor was too small to pass his notice—from rugs to wallpaper.
When the White House called York Wallcoverings in Pennsylvania to tell them the President wanted an order for the Oval Office delivered by 7 P.M. that same day, they thought it was a prank at first. When they were assured that this was a personal request from the new commander in chief, they panicked. They’d stopped making the pattern that Trump personally selected three years before. So the good folks at York had to stop everything else they were working on, hand-mix the inks, print ninety-six double rolls of out-of-stock fabric, and make the two-hour drive to deliver the product, all before dinnertime. Which, miraculously, they did.
The President also, with great pride and concentration, selected the color palette for the rest of the West Wing and ensured that decorations in each room were from a corresponding time period. In those changes he was a little more patient.
Something else also caught his eye in the Roosevelt Room, a modest-sized conference room just across the hall from the Oval Office. Along the wall on the south side of the room stood eight flags: the U.S. flag, the presidential and vice presidential flags, and flags for each of the five branches of the military—Army, Air Force, Coast Guard, Marines, and Navy. The President especially liked the military flags, because they included streamers—long pieces of fabric—embroidered with the major campaigns in which each branch had fought.
Trump, who had never served in the military, held the armed forces in highest esteem. He famously referred to military leaders as “my generals” and was drawn to anyone in uniform. As President, he liked being chief executive—it was a role he’d been filling for decades—but he loved being commander in chief.
In the early days of the administration, aides would sometimes come into the Roosevelt Room and realize the flags were mysteriously missing. Invariably they would come to find out that Trump had requested they be moved into the Oval Office and placed along the walls behind his desk. So then they’d have to move them back into the Roosevelt Room for public events, once again prompting the President to ask for them to be returned to the Oval once he realized they were gone. Eventually they acquired a second set so the President could enjoy them encircling his office and the Roosevelt Room could be left in peace.
Once the renovations were completed, the President enjoyed giving tours of his private suite in the West Wing, including the rooms connected to the Oval Office that most Americans and staff members in previous administrations had rarely seen. He occasionally delighted in pointing out the history of one room in particular.
After being interviewed by Maria Bartiromo in the Roosevelt Room, the President invited the Fox Business Network host across the hall into the Oval for a quick tour. Turning right down the suite’s hallway, he paused to turn on the light in the bathroom—the place where Lyndon Johnson famously used to give orders to his staff while sitting on the toilet. The flawless white marble glistened in the light and the President remarked on the craftsmanship. “Simply beautiful.”
But that wasn’t the room that interested him most.
A few steps farther on the other side of the hall, the President popped open the door to his private study. It’s a small room, which his predecessors tended to use as a working office when the Oval felt too formal. Light poured into the study through the two floor-to-ceiling windows, and Trump had installed several plush, comfortable chairs. He didn’t use the room very often, though as I would later experience, it was the ideal place to have private conversations that couldn’t even be heard by the curious ears of executive assistants.
“I’m told this is where Bill and Monica—” Trump began, stopping himself before his sentence reached completion.
He shrugged and then moved on to the private dining room. “This place was a disaster when I got here,” he said, “hole in the wall and many other problems.” He’d had the room stripped down to its studs and refurbished in spectacular fashion. He purchased a giant crystal chandelier with his own money—which he called his “contribution to the history” of the White House—and had it hung above a table that was usually covered in crisp white linen. The carpet was deep red with golden stars every few feet. The seats of the wood-backed chairs were upholstered to match the stars. Large historical paintings were hung in gilded wooden frames. And suspended on the wall above the fireplace was his favorite toy: a sixty-plus-inch flat-screen television. “It’s got, like, a super TiVo,” he said as he grabbed the remote and scrolled through the day’s clips that had been queued up for him. “I think it’s one of the greatest inventions.” He said this with a smirk, as if to acknowledge his reputation as a television addict.
He loved showing off the residence, too, and seemed genuinely awed by the sheer coolness of living at the world’s most illustrious address.
The second week we were in the White House, Trump came out of the Oval late in the evening and, with raised eyebrows, said something that many of us never expected to hear, especially from him.
“This job is a lot harder than I thought it’d be.”
It occurred to me pretty early on that the presidency is like an iceberg. The parts you see—the speeches, the ceremonial duties, the interviews, the walks out to Marine One, the photo ops before or after meetings—those are like the tip of the iceberg sticking out of the water. The other 90 percent of the job exists out of sight in the murky depths below. Intelligence briefings, policy briefings, legislative strategy briefings—briefings, briefings, and more briefings. And mountains of paperwork.
One afternoon after an event in the East Room, Staff Secretary Rob Porter was waiting for the President in the Green Room with a stack of official actions that needed to be signed right away.
“Here he is again,” the President said, half joking but somewhat annoyed. “You’ve never seen somebody have to sign as many documents as me—big ones, little ones. It never ends.” Porter laughed dutifully and explained why this particular stack couldn’t wait.
Any decision that makes it to the President’s desk is significant, otherwise it would have been handled by someone lower down the chain of command.
Though it may surprise people accustomed to Trump’s “I’m a genius who can handle anything” public persona, in private, this new reality was not totally lost on him. Of course, I doubt anyone really knows what they’re getting themselves into when they sign up to be Leader of the Free World.
During our early days in the West Wing, there was an entire genre of reporting devoted to Trump’s “chaotic” management style. This was not “fake news.” A lot of it, anyway. Press reports about it being the Wild West were somewhat overblown, but the underlying premise was generally accurate. We were all figuring it out as we went along.
In The Art of the Deal, Trump wrote that it’s hard to be “imaginative or entrepreneurial if you have too much structure.” Right away, his freewheeling approach collided with the presidency like an unstoppable force running into an immovable object. Anyone could see why it would pose such a challenge to someone in charge of managing the office—like Reince Priebus or, later, John Kelly.
His official schedule was more of a loose outline than a strict regimen. If the President was scheduled to come down from the residence first thing in the morning for a filming session, I’d wait for him on the ground floor outside his private elevator. It wouldn’t be abnormal for him to be upstairs working the phones and ultimately come down a half hour, or even a full hour, later than anticipated. The same could be said of the evenings, when he’d linger in the Oval until after dusk, continuing to work long after his “official schedule” had concluded.
During the day, the Oval Office suite was a hub of activity.
In the “Outer Oval,” the President’s executive assistant, Madeleine Westerhout, shared a work space with Hope Hicks, whose title was Director of Strategic Communications but who was, in reality, whatever Trump wanted her to be that day. Like pretty much everyone else.
Madeleine had previously been an executive assistant at the RNC. She’d first captured the public’s attention—and Trump’s attention as well—during the transition. Ever the showman, Trump paraded potential cabinet members in front of the cameras in the Trump Tower lobby and at his golf club in New Jersey. Ushering each one of them to meet the boss was a twenty-six-year-old brunette, smiling and making small talk along the way. That was Madeleine.
During the transition, campaign aides jokingly referred to her as “The Mockingjay,” the young woman who came to symbolize a rebellion in the Hunger Games novels. In our case, she symbolized a broader push for RNC aides to swoop in and claim White House jobs that might have otherwise gone to campaign staffers. It was tongue in cheek—nothing personal against her. In fact, she was nothing but nice to me when we first arrived. But others who’d been with Trump much longer than me viewed her with deep suspicion. They believed Priebus and his top deputy, Katie Walsh, had installed Madeleine in such a sensitive role—within earshot and with full visibility of everything happening in the Oval—to act as their personal spy.
Hope’s desk, sitting parallel to Madeleine’s, was the closest to the Oval Office. The President would call out for “Hopey” to come in to see him countless times each day. She’d assess the press coverage for him, give recommendations on which interviews to do and which to turn down, and advise him on how to respond to the media crisis of the moment. Trump has a reputation for surrounding himself with beautiful women. Hope was no exception to this rule. She was a twenty-eight-year-old former Ralph Lauren model, after all. But that shouldn’t be taken to imply that she wasn’t a pro. While Spicer was engaged in a blood feud with the entire Washington press corps and the President was publicly calling them “the enemy of the people,” Hope maintained strong relationships with almost all of them. Most important, the President trusted her completely. The reason was simple: unlike so many others in Trump’s orbit, she’d proven time and again that she only acted in his best interest. She wasn’t trying to build her brand or get famous. In fact, she longed for the anonymity she had enjoyed before politics. She was there to serve him.
She became one of my best friends in the White House. In my text conversations, I didn’t refer to her by her name, I’d just type the diamond emoji—a symbol inspired by the famous Hope Diamond on display in the Smithsonian. We’d later sit by the pool at Bedminster and talk at length about our jobs, the White House, and life in general, but in the early days of the administration we didn’t have time to slow down.
In an even smaller office inside the Outer Oval, the President’s personal aide, or “body man,” Johnny McEntee, and his longtime bodyguard, Keith Schiller, shared a work space.
McEntee was a former University of Connecticut quarterback in his mid-twenties. His claim to fame was a YouTube video in which he showed off his accuracy and arm strength by performing tricks, like throwing a football into a basketball hoop from the upper deck of UConn’s basketball arena. The video garnered almost eight million views. As an intern at Fox News, he’d watched Trump’s freewheeling campaign announcement on TV and knew immediately he wanted to join his team. He sent messages to the campaign’s public email address and eventually got a response inviting him to come on board. He became more than a political staffer; he was like an adopted family member. He was by the President’s side sixteen hours a day. He’d later become a heartthrob throughout the Arab world when photos of him with the First Family went viral during the President’s trip to Saudi Arabia. Arab newspapers didn’t know his name, referring to him only as “the man in the red tie.” “This man in the red tie shouldn’t leave Saudi Arabia!” one woman said, according to Arab News. “Just give me the man in the red tie and throw me in the sea,” another tweeted.
Though most outsiders didn’t know it, Johnny’s office mate, Keith Schiller, was the most important person on Trump’s staff. His official title was Director of Oval Office Operations, but he may have been more accurately described as First Friend. In his late fifties, Keith’s relationship with “the boss,” as he always called him, went back further than anyone else’s in the White House. He was tough as nails. As a New York City narcotics officer in the early 2000s, his job had been to kick in doors during drug raids. When a protester outside Trump Tower came after him from behind during the campaign, Schiller had turned around and smacked him so hard, he immediately cowered in fear. “He was reaching for my gun,” Schiller later told me. He had served as Trump’s head of security since 2004. He’d been at Trump’s side through the good times and the bad, and he was one of the only nonbillionaires that Trump viewed as a peer.
Every president needs someone in whom they can confide, someone who will shoot straight with them—say things that other staffers could never get away with. That was Keith. He was always very respectful and deferential to the President, but he was an honest and trusted voice. He went up to get the President in the morning, then walked him back up at night, often making him the first and last staffer Trump would see. The two chiefs of staff that I worked with in the White House both resented his relationship with the President and tried to sideline him in any way they could.
Madeleine, Hope, Johnny, and Keith were the aides who kept the Oval Office humming and made sure the President always had what he needed. Participants in official meetings funneled through their office on the way in to meet with the President. In between meetings, aides who wanted to pop in for a second were often summoned when the President would notice them standing just outside. He fed off the energy of being around other people. He liked bouncing from issue to issue in quick bursts.
In the early days of the administration, my primary role in such meetings was something of a fact-checker for the press and communications team. Sometimes reporters would claim to have sources describing conversations that took place in the room. In those instances, I was able to quickly tell press aides, yes, that happened; or no, that did not happen; or well, there is a shred of truth there, but it is taken out of context. Then they could formulate a plan for how to respond.
There were very few people on the original Trump White House staff who had any experience in the West Wing. We would sometimes laugh about the differences between The West Wing television show and reality. Perhaps most notably, the halls of the real-life West Wing are nowhere near wide enough to accommodate the television series’ famous walk-and-talk scenes, and in fact the entire place is much smaller and more cramped than it’s often portrayed.
But as I tried to find my place in Trump’s orbit, one West Wing episode—“20 Hours in America”—frequently came to mind.
In the episode, Deputy Chief of Staff Josh Lyman (Bradley Whitford) is left behind by the presidential motorcade after President Josiah Bartlet’s (Martin Sheen) speech in Indiana. As a result, Deputy Communications Director Sam Seaborn (Rob Lowe) has to stand in for Lyman and staff the President once he returns to the White House.
Terrified, Sam explains, “There are going to be any number of areas on which I can’t give him expert advice.”
“Welcome to the club,” Josh replies.
For the rest of the day, Sam desperately tries to staff the President from meeting to meeting, topic to topic. By the end of the episode, he’s exasperated and reflecting back on what he has experienced.
“Until you sit in the room all day, you can’t comprehend the chaos of the Oval Office,” he says. “I had one good moment … but that was it. The rest of the day was just keeping up. And this was a pretty light day.”
But in spite of being overwhelmed and feeling incredibly unprepared for the breadth of issues and the depth of each conversation with the President and his expert advisers, his one takeaway is “I’ve got to get back in there. That’s where it’s happening.”
TV shows don’t tend to get much right about what it’s really like to work in the White House—at least in the Trump White House—but The West Wing’s writers were spot-on with this one. All of the action is in the room. Decisions are made in the room. If you want to matter—if you want to be a player—you’ve got to get in the room.
With that in mind, I attended presidential meetings on an insanely broad range of subjects and quietly took notes. I didn’t say much for the first couple of weeks, but before long I was able to occasionally offer perspective that others didn’t have. As a result, the President grew to know and trust me, and I never violated his trust.
This proximity also helped me in my official role as Director of White House Message Strategy. Unlike most politicians, who like staffers to bring them fully fleshed-out briefing papers and poll-tested talking points, Trump’s communications strategy and messaging was all based on pure gut instinct. Being around him helped me get a sense of how he instinctively talked about various issues. And since there really isn’t a “private” version of Trump, you could bet that anything he said behind the scenes was eventually going to find its way into his public comments.
The more time I spent around the President, the more I picked up on his quirks.
For one thing, I noticed that he had a strange habit of moving any item that was set in front of him. If a waiter placed a glass down beside him, he would immediately reposition it. If his name placard was directly in front of him, he would move it off to the side. If he was referencing notes in front of him, he would shift them from position to position while other people were talking. And if his silverware was not exactly perpendicular to his plate, he would carefully align it—an OCD habit that I subconsciously picked up myself, driving my wife insane. Sometimes he would actually do the same for his guests. When Wayne LaPierre of the NRA sat down beside him at the table in the Roosevelt Room, for example, Trump even slid LaPierre’s own drink and coaster a few inches to the left. Maybe this was all subconscious, maybe it was a subtle power move. In any event, it happened all the time.
The staff often scheduled larger meetings with the President in the Roosevelt Room. He didn’t like to venture far from his domain during the day, but just across the hall was acceptable. Regardless of who he was meeting with, or for how long, the President had a habit of ending the discussions the same way. When he became too bored and was ready to move on, he would interject, “Has anyone here ever heard of a place called the Oval Office?”
His guests would smile and nod. “Oh, of course, I’m sure you’ve all been to the Oval Office many times, right, as important as you all are?” he’d tease. With some exceptions, most had not.
“You know, the crazy thing is,” he would continue, “President Obama didn’t like to bring people into the Oval Office; he didn’t want people to see it. I have no idea why, because it’s just right through that door.” It was unclear to us whether this was true or not, and I have no idea where the President heard that. But as I had noticed many times by then, he enjoyed making comparisons to Obama that made him look better in the telling.
The President would then look over his right shoulder and nod or point to the curved door on the southeast side of the room. “Would you like to see it? You know what? Let’s go.” And with that, the President would parade the group across the hall into the most famous office in the world. After all, was someone going to say, “No, thanks, Mr. President”? Of course not. It was a fail-proof, and clever, way to end any meeting early and on a good note.
His other recurring bit took place during meetings in the Oval Office itself, and it was by far my favorite.
The President liked to preside over small group meetings while sitting behind the Resolute desk. The desk itself was an extraordinary historical artifact. It was ornately carved out of English oak timbers from the HMS Resolute and had been given by Queen Victoria to President Rutherford B. Hayes in 1880. Presidents Kennedy, Reagan, Clinton, Bush, and Obama all used the desk in the Oval Office, and it combined the two things Trump appreciated most in White House furniture: history and luxury.
Out in front of him, on the other side of the desk, four wooden chairs—historic, I’m sure, but fairly uncomfortable—would be set up in a semicircle. On many days, stacks of briefing papers, newspapers, and locked bags designed to carry classified documents would be stacked on the desk around the telephone. “I actually do work in here, unlike some of the ones before me,” the President would say as an assistant would clear off the desk.
But always left behind, no matter what, would be a small wooden box, approximately nine inches long and three inches wide. A golden presidential seal was imprinted on top of it right in the middle, with a small red button right beside it, about the size of a penny.
The box with its bright red button would often catch the attention of guests, who would look at it silently as their minds raced.
What happens if he presses that red button? I’m sure many a first-time visitor wondered to themselves.
If Trump noticed someone glancing at the box—and sometimes completely unprompted—he would pick it up and move it farther away from himself. “Don’t worry about that,” he’d say. “No one wants me to push that button, so we’ll just keep it over here. Now, what were you saying?”
Guests would laugh nervously and the conversation would continue, until several minutes later Trump would suddenly move it closer to him without actually saying anything about it. Then, later in the conversation, out of nowhere, he’d suddenly press the button. Not sure what to do, guests would look at one another with raised eyebrows. Moments later, a steward would enter the room carrying a glass filled with Diet Coke on a silver platter, and Trump would burst out laughing. “That red button!” he’d exclaim. “People never know what to think about the red button! Is he launching the nukes?!” Most guests would double over laughing at the prankster in chief. The prank also offered a subtle sense of self-awareness—there were people who thought Trump was volatile enough to start a nuclear war.
In addition to all the outside groups rolling through, cabinet secretaries also began sitting down with the President to discuss the vision for their agencies.
One of the most memorable exchanges I witnessed was with Dr. Ben Carson, Trump’s former presidential rival turned supporter. He was now Secretary of Housing and Urban Development, despite having little to no experience running such a massive organization. That didn’t matter to Trump; Carson was his guy. And he seemed to have genuine affection for him. Long gone were the days when Carson threatened him in the polls, when Trump had said he had a “pathological temper” that made him incurable, like a “child molester.”
“My precious Ben,” Trump said softly, swiveling his chair around to greet the Secretary.
During the 2016 campaign, Trump very famously diminished rival Jeb Bush by calling him “low energy.” Next to Ben Carson, Bush was a rocket engine of excitement. Everything about his movements, his demeanor, even the somewhat sleepy look in his eyes seemed designed to lose your interest. In another life, he was an acclaimed neurosurgeon. Some people joked that was perhaps because he could put patients to sleep without the need for anesthesia.
Carson sat in front of the Resolute desk with a folder in his lap, feet neatly tucked under his chair, like an attentive student. I took a seat along the wall, figuring there might be a moment for me to slip out and return to my desk to catch up on the emails piling up in my in-box. There aren’t many places I’d rather be than sitting in the Oval—in the middle of the action—but it was hard to imagine HUD policy capturing my attention for very long. Turns out I wasn’t the only one in the room who felt that way.
The President leaned back in his chair, crossed his legs, and took a swig of his Diet Coke. Large cubes of ice clinked against the inside of the glass, which was running low on Trump’s favorite dark brown liquid.
“So what’re we going to do, my Ben?” Trump asked genially.
The Secretary’s voice was so soft that I struggled to make out some sentences. Words left his mouth and seemed to evaporate once they hit the open air.
Referencing his notes, Carson began casting his vision for a department that would help lift people out of poverty through various programs that brought the public and private sectors together. Literacy was a focus. This came as no surprise to me. Carson’s nonprofit had opened well over a hundred “reading rooms” around the country, a fact I’d learned when crafting the messaging around Carson’s nomination.
I could see Trump starting to lose interest as Carson continued articulating the detailed plans inside his notebook. First, the President shifted in his chair and readjusted a small pillow he’d placed behind his back. Then, as Carson talked about different phases of his program and whatnot, Trump glanced around the room. At some point he noted his Diet Coke was nearly gone and went back to his button routine, but his heart wasn’t quite in it this time. “People always wonder about this button,” he told a confused Carson.
Finally, he pressed it again. Diet Coke arrived and Trump was done.
“That sounds wonderful, Ben,” he interjected at one point. “I trust you to do it right.” I had no idea what Trump had just approved, and I’m not sure he did, either. But he stood up, signaling the meeting was coming to an end. He shook Secretary Carson’s delicate, valuable right hand, the one that had saved so many lives during his decades as a surgeon, and sent him on his way. The whole meeting lasted, maybe, ten minutes.
In other early strategy meetings, however, Trump was much more engaged.
“Get in here, Steven!” the President said, seeing Treasury Secretary Steven Mnuchin waiting just outside his office. “They said we’d never do it, but here we are in the Oval Office, raised more money than they ever thought. Saw the whole country—and they loved us, right, my man?”
“That’s right, sir, we did,” Mnuchin replied in his typical, low-key style. “I have some people that I want you to meet.”
Behind Mnuchin filed in about a half-dozen men in expensive suits. “Holy crap,” one of them said under his breath, pointing up at the eagle and stars intricately carved into the ceiling. It was the first time any of them had been in the Oval, an experience that gives pause to even kings, prime ministers, and presidents, much less the rest of us mere mortals.
“Welcome to the famous Oval Office,” Trump said with a twinkle in his eye. “I’m sure you’ve all been here many times before.”
With the Treasury Department’s new senior aides now arrayed in front of the President, Mnuchin started introducing them one by one. Trump occasionally interjected with questions about their résumés and backgrounds, but mostly casually listened while sipping his Diet Coke.
After the introductions, Trump thanked the new staffers for joining the team and seemed like he was about to wrap it up. Then he suddenly stopped midsentence, sat up straight, and asked the group the first and only policy question of the meeting.
“Should I label China a currency manipulator?”
It was one of Trump’s central foreign policy promises of the campaign. Now, in office, he took great pride in keeping his word to voters and was eager to check this one off his list.
“No, sir, you shouldn’t,” one of the aides said without hesitation as the rest of the group traded uncertain glances.
Surprised, Trump’s head snapped around and he locked eyes with this new adviser, who was now probably worried this would be his first and last trip to the Oval.
“Really?” the President asked with great curiosity. “Why not?”
“We’re developing a report for you that lays out in detail our economic relationship with China,” the Treasury staffer said. “Using Treasury’s criteria, China’s worst offense is its massive trade surplus, but based on our research it does not appear to be actively manipulating its currency.”
“Who the hell is this?” Trump asked with a laugh, looking over at Mnuchin.
“This is Dan Kowalski,” the Secretary replied with trepidation. Kowalski had been a senior staffer on the campaign’s policy team after working on the Hill for two decades. He was intimately familiar with Trump’s history on this issue, and he was now one of the newly minted counselors to the Secretary.
“All right, Dan,” the President said, leaning forward. “Talk to me about this. They’re killing us—I mean absolutely killing us.”
Mimicking his cadence on the campaign trail, Trump mock-yelled, “‘China’s beating the hell out of us! And I’m not going to let them do it anymore!’ That’s what I said, all the time, and the people would go crazy. Steven, you were there. You saw it. The people would go wild, I mean absolutely wild. And now you’re telling me something different?”
“No, sir,” Kowalski said. “There are a lot of tools at your disposal to push back on China, and you should use them. But our research shows that they are not currently manipulating their currency. We have a list of countries we watch closely—six of them, if I remember correctly—and China is one of them. They have a history of foreign exchange intervention. It’s hurt us in the past, you are absolutely right. They undervalued their currency for a long time, so it did not appreciate even though its trade surplus soared. But that is no longer the case.”
“I’m going to have to see this report,” Trump replied, looking over at Mnuchin. “I want to see it. We’ve got to do something about China, I’m just telling you. We have no choice. So I need to see this report.”
In the coming weeks, the President held meetings with numerous officials throughout the executive branch, including senior members of the National Economic Council, National Trade Council, and National Security Council. Then, less than a month after the meeting in the Oval Office with Mnuchin’s team, Trump announced he would not label China a currency manipulator.
This was my first memorable exposure to one of Trump’s core operating principles, which could probably be best described as strong opinions, weakly held. He had strong opinions on pretty much everything under the sun, and he wasn’t afraid to share them with the world. But the only two issues on which he seemed to have deeply ingrained, long-held beliefs were immigration and trade. On everything else he was willing to be convinced, with compelling evidence, that he should change his position. This was different from flip-flopping, which politicians do for political expediency. There’s no doubt he changed his position, but from my vantage point he did it because he was presented with new information. And isn’t that what we want from our leaders? Of course, we also needed China to ratchet up pressure on North Korea to abandon its nuclear weapons program. Navigating geopolitics is a lot more complex than campaigning, and I’m sure that played a role, too.
The West Wing adapted Trump’s laissez-faire style, but there was sometimes uncertainty about who exactly was in charge and empowered to do what.
A traditional White House structure starts with the Chief of Staff at the top, followed by a couple of deputy chiefs, then the heads of departments (Communications, Legislative Affairs, Political Affairs, Intergovernmental Affairs, the National Economic Council, National Security Council, etc.), then their deputies, and so on.
But from the very beginning, Trump created something of a three-headed monster at the top with Reince Priebus holding the title of Chief of Staff, Steve Bannon as Chief Strategist, and Jared Kushner as Senior Adviser. Each of those individuals came in with staff who were loyal to them for various reasons, whether ideological or personal.
The selection of Priebus was puzzling to a lot of people—especially to anyone trying to reconcile his hiring with Trump’s well-known obsession with loyalty. He knew, after all, that Reince had all but bailed on him after the Access Hollywood crisis. Maybe his selection of Priebus for the traditionally powerful post of Chief of Staff was meant to show that he was more open-minded and forgiving than the conventional wisdom suggested. Maybe it was a recognition that Trump needed an insider to help him govern, especially given Reince’s close relationship with House Speaker Paul Ryan. Maybe it was done just so that Trump could torment Reince on a daily basis. Or maybe—and this tended to be my view—Trump didn’t think much of titles. “Chief of Staff” meant little to him.
It quickly became obvious to everyone working with Trump that there was the official organizational chart, and the unofficial—also known as the real—organizational chart. The official org chart looked like a typical White House, perhaps just a little more top heavy. The real org chart, however, was basically Trump in the middle and everyone he personally knew connected to him—like a hub and its spokes. This exacerbated staff tensions when the official hierarchy was upended by the reality of how Trump operated.
As Director of Legislative Affairs, for instance, Marc Short was technically subordinated to Deputy Chief of Staff Rick Dearborn, whose portfolio included the White House’s relationship with Capitol Hill. But in practice, Short was the President’s go-to guy when dealing with lawmakers, and he operated mostly autonomously. This wasn’t a big deal in Dearborn’s case—he was comfortable enough in his own standing, and in his own skin, to not recoil at Short’s spreading his wings a little bit.
Kellyanne was another one. As Counselor to the President, she managed to land a job with no fixed responsibilities. “What exactly does Kellyanne do?” was a question people asked all the time. So she was able to continue being the President’s pit bull on TV—a job that never goes out of fashion in Trump World—and otherwise just dabble in areas that piqued her interest. She would later focus her efforts on the opioid crisis and veterans’ issues, but early on she was content—very content—to sit back, go on TV, and let rivals eat one another alive.
And then there was Dan Scavino, one of Trump’s longest-serving aides. Dan was the rare person in the White House who was universally liked by all the staff. He’d worked his way up from being Trump’s golf caddy, to general manager of Trump National Golf Club in Westchester, to social media director on the campaign and then in the White House. He was glued to Trump’s side, capturing nearly every moment with his cell phone camera and blasting it out on social media for the world to see. He was the only person other than Trump himself who always maintained access to the @realDonaldTrump Twitter account. On his personal account, he was known as the unofficial conductor of the Trump train, and his online persona was a mirror image of Trump—bombastic, controversial, a hot-take machine. In person he was quiet, humble, and carried himself with a gentle spirit.
Any time Scavino’s name would come up in conversations—which happened regularly; the guy was famous among Trump’s followers—people would inevitably ask about “the tweets.” Is it really Trump? Does he give anyone advance notice what he’s tweeting? Tell us how it works!
This shouldn’t come as a surprise to anyone: it’s Trump. He’d fire off tweets from the residence at all hours and usually without any advance notice to staff. During the day, he would often call Dan into the Oval to dictate tweets, complete with punctuation instructions—dash, dash, “sad,” exclamation point—and his own unique way of capitalizing seemingly random words for emphasis.
Early on, there wasn’t an official channel to submit recommended tweets, but Dan would come in with a printout of various options. Trump would approve them, disapprove them, or make tweaks, but you can rest assured that he wasn’t letting anything go out without his sign-off. In that regard he was like a publisher, fiercely protective of his brand and loyal to his audience—he only wanted to put out things they’d want to read. Over time I got really adept at tweeting in Trump’s voice. Policy and communications aides would bring their topics to me and I’d craft the most Trumpian tweet I could, then submit it for approval, with a pretty good success rate.
In retrospect, I was both empowered and hurt by the unofficial org chart. Because of my relationship with Trump—and Hope, Keith, Jared, and Bannon, to name a few—and my status as a campaign “loyalist,” I had wide latitude to be a part of meetings, to fly on Air Force One, to interact with the President, and later to play a leadership role in major efforts like tax reform. These were extraordinary, once-in-a-lifetime experiences, the kind you dream of when you think of what it must be like to work at the White House. Like the time I suddenly found myself organizing a videoconference call between the President and astronauts aboard the International Space Station.
In the first couple of months we were in the White House, NASA Communications Director Jen Rae Wang reached out to me and asked if the President might participate in some type of event celebrating astronaut Peggy Whitson’s breaking the record for the most cumulative time in space. She was currently aboard the ISS and was set to break the record on April 24, 2017.
“I’ve seen past presidents call the Space Station before,” I said. “Could he do that?”
“Oh, yes,” she replied, clearly excited. “We could set up a videoconference anywhere you want and broadcast it live.”
“The Oval Office?” I asked.
“Yes, of course, that would be amazing,” she said.
The next day, standing on the patio just off the Oval Office, I asked the President if he was interested in doing the call. He was all in. “We don’t capture people’s imaginations anymore,” he said, in a rare moment of wistfulness. “We used to do big things—incredible things. No one could do the things we could do. You have to inspire people. They went to the moon. But the call would be great. Honestly, how cool is NASA?”
Over the next few weeks, I brought in NASA engineers, who produced diagrams of the Oval Office with all the production equipment positioned where it would be. We went into the Oval and did a walk-through of exactly how it would play out. And we coordinated with NASA’s spaceflight team to pinpoint the exact time the call would need to take place. This, as it turns out, was much more important than I initially realized. One of the engineers explained “orbital mechanics” to me, which boiled down to: When the Space Station flies around the curvature of the planet, we lose touch with it. That meant we had a very defined window of time—about twenty minutes—to make this happen. The President would have to be right on time, a rarity.
The day of the event, there was a buzz of excitement in the Oval suite. For staff, this was going to be one of those How cool is this? moments. With the production team setting up in the Oval, I pulled the President into the Private Dining Room for a final briefing on the sequence of events.
Also around the table with me were Secretary of Education Betsy DeVos (we had partnered with her to encourage teachers around the country to let their students watch the videoconference from their classrooms), astronaut Kate Rubins, and Acting NASA Administrator Robert Lightfoot Jr. We had about ten minutes before the broadcast, which I stressed to the President had to start and end exactly on time.
The President was sitting at the head of the table wearing a dark red tie, a small stack of newspapers and briefing folders sitting just to his right. I sat down in the chair just to his left. The giant flat-screen TV hanging on the wall was tuned to Fox News, on mute.
I started walking the President through the sequence of events as he scanned over his prepared remarks, crossing out some of the text with a Sharpie. He wanted to know the positioning of the cameras, which side of his head would be most prominently featured. I had made sure the press cameras would be positioned on the right side, his preference, and he nodded his approval. He also wanted to make sure the television audience would see both him and the astronauts in space, which I assured him they would.
As I continued working my way through the briefing sheet, he suddenly appeared distracted, distant. I could sense the gears inside of his head starting to turn. I was losing him. And he soon revealed why. With our small window of time for prep closing, the President suddenly turned toward the NASA Administrator.
“What’s our plan for Mars?” he asked.
Mars? Where did that come from?
Mr. Lightfoot sat up straight, cleared his throat, and explained that NASA’s plan was to send an unmanned rover to Mars in 2020, then to try for manned spaceflight to the red planet by the 2030s.
Trump bristled. “But is there any way we could do it by the end of my first term?” he asked.
Lightfoot shifted in his chair and placed his right hand on his chin. With hesitation, he politely told the President that he didn’t believe that time frame was possible. A man on Mars in 2020 would be a logistical impossibility. He laid out all the challenges—distance, fuel capacity, etc. Also the fact that we hadn’t landed an American anywhere remotely close to Mars ever.
I was getting antsy. All I could think about was that he had to be on camera in three minutes. We still hadn’t yet discussed several key details, and yet we’re in here casually chatting about shaving a full decade off NASA’s timetable for sending a manned flight to Mars. And seemingly out of nowhere.
Trump dropped his briefing papers down in front of him. His head cocked to its side and he leaned forward. “But what if I gave you all the money you could ever need to do it?” Trump asked. “What if we sent NASA’s budget through the roof, but focused entirely on that instead of whatever else you’re doing now. Could it work then?”
With a subtle, uncomfortable laugh and a bewildered look, Lightfoot said, basically, “No.” He was sorry, but he just didn’t think it was technologically possible.
Trump was visibly disappointed, but I tried to refocus him on the task at hand. We were now about ninety seconds from going live.
The President and I walked down the narrow hallway connecting the dining room to the Oval, but just before we walked through the door, he decided to stop in his white-marbled bathroom for one final check in the mirror. Optics. “Thirty seconds, Mr. President,” I said, now nearing full-on panic.
“Space Station, this is your President,” he said to himself, smirking in the mirror. “Go ahead,” he continued calmly, without even a hint of concern in his voice. “I’ll be right in.”
When he finally hit the door, camera shutters snapped in a flurry as I counted down “Five … four … three…” He sat down, perfectly positioned as the broadcast began. Nineteen minutes later I signaled for him to wrap it up, and we finished the broadcast just before the Space Station flew over the horizon and out of reach. If I’d ever doubted that his showbiz background actually brought any value to this job, I certainly never would again.
I wouldn’t trade such experiences for anything, but this access also bred resentment, especially among people above me in the official org chart who weren’t afforded the same opportunities, or thought I was too big for my britches, as they say in the South. This earned me extra enemies. And I didn’t need any more of those, considering the tension that already existed between former campaign and RNC staffers. The list would grow longer over time, for various reasons.
On the press and communications teams, our official schedule was bookended by an all-staff morning meeting at seven thirty and an evening meeting at six, both of which almost always started well behind schedule. For a while we kept a running tally of the total man-hours wasted standing outside of Sean’s office waiting for the meeting to begin. We quit a couple of weeks in when it reached into the hundreds and we gave up keeping track. Thirty people all waiting together adds up in a hurry. Once the meetings finally began, people would go around the room mentioning things they were working on, and their superiors—or anyone else, really—would play armchair quarterback, explaining why what they were doing was wrong.
I was often reminded in these meetings of a conversation I had with Secretary of Defense James Mattis while he was waiting to see the President. While he could go toe-to-toe with any warrior on the planet, it was his intellectual approach to his life and work that truly set him apart. In addition to “Mad Dog”—a nickname the President loved more than Mattis did—he was also known as the “Warrior Monk.” Throughout his military career, he would bring his roughly seven-thousand-volume library with him as he traveled from post to post. So on the rare occasion there was an opportunity to pick his brain, I didn’t miss it.
On one such occasion he launched into an explanation of “commander’s intent.” This is a well-known concept in the military that essentially boils down to everyone having a clear understanding of the team’s goals and objectives. If the commander has made it clear what success looks like, no one needs to be micromanaged along the way. General Mattis recalled leading Marines into battle as they swept across Iraq on the way to Baghdad. To his memory, he only gave a handful of direct orders over the course of a few weeks. He’d made his intent clear, and his men were empowered to make the right decisions on how to achieve it as they went. He also explained that he preferred to spend time with his men in the field, seeing their challenges firsthand, rather than remaining far removed from them and being briefed after the fact.
Mattis’s approach to leadership was diametrically opposed to what we experienced in the press and comms office. Roles, goals, and objectives weren’t clearly defined. Spicer went weeks without interacting with the broader team “on the front lines,” if you will. And every effort someone made was nitpicked and ridiculed in front of everyone else.
These meetings set the tone for the entire team, creating a culture of frustration and distrust, and ultimately leading to the entire operation being justifiably viewed internally—and, with time, externally as well—as a disaster. It was already a challenge for me going from being the CEO to working under someone else. Now I felt like I wasn’t working in a meritocracy, or on a team, or with a press secretary who even cared about his people’s well-being or success.
This is best illustrated by a story that started as an internal incident that made everyone just shake their head or roll their eyes, but ended up becoming the lead anecdote of a viral article in The Wall Street Journal and a major point of contention in Spicer’s White House memoir.
The third week we were in the West Wing, Spicer came out of his office and complained to his secretary—whose desk was about five feet from my own—that he didn’t have a mini fridge to keep his drinks cold. He had requested one, and I’m a little unclear on the backstory, but it sounded like he had been told by the staff who managed the facilities that they weren’t allowed to give him one in the West Wing because of concerns about mold.
“I’m going to go across the street, because I know they have one over there,” he said. This meant a visit to the Eisenhower Executive Office Building. The overwhelming majority of people who work at the White House actually work out of offices in the EEOB, located across West Executive Drive, a narrow private road. The research team worked there out of a large, open room with eight desks lined up in two rows. Real estate in the West Wing was highly coveted—proximity to the Oval was often an indication of stature. But the EEOB had its advantages as well, most notably the fact that the offices were massive by comparison. The furniture was old, the carpet was faded, but light cut through the rooms thanks to massive external windows, and there was a much calmer atmosphere overall.
In the back left corner of the research team’s office sat Andy Hemming, the White House’s Director of Rapid Response. “Hemm-dog,” as he was known, had stuck with the Trump campaign even when many of his RNC compatriots had bailed. So he maintained a foot in both camps. He was quite a character, often blurting out jarring or inappropriate things during meetings—which we’d usually laugh about later—and he maintained something of a shrine to disgraced former Congressman Anthony Weiner on the wall beside his desk.
Weiner, who also happened to be married to Hillary Clinton’s top aide Huma Abedin, had gotten himself embroiled in various scandals over the years. He’d sent explicit photos of himself on Twitter and via text message—photos that were later released publicly. He ended up being sentenced to almost two years in prison for sending obscene material to a minor, for which he also had to register as a sex offender. Every time Weiner found himself in trouble, the New York tabloids would run double entendre headlines on their front pages. Hemming had every one of them hanging on his wall, along with an accompanying @realDonaldTrump tweet.
Hemming was also keeper of the office mini fridge, where various junior staffers kept their Lean Cuisines and lunch-meat sandwiches. The West Wing had the Navy Mess. We could call down at almost any point during the day and order up a wide variety of made-to-order meals or snacks. The EEOB crew had a serviceable cafeteria that was open on a much more limited basis. But Spicer wanted their mini fridge for himself, nonetheless.
Hemming rebuffed him, and according to multiple people who witnessed it, Sean just kind of laughed and went on his way.
Then, a few days later, two other staffers approached Hemming and said that Sean had asked them to tell him to bring the mini fridge to his office. Again, multiple people who witnessed this conversation said that Hemming told them he wouldn’t do it, and that if Spicer really wanted it then he could come get it himself.
One evening around 8 P.M. I got a call from a member of the comms team who worked in the EEOB. “Dude, I just saw the strangest thing,” he said. “I walked out into the hallway and Sean was carrying a refrigerator out of the building with, like, the power cord dragging on the ground behind him.”
The following day, Hemming returned to find their mini fridge missing. And upon attending the morning meeting in Spicer’s office, he saw where it had gone.
The story became a symbol internally of Spicer’s leadership style, but unlike most incidents in the building, it didn’t find its way into the press. That is, until one night when a group of White House comms staffers went out for drinks with Mike Bender, a reporter for The Wall Street Journal. Although I wasn’t there, I was told that the mini fridge story came up in the conversation—off the record. Bender pushed for them to let him write about it, but they refused. After a lengthy back-and-forth, they finally agreed to let him have the story, but not until after Spicer had left the White House.
In a twist of fate, Spicer resigned the very next day, and the lead anecdote in his resignation story was the mini fridge. It set the internet ablaze.
Spicer later wrote about the incident in his memoir, The Briefing: Politics, the Press, and the President, released a year after he left.
While expressing frustration with the media manufacturing “national moments of outrage or ridicule,” Spicer wrote that “Mike Bender of The Wall Street Journal falsely accused me of taking a mini fridge from junior staffers.”
I saw the press get a lot of things wrong during my time in the White House. That wasn’t one of them.