Donald Trump’s presidency was always going to be … atypical. But few, if anyone, outside his orbit got as early a taste of what was to come as Brian Mosteller.
Described by colleagues as fastidious almost to the point of obsessiveness, Mosteller served as President Barack Obama’s special assistant and director of Oval Office operations. That meant that on the day of Trump’s inauguration in 2017, he was one of just a handful of aides left there to help with the transition.
On that Jan. 20 morning, Mosteller recalled Trump and Obama, along with a smattering of top political leaders, congregating in the Blue Room of the White House for the ceremonial tea. As the group began filtering out to get into their motorcade for the trip to the Capitol, the incoming and outgoing president lingered in the Grand Foyer. There, Obama quickly briefed Trump on a pending national security matter.
“Trump,” Mosteller recalled, “says, ‘Well what would you do in this situation?’”
To Mosteller it was unnerving; not just because Trump hadn’t given much thought to the issue, but also because “it was evident that he wasn’t really interested in the answer.” He exchanged a glance with Obama’s longtime photographer Pete Souza. “We had this realization that this was really bad,” Mosteller said. “If this is the question taking place discreetly behind closed doors on day one, the country is going to be in rough shape.”
A solitary vignette before a historic ceremony does not foreshadow an entire presidency. But as Trump’s tenure comes to a close this Wednesday, fewer days are as symbolic of his time in office as the first: the jubilation of the fans, the dread of the foes, the bellicosity of the rhetoric, the unorthodoxy of the approach, disruptiveness as a tactic, chaos as a byproduct, and the petty obsessions that colored it all.
“Jesus that day sucked,” said Ben Rhodes, Obama’s longtime adviser, who was with him that day.
For the Obama team, it was all somber. Many of those who were at the White House that day were finishing up eight-year stints. Some had slept on their office floors overnight for fear that the security clampdown in the city would make it impossible to get to work on time. Aides recall an intense exhaustion that mixed oddly with the depression they felt — the mind jolting the body to remind it that things had gone awry.
“I was worn out after doing that job for eight years and was looking forward to being done with the job,” Souza said. “At the same time, I was concerned for the country really, who we were turning the keys over to. It was just a weird set of dual emotions playing out that day.”
The day was not without its routines. When Obama came down from his residence to the Oval Office, he was handed his morning briefing book with a schedule memo for the day. It was thinner than usual. And all of his personal stuff was gone from the room save roughly 30 or so photos on the Resolute Desk.
At some point, Obama took a handwritten letter he’d composed for Trump out of the desk, put it in an envelope and placed it back in the drawer. He then went back up to the residence and had a ceremony in the State Dining Room with the ushers’ office. They presented him with the flag that had flown atop the White House that day.
“He was spiritually in the right space. He was ready to walk away,” said a former aide with him that day. “It was a rite of passage, he emphasized. That’s just how it goes.”
Shortly thereafter, the incoming president arrived and the mood tensed. There was an awkward moment when Trump left Melania behind as he walked up the steps to greet Obama. It was followed quickly by another when Melania brought a gift, which — while well intentioned — violated the explicit instructions for there not to be any exchange of such kind.
Inside the White House, the Obama aides still there were almost overwhelmed by Trump’s bravado. Mosteller recalled Trump as acting as if he’d “just won an award.” Souza was more merciless. “I just felt I was in the presence of the mafia,” he said. “It’s kind of hard to explain. He has this way about him that just reeks of narcissism.”
The group had their ceremonial tea before jumping into the motorcade to head to the Hill. Riding in a separate vehicle from the outgoing and incoming presidents, Souza looked around. “There is nobody in the parade stands,” he thought to himself. “That’s kind of odd.”
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When they got to the Capitol, Trump and Obama went to separate holding rooms. In his, Obama signed his last official bill and his staff gave him a joking applause. Then they moved to the hall — stuffed with people — waiting to be called out to the podium. At that precise moment eight years earlier, Obama had paused and closed his eyes before heading out to his inaugural crowd. And not just a quick blink either. “He closed them for several seconds,” Souza said. “It was clear to me that he was saying a prayer.”
Before heading out this time, there was no apparent attempt to summon the divinities.
“I don’t remember him closing his eyes,” Souza said. “Maybe he should have.”
Hoping to get a good shot, Souza defied orders and snuck out onto the platform as well. When Trump finally came out, the two men were just five feet apart. The soon-to-be-sworn-in president took a pause of his own, however brief, and raised his fist in triumph.
“My heart just sank,” Souza said. “I was sick to my stomach.”
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From the vantage point of the Trump team, the day was, naturally, quite different. Few if any had expected to win the election. So the actual act of assuming control of the White House had a surrealist vibe to it. “It was like looking over your shoulder waiting for someone to tell you ‘Stop, no you can’t do that,’” recalled a staffer for Mike Pence, who had driven up to the North Portico through the White House front gates that morning. A person involved in the inauguration described Trump’s mood as “absolutely jubilant and euphoric.”
But even by that point, it was evident that Trump’s presidency would be unconventional. His daughter Ivanka had to persuade him not to stay in his own hotel down the street from the White House the night before, and instead keep with tradition by sleeping at Blair House on the other side of Lafayette Square. His ex-wives, Marla Maples and Ivana Trump, had both asked to attend the inauguration. So Trump gave “clear instructions” to put them on opposite sides of the platform, in sections toward the back. “They had to be in the same row and same chair in case one saw the other,” said one of the people involved in the inauguration.
And fear of punctuality was profound enough that Trump’s staff stressed to him that the vice president could theoretically become the acting president for a few minutes if he was late to take the oath of office.
“[H]e loved the number 45, and we said if you’re late, you could in fact be the 46th president,” said the person involved, “and of course he didn’t like that at all so he said he wouldn’t be late.”
By the time Trump stepped to the crowd and gave that fist pump that left Souza so dispirited, the tensions that would pervade American politics for the next four years were already apparent. One aide who worked on the inauguration recalled rushing home as the crowds swelled to change coats, only to be confronted by protesters because of the badge she was wearing. “I put my credentials away and didn’t advertise where I worked,” she said.
Dozens of Democrats, meanwhile, had refused to come in protest — a slight not lost on the incoming president’s team. Nor was it lost on them that they’d been snubbed by A-List celebrities. Elton John had tentatively committed to performing at the inauguration, an aide said. But after financier Anthony Scaramucci, then a vocal Trump fan, inadvertently leaked it too early, he had pulled out. Italian tenor Andrea Bocelli had dropped out after he started getting death threats. Instead, the committee booked Jackie Evancho, a runner-up on “America’s Got Talent,” to perform the national anthem.
The new president’s speech only inflamed matters. It was an address with designs for shock, not sweeping oratory. David Shulkin, who was Trump’s nominee to be Veterans Affairs secretary, watched the now president describe an era of “American carnage” and was taken aback by the brimstone.
“That became a precursor of what we saw throughout the administration, which was that there were many many of those missed opportunities to bring the country together,” Shulkin said.
Looking back, the Trump team argues that the more uplifting themes of the speech—the invocation of the forgotten man and women—were overshadowed by the carnage line. But when it was done, the crowd seemed at once confused and unnerved, wondering (not for the last time) whether there was some greater meaning or purpose that they’d missed. “Well, that was some weird shit,” George W. Bush reportedly said to Hillary Clinton, the most aggrieved attendee of all.
“I’ve been in a similar position for every inauguration going back to 2001,” recalled Jon Karl, ABC’s White House correspondent, “and it’s usually quite a celebration, and there’s a lot of palling around, they’re all getting together, and this is the one time partisanship is put aside and everybody’s all smiles. Not this time. It was grim.”
At the ceremonial luncheon after the speech was over, the mood seemed to lighten. Trump signed formal nomination papers and took what one person there described as a child-like delight in trying to hand out pens to congressional leaders. The parade down Pennsylvania Avenue had no notable drama or surprises. In fact, one aide to Trump said the president had no real understanding of how sparsely attended (relative to other inaugurations) his ceremony had been. The infamous press conference in which press secretary Sean Spicer would declare it “the largest audience to ever witness an inauguration, period,” would actually come on Day 2; ordered up only after Trump watched news coverage of his crowds that morning.
But, as would quickly become the norm, the periods of calm were just a short reprieve from the chaos. Back at the White House, newly arrived aides scrambled to figure out where to go and how to make the office—quite literally—work. Phones would ring with no one sure who was to pick them up.
Trump had instructed staff that he wanted to make a show of moving swiftly. And by the afternoon, the press corps was summoned into the Oval Office to document his first official acts. At 7:31 p.m. a pool report was filed declaring that the bust of Martin Luther King Jr. that had been on display during the Obama years was no longer there. In fact, it was merely obscured by a curtain and a Secret Service agent. Zeke Miller, the reporter responsible for the erroneous report, tweeted out a correction within an hour. But by then, condemnation had been pouring in and Trump was livid.
“I spent six hours tamping down racial flames,” one staffer remembered. Trump’s campaign manager Kellyanne Conway described the moment as a harbinger for four years of frosty media relations. “So much of that day was a metaphor for what happened next,” she said. “The press came into the office looking for trouble.”
Outside the White House, everyone else was getting adjusted to the tectonic shift in power dynamics that had just occurred. One former White House official recalled attending the inaugural balls, where “a lot of random people” kept shoving their business cards at him asking for jobs.
“There were so many people who didn’t support Donald Trump and were worried about it, from members of Congress and donors, to Bush cabinet and administration people who called,” said Conway. “They’d say, ‘Oh, I was a little rough on Trump and I want to support him now.’ There were many calls like that.”
Souza and Mosteller by that point were on a plane ride with Obama. They kept the TVs off—unable or, perhaps, just unwilling to watch coverage of the balls. There was relief, Souza said, that the job was ending. “But all the while, I was just holding my breath, wondering what was going to happen during the next few months and the next four years.”
And then, a different reality set in. Heading for Palm Springs, the aircraft was unable to land because of terrible fog. It would descend and then take off again.
“A couple of people were freaking out a bit,” recalled the former Obama aide, who was on the flight as well. It was so bad that the now former president came back to tell the others that they would likely have to re-route and find a landing spot elsewhere. Eventually, they did. Once there, the Obamas quickly took off in a motorcade for their vacation destination.
“There was no grand goodbye,” Mosteller said. They knew they’d see each other again.
“It was like going on a great vacation and then getting in the car ride back from the airport,” the aide recalled. “It was sobering and quiet and we knew it was just never going to be the same.”