It was simpler for Eric and his wife Lara. At the time, it was just the two of them. Lara got pregnant in the midst of the campaign, so for months there was no extra detail to coordinate, and they had forty weeks to plan for an eventual detail.
Tiffany’s detail was perhaps the laxest of all. One morning at the end of May, she walked in the front door of the Golden Pear in East Hampton, a tiny, teeming see-and-be-seen spot smack in the middle of Newtown Lane, the town’s little main street. The Golden Pear is some two hundred feet from the Monogram Shop, a little personalization store that, each year since the 2004 presidential election, has sold plastic cups labeled with campaign logos for each major party candidate, sold for $3 apiece to Hamptonites to display on their marble islands or pass around at their catered beach barbecues. The shop owner starts keeping track after the Super Tuesday primary contests in March, and at the close of business each day, she handwrites the total number of cups sold for each candidate on a piece of paper that she hangs in her store window.
Since this custom started, the cups had accurately predicted the winner—first with George W. Bush, then with Obama, twice. But this cycle, the cups, like every pollster and expert and analyst, got it wrong. Up until the weekend before Election Day, the Monogram Shop sold 4,946 for Hillary Clinton, and just 3,388 for Donald Trump.
Tiffany didn’t stop in to buy one of her father’s cups that morning, as Chelsea Clinton once did the year her mother ran against Barack Obama in the primaries. She chose to spend her $3—likely four times that, given their prices—on four iced coffees with her boyfriend. She dropped one iced coffee, and no one flinched or helped her pick it up—not even her detail, who was standing at a nearby table noticeably playing a game on his phone.
Most people didn’t notice her, besides the brief spill disturbance. She was in a baseball cap, and her security presence was so minimal that other customers readily came in and out both the front and back doors without so much as a glance. At one point someone did approach her, at which point she perked up, expecting some sort of comment—though who knows which way that would have gone. Her detail didn’t step in to block the approach, which would have been unnecessary, anyway, since the patron was simply asking if he could steal the extra chair at her table.
One customer that morning had also been in the Golden Pear one day in the 1990s when Chelsea Clinton and her several Secret Service agents walked in. “The world basically stopped,” he recalled. “For Tiffany, no one really noticed, and the people who did were intentionally looking the opposite direction.”
POLICE SHUT down Fifty-Seventh Street between Second and Third Avenues midmorning on Election Day for the Trump motorcade. The cars slid up in front of Public School 59, a school turned polling station for the day, just blocks from Trump Tower. Red and blue lights flashed against silver barricades set up to hold back the dozens of people who’d gathered outside to get a glimpse of the candidate and both cheer and boo him before he cast his ballot. He and Melania stepped out of a black SUV, Ivanka, Jared, and their daughter Arabella following seconds behind. They all went down to the school’s gymnasium, filled at that point with agents in boxy suits and earpieces, cameramen clicking away, and reporters shouting questions at the Trumps. The family, in all neutrals, popped against the gym’s baby-blue-and-banana-yellow walls. Apart from Donald, who’d walked in wearing only a suit jacket, all of them kept their coats on inside. Melania’s Balmain coat, with its wide lapel and gold buttons, hung on her shoulders, leaving her arms free. Ivanka kept her cream trench coat belted tightly over her black turtleneck and pants. Jared’s green utility coat remained over the gray V-neck he’d layered over blue button-down, black jeans, and white Common Project sneakers.
Ivanka approached the registration table first. “Here you go,” the lady behind the table told her. “What you’re going to do is fill out the ballot in one of the privacy booths behind you. When you’re done with that, you bring it to the scanner under the basketball net.” The woman asked Arabella if she wanted a sticker, and Ivanka smiled and brushed her daughter’s hair back as she thanked the woman. She picked up the ballot and showed it to her father. They locked eyes. This was really happening. Melania was next to approach the table, followed by Donald himself. Jared went up last. “Last name Kushner,” he told the woman.
Don Jr., his wife, Vanessa, and four of their five kids showed up to the same polling station a little while later.
Election Day happened to be Eric and Lara’s second wedding anniversary, and the two voted a few blocks south, at the Fifty-Third Street Public Library. Eric proudly took a photo of his filled-in ballot, and tweeted it out to his followers. It is, of course, illegal to take photos in the voting booth in New York, a fact that many of his nearly two million followers were quick to point out. He later deleted the tweet.
They all wound up back at Trump Tower. Don Jr. did a bunch of local radio hits. They made calls to supporters and took calls from busybodies wondering what the mood was like inside. By around five o’clock, when the first dismal round of returns started rolling in, the three eldest kids started calling in to local stations in battleground states to make a last push. Jared made calls to a few media friends. He asked one high-up executive at a major media organization who’d known Kushner both professionally and personally for years what he was hearing about Florida, which at that point was their last hope for any path to victory that night. The executive told him it didn’t look great, but what did he expect? “Did we get your support?” Jared asked. “No,” the executive told him. “No you did not.” Jared hung up and called Matt Drudge, another macher in the media circle he’d accumulated. The media had been off about the Trump campaign the whole time, Drudge told him. Wait until the next couple rounds of exit polls come out, he said. That’s when things could start to shift.
Since before five o’clock that morning, campaign officials had been huddled on the fifth floor of Trump Tower—essentially an expansive unfinished utility closet with concrete floors and no heat, which staffers in the early part of the campaign used as a makeshift headquarters. By the time the sun set that evening, dozens of people packed the room as then national field director Bill Stepien zeroed in on the campaign model, mostly focused on Florida, and Jared and Ivanka and Eric and Don began milling about, poring over maps and models and numbers coming in from their guys on the ground and officials in Florida feeding them what they knew. Donald was up in his triplex atop the tower until after eight o’clock, when he called Ivanka, asking where she was. He told her to leave the fifth floor and come up to the fourteenth—the official headquarters—and he would meet her there.
They looked like sardines, the lot of them. Donald, Melania, the kids, Pence, Kellyanne Conway, Steve Bannon, Reince Priebus, Chris Christie, Mark Shot—the whole MAGA mod squad, stuffed into that corporate-looking office, cramped around giant screens and projections and TV screens as campaigners explained the numbers coming in and the New York Times prediction needle shifted slightly in Donald’s direction. They stayed there until after eleven, when networks and wire services called Florida for him and the tide started turning in other battleground states. They took the executive elevator straight to the triplex—the family, the Pences, Conway, Christie and his son Andrew, Bannon, Stephen Miller, Priebus, Dave Bossie. The rest either stayed on the fourteenth floor or started to make their way a few blocks west to the victory party at the Midtown Hilton.
Miller sheepishly approached a few of them and told them he had prepared an exquisitely drafted concession speech. “What do we have on the victory speech?” someone asked Miller. “Bullet points,” he said.
So