Election 2016: Inside Donald Trump’s Unlikely, Stunning Victory Party

A little after 9:30 p.m., they began to distribute the red hats.

By the end of the late, late night, the Make America Great Again hats would flood Donald Trump‘s victory party at the New York Hilton in midtown Manhattan. Men in a VIP section doubled up on brims, hooted, and slapped Trump’s brother Robert on the back when he was thanked in the candidate’s victory speech. Women stuffed stacks of five into their purses.

It had started out slow. A blond boy might just hand you one optimistically—”Here you go!”—but it seemed premature, maybe even unrealistic. The room was only halfway full and Trump had yet to win Ohio.

“Oh f–k, are we up in Ohio?” Carl Paladino asked a friend, as they stared at the screen. The real estate developer and former New York gubernatorial candidate high-fived his friend. “F–k yeah we are.”

Paladino’s optimism seemed as out of place as the early free hats. The crowd at the party was thin and typically Trump-eclectic, with Omerosa, The Apprentice contestant and Trump surrogate, as the most colorful personality in the room besides “The Sassy Ladies,” group of sixty-somethings from San Diego who travel the world together and do not care about sexual assault. There was also Seanna Pereira, the 10-year-old singer of anthems at Trump rallies whose mother and producer insisted on an interview and who offered that “the media is, like, not fair. It’s not half Republican, half Democrat; it’s all Democrat, which is not fair so they should really change that.” Or the Orange County sports marketer who said a Hillary Clinton presidency would mean that he would be able to distribute fewer freebies to professional athletes.

Paladino was annoyed that New York had already been called in her favor when, as New York campaign chairman, Paladino had promised New York to Trump, and still thought he could deliver. “He left a voicemail for me two days ago,” Paladino said. “I didn’t have my phone with me. But he was very positive.”

Slowly, the victory crept up on a room that, like its leader, had already been so convinced of victory as to appear delusional. Around the time Virginia went to Clinton, former Connecticut gubernatorial candidate Joe Visconti even attributed Trump’s success in general to his affinity for “The Power of Positive Thinking,” shortly after yelling “Shut up!” and “We Hate You!” at Megyn Kelly on one of Fox News screens surrounding the headquarters.

And with the escalating sense of victory: the hats. A steadily climbing percentage of the room suddenly wore the hats – a quarter, a half – from a person named Conway Wilcox to the woman with a a photo of herself in a bra as her phone’s background.

“Well, isn’t that something,” crowed Stephen Baldwin sometime after 10:30 p.m., not long before Florida went Trump. “Isn’t that just the dangdest thing?”

I said I’d been texting with my family a lot over this, and asked if he’d texted Alec, his brother who’d been playing Trump on Saturday Night Live. “Oh we’re on radio silence, my friend, radio silence. Alec and Billy are sweatin’ bullets right now, bro. And you can put that,” he paused for effect “in writing!”

Not all wanted to own the gains. Outside the ballroom, conservative prankster James O’Keefe took a break from hearing from a fan about how the failures of the financial markets boded well, to explain his distance from the campaign.

“I’m a journalist,” he said. “I express things but this is what happens when a system is broken. This is what happens when things go awry.” As O’Keefe said this the ballroom exploded and the screens called Florida for Trump. Then he turned to me. “And now he’s gonna be the next president.”

It wasn’t a gloat, just a statement of fact. How did that news make him feel? “I will say it’s – it’s gonna be maybe a baseball bat to Washington, maybe.” Was that a good thing? He paused. He was tired from some journalism he’d perpetrated in Pennsylvania earlier that day. “That’s not my question to answer.”

“I knew he was going to win the day I joined the campaign,” Rudy Giuliani told a group of reporters as he left a TV interview.

“Senator!” Rep. Steve King yelled, breaking away from a media scrum around midnight. He’d seemed to have been avoiding direct comparisons to Brexit. “Jeff!” He ran over to a passing Senator Jeff Sessions for what looked like a congratulatory hug but may have been a distribution of talking points to King, who had been on camera since the win looked solid. King pulled away from what Sessions whispered in his ear and looked at the senator.

Sessions shrugged. “Just go with it,” he said.

King returned to his scrum. “I think Britain will be fine,” he said, “and I say that as an Irishman!”

Chants of “lock her up!” and “call it!” followed as uncertainty about what came next took the room. Milo Yiannopoulos and his publicist started screaming at a Buzzfeed reporter with the theory that, had Trump not been elected, “the person who might have come next would have been much worse.” But they also implied that the reporter was also somehow at fault for triggering this, apparently, best case scenario. Everyone besides the reporters had been drinking.

If John Podesta’s 2 a.m. announcement from the Javits Center was confusing it also at least diffused tension. John “Tig” Tiegen, who defended the Bengazi embassy the night of the raid there and who spoke at the Republican convention stood alone as he watched Podesta. He shook his head.

“It’s the same thing as that night in Bengazi,” Tiegen said. “She’s talking and running.” Just before that Eric Prince, the founder of security firm Blackwater, had slipped him a business card, saying: “Hey. Shoot me an email, all right?”

Trump’s address came some time after Podesta’s, but everyone hugged the stage, which was flanked on both sides by two of those red hats, this time on pedestals and in ornate wooden cases. Ten minutes before Trump came out, Sarah Palin and her family went across at ground level, alone and then went back in an apparent false start. When Trump did take the stage, his entourage of at least 25 was so long that people in the crowd could yell things to individual members of the scrum, like “Shut out the press!” and, to Giuliani, “Hey Attorney General! Lock her up!” Giuliani heard this, giggled at it, and waved it away.

The speech happened. You know what it’s like. “Thank you. Thank you very much, everybody. Sorry to keep you waiting. Complicated business. Complicated. Thank you very much,” Trump started.

Then came the task of getting everyone off the stage. Just about the only person not in the procession was Jerry Falwell Jr. As the crew left the stage, Falwell shoved through the crowd with his wife and tried to follow the group through the exit, to what he seemed to think was a VIP reception. There he bumped into a NYPD detective working security.

“Hey, is the VIP reception in there?”

“No.”

“Do you know if it’s upstairs?”

“No.”

Falwell turned to his wife. “Baby, see, I told you we got to get upstairs.”

The crowd massed near the main entrance of the hotel, blocked by the secret service until the president-elect had cleared the building. A young woman in a red dress pounced on Yiannopoulos and straddled his mid section in a kind of hug. “Melania!” She screamed. “Is the First Lady! We have! The hottest! First Lady!”

Scraps of conversation between Yiannopoulos and a blond friend carried as the crowd walked up Sixth Avenue because, well, they were shouting at each other. The subjects under discussion were unclear, but phrases included: “I hope they Livestream it so I can jerk off to it!” “I will lay the first brick!” “The streets will be washed clean!”

They lowered their voices a few blocks up as a film crew, and the comedian Robert Smigel, wearing his Triumph the Insult Comic Dog puppet, captured those exiting the victory party.

“Truuuuump’s Ameeeerica,” Triumph intoned in his weird accent, putting his face next to passersby, as cameras scanned them, likely an attempt to create a tableau for the Conan show.

“Hey, that’s a cool dog,” Milo’s blond friend said, his nose an inch from Triumph’s cigar. “I think I’ve seen it somewhere.”

“I’m sure you have,” Triumph began. And then that was it. Triumph seemed at a loss for words. The Republicans walked away.

Smigel lowered his puppet and sighed. “Trump’s America,” he said.

Photos by Thomas McCarty.