It did not seem likely, even as supporters slowly filed into his Midtown Manhattan victory party. The Grand Ballroom at the New York Hilton – a quick jaunt from the President-elect’s golden tower – is a small room, after all, and the campaign did not announce the event until six days before election night.
Did Mr Trump even expect to win?
Leading up to the election, Democratic nominee Hillary Clinton was up in most major polls. Meanwhile, Mr Trump's campaign was spiralling out of control following the release of Access Hollywood tapes, wherein he bragged about sexually assaulting women – footage reinforced by more than a dozen women who came forward to say they were victims of the very acts he boasted.
But then the unexpected happened – he won. Around 2.30am, all major news organisations called the state of Pennsylvania for Mr Trump, and his opponent Mrs Clinton conceded. The crowd roared.
At first, the Hilton ballroom only murmured with the sound of Fox News analysts from the giant television screens mounted on every wall – only peppered with the laughs of a few diehards in two-piece suits, evening dresses, and red baseball caps with Mr Trump’s ominously nostalgic slogan, “Make America Great Again”.
Within two hours, a sea of red hats filled the predominantly white VIP section in front of the flag-adorned stage. Fox gave Mr Trump an early lead, announcing states like Kentucky, Indiana, and West Virginia. And with each announcement came huge cheers.
“So far, not really [surprised about the results],” an 18-year-old Fordham University student named Arthur told The Independent. “I think that once the real swing states start to come around for Trump, we’ll start to see a big change.”
Then Fox projected a series of key swing states one after the other. Mr Trump took Ohio, although that was expected; he won North Carolina, a controversial result after the state passed new voter laws that resulted in a lower turnout of black voters; and then, finally, Florida went to the former reality television star, completely changing the game.
The Hilton finally began to feel like a party. It was a different story in the press pins and behind-the-scenes in the near-empty dining room, as reporters typed furiously on their laptops stories they most likely did not plan to write.
Still, Mr Trump’s supporters in attendance did not expect he would make it this far. Even staffers had to open new boxes of red hats to pass out in light of the unexpected turn the night had taken.
“Yeah, I’m surprised he was able to pull through all of the shenanigans,” said James Branden, 69, an American businessman who lives in Singapore. “You had CNN feeding her the debate questions. If he had done that, they’d have run him out of the race.”
Mr Branden took issue with the political press’ reporting of Mr Trump, who launched his campaign with a hardline stance against Mexican immigrants.
“He said that the illegal aliens coming across the border were rapists and drug dealers – which is accurate,” he added, despite studies that show low crime rates among first-generation Mexican immigrants. “The media said the immigrants from Mexico were rapists. That’s not what he said. …
“The Democrats don’t want to [stop undocumented immigration] because they want that voting block.” He clarified: “The Latin, uh, you know, the Latino voting block.”
As the clock struck midnight, Mr Trump had all but won the election. When he clinched Wisconsin, Mrs Clinton’s once-certain path to victory seemed impossible.
So, what now? Will Mr Trump build his great wall between the US and Mexico? Will he bar Muslims from entering the country? Will he deport millions of people in his first hour in office, as promised?
One supporter, a property developer who splits his time between the US and UK, thinks not.
“He’s a businessman, and I think he said a lot of controversial stuff to get publicity and to get recognised and maybe not meaning everything he said,” said 32-year-old Teddy Cooper. “I think once that he gets into president [mode] … I think that he’ll numb down a lot of what he said and fall into line a little bit. …
“I don’t think that he’s going to do extreme things as people think he’s going to do.”
In his acceptance speech, Mr Trump called for unity. “It is time for America to bind the wounds of division,” he said.
He thanked his family, his staff, and his supporters – people, he said belong to a “movement” of “all races” and made his familiar promise of making “things” great.
“We are going to dream of things for our country. And beautiful things, and successful things once again,” he told the room full of ecstatic supporters, leaving the stage to the Rolling Stones’ “You Can't Always Get What You Want”.
Mr Trump plowed through the electoral college – pulling off one of the biggest upsets in US history in the process – yet it still remains unclear which version of the President-elect will be assuming the office: the controlled man who took to the stage at 3am; or the demagogue who insulted his opponents, bragged about sexually assaulting women, and ignited the most fringe white supremacist elements of the US.
As President-elect Trump prepares to take his seat in the Oval Office, all anyone knows is that he wants to make America great again – whatever he means – somehow.