But on the 26th floor of a golden Manhattan tower that bears his name, Trump was coming to the conclusion that his own moment was at hand.
And in typical fashion, the first thing he thought about was how to brand it.
One after another, phrases popped into his head. “We Will Make America Great.” That one did not have the right ring. Then, “Make America Great.” But that sounded like a slight to the country.
And then, it hit him: “Make America Great Again.”
“I said, ‘That is so good.’ I wrote it down,” Trump recalled in an interview. “I went to my lawyers. I have a lot of lawyers in-house. We have many lawyers. I have got guys that handle this stuff. I said, ‘See if you can have this registered and trademarked.’ ”
Five days later, Trump signed an application with the U.S. Patent and Trademark Office, in which he asked for exclusive rights to use "Make America Great Again" for "political action committee services, namely, promoting public awareness of political issues and fundraising in the field of politics." He enclosed a $325 registration fee.
His was a vision that ran against the conventional wisdom of the time — in fact, it was “much the opposite,” Trump said.
To save itself, the Republican establishment was convinced, the GOP would have to sand off its edges, become kinder and more inclusive. “Make America Great Again” was divisive and backward-looking. It made no nod to diversity or civility or progress.
It sounded like a death wish.
But Trump had seen something different in the country, and in the daily lives of its struggling citizens.
“I felt that jobs were hurting,” he said. “I looked at the many types of illness our country had, and whether it’s at the border, whether it’s security, whether it’s law and order or lack of law and order. Then, of course, you get to trade, and I said to myself, ‘What would be good?’ I was sitting at my desk, where I am right now, and I said, ‘Make America Great Again.’ ”
Democrats slammed it.
“If you’re looking for someone to say what is wrong with America, I’m not your candidate. I think there is more right than wrong,” Democratic nominee Hillary Clinton said. “I don’t think we have to make America great. I think we have to make America greater.”
Her husband, former president Bill Clinton, went so far as to declare it a racist dog whistle.
“I’m actually old enough to remember the good old days, and they weren’t all that good in many ways,” he said at a rally in Orlando. “That message where ‘I’ll give you America great again’ is if you’re a white Southerner, you know exactly what it means, don’t you?”
The slogan itself was not entirely original. Ronald Reagan and George H.W. Bush had used “Let’s Make America Great Again” in their 1980 campaign — a fact that Trump maintained he did not know until about a year ago.
“But he didn’t trademark it,” Trump said of Reagan.
His decision to claim legal ownership reflected a businessman’s mind-set. “I think I’m somebody that understands marketing,” Trump said.
Trump Organization lawyer Alan Garten said Trump holds upward of 800 trademarks in more than 80 countries.
The trademark became effective on July 14, 2015, a month after Trump formally announced his campaign and met the legal requirement that he was actually using it for the purposes spelled out in his application.
Having won the trademark, Trump was aggressive in protecting his idea. When his GOP primary rivals Sen. Ted Cruz (Tex.) and Wisconsin Gov. Scott Walker began tucking “make America great again” into their own speeches, Trump’s lawyers fired off cease-and-desist letters.
Trump was an impulsive and erratic candidate who ran a chaotic campaign. The one constant, it often seemed, was “Make America Great Again.”
“I didn’t know it was going to catch on like it did. It’s been amazing,” Trump said. “The hat, I guess, is the biggest symbol, wouldn’t you say?”
There were plenty of snickers when his Federal Election Commission filings showed that his campaign was spending more on “Make America Great Again” trucker caps than on polling, political consultants, staff or television ads.
"An appropriate icon for his failing campaign," the Washington Examiner's Philip Wegmann wrote in late October. "The millions of hats will make excellent keepsakes for those who thought his populist bravado could overcome Clinton's unimaginative and conventional but well-oiled political machine."
Trump saw the hats as a fundraising and advertising vehicle. He was thrilled when his campaign headgear landed in the New York Times Style section — during Fashion Week, no less.
“In the Style section, it was the ornament — what do you call that? — an accessory. They said the accessory of the year. You know the hat. You’d see people going to the fanciest balls at the Waldorf Astoria wearing red hats,” he exulted.
As is often the case, Trump’s description is more than a little hyperbolic. What the newspaper actually wrote was that the “old-school” caps had become “the ironic must-have fashion accessory of the summer,” favored by hipsters for their “uncanny ability to capture the current absurdist political moment.”
None of which fazed the celebrity billionaire who had debuted the hats by wearing one during a July 2015 trip to the Mexican border — or the legions of supporters who raced to snap them up. Trump had designed them himself, he said. The basic models sold through his campaign website were priced at $25.
“How many did we sell? Does anyone know? Millions!” Trump said in the interview.
“It was copied, unfortunately. It was knocked off by 10 to one. It was knocked off by others. But it was a slogan, and every time somebody buys one, that’s an advertisement.”
However many hats he sold, what cannot be disputed is that “Make America Great Again” caught on. It was the most effective kind of political message, bite-sized and visceral.
“It actually inspired me,” Trump said, “because to me, it meant jobs. It meant industry, and meant military strength. It meant taking care of our veterans. It meant so much.”
That kind of mission statement was something that Clinton’s campaign — for all its poll testing and high-priced advice from Madison Avenue — struggled to articulate.
Her strategists considered 85 possibilities for a general-election campaign slogan before settling on “Stronger Together,” according to an email from the account of campaign chairman John Podesta that was published by WikiLeaks.
What they were up against was nothing short of “a marketing genius,” said David Axelrod, who had been Obama’s chief political strategist. Trump “understood the market that he was trying to reach. You can’t deny him that. He was very focused from the start on who he was talking to.”
While Clinton carried the popular vote, Trump lined up the states he needed to win what mattered: the electoral college.
“In terms of galvanizing the market that he was talking to,” Axelrod said, “he did it single-mindedly and ingeniously.”
Halfway through his interview with The Washington Post, Trump shared a bit of news: He already has decided on his slogan for a reelection bid in 2020.
“Are you ready?” he said. “ ‘Keep America Great,’ exclamation point.”
“Get me my lawyer!” the president-elect shouted.
Two minutes later, one arrived.
“Will you trademark and register, if you would, if you like it — I think I like it, right? Do this: ‘Keep America Great,’ with an exclamation point. With and without an exclamation. ‘Keep America Great,’ ” Trump said.
“Got it,” the lawyer replied.
That bit of business out of the way, Trump returned to the interview.
“I never thought I’d be giving [you] my expression for four years [from now],” he said. “But I am so confident that we are going to be, it is going to be so amazing. It’s the only reason I give it to you. If I was, like, ambiguous about it, if I wasn’t sure about what is going to happen — the country is going to be great.”
All of which raises the questions: How can greatness be measured and sensed? What does it even mean?
“Being a great president has to do with a lot of things, but one of them is being a great cheerleader for the country,” Trump said. “And we’re going to show the people as we build up our military, we’re going to display our military.
“That military may come marching down Pennsylvania Avenue. That military may be flying over New York City and Washington, D.C., for parades. I mean, we’re going to be showing our military,” he added.
But Trump acknowledged that slogans and showmanship will not be the ultimate tests of whether the country is “great again.”
The president-elect has an ambitious to-do list for the next four years: building stronger borders, keeping the country safe against terrorism, producing more jobs, repealing the Affordable Care Act, replacing it with something better, promoting excellence in engineering and science, investing in modern infrastructure.
Ultimately, it will be up to the people for whom “Make America Great Again” was a covenant, not a slogan, to decide whether the 45th president has lived up to his promise.
“I think they have to feel it,” Trump acknowledged. “Being a cheerleader or a salesman for the country is very important, but you still have to produce the results.”
“Honestly, you haven’t seen anything yet. Wait till you see what happens, starting next Monday,” he said. “A lot of things are going to happen. Great things.”
Alice Crites contributed to this report.