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Trumpology

Donald Trump’s Lifelong Obsession with Comebacks

Other people call it losing. For Trump, it’s a transitional state between wins.

President Donald Trump points as he departs after a White House National Day of Prayer Service in the Rose Garden of the White House, Thursday, May 7, 2020, in Washington.

Donald Trump is trying to win a second term by touting a comeback to come.

“We’re making a comeback,” the president said last week in the Rose Garden. “I think it’ll be a tremendous, tremendous comeback.”

“We’re coming back,” he said the next day, “and we’re coming back strong.”

“American Comeback,” the Trump campaign titled a new ad out this week. “THIS NOVEMBER,” the ad proclaimed, making clear the comeback he is referring to is not just the country’s struggle with the coronavirus pandemic but the restoration of his own political fortune, “THE GREATEST COMEBACK STORY IS WRITTEN.”

That Trump—in the throes of the worst public health crisis in more than a century and the most devastating economic downturn since the Great Depression—is writing rosy history long before it has actually happened might seem audacious. It borders on the fanciful when considering the slew of numbers—the steadily mounting death toll, near-record unemployment and a majority of Americans dissatisfied with his handling of the crisis—that sketch a future trending in the opposite direction. But this is a page from a playbook Trump has used many times before.

At key points in Trump’s long and public life—from his nadir in the 1990s to “The Apprentice” more than a decade later to his embattled campaign a decade after that and finally to his tumultuous presidency—Trump has used the idea of the comeback as a critical weapon in his arsenal of self-invention. A believer in a binary worldview that was a core teaching of his flinty father—there are winners and losers, and he always must be the former, not the latter—Trump has used “comeback” as a fortifying piece of rhetoric that masks periods of failure, delaying a reckoning until there’s something to brag about. Others might wait for actual evidence that a comeback has occurred, but Trump repeatedly has advertised his comebacks months and even years in advance. He has used it to bend in his favor unflattering media narratives—to tweak perception, to alter reality—to conjure power, positivity and a sense of propulsion, especially at junctures when he’s running low on all three.

“The world that he lives in and projects, there are just two roles in it,” Trump biographer Gwenda Blair told me. “You’re a winner or a loser. And if there’s a moment that you’re not quite a winner, you’re almost a winner. You’re practically a winner. It’s a cloak that contains winning as a part of it.”

“It’s his way of saying, ‘I had a setback, and now I’m coming back’—but he never says he had a setback,” former Trump publicist Alan Marcus told me.

“He also uses it as a starting off point to build momentum,” added Marcus, who worked for Trump from 1994 to 2000. “It was a word that he pushed off on.”

“Comeback,” said Sam Solovey, a contestant on the first season of “The Apprentice,” who prepped for the show by reading every Trump book and biography, “is the placeholder until victory is at hand.”

It helped him get to the White House. And now, forced by circumstance to abandon his victory lap messaging of “Keep America Great,” Trump is reaching for it again as he tries his hardest to stay there.

“It’s just as critical to 2020 as it was in 2016, if not more so,” former Trump aide Jason Miller told me. “If he’s the outsider, if he’s the insurgent, he wins reelection. If he’s viewed as the insider, the one who’s the power holder in a tumultuous time, then winning becomes much tougher.”

“My name is Donald Trump,” he said in the intro of the first show of the first season of “The Apprentice,” launching into a quick series of words and pictures associated with success. For Trump, the reality television show on NBC, which debuted in 2004, was a chance to cement his comeback tale—and to do it in the way that he wanted, sandwiching what he took to calling his “glitch” or his “blip” basically between brackets of unfettered triumph. “But it wasn’t always easy,” he explained. “About 13 years ago, I was seriously in trouble. I was billions of dollars in debt. But I fought back. And I won.”

In the first half of the ’90s, Trump constantly skirted financial ruin, facing for years the possible permanent tarnishing of the image he had cultivated in the ’70s and ’80s as an infallible deal-doer. “Donald was broke,” Stephen Bollenbach, the CFO Trump’s lenders made him hire, would say. “He was worse than broke. He was losing money every day.” Even so, Trump talked about his comeback, not when his struggles began to wane but practically from their start.

“All Donald knew was that he was still a story,” Wayne Barrett wrote in his seminal biography. In the spring of ’91, according to Barrett’s reporting, Trump announced to a consultant that he was determined to return to the cover of Time. “He said he would be the comeback of the century.”

In 1992, he redoubled his efforts, earning honeyed headlines on the cover of New York magazine and on the front page of the Washington Post. He refused to reflect on the past, skated through the present and relentlessly spun toward the future. “I’m not going to look back and say it was tough and blame myself,” he told the Sunday Times of London. “I could be even bigger than ever.”

Gossip columnists marveled at Trump’s ability to shape the nature of the story. “I mean,” Linda Stasi of the New York Daily News told the Boston Globe in 1994, “it’s not like he’s the president.”

Business bigwigs, meanwhile, marveled at it because … it wasn’t true. “I think his recovery is an illusion,” a real estate executive who did frequent business with Trump said to the reporter from the Globe. “It’s like the emperor has no clothes. I guess if you keep repeating it long enough people begin to believe it.”

And he did. And they did.

And it worked.

In 1995, not quite five months after Trump successfully started selling stock in his failing casinos in New Jersey and his resurgence was looking legitimately less and less like a mirage, some of New York’s business and government leaders honored Trump at a luncheon in Manhattan for what they dubbed “the comeback of the decade.” The lieutenant governor called him “the comeback kid.” Bill Fugazy, a limo company tycoon and onetime Roy Cohn crony, gave Trump a glass-encased boomerang. “You throw it,” he said, “and it always comes back.”

In 1996, in articles about Trump, the Daily News and the New York Times used “comeback” in headlines. By this time, thanks to the casino deal plus at-long-last development on a plot of land he was involved with on the Upper West Side, those headlines were no longer wrong. “I think it says,” Trump said, “what I’ve been doing over the years has been right.” (Sound familiar?)

And in 1997, out came The Art of the Comeback, the sequel of sorts to The Art of the Deal. “It never occurred to me to give up, to admit defeat,” Trump (really Kate Bohner) wrote. “He simply skips over the losing part. It is the unspoken chapter in the ongoing narrative,” said Solovey, the first-season “Apprentice” contestant. “He left out the Art of Losing.”

Hence the intro to the show in ’04. That same year, too, on multiple occasions, he made the claim that the Guinness Book of World Records listed him as having made the greatest personal financial comeback of all time. It’s true. It did, in 1999 and 2000, a Guinness World Records spokesperson told me, before “the Records Management Team” decided “the concept of a ‘comeback’” was not “standardizable across the globe.” To use it the way he wanted to use it, he didn’t need it to be.

He kept “comeback” as a cudgel, of course, when he turned toward politics.

In 2015, a little more than a month before he came down the escalator and officially entered the fray as a presidential contender, he gave a speech to the Republican Party of Sarasota County, Florida. “Our country is not going to have a comeback,” he said, “with any politician.”

The rest of 2015 and into 2016, for most of the campaign, he didn’t use the word that much—until he needed it, in October, when polls pointed to him losing to Hillary Clinton and perhaps by a lot. “I know how to make a comeback,” he said in a speech October 3 in Loveland, Colorado, referring to his experience in the ’90s. “I don’t even think of it as a comeback,” he said that same day in a speech in Pueblo, Colorado. “It was just, like, you know, we had tough periods, good periods, tough periods. We just knew that things were going to be just fine.”

“America’s comeback begins on November 8,” he said in a speech in Portsmouth, New Hampshire, on October 15, a week after the uncovering of his lewd comments on the “Access Hollywood” tape, when many figured his candidacy surely was doomed.

He’s never stopped using the word as president. But it started to tick up at the turn of the year. He was always going to run in 2020 by talking about a “comeback.”

But he wanted to run on one he was saying had just occurred—and that he had engineered. “Three years ago, we launched the great American comeback,” he said in his State of the Union address the first week of February. “We’re in the midst of the great American comeback,” he said repeatedly that month and into early March.

At that point, though, the dire reality of the coronavirus and its consequences began to become clear. It was no longer a credible pitch. The Trump campaign this year was going to be about KAG—Keep America Great—but now it’s another round of MAGA. Make America Great Again. Again. Trump not only has not shied away from using the word “comeback” but has doubled down, simply shifting from trumpeting one to forecasting another—to trying, as is his wont as a devotee of Norman Vincent Peale, to speak it into existence, never, ever losing, always either winning or on the way.

“There’s going to be a comeback very, very quickly, as soon as this is solved,” he said in a coronavirus briefing on March 18. “And it will be solved. We will win. And there will be a comeback.”

“We’re going to have a very quick comeback,” he said on Fox News on March 24.

“We’ll be the comeback kids,” he said in the briefing on April 15. “All of us. All of us.”

“He has very few moves,” Marcus, the former Trump publicist, told me, “and one of those moves is the comeback move.”

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