Illustration by The Red Dress
Michael Kruse is a senior staff writer for POLITICO.
His audacity masked his desperation.
It was the spring of 1995. Donald Trump was this close to finished. He had spent the previous five years constantly, and barely, avoiding financial ruin and what he worried would be a permanent stain of personal bankruptcy. In that time, his marriage had collapsed, he himself had incurred debts of almost a billion dollars, all three of his casinos in Atlantic City had filed for bankruptcy, and the best of the three, Trump Plaza, was losing almost $9 million a year.
The aura of success was gone. Banks wouldn’t lend him anymore the kind of money he needed. From this crouch, Trump hatched a bold, almost absurd plan: He chose this moment to take his company public—and sell stock in his casinos. He created a new company, Trump Hotels & Casino Resorts, Inc., and hoped to rustle up about $300 million from stock and junk bonds to expand the Plaza, develop a riverboat casino in Indiana and reduce his personal debt.
Analysts frowned on the idea. “We are not entirely confident,” one from Standard & Poor’s warned, “that Mr. Trump will respect the interests and preserve the capital of equity investors in his properties.” The media was harsher, a columnist at Newsday portraying Trump as part carny, part con man. “Step right up, cries the barker with the jaunty derby and twirling cane,” Sydney Schanberg wrote that April. “Donald Trump has a deal for you.”
A quarter of a century has passed. Trump, of course, is no longer the cash-strapped operator of gaudy gambling halls on the New Jersey shore but the president of the United States. Once again, though, he is in dire straits. Thanks to the coronavirus pandemic and its attendant economic wreckage, the possibility that he could be re-elected has never seemed less certain. The annals of American history are littered with presidents brought down by their failures to deal with a national crisis, from Herbert Hoover and the Great Depression to Lyndon B. Johnson and the Vietnam War to Jimmy Carter and the Iran hostage affair and the oil shock.
Those presidents, though, had something else in common, too. They were not Donald Trump.
Because from the early ‘90s, when bankers and lenders in New York and state regulators in New Jersey could have all but ended him, to his herky-jerky presidential campaign in 2015 and ’16, to his aberrant, hyperactive presidency, Trump has built an astonishingly consistent record of surviving crises, of dodging the comeuppance everyone assumes is coming his way, and then turning seeming calamity into his next great opportunity—and emerging not just intact but emboldened.
He dodged the “Access Hollywood” tape fiasco. He evaded the noose of impeachment over the Ukraine deal. Those might now seem minor compared to the challenge of trying to get reelected during a worldwide health crisis and a looming depression—but if one acknowledges that he has been training in some sense for this sort of a jam for the bulk of his adult existence, then this nightmarish predicament starts to look less like an uncrackable problem than a potential capstone accomplishment.
“He’s a magician that way,” said Jennifer Mercieca, a professor at Texas A&M University and the author of the forthcoming Demagogue for President: The Rhetorical Genius of Donald Trump. “Other people would stop and recognize that they were defeated. Or that they should be shamed. He refuses.”
George Arzt, a Democratic consultant in New York, who’s known Trump for going on 50 years, likens him to the world’s most noted escape artist.
“Houdini,” he said.
Few chapters exhibit this talent of Trump’s better than what happened in 1995. In the first week of June, Trump stood on the floor of the New York Stock Exchange and watched over the successful debut of his publicly traded casino company, the stock symbol his initials—DJT. He got the low end of the price he wanted, $14 per share, but enough to bring in $140 million, plus an additional $155 million in 10-year junk bond notes for a total haul of just shy of $300 million.
Trump’s casinos could have been concrete blocks lashed to his ankles. But at that perilous juncture he somehow transformed them into a personal lifeline. From that point until 2009, when Trump stepped down as the company’s chair, his Trump Hotels & Casino Resorts would pay him $44 million in salary and $82 million overall. The people who invested, who threw him that lifeline, didn’t do so well: The company lost $1.1 billion over that time, filing for bankruptcy twice. The stock would peak at $35.50 in 1996—and ultimately fall to as low as 17 cents a share. “People who believed in him, that listened to his siren song,” the uber-investor Warren Buffett would say, “came away losing well over 90 cents on the dollar. They got back less than a dime.”
That day on Wall Street, though, was nothing short of a bounce-back win. The government-mandated “quiet period” surrounding an initial public offering meant Trump couldn’t make any comments. But he didn’t have to. The look on his face, according to reporting at the time, was all that needed to be said. He beamed. “He was,” said somebody who was there, “absolutely ebullient.”
And now, in his scattershot response to this once-in-a-lifetime crisis—his shoutfests with reporters, his back-and-forth proclamations and policy impulses, his odd tweets about miracle drugs—Trump’s aghast critics see a president backed into a corner, desperate and unmanned, in a frantic, final freefall. But people who’ve watched him for years, who’ve witnessed the dizzying pivots, the great escapes, the gobsmacking victories in the face of arguably more unforgiving audiences than American voters—what they see is Trump deploying tools and tactics that have worked before and could work again.
Before his campaign (calling John McCain “not a war hero,” stating he could shoot somebody and not lose supporters, boasting that he could “grab ‘em by the pussy”), and before his presidency (the Mueller report, his impeachment, so much of everything else over these last three years and not quite three months), Trump had no shortage of experience doing things that could have spelled doom—but did not.
He spent too much money that wasn’t his on too much stuff he didn’t need. The Plaza Hotel. The airline. The yacht. And by the early ‘90s it became exasperatingly clear to the bankers that Trump’s debilitating issues weren’t just his. They were theirs, too. His creditors had so enabled him that they were now “partners,” as a bankruptcy lawyer put it to the Boston Globe. “Because he owed all this money,” his longtime political adviser Roger Stone once said, “he had the leverage!” He had, thanks to the banks, gotten bigger and bigger and bigger—until he was “too big to fail.” For Trump, though, this was not an admonishment. It was a revelation. I’m in trouble. But so are you. And so you can’t get rid of me now.
Ditto for the New Jersey gaming regulators. Throughout the first half of the ‘90s, they could have stripped Trump of his casinos, on account of his manifest lack of “financial stability.” The assessments of Trump by the Casino Control Commission and the Division of Gaming Enforcement were stark. The Trump Organization was “near insolvent.” His “fiscal health” was “worrisome.” His casinos’ ability to obtain the necessary credit and funds was “significantly diminished.” Trump, the division reported to the commission, was on track to have personal income of $1.7 million in ’91. Then $700,000 in ‘92. Then $300,000 in ’93. Trump was, the numbers made plain, in the throes of financial death. “Unsettling,” understated one member of the commission. In the end, though, the gatekeepers always gave Trump green lights, granted leeway, extended deadlines. They cited his “progress,” which always was more wishful thinking than defensible fact. They let Trump live because they feared a dead Trump would lead to a dead or at least severely staggered Atlantic City. “Too big to fail”—again.
What played out around this time on Manhattan’s Upper West Side was a version of the same. Trump had tried for years to put on a sprawling tract of land that he owned a mammoth development anchored by the tallest building in the world. He wanted to call it Trump City. But he was stymied by neighborhood resistance and his own persistent spats with government officials. This property, like his casinos, could have been a waterloo. Thanks, though, to investors from Hong Kong, it proved to be the opposite. His grandiose vision had to be ratcheted down to a more modest project, but the collection of buildings (formerly) known as Trump Place made the plot a money-maker instead of a money-loser. Here, too, Trump had jimmied his way out of a tight spot, and with a product to promote.
“Donald is pretty fast on his feet,” Kent Barwick, who clashed with Trump as the president of the Municipal Art Society at the time, told me. “I mean, he may not be a Mensa candidate, but he’s shrewd.”
“The dodging and the weaving and the bullshit,” said Steve Robinson, an architect involved in the Upper West Side resistance, recounting Trump’s methods.
Indeed, Trump spent the first half of his worst decade not just scrambling to survive but constructing a runway of rhetoric for what he eventually was able to pull off with the IPO of ’95.
“What Donald Trump has done, essentially, is sell some assets and reduce debt,” Trump wrote in 1991 in a letter to the editor in the Washington Post. “Donald Trump is doing very well.”
The Taj filed for bankruptcy that year. The Plaza did the next year. So did the Castle. It didn’t matter. Trump, undaunted and unabashed, began hammering away about a “comeback.” And he didn’t do it on his own. He had help. Because for all of the media’s harder-hitting, stacks-of-facts chronicling of his failures, and for all the many occasions Trump disparaged “sick” and “nasty” reporters who “should be ashamed,” journalists at times also helped push his preferred version of himself. “He’s Ba-ack,” Business Week said as early as 1992. “You’ve got to hand it to Donald Trump. He’s one of the few shooting stars from the ‘80s who can boast of a comeback in the ‘90s,” ABC News’ Sam Donaldson said on “Primetime Live” in 1994.
“I think he is the world’s greatest promoter and P.R. person,” Wilbur Ross, who is the Secretary of Commerce now but was a prominent investment banker then, told Vanity Fair that year. “He has captured the public imagination and turned it into a resource for himself. People may joke that he’s always promoting himself, but he’s figured out a way to make it more than an ego trip.”
Underwriters of the stock deal had promoted the sheen of Trump’s well-known name and the sway it held with his typical day-tripping, relatively small-sum customers. “Defying reason,” Forbes said that fall, investors bit. “There’s a lot of brand equity in Trump’s name,” a stock analyst told USA Today in November of 1995, “in middle America.” Trump was quoted in the article, too. “The general public loves Trump again. They really never stopped loving Trump,” he said.
Trump spun from the confidence of a certain portion of the population money for himself. “The ’95 thing injected him with new cash,” said David Cay Johnston, the Pulitzer Prize-winning reporter who covered Trump and his casinos for the Philadelphia Inquirer and then the New York Times, “and allowed him to argue that he was this great genius.”
That in turn allowed him in ’96 to fold into his publicly traded company his other two Atlantic City casinos, first his Taj Mahal, then his Castle. And maybe equally importantly, people buying what Trump was selling let him buy time—time, it turned out, until 2004, when television impresario Mark Burnett began to re-pitch him to watchers of “The Apprentice” on primetime as the epitome of American business brawn. Buffed and on screen, Trump appeared to be an infallible, decisive CEO with a Midas touch past.
That catchy pop-culture depiction buried the much less flattering reporting repeatedly laid out in the business pages of the biggest and most mainstream newspapers and magazines. Gauged as a whole, Trump Hotels & Casino Resorts was “a flop,” Shawn Tully of Fortune wrote in March of 2016, as Trump as a presidential candidate left in his wake the Republican primary pack and began to take aim at Hillary Clinton. It “damaged thousands of shareholders, bondholders, and workers.” Losers everywhere. “The sole ‘winner,’” explained Tully, an experienced financial scribe, “now packs arenas across America, mesmerizing tens of thousands of cheering fans with tales of his business triumphs.”
Tales remains the operative term. Because the contest at hand is not only between Trump and the ravages of Covid-19, or Trump and “Democrat” governors, or Trump and any of the reporters spread out in the seats in the briefing room these evenings at the White House. All of it is part of the larger war for Trump between the numbers and the narrative. Will this president, as has been the case with prior presidents, be punished at the ballot box for a woeful reality, not always of their making—or will enough of the voters of 2020, like the investors of the mid-1990s, be susceptible to Trump’s proven brand of brazen persuasion?
There are people I talked to for this story who side with the implacable numbers. Death tolls and unemployment rolls and impossibly long lines at food banks, they say, simply can’t be swamped by even the most tenacious attempts to scramble storylines.
“I am definitely in the camp of not this time,” said political scientist Rachel Bitecofer, who predicted with startling accuracy the results of the 2018 midterms. “Body bags,” she said, leave “an indelible impression.”
“The Trump magic only works if he’s got gullible audiences, or at least curious audiences,” said Mercieca. She’s the author of the book due out this summer about the “rhetorical genius” of Trump. But she still thinks this skillset has its limits. “And if we’re really miserable in November and we may well be very miserable, then I think people probably are going to associate that with Trump.”
There are also, though, those I spoke to who believe Trump has the capacity to cloak the numbers and recast them as positives, not negatives—that he, in essence, totally could talk his way out of this by telling a better story. Could Trump get reelected? In spite of a plague? In the midst of wide-ranging economic devastation? These people all but sighed when I asked.
“Yes,” said former Trump casino executive Jack O’Donnell.
“Yes,” said Tim O’Brien, the Trump biographer who’s a columnist for Bloomberg Opinion and served as a senior adviser for Mike Bloomberg’s presidential bid. “He is so uniquely pathologic and uniquely remorseless, and I think it gives him this reptilian energy to continuously deny, spin and move forward,” O’Brien continued. “And November’s a long way off.”
O’Donnell, O’Brien and others see him doing what he did in those years leading up to that spring and summer of 1995.
“Trump is a simple guy with a few basic moves,” former Trump P.R. man Alan Marcus told me. “He always goes back to what’s worked in the past.”
“He’s obviously positioning himself for the long haul here,” O’Donnell said. “For all his lack of knowledge about so many things, he’s pretty darn media-savvy, and he’s working this right now almost brilliantly to the extent that he realizes the value of putting himself out there every day, and even if he doesn’t say the right thing every day, and even if he contradicts himself, what he’s doing is he’s laying a framework to defend himself. He’s spinning this every day now: 2 million would have died if it wasn’t for me—and it’s pretty clear it’s not going to get to 2 million—so whatever that number is beneath it, whether it’s 100,000 or 200,000, which is just horrible, to him it’s a victory. And he’s going to present it as that.”
It’s what he’s done for decades, hawking these kinds of alternative narratives—first and foremost the lie that he’s a self-made man—and these narratives have been remarkably successful, and protective, too.
“He also has been uniquely insulated from the consequences of his own mistakes his entire life,” O’Brien explained, “first by his father’s wealth that insulated him from his educational and then business mistakes; and then celebrity, which insulated him from being forgotten, even though he was a joke as a businessman at that point; and then this third ring of fire—the presidency—which has insulated him legally from the consequences of his corrupt behavior. And I would say there’s a likelihood that in 2020 he gets insulated from being defeated because he’s able to make a pandemic a winner for himself.”
Many people I talked to said Trump’s already turned this calamity into opportunity, pointing to his nearly daily briefings, which by some accounts are like his rallies only better—because they happen more often and are watched by more people. Their efficacy is very much an open question. Polling is showing the benefits are fading, as the briefings have gotten longer, less focused and more contentious. Struggling with mounting coverage painting him as a heedless, feckless ditherer who ignored numerous dire warnings, Trump has stuck unwaveringly to a characteristic P.R. offensive, accepting no “responsibility,” claiming “total” authority, and presenting himself as an on-it and unassailable manager—putting his name on mailed-out CDC guidelines and stimulus checks while at the same time relentlessly shifting blame for this “invisible enemy” to the World Health Organization, China, states he says weren’t prepared enough, governors he thinks don’t thank him enough.
“Never underestimate Donald Trump,” said Sam Nunberg, a Trump adviser during the 2016 campaign. “He’s able to adapt to any situation.”
In the past, too, Trump stared down these existential threats with small, sometimes seat-of-the-pants teams on the 26th floor of Trump Tower, not as an incumbent president backed by a sweeping, sophisticated, funds-flush reelection operation—his campaign and adjacent entities raised $212 million in the first quarter and have raked in more than $1 billion overall—well-equipped, ready and willing to fight these next six and a half months on a narrowed, drastically altered front, a “virtual” campaign that could be defined by screens and fear.
Come November, Trump could win again, say political strategists associated with both major parties, not in spite of the coronavirus but because of it.
“If I was Brad Parscale,” Greta Carnes, the national organizing director for Pete Buttigieg’s presidential campaign, told me, referring to Trump’s campaign manager, “I would be salivating right now, because this is the exact kind of environment where Trump will do well.”
Anger, anxiety and an onslaught of misinformation online were engines of Trump’s political ascent, and this unprecedented, disjointed general election is shaping up to be rife with all three.
“This year is going to be so scary, so volatile, so anxiety-inducing,” Carnes said, “I just think in my heart of hearts that it’s going to take a really uphill battle for people to want to pick somebody else”—an extreme version, perhaps, of what saved post-September 11 George W. Bush in 2004, the strong pull to not change course even during a deeply unpopular war.
Presumptive Democratic nominee Joe Biden “before Covid actually had a better chance of being elected than he does now,” Rick Wilson, an anti-Trump Republican strategist, told me. Wilson’s reasoning: Biden’s comparatively absent from the national conversation right now—and Trump is making sure of it. “Trump’s numbers depend in part on Trump absorbing all of the spotlight. We learned this in ’16,” Wilson said, “and right now he’s absorbing all of it.”
Attention can be good or bad, but a central gambit of the life of Trump is that that’s actually not true. That it’s all good. That attention is power. That if you’re watching, he’s winning.
“Anybody who studies him and studies the nature of power and propaganda when melded together should understand that this is not going to be easy,” veteran Democratic strategist Hank Sheinkopf said of his party’s shot to make Trump a one-term president.
“Americans are suckers for a good story,” he said. “Donald Trump is going to give ‘em a good story.”
And that story is?
“The story is,” he said, shifting into the ominous voice of a classic political ad narrator, “the nation faced its greatest crisis since the Second World War. And we were led by a president who had been hobbled by people who had tried to destroy him from day one. The economy was in tatters. Millions were out of work. What did Donald Trump do? He did what all great American leaders have done. X, Y, Z. Now, despite what we’ve been through, this most extraordinary nation, blessed by God, is on its way back. It won’t be easy, but we’re going to get there, because Donald Trump is leading the way.”
The video the president showed at the beginning of Monday’s briefing that many described as propaganda marked an escalation in this effort and a likely preview of what’s to come. “PRESIDENT TRUMP TOOK DECISIVE ACTION,” the screen said.
And on Thursday, on the heels of the latest dismal unemployment numbers, the Trump campaign blasted out an email, with a quote attributable to its communications director, trying to flip the narrative. It echoed Sheinkopf’s mock script. “Under the president’s leadership the economy reached unprecedented heights before it was artificially interrupted and it will be though his guidance that we’ll restore it to greatness …”
Don’t believe this can work?
Don’t believe Trump can win?
“Talk to President Hillary Clinton,” Sheinkopf said.
Donald Trump’s Greatest Escape
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