Michael Kruse is a senior staff writer for Politico.

“Well,” the newswoman said to Donald Trump, “you’re under a tremendous amount of pressure lately.”

“Why do you say that?” he asked.


It was April 6, 1990, and Paula Zahn on CBS actually had plenty of reasons to think Trump might be feeling anxious. It hadn’t been two months since the hyper-public, tabloid-tawdry revelation that his philandering had shattered his marriage to the mother of his first three children. He and his executives were grappling with the flawed, frantic opening of the newest, gaudiest, most expensive and most debt-bloated of his three casinos in Atlantic City. And reporters who covered money instead of celebrity had started to suss out the unsteadiness of Trump’s overall financial state.

“Both in your professional life and your personal life,” Zahn offered.

She asked how he was doing.

“I feel great,” Trump replied. “I’m doing well.”

Nearly three decades have passed. Even in Trump’s perma-perilous presidency, this is a juncture that pulses with risk. Newly empowered Democrats in Congress are ramping up multiple investigations, and talk of impeachment is impossible to avoid. Looming largest over this tumultuous battlefield, though, is the report special counsel Robert Mueller appears poised to submit to Attorney General William Barr—the culmination of nearly two years of labor and the subject of immeasurable speculation. While Trump often awards himself and his administration “A-plus” grades, many others question whether he will be able to sustain his rosy self-assessment once the details of Mueller’s findings become public.

Trump in the ’90s: Amidst a period of highly-public personal philandering, Donald Trump—pictured bottom left with his first wife Ivana in 1989, the year he began his affair with his to-be second wife Marla Maples, pictured bottom right with their newborn daughter Tiffany in 1993—would open and drive into incredible amounts of debt multiple casinos in New Jersey’s Atlantic City, including the Trump Taj Mahal, pictured above at its grand opening in 1990. | AP Photo/Mike Derer, SWERZEY/AFP/Getty Images, AP Photo

Every flurry of tweets from the president—and last weekend’s two-day grievance bender against late-night comedy and cable news shows was a particularly strong example—begets new pronouncements that Trump is coming unglued from the strain. George Conway, husband of close Trump adviser Kellyanne Conway, hauled out the clinical definition of narcissistic personality disorder to make the case that Trump is not only unfit for office but becoming catastrophically worse. And psychiatrists are speaking with dire predictions about the potential for a deranged person with extraordinary powers to create global mayhem and destruction.

“He has very poor coping mechanisms when he is criticized or when he feels humiliated,” Bandy Lee, a forensic psychiatrist from Yale and the editor of The Dangerous Case of Donald Trump, the second edition of which is out this month, told me, “and at these points he generally goes into attack mode and he threatens others or tries to get revenge. The Mueller report is of a scale that is probably unlike what we have seen him undergo before.”

Worst-case scenario? “Obliterate observing eyes of his humiliation,” Lee said. Meaning? “Destroying the world. That, very quickly, becomes an avenue, a perceived solution … for individuals with his personality structure.”

Make what you will of such medical predictions, but the historical record tells a different story. The back-and-forth with Zahn is an instructive (and comforting?) reminder about overstating Trump’s fragility. The Trump campaign in 2015 and ’16 careened from kill shot to kill shot, of course, and just kept going, right to the White House—and that was not the first time he flashed his ability to mitigate calamity and deftly skirt what might have seemed like an inevitable comeuppance. Whether or not Trump could remain not only financially solvent but reputationally intact was an open question for the entirety of the first half of the 1990s. So many times, he could have been snuffed, stopped, rendered a relative footnote, his place in the history of this country limited to status as a gauche totem of a regrettable epoch of greed. That, needless to say, is not how the tale played out. Trump is many things. A developer. A promoter. A master media manipulator. A grown-old rich kid. The president of the United States. Above all else, though, he is a survivor.

“The ultimate survivor,” former Trump casino executive Jack O’Donnell told me recently.

Trump’s Trophies: Trump had a tendency to spend on things he couldn’t afford—like his Manhattan Plaza Hotel, left, a luxury yacht, top right, and his 1989 airline Trump Shuttle, bottom left—mostly with borrowed money. | AP Images, AP Photo/Marty Lederhandler, JetPix/Wikimedia Commons

But it’s not just that Trump has survived that’s important to consider at this moment—it’s how he has done it. Armed with extraordinary audacity, constitutional sangfroid, a stomach for tumult, an acumen for recasting obvious losses into strange sorts of wins, and the prodigious safety net bequeathed by his wealthy, wily father, he has plowed past myriad hazards. And he did it by tying himself tightly to his bankers and lenders in New York and to gaming industry regulators in New Jersey—who let him live large until they couldn’t let him die without fatally wounding themselves. He effectively inhabited hosts, using them to get bigger and bigger in the ’80s until he was practically perversely invincible by the ’90s—not only “too big to fail,” as the late Wayne Barrett once told Susan Glasser and me, but “too big to jail.”

Perhaps his past escapes are the reason he appears oddly calm as most of the country leans forward, awaiting word of bombshells from Mueller. Over the weekend, when outsiders perceived mounting anxiety in Trump’s Twitter barrage, people who spoke to Trump by phone told reporters that “he seemed to be in good spirits.” The volume of tweets, they surmised, was just a product of too much time on his hands in the White House.

His bravado and bluster can’t mask, his critics say, the true jeopardy he faces. The stakes now are too high, the arena too large, the political currents too strong, for Trump to expect the same results. But if he does fail, pinned to account by the weight of evidence uncovered by Mueller, one thing is certain: It will be the first time.



***

Those who believe in the power of Trump’s survival skills to protect him from even this unprecedented threat draw an analogy between the Republican Party—its members of Congress and especially the Senate—and the institutions that have enabled him in the past.

“The banks were heavily invested in Trump, and they couldn’t have him go down,” former Trump campaign staffer Sam Nunberg told me, “and the Republican Party can’t have him go down.”

“I think he believes that the presidency is too big to fail, too powerful to be taken down,” O’Donnell added. “And I think that this is kind of something that he learned in the ‘90s, where the banks basically said to him, ‘You’re too big to fail, we have to back you.’ And they did it, time and time again, in Atlantic City.”

To be determined in the coming weeks and months: how well those lessons will hold up.

“This is a man who has lived dangerously for decades by flirting with the boundaries of propriety, legality and civility,” Trump biographer Tim O’Brien told me. “And he is now faced, after years and years of getting away with it, with consequences that are far beyond anything he’s encountered before. … The things that I think have allowed him to survive in the past will be of practical, personal use here in terms of him maintaining a stiff upper lip, if he’s able to.” But the more material applicability of the Machiavellian takeaways from his ‘90s scrapes? “I think they’re going to be absolutely of no use if the legal consequences are realized at their full magnitude.”

Trump the Builder: The New York real estate mogul, above in 1987, partnered with Hong Kong investors to develop buildings on the Upper West Side, below, that would have been Trump City but were later called Trump Place, until recently tenants voted to remove the president’s name. | Joe McNally/Getty Images, Oliver Morris/Getty Images

Others who know Trump well aren’t so sure.

“No matter what they do, he survives. No matter what they try, he survives,” longtime New York Democratic strategist Hank Sheinkopf told me. “Can Trump survive this? He absolutely can.”

In the middle of 1990, after all, he was more than $3 billion in the red. He had for years spent too much to buy too much, all with mostly borrowed money. The yacht, the airline, Manhattan’s Plaza Hotel. “Trophies,” he called them. And his casinos, first two, now three with the lurching launch of the Trump Taj Mahal, cannibalized each other. Even record rakes of cash weren’t enough to simply service all of Trump’s debt. On the horizon was the first of his six corporate bankruptcies.

“Trump is on his way down—and probably out,” business journalist Allan Sloan wrote that June in Newsday.

People didn’t stop at mere predictions. They also poked fun.

“I envision Donald Trump a year from now doing the ads for stomach-flatteners or ginsu knives on late-night TV. Or as a Worldwide Wrestling Federation commentator,” Gail Collins, then a columnist for the New York Daily News, told David Von Drehle, then a reporter for the Miami Herald.

Vanity Fair editor Tina Brown likened Trump to late-in-life Elvis. “He probably will wind up in that sort of Graceland, you know, wearing a diaper,” she told Steve Kroft of CBS News.

Spy, the puckish satirical magazine and inveterate needler of Trump, in its August 1990 issue took a tongue-in-cheek look at what they foresaw as a sad, middling future for a balding, paunchy Trump. Their crystal ball, though, was not all wrong. They anticipated a Chapter 11 bankruptcy filing, and a rough version of reality television, too—and a public offering that would permit Trump to use money from shareholders to make money of his own (“Now YOU can own a piece of the Trump!”).

But beyond the smart set’s schadenfreude were Trump’s real-life results.

After weeks of negotiations, the cluster of 70-some-odd banks that had loaned him billions of dollars gave him an additional $65 million loan. It was the first in a yearslong sequence of bailouts and extensions and breathing-room reprieves. They had loaned him so much money, it was no longer only his problem—it was theirs. He all but dared them to take him down. “He has a good bit of leverage over the institutions,” a Harvard Business School finance professor told the Boston Globe at the time. “His adjusted net worth is minus several hundred million dollars, by my estimate, and he is alive only because his bankers are too red-faced to pull the plug on his life-support system,” the chairman of a money management firm wrote in the New York Post. “The most important thing,” an official in the office of one of his lenders said in The American Banker, “is to make Trump survive.”

Trump the Candidate: Despite a number of incidents that might have taken any other candidate down—including the infamous “Access Hollywood” tape, pictured above, in which he swaggered about sexual assault—Trump was elected president on Nov. 8, 2016 and delivered his acceptance speech, pictured below, in the early hours of the following morning. | YouTube, Spencer Platt/Getty Images

The banks over time clawed back a passel of Trump’s possessions (the yacht, the planes, the Plaza), but they didn’t take his casinos—because they didn’t want them. “The last thing they want to do is manage casinos,” an analyst from Moody’s Investors explained to the Associated Press. And the last thing the gaming officials and city leaders in New Jersey wanted was to have them close. The relationship was the same as with the banks back in New York. Desperate to prop up the flagging gaming industry, looking continually to the casinos to inject into the struggling seaside town at least the appearance of vitality and prosperity, they needed Trump as much as Trump needed them. A prerequisite to owning a casino in Atlantic City, understandably, was financial stability, and regulators could have stripped Trump of his—repeatedly—but of course didn’t. Trump’s casinos amounted to roughly a third of the market. “The whole economic development of the town,” said O’Donnell, “it was dependent on this. And so they just—they caved.”

Trump had managed to turn an apparent weakness into a significant advantage. The banks put him on an allowance … of $450,000 a month. The Trump Tower triplex was safe.

“The man is a Sherman tank in a Brioni suit,” New York Post gossip columnist and Trump pal Cindy Adams told USA Today.

“Hey, look, I had a cold spell from 1990 to ’91,” he said in 1994 in New York. “I was beat up in business and in my personal life. … But you learn that you’re either the toughest, meanest piece of shit in the world, or you just crawl into a corner, put your finger in your mouth, and say, ‘I want to go home.’” And Trump didn’t want to go home.

He wasn’t entirely in the clear, though, until 1995 and ’96, when his need for money finally superseded his desire for absolute control and he took his casinos public. He sat in his office and looked at O’Brien, then a reporter for the Wall Street Journal. He was “back,” he said. People bought stock in Trump and lost money in droves. Trump Hotels and Casino Resorts proved to be a good investment for just one person—Trump. “It was to get other people to get him out of that debt,” a former member of the Trump Organization told me. In addition to his selling of his stake in his foundation-laying Grand Hyatt and tens of millions of dollars of wrangled, well-timed loans from family trusts, it’s what saved Trump—along with a partnership with Hong Kong investors that turned his long-held plot of land on the Upper West Side that always cost him money into one that began to actually make him money. Construction on what would have been Trump City and now would be called Trump Place (and then wouldn’t) started in 1997. And two years later, in front of some of the buildings, Trump let the magician David Blaine get “buried alive” for a week in a plexiglass coffin. It was, said Blaine, a stunt famed illusionist Harry Houdini always wanted to do. For Trump, the publicity ploy made for an apt ode to the art of escape.

Trumpologists and culture critics frequently cite showman P.T. Barnum as Trump’s preeminent antecedent, but another, less noted inspiration was Houdini, the author of a forthcoming Houdini biography told me. “He always found—especially when it just seemed like it was over for him—he found some new chapter, and some new way to sort of get his success going again,” Joe Posnanski said. “He created this handcuff act, and the handcuff act becomes huge, and then that sort of runs its course. And then he comes up with the milk can, and the milk can sort of runs its course. And he comes up with the Chinese water torture cell, and that runs his course. And he starts hanging upside down and escaping from straitjackets.”

It makes Posnanski think of Trump.

“With Trump, you just think, ‘OK, this is it. This is totally it, you know?’” he said. “He’s bankrupt, people are laughing at him, he’s this, he’s that—but it’s never over for him.”

“Trump,” said Sheinkopf, the Democratic strategist, “is incessantly pulling Houdini acts.”

Recall all the “gaffes” that were to have torpedoed his indelicate, unorthodox 2016 presidential bid—peaking, of course, with the “Access Hollywood” tape revealed in early October in which he swaggered about sexual assault.



***

Those who predict Trump will ultimately fall don’t disagree that he has benefited from well-placed safety nets before. This time is different, they insist, because his high-wire act is being performed at unprecedented heights.

Under Investigation: An investigation run by Robert Mueller, left, has hung over Trump’s presidency for nearly two years and led to the arrest of multiple of the president’s associates, including his former attorney Michael Cohen, top right, and his long-time advisor Roger Stone, bottom right. | Zach Gibson/Bloomberg via Getty Images, Alex Wong/Getty Images, ANDREW CABALLERO-REYNOLDS/AFP/Getty Images

“Significantly higher,” O’Brien said. “He’s been on a financial tightrope, and a familial tightrope, but he’s never been on a legal tightrope like this one. Not even close. This is fundamentally new because of the legal consequences, and those legal consequences don’t end with the filing of the Mueller report. He still has issues that are still very serious in the Southern District of New York; in some ways, they may be more serious than the Mueller investigation in terms of potential consequences and how far they dig into his world.”

Bandy Lee is worried. The forensic psychiatrist from Yale has studied thousands of people with the mental disorders she perceives Trump has. Their behavior, untreated, had predictable and unpleasant results. She foresees a similar unraveling for Trump, albeit with a wild card she has never encountered in any of her patients: the awesome power of the commander in chief.

“Under stress, we can see the limits of one’s ability to cope, and we can see that the president has reached his limits fairly rapidly, in terms of not being able to sit with the advancing special counsel’s investigation. You can see there is a heightening of activity and creation of crises, distractions, if you will, in order to distract both themselves as well as the public away from the bad news he is continuing to receive,” Lee said.

“He has very poor coping mechanisms when he is criticized or when he feels humiliated,” she continued, “and at these points, he generally goes into attack mode, and he threatens others or tries to get revenge.”

Our conversation took place before Trump resurrected his feud with the late John McCain, but I couldn’t help thinking of Lee’s warning as I listened to the president on Wednesday belabor his grudge before a crowd of workers who were expecting some good news on the economy, not a hit job on a war hero. Maybe this, just like the days of name-calling with George Conway, really are the signs of a mind in turmoil.

Trump the Survivor: President Trump departs the White House earlier this year, while talk of his impeachment by a newly-Democratic House is impossible to avoid. He’s teetered on the brink before and never succumbed. Will he be able to do it again? | Win McNamee/Getty Images

And yet—and this is just the reality of the record—Trump shrewdly, bullheadedly, even blithely pushed past crises in the ‘90s that would have felled almost anybody else. And then, perhaps convinced of his own invincibility, he blew through a litany of accepted social and political checkpoints on his way to the Oval Office and his high-backed chair behind the Resolute desk.

“Pressure,” Trump said in an extended interview in Playboy in 1990, “doesn’t upset my sleep. … I like throwing balls into the air—and I dream like a baby.”

That same year, on June 14, he turned 44. The next day, he missed about $45 million in debt payments for his casino called Trump Castle. “He is absolutely on knife’s edge,” James Grant, the editor of Grant’s Interest Rate Observer, told Newsday. The day after that, Trump had a party. More than a thousand employees in Atlantic City showed up at the bash on the boardwalk, according to news reports. “We love you, Donald!” they cried. He was presented with a chocolate cupcake, a 12-page birthday card and an 8-foot-by-10-foot portrait of himself.

“Nobody wants to write the positives,” Trump told the cheering crowd. “Over the years, I’ve surprised a lot of people. The largest surprise is yet to come.”

True.