Is Trump Cracking Under the Weight of Losing?

Over the course of a lifetime of professional and personal transgressions and failures, channeling lasting, curdled lessons of Norman Vincent Peale and Roy Cohn, Trump has assembled a record of rather remarkable resilience. His typical level of activity and almost animal energy has at times lent him an air of insusceptibility, every one of his brushes with financial or reputational ruin ending with Trump emerging all but untouched. His current crisis, though, his eviction from the White House now just a month out, is something altogether different and new.

“He’s never been in a situation in which he has lost in a way he can’t escape from,” Mary Trump, his niece and the author of the fiercely critical and bestselling book about him and their family, told me. “We continue to wait for him to accept reality, for him to concede, and that is something he is not capable of doing,” added Bandy Lee, the forensic psychiatrist from Yale who’s spent the last four years trying to warn the world about Trump and the ways in which he’s disordered and dangerous. “Being a loser,” she said, for Trump is tantamount to “psychic death.”

The combination of an unprecedented rebuke meeting an uncommonly vulnerable ego has some people wondering if there is a chance that Trump’s unusual actions suggest something potentially more dire. Could he be on his way to a mental breakdown?

Sam Nunberg dismissed the notion. “No,” the former Trump political aide said in a text.

Same with Anthony Scaramucci, who very briefly and semi-famously was his top White House spokesperson. “No chance,” he said.

But that’s not consensus. Louise Sunshine, for instance, has known Trump longer than just about anybody. She started working with him in the early 1970s—so I sent her a text asking her the question. “Maybe,” she responded.

Everybody, after all, has a breaking point. “And he’s not indestructible,” said Barbara Res, a former Trump Organization executive vice president who was the construction manager for Trump Tower and just wrote a book called Tower of Lies. “I do think Trump is struggling,” Tony Schwartz, the actual author of The Art of the Deal, told me, “and that this is far and away the toughest time he’s ever had.”

“His fragile ego has never been tested to this extent,” Michael Cohen, his former personal attorney and enforcer before he turned on him, told me. “While he’s creating a false pretense of strength and fortitude, internally he is angry, depressed and manic. As each day ends, Trump knows he’s one day closer to legal and financial troubles. Accordingly, we will all see his behavior deteriorate until it progresses into a full mental breakdown.”

“Psychological disorders are like anything else,” said Mary Trump, who’s also a psychologist. “If they’re unacknowledged and untreated over time, they get worse.”

In Lee’s estimation, it’s not something that could happen. It’s something that is happening, that’s been happening for the past four years—and will keep happening.

“His pathology has continued to grow, continued to cause him to decompensate, and so we’re at a stage now where his detachment from reality is pretty much complete and his symptoms are as severe as can be.” She likened Trump to “a car without functioning brakes.” Such a car, she explained, can look for a long time like it’s fine, and keep going, faster and faster, even outracing other cars. “But at the bottom of the hill,” Lee said, “it always crashes.”

Trump is who and how he is first and foremost because of his parents. His unwell mother couldn’t and didn’t give him the attention he wanted and needed, while his domineering father gave him attention but a wrong and warping kind—instilling in him a grim, zero-sum worldview with the dictate that the only option was to be “a winner.” Ever since, he responded so relentlessly to these harsh particulars of his loveless upbringing—the insatiable appetite for publicity, the crass, constant self-aggrandizement—that he became the president of the United States and arguably the most famous person alive. But from the time he was a boy, the way Trump has coped with the void he’s felt ultimately has been less a solution than a spotlight—it’s what’s made his most fundamental problem most manifest.

“His problem is that he has grown up with vulnerability in terms of his self-worth, self-esteem and a clear sense of himself,” Mark Smaller, a past president of the American Psychoanalytic Association, told me. “Somebody with these kinds of vulnerabilities, affirmation, being the center of things, is never enough. Because you can’t solve these old wounds, these old, narcissistic wounds—you cannot solve them with affirmation, with being at the center of things. You can’t because they persist, so that you need more attention, you need more affirmation, you need to be more at the center of things, all the time, more often. And when realities start to interfere with getting that kind of affirmation, you just want more.”

The only moment in Trump’s life that remotely compares to what’s happening right now is in early 1990.

He was mired in a tabloid-catnip marital breakup on account of an affair with the B-movie actress who eventually would become the second of his three wives and the mother of the fourth of his five children. He also was a staggering $3.4 billion in debt—personally liable for nearly a billion of that—his business affairs in New York and with his casinos in Atlantic City, New Jersey, in absolute shambles. “I would have been looking for the nearest building to jump off of,” Steve Bollenbach, the financial fixer banks made Trump hire, once told biographer Tim O’Brien. That spring, according to Vanity Fair, Trump ordered in burgers and fries and stayed up late in bed, staring at the ceiling. At risk of becoming a has-been and a punchline, Trump nonetheless boasted about future prospects—of national magazine covers and a comeback to come. “All Donald knew,” Wayne Barrett wrote around the time, “was that he was still a story.”

He sat at his desk paging through periodicals looking for his name. “Even if it was the same AP article in every single newspaper, he wanted to see it,” former Trump casino executive Jack O’Donnell told me. “That’s how he survives.”

“Did he collapse? No. He did not collapse,” veteran New York Democratic strategist Hank Sheinkopf said. “He just continued.”

Trump was able to do that, of course, principally due to the sprawling, near-foolproof safety net his father’s wealth allowed. Lenders in New York and regulators in Atlantic City, too, let him skate, both groups as beholden to him as he was to them.

Still, en route to averting comeuppance, he proceeded to weave this self-inflicted calamity into a preferred tale of a certain toughness he possessed. “Most people would have been in the corner sucking their thumb,” he said to a reporter from the Sunday Times of London. “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,’” he told a writer from New York. “You never know until you’re under pressure how you’re gonna react.”

But the biggest difference between then and now: Even when Trump was all but broke, even as bankers clawed back some of his “toys,” the “props for the show,” as he once put it in Playboy, they gave him an obscene $450,000-a-month allowance. And the most important thing? He got to keep Trump Tower. He got to remain living in the penthouse of the building that he had built, that had made him famous, and that served above all as the preeminent stage for how he wanted to be seen.

“He was always there in his office,” Alan Marcus, Trump’s publicist later on in the ‘90s, told me. “He was always there in his castle.”

This time, on the other hand, he’s getting kicked out. No more Oval Office photo ops. No more two-scoop nights watching Fox News in his room in the residence. In a month’s time, for most likely the last time, the door of the White House will close behind him.

This looming reality colors his interactions in these waning days.

Earlier this month, the Medal of Freedom ceremony to honor Dan Gable, the fabled Iowa wrestler and coach, seemed precisely the sort of pomp Trump liked the most throughout his single term. “He couldn’t stand the feeling of losing,” he said of Gable, reading from prepared remarks, standing behind the lectern festooned with the presidential seal, surrounded by Gable, Gable’s family and members of Congress from Iowa, reporters and photographers.

“Before matches,” Trump continued, “Dan would repeat the words ‘cakes, carries, ducks, picks, shucks, sweeps’ over and over again. I’ll have to ask Dan why. Why, Dan?”

“Because they’re all moves that end the match,” Gable said.

“Oh,” Trump said.

Toward the end of the event, though, when one of the reporters asked if he was still “looking to change the outcome of the election,” Trump called the election “rigged” and the United States “third-world” before turning to thank Gable again—and then abruptly walked out.

Gable, seeming surprised and still standing in the Oval, looked at the gathered press and held his hands up. He said all that was left to say.

“He’s gone.”

“So,” Brian Kilmeade of Fox asked Trump last weekend in one of the vanishingly few interviews the president has consented to since he lost, “would you show up at the inauguration. Will you?”

“I don’t want to talk about that,” Trump said. “I want to talk about this: We’ve done a great job. I got more votes than any president in the history of our country—in the history of our country, right? Not even close: 75 million”—actually a little more than 74—“far more than Obama, far more than anybody. And they say we lost an election. We didn’t lose.”

This is true, obviously, only if one ignores the more than 81 million people who voted for Joe Biden and the 306 Electoral College votes he was awarded as a result.

The people who’ve known Trump well, the people who’ve watched him for a long, long time, the mental health professionals—they’re worried, they told me, about what’s to come, in the next month, and in the months and years after that.

“There’s no reckoning with reality,” biographer Gwenda Blair said. “He’s going to continue to frame it that he won, he was cheated, he’s the victim, and he’s going to continue to bend reality as best he can.”

“He’ll continue to rage against the results, and he’ll continue to solidify in the minds of millions more Americans that the democratic process was corrupted, and that’s going to have a long-lasting tail that we’ll have to deal with in American politics for many, many years,” said Miles Taylor, the former chief of staff at the Department of Homeland Security who was “Anonymous” before he revealed his identity in October. “I don’t expect that the president is going to chain himself to the Resolute Desk and refuse to leave, but also, given what we’ve seen the past few weeks, I wouldn’t totally put it past him.”

“The probability of something very bad happening is very high, unacceptably high, and the fact that we don’t have guardrails in place, the fact that we are allowing a mentally incapacitated president to continue in the job, in such an important job, for a single day longer, is a truly unacceptable reality,” said Lee, the Yale psychiatrist. “We’re talking about his access to the most powerful military on the planet and his access to technology that’s capable of destroying human civilization many times over.”

“You have to remember,” said Cohen, his former attorney. “Trump doesn’t see things the way that you do. He sees things in his distorted reality that benefits him. He’s able to right now embrace that distorted reality because he still wakes up in the White House. But what happens each and every day as he gets closer to not only leaving, but also it comes with a sense of, in his mind, humiliation, right? And he knows that he is destined for legal troubles.”

“He’s looking down the barrel” of legal and financial difficulties, Mary Trump said. “But perhaps more troubling for him or more terrifying for him is the fact that he is in danger of losing his relevance.”

And that is not something Trump will ever be able to abide.