Is Trump Cracking Under the Weight of Losing?

“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.

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