Confidence Man: The Making of Donald Trump and the Breaking of America

by Maggie Haberman

Over the years, those who got closest to him and chose to stay there often suggested they had been sucked in by a version best described as the “Good” Trump. The Good Trump was capable of generosity and kindness, throwing birthday parties for friends and checking on them repeatedly when they fell ill, calling the daughter of a political ally who was suffering from breast cancer for a surprise chat from the White House. The Good Trump could be funny and fun to be around, solicitous and engaged, able to at least appear interested in the people in his company. The Good Trump could heed advice from aides hoping to curb his self-destructive impulses and could seem vulnerable. That version of Trump won the loyalty of many people over decades.

Over time, Trump has had both the thickest skin and the thinnest skin of any public figure I have ever covered, sloughing off a barrage of negative coverage in one moment, while zeroing in on a perceived minor slight made against him by a talking head on television in the next.

Over the course of the negotiations, Trump developed something akin to friendship with the development-agency official on the other end of the talks, Michael Bailkin. They would get drinks at a Third Avenue bar, where Trump would occasionally offer Bailkin a glimpse into his inner life, such as it was, by talking about his brother Freddie’s struggles with alcoholism. During one conversation Bailkin told Trump, “You’re a very shallow person.” Trump replied, “Of course. That’s one of my strengths. I never pretend to be anything else.”

Nearly thirty years later, after more than a dozen allegations of sexual harassment emerged, as well as a tape of him talking with a TV host about grabbing women’s genitals, Trump would call it “locker-room talk” and not indicative of who he was. But his discussion of people’s looks and behavior in coarse detail was a constant through his adult life.

Trump seized the promotional opportunities that his new property provided him. When the director Chris Columbus was filming a sequel to Home Alone and wanted to use the Plaza’s lobby, Trump forced his way into the film. “The only way you can use the Plaza is if I’m in the movie,” he said. Columbus thought of cutting the cameo, but Trump’s appearance drew applause from the test audience.

If the Post’s “Best Sex I’ve Ever Had” cover helped to relieve Trump’s insecurities, The Wall Street Journal’s choice of headline went right at them: trump may have to borrow funds from his father.

What’s that on your face?” Trump was asked. The question came from Ribis, who sometimes worked out of an office next door to Trump’s on the twenty-sixth floor of Trump Tower, convenient for winning the boss’s attention on a particular matter. Ribis was in the middle of a phone call, with Marcus on the line, when Trump wandered by his open office door and poked his head in. “Makeup,” Trump replied. “Why?” asked Marcus, inserting himself into the conversation over speakerphone. In later years, Trump would routinely put orange-hued foundation over his rosacea-afflicted skin, but at forty-nine, this was a striking sight. “Oh, stage makeup,” Trump replied. “I did a commercial.”

One middle-aged man gave me a strange look when I asked and assured me he would be casting a ballot for Trump at the caucuses. I asked him why he planned to do that. Without missing a beat, he looked at me and said, his voice earnest, “I watched him run his business.”

When the video was broadcast on cable-news channels, Trump told his aides that what had happened was horrible. He appeared genuinely outraged, and told Barr to do everything he could to bring justice in the case. As was often the case with Trump, he found sympathy for individuals, such as Floyd, whom he otherwise categorized by general and often unflattering stereotypes. But that would have no bearing on how he saw the protesters loosely affiliated with the Black Lives Matter movement who gathered in Minneapolis, and eventually cities nationwide.

The objective was to humanize a politician who resisted being humanized, to project a sense of empathy onto a man notoriously devoid of it. Trump had sought his first term on promises to “drain the swamp.” Now he was holding fast to Washington’s most visible icons in an increasingly desperate effort to win a second.

Yet there it was: reflecting on the meaning of having been president of the United States, his first impulse was not to mention public service, or what he felt he’d accomplished, only that it appeared to be a vehicle for fame, and that many experiences were only worth having if someone else envied them.

The political shifts that in 2016 first appeared to be a function of Trump’s personality-driven populism began to look like part of a permanent realignment, with party coalitions sorting on the basis of education levels, culture, and a growing urban versus exurban geography, rather than the old divides of religion, income, or even ideology. Those trends polarized issues that once were largely removed from politics; after Trump was booed at rallies for recommending coronavirus vaccines, he complained privately that he couldn’t get proper credit for their existence due to opposition from what he called the “radical right.”

Trump loyalists quickly began trying to tear down Hutchinson’s credibility. Yet even as some contradicted specific elements in her testimony, she had painted a familiar portrait of Trump, one that dozens of people who worked for his company, political campaigns, and government tried masking over four decades: a narcissistic drama-seeker who covered a fragile ego with a bullying impulse and, this time, took American democracy to the brink.

The reality is he treats everyone like they are his psychiatrists—reporters, government aides, and members of Congress, friends and pseudofriends and rally attendees and White House staff and customers. All present a chance for him to vent or test reactions or gauge how his statements are playing or discover how he is feeling. He works things out in real time in front of all of us. Along the way, he reoriented an entire country to react to his moods and emotions.