“The Apprentice,” a new movie that dramatizes the early years of Donald Trump’s career, ends with a scene between Mr. Trump and an actor who plays me. The year is 1986 and I’m interviewing Mr. Trump for the first time, to begin ghostwriting “The Art of the Deal,” a book that I view today as an unintended work of fiction.
Since my time collaborating with Mr. Trump, I’ve spent my adult life studying, writing about and working with leaders and other high achievers. I’ve focused especially on how their early childhood experiences have influenced their adult lives — mostly unconsciously — and on exploring the often vast gulf between how they present themselves on the outside and how they feel on the inside. Mr. Trump, for me, has always been Exhibit A.
Watching “The Apprentice” crystallized two big lessons that I learned from Mr. Trump 30 years ago and that I’ve seen play out in his life ever since with more and more extreme consequences. The first lesson is that a lack of conscience can be a huge advantage when it comes to accruing power, attention and wealth in a society where most other human beings abide by a social contract. The second lesson is that nothing we get for ourselves from the outside world can ever adequately substitute for what we’re missing on the inside.
“The Apprentice” tells Mr. Trump’s story through the lens of the two men who most influenced him: his father, Fred, and Roy Cohn, his longtime lawyer and one of the most notorious and disgraced fixers of the 20th century. What they had in common, and passed on to Donald in spades, was their shamelessness when it came to winning and dominating others, whatever that took. The end always justified the means.
The film starts with a disclaimer that some events have been “fictionalized for dramatic purposes,” and the filmmakers clearly took artistic liberties. Journalists, historians and critics can debate which specific scenes in “The Apprentice” actually happened and which ones did not. For me, the movie felt emotionally true — and consistent with the Donald Trump I came to know three decades ago. “The Apprentice” is less about how Mr. Trump rose to power than it is about the generational impact of his family’s trauma and dysfunction, and how it shaped the person Mr. Trump became and the impact he’s had on an entire country.
During my time working on “The Art of the Deal,” Mr. Trump would call me most evenings from his Trump Tower apartment, and nearly every call began the same way. “Can you believe it, Tony?” he asked, rhetorically. “Bigger than ever.” Then he would go on to talk about some triumph he’d had that day or a hapless competitor he’d vanquished.
On the face of it, he was riding high in the mid 1980s. He had just built Trump Tower at 57th Street and Fifth Avenue, he owned two large casino hotels in Atlantic City and was on the verge of buying a third, and he traveled around in a limousine, a helicopter, a yacht or a private plane.
What Mr. Trump never let me know was that amid all those glittering external signs of success, he was in increasingly desperate financial trouble, drowning in debts that would lead him into a series of bankruptcies. I did not yet realize that he routinely lied as easily as he breathed, including to me for his own memoir, and without a hint of a guilty conscience.
What struck me from the first day I met Mr. Trump was his unquenchable thirst to be the center of attention. No amount of external recognition ever seemed to be enough. Beneath his bluster and his bombast, he struck me as one of the most insecure people I’d ever met — and one of the least self-aware. He’d crossed the bridge from Queens to Manhattan but he remained the product — and even the prisoner — of his childhood experiences. As he told a reporter in 2015, “When I look at myself in the first grade and I look at myself now, I’m basically the same.”
I buy that.
Children aren’t born seeking external success, power, wealth or dominance. What Mr. Trump seems to have buried as he grew up was the core emotional need that all human beings experience from the day they’re born: to feel safe, secure and worthy because they’re loved unconditionally by their primary caretakers. From my observations — and what the movie details — that kind of love was never available to Mr. Trump or to his siblings.
Mr. Trump’s father, Fred, was openly disdainful of any acknowledgment or expression of weakness or vulnerability. He had amassed a fortune building low-income, government-supported housing and, along the way, he developed a harsh, zero-sum view of the world: You were either a winner or a loser in life. If you weren’t a killer, you were forever at risk of being victim and a sucker. Brutality, in the service of winning, was no vice.
“The most importance influence on me, growing up, was my father,” Mr. Trump told me for “The Art of the Deal.” “I learned about toughness in a very tough business.”
Mr. Trump also learned lessons about how to earn his father’s approval and avoid his wrath by observing the fate of his older brother, Fred Jr., who was expected from an early age to someday take over his father’s business. When he chose instead to follow his passion to become a pilot — and to leave the family business — he lost the respect of his father, who began referring to him dismissively as a “glorified bus driver.” Fred Jr. died from the effects of alcoholism, at the age of 42.
“Fortunately for me,” Mr. Trump explained in “The Art of the Deal,” “I was drawn to business very early, and I was never intimidated by my father the way most people were. I stood up to him and he respected that. We had a relationship that was almost businesslike.”
I still remember the chill I felt when Mr. Trump said those words, as if it was fine to have an almost completely transactional relationship with his father.
When children can’t get what they need from their primary caretakers, they eventually turn to other means. For Mr. Trump, that seemed to manifest in relentlessly seeking attention and recognition from an early age, and measuring his value comparatively and by the numbers — whether it was his net worth, the height of his buildings or the number of people who attend his rallies. Early on, Mr. Trump figured out that sufficient bravado and bold assertions — even if they were false — could often substitute for actual accomplishments, especially if he repeated them often enough.
What “The Apprentice” captures most evocatively is Mr. Trump’s transition from pleasing his father to enlisting Mr. Cohn as a mentor and role model. Mr. Cohn’s role was to help Mr. Trump outdo his father, even as Fred used his vast wealth and political connections to clear Donald’s path. At the time that Mr. Trump first met Mr. Cohn at a private club in 1973, Fred and Donald had just been sued by the Justice Department for refusing to rent to Black people and other minorities at their Trump Village apartment buildings in Brooklyn.
The evidence of racism was overwhelming. But Mr. Cohn urged Mr. Trump to fight back rather than settle. “The Apprentice” distills Mr. Cohn’s worldview into three life lessons he shared with Mr. Trump: Attack, attack, attack; admit nothing and deny everything; and claim victory and never admit defeat. Mr. Trump took those principles to heart.
“Whatever else you could say about Roy, he was very tough,” Mr. Trump told me for “The Art of the Deal.” “Sometimes I think that next to loyalty, toughness was the most important thing in the world to him.”
Loyalty and toughness were two qualities Mr. Trump revered, and he concluded his assessment in “The Art of the Deal” with the highest praise: “Roy was the sort of guy who’d be there at your hospital bed, long after everyone else had bailed out, literally standing by you to the death.”
For Mr. Trump, however, loyalty went only one way. By the time we began work on the book, he had long since bailed on Mr. Cohn, who had been diagnosed with AIDS. It didn’t seem personal for Mr. Trump because in my experience nothing was personal for him. It was all business, and Mr. Trump seemed to have no further use for his longtime lawyer, mentor and friend.
Mr. Trump did encourage me to interview Mr. Cohn for “The Art of the Deal,” and I went to see him in his last days. Over two rambling hours, Mr. Cohn shared an odd blend of hurt, bitterness, resignation and a certain awe at how easily his longtime student had walked away from their relationship. “Donald pisses ice water,” is the way he’d put it to one reporter.
It’s long been deeply unsettling to me how many behaviors associated with psychopathy Mr. Trump exemplifies. There are seven characteristics associated with “antisocial personality disorder,” according to the Diagnostic and Statistical Manual of Mental Disorders: deceitfulness, impulsivity, failure to conform to social norms with respect to lawful behaviors, irritability and aggressiveness, reckless disregard for the safety of self or others, consistent irresponsibility and lack of remorse. I’ve observed all seven in Mr. Trump over the years, and watched them get progressively worse. It’s the last one — lack of remorse — that gives him license to freely exercise the other six.
The past is prologue and, as Mr. Trump has said, he’s essentially the same person today that he was as a child. That is the central warning “The Apprentice” poses, and it comes just five weeks before the election.
Ever since Mr. Trump announced in 2015 that he was running for president, I’ve argued publicly that the only limitation on his behavior as president — then and now — is what he believes he can get away with. Mr. Trump has made it clear that he believes he can get away with a lot more today. If he does win back the presidency, it’s hard to imagine that he’ll have much more on his mind than revenge and domination — damn the consequences — in his doomed, lifelong quest to feel good enough.
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