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Donald was enabled from the beginning, every one of his projects funded and supported by Fred and then by myriad other enablers right up to the present.
In June Donald, then eighteen and freshly graduated from the military academy, and Robert, sixteen, still a student at Freddy’s alma mater, St. Paul’s, drove up to Marblehead for a visit, arriving in Donald’s new sports car, a high school graduation present from his parents—a step up from the luggage Freddy had received when he had graduated from college.
Since September 1964, Donald had been living at the House and commuting thirty minutes to Fordham University in the Bronx, his attendance at which he’d avoid mentioning in the years to come.
Going from the regimented life at New York Military Academy to the relatively relaxed structure of college was a tough transition for Donald,
With Freddy’s apparent fall from grace, Donald saw an opportunity to take his place as their father’s right-hand man at Trump Management.
Unable to accept responsibility, much as Donald would later be, Fred blamed Freddy for the failure of Steeplechase. Eventually, Freddy blamed himself.
he suddenly found himself a small fish in a big pond.
Donald had survived the first couple of years as an underclassman by using the considerable skills he’d acquired growing up in the family house: his ability to feign indifference in the face of pain and disappointment, to withstand the abuse of the bigger, older boys. He hadn’t been a great student, but he’d had a certain charm, a way of getting others to go along with him that, back then, wasn’t entirely grounded in cruelty.
When they were younger, Donald had been both a bystander and collateral damage. Now that he was older, he felt increasingly confident that Freddy’s continuing loss of their father’s esteem would be to his benefit, so he often watched silently or joined in.
Donald graduated from the University of Pennsylvania in the spring of 1968 and went straight to work at Trump Management.
Second, it helped consolidate Donald’s de facto position as heir apparent.
Donald was, in Fred’s eyes, “the cat’s meow.” But after the summers and weekends Donald spent working for his father and visiting construction sites, Fred exposed his younger son to the ins and outs of the real estate business. Donald discovered he had a taste for the seamier side of dealing with contractors and navigating the political and financial power structures that undergirded the world of New York City real estate.
Donald dedicated a significant portion of his time to crafting an image for himself among the Manhattan circles he was desperate to join. Having grown up a member of the first television generation, he had spent hours watching the medium, the episodic nature of which appealed to him. That helped shape the slick, superficial image he would come to both represent and embody.
My grandfather had never been sick a day in his life; he had never missed a day of work; he had never been sidelined by depression or anxiety or heartbreak, not even when his wife was near death. He appeared to have no vulnerabilities at all and therefore couldn’t recognize or sanction them in other people.
Ironically, the defenses he had developed as a young child to protect himself against the indifference, fear, and neglect that had defined his early years, along with his being forced to watch the abuse of Freddy, primed him to develop what his older brother clearly lacked: the ability to be the “killer” and proxy his father required.
In interviews in the early 1980s, Fred claimed that Donald’s success had far exceeded his own. “I gave Donald free rein,” he said. “He has great visions, and everything he touches seems to turn to gold. Donald is the smartest person I know.” None of that was true, and Fred must have known that a decade before he said it.
I grew up thinking that Donald had struck out on his own and single-handedly built the business that had turned my family name into a brand and that my grandfather, provincial and miserly, cared only about making and keeping money. On both counts, the truth was vastly different.
it was as if Donald Trump had his own Money Store.
Over time that attitude—that he knew better—would become even more entrenched: as his knowledge base has decreased (particularly in areas of governing), his claims to know everything have increased in direct proportion to his insecurity, which is where we are now.
For Donald, too much of a good thing was a better thing;
operating a casino, unlike the Grand Hyatt and Trump Tower, which were development projects that were ultimately managed by other entities, would be an ongoing business. As such, it would have been Donald’s first opportunity to succeed independently of his father.
Of course, his casinos were competing with one another and eventually would be cannibalizing one another’s profits.
the three properties carried $94 million in annual debt, and the Taj alone needed to pull in more than $1 million a day to break even.
The possibility of more defaults and bankruptcies still loomed, and a solution had to be found that would protect Donald’s image, which, in turn, would protect the banks’ money. Without the veneer of success and confidence he projected (and had projected for him), the bankers feared that his properties, already in trouble, would lose even more value.
As much as Donald complained to Robert that the banks were “killing” him, the truth was that he was beholden to them in a way he had never been to his father: he had never been on a leash before, let alone a short one, and it chafed.
In a way, you can’t really blame Donald. In Atlantic City, he had become unmoored from his need for his father’s approval or permission. He no longer needed to talk himself up; his exaggerated assessment of himself was simultaneously fueled and validated by banks that were throwing hundreds of millions of dollars at him and a media that lavished him with attention and unwarranted praise. The two combined rendered him blind to how dire his situation was. My grandfather’s myths about Donald were now being reinforced by the world at large.
When his ability to charm hit a wall, he deployed another “business strategy”: throwing tantrums during which he threatened to bankrupt or otherwise ruin anybody who failed to let him have what he wanted. Either way, he won.
The more New Yorkers wanted spectacle, the more willing the media were to provide it—even
If the media could deny reality, so could he.
Donald’s talent for deflecting responsibility while projecting blame onto others came straight from his father’s playbook.
Finally, there was the slow-rolling toll that his as-yet-undiagnosed Alzheimer’s was beginning to take on his executive functioning. Already susceptible to believing the best of his worst son, it became easier over time for him to confuse the hype about Donald with reality.
Maryanne would say years later, “We would have been penniless. Elizabeth would have been begging on a street corner. We would have had to beg Donald if we wanted a cup of coffee.” It was “sheer luck” that they had stopped the scheme. Yet the siblings still got together every holiday as though nothing had happened.
It wasn’t until later, when I reread the letter, that I understood why Donald thought it would be a good idea to hire me—not because it was “fantastic” but because it demonstrated that I was really good at making other people look really good.
The idea that anyone else was entitled to money or support he or she wasn’t obviously earning was impossible for Donald and my grandfather to fathom.
But his kindness had become so warped over time—through lack of use and Fred’s discouragement—that what he considered kindness would have been practically unrecognizable to the rest of us.
It wasn’t enough for me to volunteer at an organization helping Syrian refugees; I had to take Donald down.
In the long run, however, my grandfather, who had one wish—that his empire survive in perpetuity—lost everything.
There is a through line from the House to the Trump Tower triplex to the West Wing, just as there is from Trump Management to the Trump Organization to the Oval Office. The first are essentially controlled environments in which Donald’s material needs have always been taken care of; the second, a series of sinecures in which the work was done by others and Donald never needed to acquire expertise in order to attain or retain power (which partly explains his disdain for the expertise of others).
Donald was to my grandfather what the border wall has been for Donald: a vanity project funded at the expense of more worthy pursuits.
Donald’s need for affirmation is so great that he doesn’t seem to notice that the largest group of his supporters are people he wouldn’t condescend to be seen with outside of a rally.
Donald is not simply weak, his ego is a fragile thing that must be bolstered every moment because he knows deep down that he is nothing of what he claims to be.
He knows he has never been loved.
It’s the effort to keep the rest of us distracted from the fact that he knows nothing—about politics, civics, or simple human decency—that requires an enormous amount of work.
When Donald became a serious contender for the Republican Party nomination and then the nominee, the national media treated his pathologies (his mendacity, his delusional grandiosity), as well as his racism and misogyny, as if they were entertaining idiosyncrasies beneath which lurked maturity and seriousness of purpose.
One of the few pleasures my grandfather had, aside from making money, was humiliating others.
His cruelty serves, in part, as a means to distract both us and himself from the true extent of his failures.
Donald continues to exist in the dark space between the fear of indifference and the fear of failure that led to his brother’s destruction.
you have to remember that the man speaking is still, in essential ways, the same little boy who is desperately worried that he, like his older brother, is inadequate and that he, too, will be destroyed for his inadequacy.
At a very deep level, his bragging and false bravado are not directed at the audience in front of him but at his audience of one: his long-dead father.
The few journalists who do challenge him, and even those who simply ask Donald for words of comfort for a terrified nation, are derided and dismissed as “nasty.”
