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). All of this has protected Donald from his own failures while allowing him to believe himself a success.
Donald was to my grandfather what the border wall has been for Donald: a vanity project funded at the expense of more worthy pursuits. Fred didn’t groom Donald to succeed him; when he was in his right mind, he wouldn’t trust Trump Management to anybody. Instead, he used Donald, despite his failures and poor judgment, as the public face of his own thwarted ambition. Fred kept propping up Donald’s false sense of accomplishment until the only asset Donald had was the ease with which he could be duped by more powerful men.
There was a long line of people willing to take advantage of him. In the 1980s, New York journalists and gossip columnists discovered that Donald couldn’t distinguish between mockery and flattery and used his shamelessness to sell papers. That image, and the weakness of the man it represented, were precisely what appealed to Mark Burnett. By 2004, when The Apprentice first aired, Donald’s finances were a mess (even with his $170 million cut of my grandfather’s estate when he and his siblings sold the properties), and his own “empire” consisted of increasingly desperate branding opportunities such as Trump Steaks, Trump Vodka, and Trump University. That made him an easy target for Burnett. Both Donald and the viewers were the butt of the joke that was The Apprentice, which, despite all evidence to the contrary, presented him as a legitimately successful tycoon.
For the first forty years of his real estate career, my grandfather never acquired debt. In the 1970s and ’80s, however, all of that changed as Donald’s ambitions grew larger and his missteps became more frequent. Far from expanding his father’s empire, everything Donald did after Trump Tower (which, along with his first project, the Grand Hyatt, could never have been accomplished without Fred’s money and influence) chipped away at the empire’s value. By the late 1980s, the Trump Organization seemed to be in the business of losing money, as Donald siphoned untold millions away from Trump Management in order to support the growing myth of himself as a real estate phenom and master dealmaker.
Ironically, as Donald’s failures in real estate grew, so did my grandfather’s need for him to appear successful. Fred surrounded Donald with people who knew what they were doing while giving him the credit; who propped him up and lied for him; who knew how the family business worked.
The more money my grandfather threw at Donald, the more confidence Donald had, which led him to pursue bigger and riskier projects, which led to greater failures, forcing Fred to step in with more help. By continuing to enable Donald, my grandfather kept making him worse: more needy for media attention and free money, more self-aggrandizing and delusional about his “greatness.”
Although bailing out Donald was originally Fred’s exclusive domain, it didn’t take long for the banks to become partners in the project. At first, taken in by what they believed to be Donald’s ruthless efficiency and ability to get a job done, they were operating in good faith. As the bankruptcies piled up and the bills for the reckless purchases came due, the loans continued but now as a means to maintain the illusion of success that had fooled them in the first place. It’s understandable that Donald increasingly felt he had the upper hand, even if he didn’t. He was completely unaware that other people were using him for their own ends and believed that he was in control. Fred, the banks, and the media gave him more leeway in order to get him to do their bidding.
In the very early stages of his attempts to take over the Commodore Hotel, Donald held a press conference presenting his involvement in the project as a fait accompli. He lied about transactions that hadn’t taken place, inserting himself in a way that made it difficult for him to be removed. He and Fred then used this gambit to leverage his newly inflated reputation in the New York press—and many millions of dollars of my grandfather’s money—to get enormous tax abatements for his next development, Trump Tower.
In Donald’s mind, he has accomplished everything on his own merits, cheating notwithstanding. How many interviews has he given in which he offers the obvious falsehood that his father loaned him a mere million dollars that he had to pay back but he was otherwise solely responsible for his success? It’s easy to understand why he would believe this. Nobody has failed upward as consistently and spectacularly as the ostensible leader of the shrinking free world.
Donald today is much as he was at three years old: incapable of growing, learning, or evolving, unable to regulate his emotions, moderate his responses, or take in and synthesize information.
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. His deep-seated insecurities have created in him a black hole of need that constantly requires the light of compliments that disappears as soon as he’s soaked it in. Nothing is ever enough. This is far beyond garden-variety narcissism; 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. So he must draw you in if he can by getting you to assent to even the most seemingly insignificant thing: “Isn’t this plane great?” “Yes, Donald, this plane is great.” It would be rude to begrudge him that small concession. Then he makes his vulnerabilities and insecurities your responsibility: you must assuage them, you must take care of him. Failing to do so leaves a vacuum that is unbearable for him to withstand for long. If you’re someone who cares about his approval, you’ll say anything to retain it. He has suffered mightily, and if you aren’t doing all you can to alleviate that suffering, you should suffer, too.
From his childhood in the House to his early forays into the New York real estate world and high society until today, Donald’s aberrant behavior has been consistently normalized by others. When he hit the New York real estate scene, he was touted as a brash, self-made dealmaker. “Brash” was applied to him as a compliment (used to imply self-assertiveness more than rudeness or arrogance), and he was neither self-made nor a good dealmaker. But that was how it started—with his misuse of language and the media’s failure to ask pointed questions.
His real skills (self-aggrandizement, lying, and sleight of hand) were interpreted as strengths unique to his brand of success. By perpetuating his version of the story he wanted told about his wealth and his subsequent “successes,” our family and then many others started the process of normalizing Donald. His hiring (and treatment) of undocumented workers and his refusal to pay contractors for completed work were assumed to be the cost of doing business. Treating people with disrespect and nickel-and-diming them made him look tough.
Those misrepresentations must have seemed harmless at the time—a way to sell more copies of the New York Post or increase the viewership of Inside Edition—but each transgression inevitably led to another, more serious one. The idea that his tactics were legitimate calculations instead of unethical cons was yet another aspect of the myth that he and my grandfather had been constructing for decades.
Though Donald’s fundamental nature hasn’t changed, since his inauguration the amount of stress he’s under has changed dramatically. It’s not the stress of the job, because he isn’t doing the job—unless watching TV and tweeting insults count. 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. For decades, he has gotten publicity, good and bad, but he’s rarely been subjected to close scrutiny, and he’s never had to face significant opposition. His entire sense of himself and the world is being questioned.
Donald’s problems are accumulating because the maneuvering required to solve them, or to pretend they don’t exist, has become more complicated, requiring many more people to execute the cover-ups. Donald is completely unprepared to solve his own problems or adequately cover his tracks. After all, the systems were set up in the first place to protect him from his own weaknesses, not help him negotiate the wider world.
The walls of his very expensive and well-guarded padded cell are starting to disintegrate. The people with access to him are weaker than Donald is, more craven, but just as desperate. Their futures are directly dependent on his success and favor. They either fail to see or refuse to believe that their fate will be the same as that of anyone who pledged loyalty to him in the past. There seems to be an endless number of people willing to join the claque that protects Donald from his own inadequacies while perpetuating his unfounded belief in himself. Although more powerful people put Donald into the institutions that have shielded him since the very beginning, it’s people weaker than he is who are keeping him there.
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. Over time, the vast bulk of the Republican Party—from the extreme Right to the so-called moderates—either embraced him or, in order to use his weakness and malleability to their own advantage, looked the other way.