Chapter Fourteen
A Civil Servant in Public Housing

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.

After the election, Vladimir Putin, Kim Jong-un, and Mitch McConnell, all of whom bear more than a passing psychological resemblance to Fred, recognized in a way others should have but did not that Donald's checkered personal history and his unique personality flaws make him extremely vulnerable to manipulation by smarter, more powerful men. His pathologies have rendered him so simple-minded that it takes nothing more than repeating to him the things he says to and about himself dozens of times a day—he's the smartest, the greatest, the best—to get him to do whatever they want, whether it's imprisoning children in concentration camps, betraying allies, implementing economy-crushing tax cuts, or degrading every institution that's contributed to the United States' rise and the flourishing of liberal democracy.

In an article for The Atlantic, Adam Serwer wrote that, for Donald, the cruelty is the point. For Fred, that was entirely true. One of the few pleasures my grandfather had, aside from making money, was humiliating others. Convinced of his rightness in all situations, buoyed by his stunning success and a belief in his superiority, he had to punish any challenge to his authority swiftly and decisively and put the challenger in his place. That was effectively what happened when Fred promoted Donald over Freddy to be president of Trump Management.

Unlike my grandfather, Donald has always struggled for legitimacy—as an adequate replacement for Freddy, as a Manhattan real estate developer or casino tycoon, and now as the occupant of the Oval Office who can never escape the taint of being utterly without qualification or the sense that his "win" was illegitimate. Over Donald's lifetime, as his failures mounted despite my grandfather's repeated— and extravagant—interventions, his struggle for legitimacy, which could never be won, turned into a scheme to make sure nobody found out that he's never been legitimate at all. This has never been more true than it is now, and it is exactly the conundrum our country finds itself in: the government as it is currently constituted, including the executive branch, half of Congress, and the majority of the Supreme Court, is entirely in the service of protecting Donald's ego; that has become almost its entire purpose.

His cruelty serves, in part, as a means to distract both us and himself from the true extent of his failures. The more egregious his failures become, the more egregious his cruelty becomes. Who can pay attention to the children he's kidnapped and put into concentration camps on the Mexican border when he's threatening to out whistleblowers, coercing senators to acquit him in the face of overwhelming evidence of guilt, and pardoning Navy SEAL Eddie Gallagher, who'd been accused of war crimes and convicted of posing for a picture with a corpse, all within the same month? If he can keep forty-seven thousand spinning plates in the air, nobody can focus on any one of them. So there's that: it's just a distraction.

His cruelty is also an exercise of his power, such as it is. He has always wielded it against people who are weaker than he is or who are constrained by their duty or dependence from fighting back. Employees and political appointees can't fight back when he attacks them in his Twitter feed because to do so would risk their jobs or their reputations. Freddy couldn't retaliate when his little brother mocked his passion for flying because of his filial responsibility and his decency, just as governors in blue states, desperate to get adequate help for their citizens during the COVID-19 crisis, are constrained from calling out Donald's incompetence for fear he would withhold ventilators and other supplies needed in order to save lives. Donald learned a long time ago how to pick his targets.

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. It took forty-two years for the destruction to be completed, but the foundations were laid early and played out before Donald's eyes as he was experiencing his own trauma. The combination of those two things—what he witnessed and what he experienced—both isolated him and terrified him. The role that fear played in his childhood and the role it plays now can't be overstated. And the fact that fear continues to be an overriding emotion for him speaks to the hell that must have existed inside the House six decades ago.

Every time you hear Donald talking about how something is the greatest, the best, the biggest, the most tremendous (the implication being that he made them so), 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.

Donald has always been able to get away with making blanket statements ("I know more about [fill in the blank] than anybody, believe me" or the other iteration, "Nobody knows more about [fill in the blank] than me"); he's been allowed to riff about nuclear weapons, trade with China, and other things about which he knows nothing; he's gone essentially unchallenged when touting the efficacy of drugs for the treatment of COVID-19 that have not been tested or engaging in an absurd, revisionist history in which he's never made a mistake and nothing is his fault.

It's easy to sound coherent and somewhat knowledgeable when you control the narrative and are never pressed to elaborate on your premise or demonstrate that you actually understand the underlying facts. It is an indictment (among many) of the media that none of that changed during the campaign, when exposing Donald's lies and outrageous claims might actually have saved us from his presidency. On the few occasions he was asked about his positions and policies (which for all intents and purposes don't really exist), he still wasn't expected or required to make sense or demonstrate any depth of understanding. Since the election, he's figured out how to avoid such questions completely; White House press briefings and formal news conferences have been replaced with "chopper talk" during which he can pretend he can't hear any unwelcome questions over the noise of the helicopter blades. In 2020, his pandemic "press briefings" quickly devolved into mini-campaign rallies filled with selfcongratulation, demagoguery, and ring kissing. In them he has denied the unconscionable failures that have already killed thousands, lied about the progress that's being made, and scapegoated the very people who are risking their lives to save us despite being denied adequate protection and equipment by his administration. Even as hundreds of thousands of Americans are sick and dying, he spins it as a victory, as proof of his stunning leadership. And in the event that anybody thinks he's capable of being serious or somber, he'll throw in a joke about bedding models or lie about the size of his Facebook following for good measure. Still the news networks refuse to pull away. 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." The through line from Donald's early, destructive behavior that Fred actively encouraged to the media's unwillingness to challenge him and the Republican Party's willingness to turn a blind eye to the daily corruption he has committed since January 20, 2017, have led to the impending collapse of this once great nation's economy, democracy, and health.

We must dispense with the idea of Donald's "strategic brilliance" in understanding the intersection of media and politics. He doesn't have a strategy; he never has. Despite the fluke that was his electoral advantage and a "victory" that was at best suspect and at worst illegitimate, he never had his finger on the pulse of the zeitgeist; his bluster and shamelessness just happened to resonate with certain segments of the population. If what he was doing during the 2016 campaign hadn't worked, he would have kept doing it anyway, because lying, playing to the lowest common denominator, cheating, and sowing division are all he knows. He is as incapable of adjusting to changing circumstances as he is of becoming "presidential." He did tap into a certain bigotry and inchoate rage, which he's always been good at doing. The full-page screed he paid to publish in the New York Times in 1989 calling for the Central Park Five to be put to death wasn't about his deep concern for the rule of law; it was an easy opportunity for him to take on a deeply serious topic that was very important to the city while sounding like an authority in the influential and prestigious pages of the Gray Lady. It was unvarnished racism meant to stir up racial animosity in a city already seething with it. All five boys, Kevin Richardson, Antron McCray, Raymond Santana, Korey Wise, and Yusef Salaam, were subsequently cleared, proven innocent via incontrovertible DNA evidence. To this day, however, Donald insists that they were guilty—yet another example of his inability to drop a preferred narrative even when it's contradicted by established fact.

Donald takes any rebuke as a challenge and doubles down on the behavior that drew fire in the first place, as if the criticism is permission to do worse. Fred came to appreciate Donald's obstinacy because it signaled the kind of toughness he sought in his sons. Fifty years later, people are literally dying because of his catastrophic decisions and disastrous inaction. With millions of lives at stake, he takes accusations about the federal government's failure to provide ventilators personally, threatening to withhold funding and lifesaving equipment from states whose governors don't pay sufficient homage to him. That doesn't surprise me. The deafening silence in response to such a blatant display of sociopathic disregard for human life or the consequences for one's actions, on the other hand, fills me with despair and reminds me that Donald isn't really the problem after all.

This is the end result of Donald's having continually been given a pass and rewarded not just for his failures but for his transgressions—against tradition, against decency, against the law, and against fellow human beings. His acquittal in the sham Senate impeachment trial was another such reward for bad behavior.

The lies may become true in his mind as soon as he utters them, but they're still lies. It's just another way for him to see what he can get away with. And so far, he's gotten away with everything.