Chapter 1: Queens, Cruelty, and Fred Trump

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The Making of Donald Trump

The Beginning: The Man Who Would Break America

Nearly all men can stand adversity, but if you want to test a man’s
character, give him power. —Abraham Lincoln

In the late 1960s, while working as a DJ and news reporter at WITL radio in Lansing, Michigan, I saw firsthand how a democratic government can rapidly erode when it’s corrupted by official lies. As a teenager who’d been expelled from high school for starting an anti–Vietnam War newspaper, and then a member of Students for a Democratic Society at Michigan State University, I was subjected to police surveillance and arrest, experiences that to this day color my understanding of government.

Which is why when Louise and I watched the Confederate flag being paraded through the US Capitol on January 6, 2021, I felt a chill. This wasn’t just an insurrection; it was the culmination of institutional erosion I’ve documented for decades on my radio show and in my books, beginning with Johnson and Nixon during the Vietnam era.

Democracies don’t typically die suddenly. They erode gradually, their foundations weakened by corruption, the predations of the morbidly rich, and the systematic dismantling of institutional safeguards. America didn’t stumble into this Trump-driven crisis by accident. We were led here step by methodical step, with Donald Trump serving as an accelerant of institutional decay that began long before he entered politics in 2015.

To truly understand how a 246-year-old democracy could find itself on the brink of fascism, we must first understand the man who pushed it to the edge; not because he’s uniquely brilliant or powerful, but because his particular pathologies perfectly matched the vulnerabilities in our system. Trump’s lifelong patterns—his craving for dominance, his imperviousness to shame, his transactional notion of human relationships—became America’s crisis once they were amplified by presidential power.

In the chapters that follow, I trace the formation of a dangerous demagogue through three critical stages. First, we’ll return to that mansion in Queens, New York, where Fred Trump created a son incapable of empathy but desperate for validation, teaching young Donald that winning justified any means. Then we’ll examine how Roy Cohn—one of America’s most notorious political operatives—transformed Trump’s raw narcissism into tactical weaponry, training him to attack, never apologize, manipulate media, and treat the legal system as a weapon for personal vengeance rather than justice. Finally, we’ll see how Trump constructed a golden façade of success that masked decades of spectacular business failures, convincing millions he was qualified to lead the world’s most powerful nation despite decades of evidence to the contrary.

This isn’t just Trump’s personal story. It’s the chronicle of how America’s elites—bankers, media executives, political strategists—repeatedly enabled and profited from a man they knew to be dangerous. The Trump we see today wasn’t born; he was made, not just by family dysfunction but by systems that rewarded his worst impulses.

I’ve spent much of my life studying the intersection of power, psychology, and democracy’s fragility. What we’re witnessing isn’t unprecedented in global history, but it is unparalleled in American experience. With these insights into the making of Donald Trump, we begin to understand how democracies fall and, perhaps, how ours might still be saved.

Because this isn’t just about one twisted man. It’s about whether the American experiment can survive the forces he unleashed.

Chapter 1: Queens, Cruelty, and Fred Trump

It is easier to build strong children than to repair broken men.

—Frederick Douglass

What if the most dangerous man in the world wasn’t born a monster but was made one, in a mansion ruled by silence, fear, and cold ambition?

It was January 6, 2021, and Louise and I watched on CNN, mesmerized, as the Capitol of America was aflame with violence.

The marble halls of the Capitol, once symbols of democratic permanence, echoed with the sounds of shattering glass and enraged voices. Confederate flags—banners of treason that never made it inside the building during the Civil War—were being paraded past statues of Lincoln and Frederick Douglass. Police officers were beaten with the very flagpoles that moments earlier had flown the American flag. A gallows stood erected on the lawn, a noose swinging in the winter wind. And in the White House, just blocks away, the president of the United States watched it all unfold on television not with horror, but with fascination and satisfaction.1

Some asked how we got here; it was certainly a common question on my radio show in the following weeks. But the wiser question is: why didn’t we see it coming?

To understand Donald Trump—to truly comprehend how a reality TV host and failed casino magnate could bring the world’s oldest continuous democracy to the brink of collapse—we must go back to where it all began. Not to the golden escalator in 2015. Not to The Apprentice in 2004. Not even to his first bankruptcy or his first full-page newspaper ad calling for the execution of the wrongfully accused Central Park Five.2

We must return to a mansion in Queens. To a father who believed kindness was weakness. To a home that punished softness, grace, and generosity. To the childhood that created a president unburdened by conscience.

Because Donald Trump wasn’t born dangerous. He was shaped into a weapon by family, by mentors, and eventually by a political system too broken and too corrupted by money to stop him.

The Fortress in Jamaica Estates

Donald John Trump was born on June 14, 1946, the fourth of five children to Fred C. Trump and Mary Anne MacLeod Trump. Their home in Jamaica Estates, an exclusively (by law at the time) white enclave in Queens, was a twenty-three-room Tudor mansion, complete with imposing façade and coldly opulent interiors.3 It stood as both symbol and incubator for the Trump family ethos: success measured in dollars and dominance, emotions seen as weakness, empathy dismissed as naïveté.

Fred Trump was not merely a successful businessman; he was a man whose worldview had been shaped by the Great Depression and who had clawed his way to wealth through a combination of tenacity, opportunism, and a willingness to skirt laws when they proved inconvenient to his ambitions.4

The Federal Housing Administration had been created in the 1930s under Roosevelt to make home ownership possible for ordinary Americans, but Fred Trump saw it primarily as an opportunity for personal enrichment. He built government-backed housing projects, cutting corners on construction while maximizing profits, practices that would eventually lead to investigations and hearings before the US Senate Banking Committee in 1954.5

Fred’s approach to business mirrored his approach to parenting: extract maximum value, show no weakness, and win at all costs. He was a man who viewed kindness as a liability, emotions as indulgences, and his children as extensions of himself, measured not by their character or compassion, but by their ability to dominate others financially and psychologically.6

“He believed the world was filled with predators and prey—and only the ruthless would survive,” recalled Donald’s niece, Dr. Mary Trump, a clinical psychologist who later wrote that Fred was a “high-functioning socio­path” whose emotional absence and relentless focus on success created a toxic environment for his children. In her book Too Much and Never Enough, she described how her uncle Donald’s personality was formed in response to this emotional desert—his grandiosity, his need for constant validation, his inability to admit mistakes, and his casual cruelty all adaptive responses to a father who viewed vulnerability as unforgivable weakness.7

Fred would tell his children—particularly his sons—“You are a killer. . . . You are a king.”8 These weren’t casual encouragements. They were imperatives. In the Trump household, success wasn’t measured in happiness or fulfillment or contribution to community. It was measured in headlines, in square footage, in defeating others. And, even more gruesomely, it was zero-sum: for you to win, someone else had to lose.

Win-win was a totally alien concept in the Trump household, as we can see in Donald’s inability to work with other nations today. In his mind, you either dominate or are dominated. Everything is hierarchy. And whoever’s willing to be the most brutal must be the top dog.

Young Donald absorbed these lessons at his father’s knee: rules were for the weak, for the “losers” who lacked the wit and will to bend them to their advantage. Money wasn’t just wealth; it was a scoreboard. And people—­especially those with less power—were either useful or obstacles.9

A Mother’s Silence

While Fred dominated the household, Mary Anne MacLeod Trump played the role of an elegant but distant presence—one young Donald desperately tried to impress but rarely reached.10

She had come to the United States from Scotland as a teenager, fleeing poverty and hoping to build a life in New York. But after giving birth to her fifth child, she suffered serious medical complications, including hemorrhaging and infection, that left her ill for years. According to family accounts, she withdrew emotionally from her children, leaving the heavy lifting of parenting—and disciplining—to Fred.11

Mary Trump describes her grandmother as “neurotic and self-involved,” noting that Donald received little comfort or maternal affection during his formative years. This maternal absence, combined with Fred’s emotional detachment, created a household atmosphere that valued superficial strength over authentic connection.12

The Trump children competed fiercely for their father’s limited approval, and Donald quickly learned that audacity, aggression, and an absolute refusal to acknowledge failure were the currencies that earned Fred’s respect. Trump’s older brother, Fred Jr., took a different path, pursuing interests that did not align with their father’s vision. The elder Fred’s treatment of his namesake son was a lesson in itself: Fred Jr.’s gentler nature and lack of interest in the real estate business were treated as moral failings rather than personal choices.13

When alcoholism eventually overtook Fred Jr., leading to his death at age forty-two, the family’s response was not compassion but judgment. Donald would later cite his brother’s fate as the reason he abstained from alcohol, but the deeper lesson he seemed to take was not about the dangers of addiction but about the price of failing to embody Fred Trump’s ruthless values.14

Weakness is fatal, Donald concluded—a lesson that would shape his worldview for decades to come and eventually, catastrophically, inform his governing philosophy.15

A Childhood Marked by Discipline

This family dynamic was playing out against the backdrop of a changing America. The 1950s and 1960s, when Donald was coming of age, were decades of profound social transformation. The civil rights movement was challenging long-established racial hierarchies. The feminist movement was beginning to question traditional gender roles. The counterculture was rejecting materialism and militarism in favor of peace and communal values.

I saw this in my own family, having grown up in the same era. My “Eisenhower Republican” father, who saw Barry Goldwater as a hero (we campaigned door-­to-­door for him when I was thirteen in 1964), walked a neighborhood girl down the aisle when her father refused to because she was marrying a Black man. He printed on his mimeo machine the underground ’zine that got me kicked out of high school (a blessing that got me into college at sixteen) and defended me when I was arrested for protesting the Vietnam War, which he supported.

But inside the Trump mansion in Queens, time stood still. The values remained those of acquisition, dominance, and zero-sum competition. The outside world might be evolving toward greater equality and social justice, but in the Trump household, might still made right.16

Fred Trump’s real estate empire was built in part on racial exclusion. In 1973, the Justice Department sued Trump Management for discriminating against Black rental applicants, a case that was eventually settled with a consent decree. Donald, who by then had joined his father’s business, was named as a defendant alongside Fred. The tactics employed were not subtle: Black applicants would be told no apartments were available, while white applicants visiting the same buildings on the same day would be shown multiple options.17

This early exposure to racial discrimination as business practice cannot be overstated in its importance to understanding Donald Trump’s later political strategy. He learned not just that racism could be profitable, but that when confronted with evidence of wrongdoing, the best defense was a good offense: deny everything, countersue, claim persecution, and never, under any circumstances, admit fault or express remorse.18

From an early age, Donald exhibited behavior that challenged authority and sought attention. His antics at the Kew-Forest School in Queens included bullying peers and defying teachers. At the age of thirteen, after numerous disciplinary issues, Fred decided to send Donald to the New York Military Academy (NYMA), hoping that the structured environment would instill discipline.19

To Donald, however, this wasn’t just parental guidance. It was rejection, a father saying, “You are too much trouble, so I’m sending you away.” And rather than learning empathy or consideration for others, Donald took a different lesson: the way to succeed wasn’t to cooperate or show kindness, but to dominate within whatever system you found yourself.20

At NYMA, Trump found an environment that in many ways reinforced the hierarchical thinking he had absorbed at home. The military structure provided clear rankings, opportunities for visible achievement through promotions, and a value system that rewarded conformity to certain behavioral codes while encouraging competition for status. Trump thrived in this environment in some ways, earning athletic honors and rising to a leadership position as a student officer. But even here, his need to dominate led to problems; he was demoted from his position for hazing younger cadets, revealing an early pattern of abusing power when it was granted to him.21

This pattern would repeat throughout Trump’s life: an ability to initially impress authority figures and gain positions of power, followed by abuses of that power that would eventually lead to downfall, only to begin the cycle again in a new arena. What never changed was Trump’s conviction, instilled by Fred, that perception was more important than reality, that “winning” was the only value that mattered, and that admitting error was an unforgivable sign of weakness.22

The Lessons of a Real Estate Empire

When Trump moved beyond the relatively controlled environments of home and military school into the broader world, first as a student at Fordham University and later at the Wharton School of the University of Pennsylvania, the values he had internalized came with him. Though he would later boast of being a “brilliant student” at Wharton, contemporaries remember him differently: as academically unremarkable, more interested in his weekend trips to New York to work with his father than in engaging with ideas or broadening his intellectual horizons.23

What Trump was studying, more diligently than any academic subject, was his father’s business model. After all, it’s hard to underestimate the power of a parental role model, both in shaping worldview and teaching skills.

When I was around ten years old, my father and his best friend, Jerry Miller, started a vitamin company in our basement, buying a high-quality custom-made multivitamin in bulk that I and my brothers helped package into bottles with customized “Millhart Laboratories” labels. Dad and Jerry were adamant that their product was one of the best on the market, with a fierce pride in both the quality and integrity of their venture.

While the company never took off, I learned from my father how to be an entrepreneur, a lesson that led me to create five successful (and two unsuccessful) multimillion-dollar businesses as well as a residential treatment facility for abused children and, most recently, a national radio/TV program.

Unlike my dad, though, Fred Trump had built his fortune not primarily through brilliant innovation or exceptional quality, but through political connections, aggressive self-promotion, creative accounting, and the exploitation of government programs meant to serve the public good. He cultivated relationships with Brooklyn’s Democratic machine politicians, whose help he needed for zoning changes and building permits. He became adept at finding ways to extract maximum government subsidies for his projects while minimizing his tax liabilities.24

Most importantly, Fred understood the power of perception. Though his business was solidly middle-class housing, he presented himself as a developer of luxury properties, understanding that the appearance of success was often more valuable than success itself in attracting investors, placating lenders, and intimidating competitors. This lesson in the power of inflated claims and strategic hyperbole would become central to Donald Trump’s later business and political strategy.25

Fred’s impact on Donald extended beyond childhood. In the business realm, Fred served as both a mentor and a financial backer. He provided Donald with substantial loans and introduced him to key figures in the real estate industry. According to a New York Times Pulitzer Prize–winning investigation, Trump received at least $413 million (in 2018 dollars) from his father’s empire, much of it through tax schemes that legal experts described as “improper” and in some cases outright “fraudulent.”26

This financial safety net allowed Donald to take risks that other developers could not afford and to weather failures that would have bankrupted those who lacked his family backing. It also allowed him to maintain the image of success even during periods when his actual business performance was disastrous. The perception of success, cultivated through constant self-promotion and inflated claims about his wealth, became its own kind of currency, allowing him to continue attracting investors and lenders even as his actual track record raised serious questions.27

From Builder to Brand

By the 1980s, Trump had established himself not just as a real estate developer but as a brand, one built more on the perception of success than its reality. His 1987 book The Art of the Deal, ghostwritten by Tony Schwartz (who would later express deep regret for his role in creating the Trump mythology), presented a carefully curated version of Trump’s business philosophy and personal narrative. The book, like much of Trump’s self-presentation, emphasized his toughness, his instinctive brilliance, and his willingness to do whatever it took to win.28

“Most people are surprised by the way I work,” Trump (or rather, Schwartz) wrote in The Art of the Deal. “I play it very loose. . . . I prefer to come to work each day and just see what develops.” This seemingly casual approach to business decision-making would later find its parallel in Trump’s approach to governance—reactive, impulsive, guided more by personal instinct and immediate self-interest than by strategic planning or coherent ideology.29

The book also revealed another aspect of Trump’s psychology that would later prove significant: his zero-sum view of human interactions. “The final key to the way I promote is bravado,” he wrote. “I play to people’s fantasies. People may not always think big themselves, but they can still get very excited by those who do. That’s why a little hyperbole never hurts. People want to believe that something is the biggest and the greatest and the most spectacular. I call it truthful hyperbole. It’s an innocent form of exaggeration—and a very effective form of promotion.”30

This passage is remarkable not just for its explicit acknowledgment of Trump’s use of exaggeration as a marketing strategy, but for its framing of deception as “innocent” and its assumption that manipulating others’ perceptions is a legitimate business tactic. The line between “truthful hyperbole” and outright lying would prove increasingly blurry as Trump’s career progressed.

The Damage Done

Trump’s first presidency revealed the full consequences of the worldview he developed under Fred’s tutelage. The most damaging aspect wasn’t his individual policy decisions or even his personal behavior, but the way he systematically undermined the institutional foundations of American democracy.

He attacked the independence of the judiciary, describing judges who ruled against his policies as biased or corrupt.31 He politicized the Justice Department, pressuring it to investigate his political opponents and to go easy on his allies.32 He undermined public trust in the electoral system, claiming without evidence that millions of illegal votes had been cast in the 2016 election and laying the groundwork for his later refusal to accept the results of the 2020 election.33

Trump’s attacks on the media as “enemies of the people” echoed authoritarian rhetoric from some of history’s darkest chapters.34 His encouragement of violence against protesters at his rallies and his defense of white nationalists after the 2017 Charlottesville rally sent the message that certain types of political violence were acceptable.35 His use of presidential pardons for political allies convicted of crimes committed on his behalf signaled that loyalty to him personally superseded obedience to the law.36

All of these actions reflected the worldview formed in that mansion in Queens, under the tutelage of a father who valued winning above all else and who saw rules as obstacles to be overcome rather than as the foundation of a functioning society. Trump brought to the presidency not just Fred’s values but his methods: divide and conquer, use fear as motivation, reward loyalty, punish dissent, admit no error, and always, always attack rather than defend.37

The consequences would eventually culminate on January 6, 2021. As Louise and I watched the Capitol breach unfold on television, it was impossible not to see it as the logical endpoint of the child formed in that Queens mansion decades earlier: a psychology that viewed compromise as weakness, dominance as virtue, and rules as applying only to others.

This is how democracies die as we’ve seen over and over again across the world; not in a single blow, but through a million small corruptions, each one making the next easier, until the infrastructure of democracy has been hollowed out from within. It doesn’t require tanks in the streets. It just requires a population willing to trade truth for tribal satisfaction, ethics for entertainment, and democracy for the promise of punishing their enemies.38

Fred Trump’s most lasting legacy wasn’t the buildings he constructed or the fortune he amassed. It was the belief system he instilled in his son, a system defined by its absence of empathy, its worship of dominance, and its view of human relationships as purely transactional.

The story that began in that mansion in Queens is still playing out before us. Donald Trump’s psychology, shaped by a father who valued dominance over decency and perception over reality, continues to corrupt American politics in profound ways as he’s now set out to fundamentally alter the nature of our American system of government.

This is the true danger: not just what Trump did, but what he made possible and is now doing.

Trump was never simply a personal anomaly. He was the product of systems: a family system that rewarded cruelty and punished empathy. A business system that valued perception over reality. A political system that had gradually surrendered to the power of money (largely as the result of a series of corrupt all-Republican-appointee Supreme Court decisions) and spectacle. A media system that prioritized outrage over truth. And a culture that had, in too many ways, confused the trappings of success with character.

Understanding how we arrived here is vital; it’s the first, necessary step in preventing what could happen next. For unless we confront the damage already done—to our institutions, to our shared understanding of truth, and to our capacity for empathy and collective action—we may find ourselves not at the end of an aberrant presidency, but at the beginning of something far worse: an America where democracy survives in name only, while power flows unchecked to those willing to abandon all principle in its pursuit.