Chapter 2: Roy Cohn’s Apprentice

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Chapter 2: Roy Cohn’s Apprentice

Power is not what you have but what the enemy thinks you have.

—Saul Alinsky, Rules for Radicals

I was twenty-two in 1973 and had just started an herbal tea company when I became entranced by the business self-help movement. Louise and I listened to Earl Nightingale tapes in the car when we’d take weekend two-hour drives up to my grandparents’ house in Newaygo, Michigan. I read books by Napoleon Hill (Think and Grow Rich) and Claude Bristol (The Magic of Believing) so many times I had entire sections memorized. I got a “pillow speaker” so I could go to sleep at night listening to their tapes.

W. Clement Stone, the insurance multimillionaire, had created a foundation that distributed posters and stickers with his slogans—“Do It Now!” and “Thinking will not overcome fear but action will!”—on them, and they decorated our apartment. I took the Dale Carnegie Course on public speaking, probably the best decision (outside of marrying Louise) of my life; it was transformational.

That was an era when many young people in business were looking for role models and mentors, a reboot of the 1930s when Norman Vincent Peale had electrified a generation of small-businesspeople with his books The Art of Living and You Can Win. My business mentor was a guy named Terry O’Connor who owned a small advertising agency in Lansing and took me under his wing; I learned a lot, we became lifetime friends, and we started two businesses that made us both a lot of money (and a third one that never really got going).

Donald Trump was, during that same time, also looking for a mentor, as his father was far too conventional and wed to his Queens properties for Donald’s taste. So, before he had a movement, a base, or a party, Donald had Roy Cohn. And that was, for him, more than enough.

It was 1973, and the Trump real estate empire faced its first major crisis. The Justice Department had filed a lawsuit against Donald Trump, his father Fred, and their company, charging them with systemic discrimination against Black renters, a serious allegation that threatened not just their business but their carefully cultivated public image. Trump, then just twenty-seven years old and eager to establish himself in Manhattan, not just Queens, needed help.1

At Le Club, a Manhattan nightspot frequented by the city’s power brokers, Trump was introduced to a forty-six-year-old attorney whose reputation preceded him—a man whose name had been infamous in American politics for two decades, whose tactics were feared, and whose absence of ethics was legendary.

Roy Marcus Cohn.

What happened next would transform not just Trump’s approach to business and, eventually, politics, but the very character of American public life. For in Roy Cohn, Donald Trump found more than just a lawyer. He found a template, a model for how to wield power ruthlessly, how to manipulate media shamelessly, and how to crush opponents mercilessly.2

If Donald Trump is the political id of twenty-first-century America—rageful, shameless, and obsessed with dominance—then Roy Cohn was his emotional blueprint and strategic godfather. Every autocrat has a tutor. Every bully, a coach. For Trump, that man was Roy Cohn: the disgraced former McCarthyite who taught him that lying was a strategy, lawsuits were weapons, and admitting fault was suicide.

Trump didn’t just admire Roy Cohn. He absorbed him. And in doing so, he inherited a political playbook so effective and corrosive that it would one day redefine the Republican Party itself and bring American democracy to the brink of collapse.3

The Making of a Monster

By the time he met Donald Trump in 1973, Roy Cohn was already an infamous figure in American political history, a man whose name was synonymous with character assassination, reckless accusation, and ruthless pursuit of power at any cost.

Born to an affluent Jewish family in the Bronx in 1927, Cohn was a prodigy of sorts, entering Columbia Law School at just seventeen and becoming a prosecutor in the US Attorney’s Office in Manhattan by twenty.4 But it was his role in the 1951 espionage trial of Julius and Ethel Rosenberg that first brought him to national attention. As the assistant prosecutor, the twenty-four-year-old Cohn pushed aggressively for the death penalty, particularly for Ethel, despite substantial questions about the extent of her involvement in her husband’s espionage. As Cohn would later boast in his autobiography, he had privately lobbied the judge for the death sentence, an extraordinary ethical breach for a prosecutor.5

Cohn’s ruthlessness in the Rosenberg case revealed something fundamental about his character that would later resonate deeply with Trump: the belief that winning justifies any means. In his pursuit of the death penalty for Ethel Rosenberg—a mother of two young boys—Cohn manipulated evidence, pressured witnesses, and engaged in ex parte communications with the judge.6

Years later, declassified Soviet cables would show that while Julius Rosenberg was indeed a spy, the evidence against Ethel was much weaker. David Greenglass, Ethel’s brother and the key witness against her, would eventually admit that he had lied in his testimony at Cohn’s urging.7 The execution of Ethel Rosenberg remains one of the most controversial judicial killings in American history (even my dad, the anti-communist Republican, was troubled by it), and Cohn’s role in it established his willingness to destroy lives in service of his ambitions.

This early triumph caught the attention of Senator Joseph McCarthy, who made Cohn his chief counsel during the infamous anti-communist hearings of the early 1950s. Together, McCarthy and Cohn embarked on a campaign of accusation, innuendo, and character assassination that ruined countless lives and careers without ever uncovering a single Soviet spy.8 Their tactics were as simple as they were devastating: make bold, inflammatory accusations; demand that the accused prove a negative; use the media to amplify fear; and never, ever back down from a claim, no matter how thoroughly debunked.

The hearings revealed another aspect of Cohn’s character that would later influence Trump: his mastery of media manipulation. Cohn understood intuitively that appearance often matters more than reality, that bold assertions frequently override facts, and that the camera loves conflict and controversy. He staged the hearings as theater, complete with dramatic revelations, confrontational exchanges, and shocking accusations, all designed to create compelling television that would keep Americans fearful and McCarthy powerful.9

The McCarthy hearings finally collapsed in 1954 during the Army-McCarthy proceedings, when the Army’s counsel Joseph Welch famously asked McCarthy, “Have you no sense of decency, sir? At long last, have you left no sense of decency?”10 It was the beginning of the end for McCarthy, but not for Cohn. He resigned and retreated to New York, where he reinvented himself as a power broker and attorney for the city’s elite—and its underworld. His client list eventually included Catholic Cardinal Francis Spellman, Yankees owner George Steinbrenner, the Roman Catholic Archdiocese of New York, and various mafia figures, including bosses Tony Salerno, Carmine Galante, and John Gotti.11

This ability to reinvent himself after catastrophic public failure would become another lesson Trump absorbed. Just as Cohn had transformed from disgraced McCarthy henchman to celebrated New York power broker, Trump would later reinvent himself repeatedly: from failed casino magnate to reality TV star, from bankrupt businessman to self-proclaimed billionaire, from tabloid joke to president of the United States. The key was never to acknowledge defeat, but to immediately claim a new victory.12

By the 1970s, Cohn had developed a reputation as a fixer who could make problems disappear, often through intimidation, threats, and his extensive connections within New York’s judicial system and media. As his former law partner Tom Bolan once explained, “Roy’s standard method was to attack, attack. Even when he was wrong, especially when he was wrong.”13

It was this man—a master of ethical corruption and aggressive counterattack—who would become Donald Trump’s most important mentor.

The Meeting of Minds

When Trump and Cohn first met at Le Club in 1973, Trump didn’t just see a potential lawyer. He saw a kindred spirit. As Trump would later recount: “I knew that Roy was the right guy for me. . . . He was a genius. He was a savage. He didn’t care what anyone said about him. He would do anything to win.”14

The meeting came at a critical juncture for the young Trump. At twenty-seven, he was eager to break out of his father’s shadow and establish himself in Manhattan real estate—a world far more glamorous and prestigious than Fred Trump’s outer-borough apartment buildings. But he faced a significant obstacle: the Justice Department lawsuit alleging racial discrimination in Trump properties.

The evidence was substantial: Black applicants were routinely turned away from Trump buildings or told no apartments were available, while white applicants were shown multiple options. Former employees testified about marking applications from Black renters with a “C” for “colored.” Testers from the New York Urban League had documented the discrimination firsthand.15

For most defendants, especially those seeking to build a reputation in New York’s high society, such allegations would have been cause for quiet settlement and reform. But Cohn saw an opportunity to teach his new protégé a different approach.

Cohn’s advice on the Justice Department’s housing discrimination lawsuit was simple and direct: Never settle. Counterattack. Sue the government for $100 million for defamation. Call the prosecutors racists themselves. According to Trump’s own account, Cohn told him, “Tell them to go to hell and fight the thing in court and let them prove you discriminated.”16

Trump followed Cohn’s advice to the letter, holding a press conference to denounce the lawsuit as “outrageous.” The Trump Organization filed a $100 million countersuit against the DOJ, a suit that was quickly dismissed by the court as frivolous. But the aggressive posture worked in the court of public opinion. After two years of legal battles, the case was settled with a consent decree in which the Trumps made no admission of guilt and committed to only nominal changes in their rental practices. Trump claimed victory, though, in reality, the case had revealed a pattern of racial discrimination that would continue in various forms throughout Trump’s career.17

For Trump, however, the takeaway was clear: Cohn’s approach—deny, attack, never admit fault—was effective. It was the beginning of a relationship that would last more than a decade, with Cohn serving as Trump’s lawyer, fixer, media handler, and most importantly, his tutor in the dark arts of power and manipulation.18

The relationship between Trump and Cohn quickly deepened beyond the professional. Trump became a fixture at Cohn’s lavish dinner parties at his townhouse on East 68th Street, where politicians, judges, mobsters, and celebrities mingled freely. Through Cohn, Trump gained access to a world of power and connection that would prove invaluable to his ambitions. Cohn introduced Trump to political fixers like Roger Stone and media power brokers like Rupert Murdoch, relationships that would later prove crucial to Trump’s political ascent.19

For his part, Cohn found in Trump an eager student, someone with the wealth, ambition, and moral flexibility to fully implement his philosophy. As journalist Ken Auletta observed after watching the two men interact at numerous social events: “There was something almost paternal in how Roy treated Donald. He was molding him, and Trump was drinking it all in.”20

The Cohn Doctrine

What did Donald Trump learn from Roy Cohn? The lessons were as simple as they were poisonous:

First, never apologize or admit wrongdoing, ever. Cohn viewed contrition as weakness and would rather die (literally, as it turned out) than acknowledge error or fault. As journalist Ken Auletta, who covered Cohn extensively, noted, “The idea that you can admit a mistake is not part of Roy’s genetic code.”21 This principle would become so fundamental to Trump’s approach that even faced with irrefutable evidence—a recorded confession of sexual assault on the Access Hollywood tape, for instance—he would deny, deflect, and attack rather than offer the slightest acknowledgment of impropriety.22

Second, always counterattack, and always with greater force than you received. When criticized or accused, Cohn’s response was invariably to hit back harder, to escalate, to make the accuser regret ever mentioning his name. As Cohn himself explained to a reporter: “I bring out the worst in my enemies, and that’s how I get them to defeat themselves.”23 This tactic became Trump’s signature move, whether attacking Gold Star parents who criticized him, mocking a disabled reporter who questioned his claims, or threatening critics with lawsuits and retribution.24

Third, use the legal system as a weapon, not a recourse for justice. Cohn taught Trump that lawsuits were instruments of intimidation, not vehicles for dispute resolution. He filed cases not to win—though winning was nice—but to punish, to harass, and to silence. The expense and stress of litigation was the point, not the legal outcome. Trump would eventually be involved in over 3,500 lawsuits—an unprecedented number for any American businessperson or politician—using the courts not to seek justice but to exhaust opponents with fewer resources.25

Fourth, manipulate the media ruthlessly. Cohn was a master at planting stories, cultivating journalists, and creating controversy to serve his ends. He understood that perception trumped reality, that bold claims often went unchallenged, and that most people would remember the accusation but not the retraction.26 Trump elevated this approach to an art form, calling reporters using pseudonyms like “John Barron” to plant favorable stories about himself, staging pseudo-events to attract coverage, and later, using Twitter to bypass media filters entirely and inject his unfiltered messages directly into the public consciousness.27

Fifth, use fear as both shield and sword. Cohn understood that people who are afraid—of communists, of crime, of social change, of the “other”—are easier to manipulate and more willing to accept authoritarian solutions. He helped McCarthy weaponize the Red Scare, stoking paranoia about secret communists undermining America from within.28 Trump would adapt this tactic to the twenty-first century, stoking fears about immigrants, Muslims, “inner city” crime, and later, a “deep state” conspiracy, always positioning himself as the only solution to these terrifying threats.29

Finally, build a fortress of loyalty around yourself. Cohn demanded absolute devotion from his clients and associates, and he repaid it in kind, at least until they were no longer useful. He created a network of mutual obligation and fear that served as both sword and shield in his battles.30 Trump’s infamous demand for loyalty—from James Comey, from his cabinet members, from Republican legislators—and his swift punishment of perceived disloyalty, all echo Cohn’s approach to power.31

Trump absorbed these lessons like a sponge. As journalist Wayne Barrett, who covered Trump for decades, observed: “Cohn’s philosophy shaped the real estate developer’s worldview and the belligerent public persona visible in Trump’s presidential campaign.”32

The evidence of Cohn’s influence is everywhere in Trump’s subsequent career. The constant lawsuits against journalists, critics, and former associates. The reflexive counterpunching. The use of nondisclosure agreements and threats. The demand for loyalty. The refusal—ever—to acknowledge error or defeat. Each is a page torn directly from Cohn’s playbook.33

But perhaps the most important lesson Trump learned from Cohn was the most dangerous: that institutions can be bent and broken if one is shameless enough, aggressive enough, and persistent enough. Cohn had repeatedly violated legal ethics, manipulated the press, corrupted judges, and intimidated witnesses—all while maintaining his position as a respected (if feared) member of New York society.34 Trump observed that the safeguards designed to protect democracy and ensure accountability—the courts, the press, regulatory agencies, ethical norms—were far more vulnerable than they appeared, especially when confronted with someone willing to attack them relentlessly and without shame.35

The End of the Relationship, but Not the Influence

By the mid-1980s, Cohn’s health was failing. His legal career was collapsing as well: he had been the subject of numerous disciplinary proceedings and was eventually disbarred in 1986 for “dishonesty, fraud, deceit, and mis­representation.”36

As Cohn approached death, Trump began to distance himself. The pattern would become familiar in Trump’s later life; the discarding of associates who could no longer serve his purposes. According to Roger Stone, a mutual associate: “When Roy got sick, Donald dropped him like a hot potato.”37

The final betrayal was particularly cruel. When Cohn was diagnosed with AIDS—a condition he denied to the end, insisting he had liver cancer—­­he reached out to Trump for support. Cohn had, after all, been Trump’s most important mentor, had guided his entry into Manhattan real estate, had protected him from the DOJ, had connected him with powerful figures who advanced his career. But Trump, sensing that Cohn was no longer useful and potentially a liability, distanced himself. When Cohn called asking Trump to find him a room at one of his hotels where he could recover, Trump reportedly promised to help but never called back.38

Cohn’s final months were a stark illustration of the transactional worldview he had helped instill in Trump. As Cohn lay dying, many of his former clients and associates abandoned him, not just because of his illness, but because his power was gone. In the world Cohn had constructed, where relationships were based on utility rather than loyalty or affection, his declining health rendered him worthless. It was the logical endpoint of the philosophy he had lived by and taught to Trump: people matter only to the extent they can serve your interests. When they can no longer do so, they are discarded.39

When Cohn died in August 1986, Trump was not among the mourners at his funeral. But the lessons Cohn had taught him—the tactics, the worldview, the absolute commitment to winning at all costs—remained. Trump had not just hired Cohn; he had internalized him. And the influence of that relationship would extend far beyond Atlantic City or Manhattan real estate.40

It would, in time, shape the American presidency itself.

“Where’s My Roy Cohn?”

In 2018, as the Russia investigation intensified and legal troubles mounted, President Trump reportedly slammed the table in the Oval Office and demanded: “Where’s my Roy Cohn?”41

The question revealed more than just Trump’s frustration with his then-Attorney General Jeff Sessions. It revealed the entire template for his view of the Justice Department, of law enforcement, of the very concept of rule of law. In Trump’s mind, shaped by Cohn’s toxic tutelage, the attorney general was not the nation’s chief law enforcement officer, bound by constitutional oath and legal ethics. He was the president’s personal fixer, his attack dog, his protector.42

This view—profoundly anti-democratic and fundamentally corrupt—­permeated the first Trump presidency. William Barr’s misleading summary of the Mueller Report, the firing of US attorneys investigating Trump associates, the persistent attacks on “disloyal” FBI officials, the dangling of pardons to silence potential witnesses: each echoed Cohn’s approach to legal institutions as tools of personal power rather than guardrails for democratic governance.43

The Trump years didn’t just damage American institutions. They exposed their vulnerability to a president willing to deploy Roy Cohn’s tactics from the Oval Office. And they revealed how quickly democratic norms and constitutional safeguards can crumble when confronted with a leader who refuses to acknowledge their legitimacy or accept their constraints.44

In the end, Roy Cohn’s lasting legacy wasn’t just his influence on Donald Trump. It was his demonstration of how American democracy could be attacked, not from outside, but from within, using the very tools and institutions designed to protect it as weapons to undermine it. Trump simply took the Cohn playbook and scaled it to national proportions.

And we’re still living with the consequences.45