Capitolo 1
The Art of Reinvention: How Trump Built an Empire on Perception
America's most polarizing president was once just a boy from Queens, standing outside his own tower on Fifth Avenue, watching for reactions from passersby. For Donald Trump, this validation became his narcotic-a craving that would drive him from local real estate developer to reality TV star to the highest office in the land. The book "Confidence Man" by New York Times journalist Maggie Haberman has become a cultural touchstone for understanding Trump's psyche, drawing praise from across the political spectrum for its unflinching examination of a man who reshaped American politics. Former President Barack Obama reportedly kept it on his nightstand, while The Atlantic called it "the most devastating portrait of Trump" ever written. What makes this work so compelling is Haberman's unique vantage point-having covered Trump for decades in New York before following him to Washington, she brings unparalleled insight into how his formative experiences in the cutthroat world of New York real estate created the template for his presidency.
Capitolo 2
The Unreliable Narrator of His Own History
Donald Trump's relationship with truth has always been complicated. One of his earliest self-mythologies involved the 1964 dedication of the Verrazano-Narrows Bridge. Eighteen-year-old Trump claimed he watched in pouring rain as elderly engineer Othmar Ammann stood ignored while politicians who had opposed the bridge received praise. "I realized then and there that if you let people treat you how they want, you'll be made a fool," Trump recalled. But almost nothing about this story was true-weather reports showed a cloudless day, Ammann was Swiss (not Swedish as Trump claimed), and far from being ignored, the engineer received special recognition during the ceremony.
This pattern of reshaping reality to fit his narrative became Trump's lifelong habit. As a Fordham freshman, his interests already extended beyond his father's real estate empire. Though he would later boast about attending Wharton, Trump had initially considered studying film at USC, maintaining a lifelong movie obsession. Unlike his father Fred's practical approach to building middle-class housing, Donald conceived of properties on an excessively grand scale, wanting to "put some show business into the real estate business."
Fred Trump cast a long shadow over Donald's life. An effective businessman who created expansive middle-class housing developments, Fred knew how to cut corners and cultivate political connections. He viewed government as existing to serve businessmen when not harassing them. Fred's approach to fatherhood-undermining his children, pitting them against each other, focusing singularly on maximizing profits-better suited overseeing a business than a family. Donald inherited this way of being, but without his father's first-generation immigrant work ethic.
The Trump family's American roots began with Friedrich Trump, who fled Germany in 1885 to avoid military service. After working as a barber in New York, he sought fortune during the Gold Rush, operating businesses catering to miners-possibly including brothels. Though he became a U.S. citizen in 1892, he was expelled from Germany after briefly returning with his wife Elizabeth, having dodged military service. The couple settled permanently in the Bronx, where they spoke German at home and where Frederick Christ Trump was born in 1905. When Friedrich died during the 1918 flu pandemic, twelve-year-old Fred inherited a substantial fortune from his father's prospecting-town holdings and Queens land parcels.
Young Donald showed signs of aggression early-at five years old, he was caught throwing rocks at a baby in a playpen. The Trump household in Jamaica Estates was materially privileged but emotionally cold. Fred Trump was formal, rigid and critical, while his wife Mary Anne MacLeod Trump remained emotionally reserved despite her social appearances. After Mary's emergency hysterectomy following her youngest son's birth in 1948, Fred instructed daughter Maryanne to continue attending school normally despite her mother's life-threatening condition. Young Donald developed a reputation for bullying, particularly targeting his younger brother Robert-once proudly gluing Robert's toy blocks together to build his own tower.
Capitolo 3
The Roy Cohn Education
In October 1973, the Justice Department sued Trump Management for discriminatory rental practices against Black tenants, naming both Fred and Donald. Investigations had found just seven Black families in Fred's 3,700-apartment Trump Village complex. Unlike developer Samuel LeFrak, who quickly settled a similar suit, Donald chose to fight, following advice from his new mentor Roy Cohn: "Tell them to go to hell and fight the thing in court."
Roy Cohn-former prosecutor in the Rosenberg spy case, chief investigator for Senator Joseph McCarthy, and now a private attorney representing mobsters and celebrities-became Trump's most influential mentor. Despite Cohn's reptilian appearance, Trump was drawn to his approach. Short, slight, with a scarred face and receding hairline, Cohn specialized in emotional terrorism and intimidation. Yet he was also charming and generous with friends, maintaining relationships with Barbara Walters, Rupert Murdoch, and Nancy Reagan.
From Cohn, Trump learned that everything could be treated as a transaction, and that a person's worth was determined by whether Cohn liked them. While Fred had given Donald access to Brooklyn and Queens power networks, Roy unlocked a bigger world of contacts in sports, politics, media, and a seamier roster of clients. Cohn taught Trump to fight more strategically rather than by instinct alone, providing a form of "lead-pipe protection" that would shape Trump's approach to conflict for decades to come.
Trump's response to the housing discrimination suit established his lifelong approach to legal challenges: defend himself with a combination of outright falsehoods and claims of victimhood. With Cohn's help, Trump countersued the federal government for $100 million, using inflammatory language comparing investigators to "stormtroopers" and conducting "gestapo-like interrogation." Though the tactics succeeded in public relations, they failed legally. In 1975, Trump signed a consent decree promising non-discrimination, but for decades afterward highlighted that there was no admission of wrongdoing-his personal victory from what was essentially a defeat.
By 1975, New York City faced bankruptcy, with mass layoffs including five thousand police officers. Public safety unions pressured Mayor Beame by distributing pamphlets warning tourists about crime, titled "WELCOME TO FEAR CITY." For a businessman like Trump seeking public backing for his projects during the city's vulnerability, this atmosphere of crisis would prove useful.
Capitolo 4
Building the Trump Brand
With PR executive Howard Rubenstein's help, Trump began reinventing himself through press conferences promoting his projects. Initially nervous before cameras, he quickly became addicted to the spotlight. A 1976 New York Times profile portrayed him as a well-liked wunderkind and "real estate promoter," where he falsely claimed to be "publicity shy" and perpetuated his father's fiction that the family was Swedish rather than German-a post-WWII tactic to avoid alienating Jewish tenants.
Trump's choice of concrete for Trump Tower meant dealing with New York's mob-infiltrated construction industry. While Fred Trump had acknowledged working with Genovese crime family associates in the 1950s, Donald accepted mob presence as an inevitable part of New York real estate, telling Haberman: "You had contractors and you don't know if they were mob or controlled... getting bids sometimes is very tough."
Despite growing up in Queens, one of the most racially and ethnically diverse places on earth, Donald Trump had few meaningful interactions with New Yorkers of color and showed little interest in the civil rights movement that coincided with his college years. His worldview reflected a transactional approach to race relations, often referring to ethnic groups as "the Blacks" or "the Hispanics"-viewing them as discrete units to be won over in business or politics rather than as individuals.
Trump's most sustained encounters with Black people came through his sports ventures. After purchasing the New Jersey Generals football team in 1983, he cultivated relationships with players, particularly Herschel Walker. In Atlantic City, Trump began hosting prizefights featuring predominantly Black boxers to attract casino guests. Don King connected Trump with Al Sharpton partly to help secure fights with young boxing phenom Mike Tyson.
As Trump expanded beyond his sheltered upbringing, he cultivated an image as a sexually voracious bachelor, frequently discussing women in crude terms and parading high-profile dates before paparazzi. Even after marriage, he continued objectifying women in coarse detail, often shocking dinner companions with inappropriate sexual comments.
Capitolo 5
The Art of the Comeback
In 1988, Trump outbid numerous investors, including the Sultan of Brunei, paying $407.5 million for the Plaza Hotel-though he publicly claimed it cost only $390 million. He didn't finance the purchase himself but personally guaranteed portions of loans from Citibank and others. Trump appointed Ivana to manage the hotel "for $1 a year plus all the dresses she can buy," similar to her previous role at Trump Castle casino.
Following the October 1987 stock market crash, New York real estate and Atlantic City casinos cooled significantly, devaluing Trump's assets while his high-interest debts remained. Yet Trump continued spending recklessly, developing a reputation for "greenmail"-making unsolicited offers for companies like American Airlines, driving up stock prices, then withdrawing. He acquired a sports team, airline, megayacht and numerous properties using borrowed money at exorbitant interest rates.
The Trump Taj Mahal Casino and Resort opened in April 1990 with Trump calling it the "eighth wonder of the world" and bringing friend Michael Jackson for publicity. But the opening week proved disastrous-few celebrities attended, guests got lost in the enormous building, room keys didn't work, and cash machines failed. Worst of all, casino employees hadn't followed state protocols for tracking slot machine cash. The Taj needed $1.3 million daily revenue just to stay afloat, and Trump's financial troubles were mounting.
By August 1990, The Wall Street Journal revealed Trump had a negative net worth of as much as $294 million. The Taj Mahal was struggling as analysts had predicted, and Trump threatened bankruptcy unless his debt was restructured. In December, Fred Trump secretly rescued his son by sending a lawyer with $3 million in cash to exchange for gaming chips at Trump Castle-an undisclosed loan that violated state regulations and resulted in fines when discovered. Despite this family bailout, Trump publicly claimed he had met his debt obligations through business strength.
Trump's marriage to Ivana deteriorated as he began an affair with Marla Maples, a stunning blonde former beauty queen and aspiring actress seventeen years his junior. Trump grew frustrated with Ivana's business ambitions and social circuit obligations, declaring "My life is shit" after her calls about dinner arrangements. On February 11, 1990, the New York Daily News broke the story of Trump's affair, ending months of rumors. The divorce became a tabloid war, with the Daily News supporting Ivana and the New York Post backing Donald.
Capitolo 6
The Television Reinvention
In 2002, Mark Burnett approached Trump at Wollman Rink with an idea for "Survivor, but with asphalt instead of jungle." NBC's entertainment president Jeff Zucker eagerly acquired the show, seeing Trump as both star and publicist. Trump was initially paid mid-five figures per episode to host "The Apprentice," where sixteen contestants competed for a job at the Trump Organization. The boardroom elimination scenes, where Trump delivered his ad-libbed "You're fired" catchphrase, became the show's centerpiece.
Debuting in January 2004, the show was a massive hit, even as Trump's casinos faced a fourth bankruptcy. When negotiating his second season contract, Trump bizarrely showed NBC executives a financial statement claiming $4 billion in wealth and demanded $1 million per episode. Though he settled for a modest raise, the show ultimately provided him over $400 million in earnings and immeasurable public validation.
The success of "The Apprentice" transformed Trump's public image. NBC publicity director Jim Dowd noted the stark difference in public reception before and after the show premiered: "He was a hero, and he had not been one before." The show established Trump as a regular media guest discussing topics far beyond business, solidifying his place in American popular culture.
Trump found comfortable rapport on Howard Stern's show, bringing along his children Ivanka and Don Jr. He discussed his sexual exploits, boasted about wandering backstage at beauty pageants while contestants changed, and engaged in sexist banter that portrayed him as an unapologetic alpha male. When pitching a race-divided season of "The Apprentice" with "nine Black contestants against nine white people, who would all be blondes," he gleefully recounted NBC executives' shocked reaction to Stern's approving audience.
In 2009, as Trump's fifteenth book was about to be published, Vanguard Press's online-marketing director Peter Costanzo introduced Trump to Twitter. Creating the @realDonaldTrump handle (since @donaldtrump was already taken), Costanzo explained that Trump would need to personally engage for the account to succeed. Twitter proved perfect for Trump-allowing him to speak directly to followers without challenge.
Capitolo 7
The Political Apprentice
After the 2010 midterm elections that saw Republicans reclaim the House, the party lacked a clear presidential frontrunner who could harness the Tea Party's energy. Mitt Romney, the establishment choice, was viewed as too moderate, while populist candidates like Michele Bachmann lacked general election viability. Into this void stepped Donald Trump, reconnecting with Roger Stone who had published a column arguing conditions were right for Trump to run in 2012.
By March 2011, Trump had fully embraced the false "birther" conspiracy, telling ABC News he had "a little doubt" about Obama's birthplace because "nobody knew him" growing up. Despite warnings from Stone that he'd be called racist, Trump deliberately escalated these claims in each interview, even falsely claiming he had dispatched investigators to Hawaii who "cannot believe what they're finding." The mainstream media's attempts to fact-check only spread the lie further, which served as coded language suggesting the first Black president illegitimately held office.
At the 2011 White House Correspondents' Dinner, Obama systematically humiliated Trump, displaying the birth certificate on large screens before delivering a scathing roast: "Now he can finally get back to focusing on the issues that matter-like, did we fake the moon landing?" Obama mocked Trump's "credentials and breadth of experience" by referencing his Celebrity Apprentice decisions. Trump maintained a frozen expression with slightly furrowed eyebrows, managing only a tight smile and small wave. Despite his team's insistence that he enjoyed being the center of attention, multiple advisers later privately acknowledged his misery at being laughed at by three thousand people.
By 2015, Trump was ready to launch a genuine campaign. His official campaign kickoff featured his theatrical escalator descent in Trump Tower before a crowd partially filled with hired attendees. Discarding his prepared remarks, Trump delivered an hour-long, rambling speech filled with unverifiable boasts, paranoid warnings about foreign threats, and grievances about trade. His inflammatory comment that Mexican immigrants were "rapists" dominated headlines, overshadowing Jeb Bush's announcement from the previous day.
Every few weeks, pundits predicted Trump's campaign would collapse over some new outrage-from declaring Iraq War deaths pointless to his misogynistic attack on Megyn Kelly to spreading conspiracy theories about vaccines causing autism. Yet Trump would simply wait out each controversy and bounce back, a phenomenon unprecedented in modern political history. His base remained loyal regardless of his statements, leading one adviser to marvel, "I've never seen a situation before where someone fucks up and their numbers go up."
Capitolo 8
The Presidency
Two days after his unexpected victory, Trump met with President Obama in the Oval Office for what was scheduled as a one-hour meeting but stretched to ninety minutes. Rather than discussing substantive policy matters, Trump approached the meeting as two political maestros exchanging notes, asking Obama how he maintained high approval ratings and boasting about manipulating media. Obama repeatedly steered the conversation back to serious matters, warning about North Korea, emphasizing the importance of personnel choices, and suggesting Trump could rebrand Obamacare as "Trumpcare" with added Medicaid subsidies.
Trump approached the White House like a family business, even trying to make employees sign unenforceable non-disclosure agreements. Reince Priebus became chief of staff while Bannon was named chief strategist with unprecedented access, including a seat on the National Security Council. Kushner established himself as a shadow president with an enormous portfolio including Middle East peace and trade negotiations, despite his stunning lack of preparation on basic governance.
Trump remade the White House to suit his tastes, adding televisions to his bedroom and bathroom, installing carpet in his bathroom like on his private jet, and displaying Trump-branded toiletries. He kept unusual hours, waking as early as 5:00 a.m. but starting his workday progressively later, eventually closer to 10:30 a.m. He spent mornings watching television and tweeting responses as if still at Trump Tower rather than leading the government. Evenings were spent in the residence watching recorded shows and making phone calls.
Trump's paranoia manifested in document handling-he tore up papers and sometimes flushed them down toilets, requiring staff to tape them back together to comply with records laws. His germaphobia was evident in his constant use of hand sanitizer that left his hands raw. Without Melania, who stayed in New York for months with their son, Trump seemed particularly anxious, having few genuine friends despite many hangers-on.
Trump was unable to compartmentalize the Russia investigations from his presidential duties, viewing them as attempts to deny his victory. His fury over the probes, combined with his warmth toward Putin, made some staff wonder about his motivations. The investigations intensified when the Times reported Don Jr.'s meeting with a Kremlin-linked lawyer during the campaign, and Mueller executed a search warrant on Paul Manafort's home.
Capitolo 9
The COVID Presidency
As the coronavirus emerged in early 2020, Trump initially downplayed its significance while focusing on other issues like vaping regulations. Despite receiving intelligence briefings about the virus threat in January, Trump resisted confrontational measures against China, with whom he had just signed a trade deal. By late January, he issued a partial travel ban from China and established the White House Coronavirus Task Force, but privately told Bob Woodward the virus was "more deadly than even your strenuous flu" while publicly insisting it would "disappear."
During a February trip to India, Trump became increasingly concerned about coronavirus coverage. Despite Melania's warnings to take the threat seriously, Trump remained focused on the massive "Namaste Trump" rally of 110,000 people arranged by Prime Minister Modi. Throughout the trip, Trump obsessively avoided eating Indian food and insisted on using special glassware, fearing contamination. On the return flight, Trump erupted after seeing CDC official Nancy Messonnier's public warning about inevitable community spread in America, bursting into the staff conference room demanding "Who is this woman?!"
Trump favored governors who praised him, telling advisers he preferred California's Newsom over Washington's Inslee: "Newsom said nice things about me, Inslee said bad things." When deciding where to send a hospital ship, Trump called Newsom on speakerphone without warning others were listening, offering him the ship because "you've been so good to me." Newsom carefully replied the ship should go wherever most needed, shocking Trump who expected him to simply grab the opportunity.
Trump transformed the daily briefings into rally-like performances lasting over two hours. He initially praised Dr. Birx for her "elegance" and silk scarves (noting she resembled his mother), but soon stopped heeding medical experts' advice. After conservatives targeted Fauci, Trump followed his base's lead, even promoting a "fire Fauci" hashtag. During one infamous briefing, Trump speculated about injecting disinfectant or bringing "light inside the body" as potential treatments, alarming health officials and Republican strategists alike.
Capitolo 10
The Final Act
In the aftermath of the November 3 election, Trump vacillated between claiming victory and privately acknowledging defeat. While publicly declaring victory, he privately asked what had gone wrong. Trump refused to concede, instead pursuing multiple strategies to overturn the results. After campaign officials Stepien and Clark outlined a mere 5-10% chance of success through legal challenges, Trump optimistically reframed it as "forty or fifty percent." He embraced Rudy Giuliani's efforts despite their legal failures, telling him "You're in charge. Go wild, do anything you want."
Trump's legal team filed sixty-five postelection lawsuits and lost sixty-four of them. As litigation failed, Giuliani and Ellis toured state capitals urging legislators to overrule election administrators. Giuliani became fixated on conspiracy theories about manipulated voting machines, including one claiming Italy used satellites to switch votes from Trump to Biden.
After failing in legal appeals, state legislature lobbying, and pressuring election administrators, Trump's network focused on one final opportunity: the January 6 certification of electoral votes by Congress. Stephen Miller promoted the idea of "alternate slates of electors" in contested states, claiming Trump needed "heroes to step up and do the right thing," despite the Electoral Count Act and Twelfth Amendment suggesting the vice president's role was purely ceremonial.
After a final heated call with Pence on January 6 where Trump reportedly said Pence could go down as a "patriot" or a "pussy," Trump addressed the rally crowd. Following inflammatory speeches including Giuliani's call for "trial by combat," Trump told supporters to "fight much harder" and march to the Capitol. Within an hour of Trump returning to the White House, rioters breached the Capitol as Pence began the electoral count. As the mob chanted "Hang Mike Pence!" and lawmakers fled, Trump watched from the White House dining room, initially resisting calls to intervene.
Trump's departure from Joint Base Andrews featured a smaller-than-hoped-for crowd despite White House efforts to round up attendees. His farewell remarks were awkward and fumbling as he told the sparse gathering, "Have a good life, we will see you soon." As Air Force One took off, Frank Sinatra's "My Way" blasted over speakers like a movie finale. For perhaps the first time in his life, there was no safety net beneath Donald Trump-"no father, no banks, no politicians or judges or customers or voters or his own salesmanship." He had finally fallen to the ground, at least temporarily.
Capitolo 11
The Aftermath and Legacy
Trump immediately began plotting his comeback, refusing to acknowledge defeat. On his flight to Florida, he vented to RNC chair Ronna McDaniel about forming his own party until she reminded him of the resources he'd lose. His second impeachment trial for "incitement of insurrection" ended in acquittal despite seven Republicans voting against him and McConnell declaring him "practically and morally responsible" for January 6.
Throughout his post-presidency, Trump granted interviews to nearly every author writing about his administration, including three with Haberman. At Mar-a-Lago, he appeared diminished after leaving the White House, following a daily routine of golf, meetings with supplicants, television, and dinner with applauding club members.
Trump's presidency created lasting changes to American politics, with party coalitions now sorting based on education levels, culture, and geography rather than traditional divides of religion, income, or ideology. His rule-breaking behavior normalized transgressions that would have previously been disqualifying, as evidenced by his casual dismissal of Senate candidate Herschel Walker's personal scandals: "Ten years ago, maybe it would have been a problem... I don't think it's a problem today." When Haberman asked why, Trump simply replied, "Because the world is changing," without acknowledging his role in that transformation.
In a moment of unexpected self-awareness during their interview, Trump acknowledged his tendency toward repetition: "One of the things I'll do, if I'm doing, like with you, for the written word, is I got to drum it into your head. So I'll repeat something six times." Later, after a meandering monologue, he smiled at Haberman and told his aides, "I love being with her, she's like my psychiatrist." Haberman observed that Trump treats everyone this way-using them to "vent or test reactions or gauge how his statements are playing." Despite his constant public presence, she concluded, "almost no one really knows him."
