Confidence Man

Confidence Man Plot Summary

Introduction

In the summer of 2015, a golden escalator descent in Trump Tower marked the beginning of one of the most extraordinary political journeys in American history. What followed was not merely a campaign but a complete disruption of political norms that would fundamentally reshape American politics. Donald Trump's rise from real estate mogul and reality television star to the presidency represents a fascinating study in personal ambition, media manipulation, and the changing nature of American democracy. This book traces Trump's evolution from his early days in Queens through his Manhattan real estate empire, his reinvention as a television personality, and ultimately his transformation into a political force. It examines how Trump's lifelong patterns of behavior—his tendency to counterattack, his obsession with loyalty, his transactional worldview—became the foundation for his political approach. For anyone seeking to understand the forces that propelled Trump to power and continue to shape American politics today, this exploration offers valuable insights into how celebrity, wealth, and an uncanny ability to channel grievance converged to create a presidency unlike any other in American history.

Chapter 1: Building the Brand: Trump's Early Business Evolution (1970s-1980s)

The 1970s marked a pivotal period for Donald Trump as he transitioned from his father's outer-borough real estate business to the glittering world of Manhattan. New York City was experiencing its worst fiscal crisis in history, creating a landscape ripe for ambitious developers. The young Trump, fresh from Wharton and eager to make his mark, saw opportunity where others saw only risk. Trump's first major Manhattan venture came with the renovation of the dilapidated Commodore Hotel near Grand Central Terminal. With the city desperate for investment, Trump secured unprecedented tax abatements worth $160 million over 40 years. The deal showcased what would become Trump's signature approach: leveraging political connections, negotiating favorable terms with government officials, and generating media attention that far outpaced his actual achievements. Mayor Abe Beame, whom Fred Trump had supported for years, proved instrumental in helping the younger Trump navigate city bureaucracy. The transformation of the Commodore into the Grand Hyatt represented more than just a building renovation; it was the beginning of Trump's carefully crafted public image. He hired the aggressive attorney Roy Cohn, known for his work with Senator Joseph McCarthy, who became Trump's mentor and taught him tactics that would define his career: never apologize, always counterattack, and use the media as a weapon. Under Cohn's guidance, Trump responded to a Justice Department housing discrimination lawsuit not with compliance but with a $100 million countersuit. By the early 1980s, Trump had established himself as a fixture in New York tabloids. The completion of Trump Tower in 1983, with its distinctive brass and pink marble aesthetic, cemented his status as a celebrity developer. His marriage to Ivana, a former model from Czechoslovakia, added to his growing mystique. Trump cultivated relationships with influential figures like Cohn, media power broker Rupert Murdoch, and political fixers from both parties, understanding that in New York, access to power was as valuable as money itself. The publication of "The Art of the Deal" in 1987, ghostwritten by Tony Schwartz but presented as Trump's business philosophy, catapulted him to national prominence. The book portrayed Trump as a master negotiator and self-made success, despite the fact that he had received substantial financial support from his father. The bestseller's success convinced Trump he had a message that resonated beyond New York, leading to his first public flirtations with presidential politics through newspaper ads criticizing U.S. foreign policy. By the late 1980s, Trump had transformed himself from Fred Trump's son into a national symbol of 1980s excess and ambition. His aggressive expansion into Atlantic City casinos, the Trump Shuttle airline, and the Plaza Hotel would soon prove financially disastrous, but the foundation of the Trump brand—built on media savvy, self-promotion, and the creation of an image larger than reality—was firmly established, setting the stage for both spectacular failures and an unlikely political future.

Chapter 2: Surviving Setbacks: Financial Troubles and Media Reinvention (1990s)

The 1990s began with Donald Trump facing financial ruin. His empire, built on excessive debt and questionable acquisitions during the 1980s boom, was crumbling under nearly $3 billion in loans. The Trump Shuttle airline was losing money, his Atlantic City casinos were cannibalizing each other's business, and the real estate market had crashed. By 1991, the Trump Taj Mahal filed for bankruptcy, followed by the Trump Plaza Hotel, the Trump Castle Casino, and the Plaza Hotel in New York. Trump's personal life mirrored his business troubles. His highly publicized affair with Marla Maples led to a bitter divorce from Ivana Trump that played out on the front pages of New York tabloids. The divorce settlement, reported to be around $14 million, added to his financial woes. Trump's carefully constructed image as a business genius was in tatters, with financial journalists revealing that his net worth might actually be negative. The fall was so dramatic that Spy magazine famously sent increasingly smaller checks to wealthy New Yorkers to see who would cash them, discovering that Trump would deposit checks for mere pennies. Yet Trump's recovery from this nadir revealed skills that would later serve him in politics. He proved remarkably adept at using bankruptcy laws to his advantage, shifting losses to investors while protecting his personal assets and licensing rights. Banks, realizing that Trump's name still held value despite his failures, kept him afloat rather than forcing liquidation. As one banker noted, "The banks were not in the business of owning and operating casinos," so they restructured his debt and allowed him to maintain control of his properties, albeit with significantly reduced ownership stakes. The mid-1990s saw Trump gradually rebuilding his brand through a series of smaller deals and licensing arrangements that required little of his own capital. He purchased the landmark 40 Wall Street building at a bargain price during the real estate downturn and converted it into office space. He acquired the former Hotel Delmonico on Park Avenue and transformed it into Trump Park Avenue condominiums. These projects were modest compared to his 1980s ambitions but helped reestablish his credibility in real estate circles. Television emerged as Trump's most effective vehicle for rehabilitation. His appearances on David Letterman's show and other programs allowed him to display self-deprecating humor about his financial troubles. This culminated in his purchase of the Miss Universe pageant in 1996 and his increasing comfort with being a celebrity rather than just a businessman. By the late 1990s, Trump had embraced his role as a pop culture figure, making cameo appearances in films and television shows, including "Home Alone 2" and "The Fresh Prince of Bel-Air." The decade ended with Trump in a far different position than where he began. Though his actual wealth remained questionable, his public image had largely recovered. He had learned valuable lessons about the power of personal branding, media manipulation, and the American public's short memory for failure. Most importantly, he discovered that perception often matters more than reality – a lesson that would prove crucial in his later political career. As he told one interviewer in 1999, "The show is Trump, and it is sold-out performances everywhere."

Chapter 3: The Apprentice Effect: Celebrity Status and Political Positioning (2000-2015)

The new millennium opened with Donald Trump's first serious foray into presidential politics. In 1999, encouraged by political operative Roger Stone, Trump briefly sought the Reform Party nomination for the 2000 election. Though this campaign was short-lived, it established themes he would return to later: criticism of both major parties, calls for renegotiating trade deals, and complaints about America being "ripped off" by foreign countries. Trump's positions during this period were notably different from his later platform – he described himself as "very pro-choice" and advocated for universal healthcare. The true transformation of Trump's public image came in 2004 with the debut of "The Apprentice." Mark Burnett, the reality TV producer behind "Survivor," cast Trump as the quintessential American business success story despite his well-documented financial troubles. The show's opening sequence featured Trump in a limousine, private jet, and penthouse, with Trump declaring, "I've mastered the art of the deal and turned the name Trump into the highest-quality brand." For millions of Americans who had never read a New York tabloid or financial news, this carefully edited portrayal became their primary impression of Trump. "The Apprentice" transformed Trump from a regional celebrity into a national household name. The show averaged 20 million viewers in its first season and ran for fourteen seasons, providing Trump with something he had never consistently had before: a steady paycheck, reportedly worth $427,000 per episode. More importantly, it gave him a platform to present a carefully crafted version of himself to middle America. Viewers who had never been to New York or stayed in a Trump hotel could now feel they knew him personally. The show's portrayal of Trump's business empire often masked the reality—producers later admitted they had to make his dated offices look more impressive for television. During this period, Trump continued to dabble in politics without committing fully. He became the most prominent voice pushing the "birther" conspiracy theory questioning whether President Barack Obama was born in the United States. Trump appeared regularly on television to demand Obama release his birth certificate. When Obama eventually did so at a White House press conference, he dismissed Trump as a "carnival barker," but the episode had accomplished what Trump wanted: it positioned him as a potential political challenger to Obama and endeared him to a segment of the Republican base that harbored deep resentment toward the first Black president. Social media, particularly Twitter, became Trump's most powerful tool during this period. In May 2009, a digital marketing specialist named Peter Costanzo had created the @realDonaldTrump Twitter account to promote Trump's latest book. Trump quickly recognized the platform's potential for direct communication with the public, bypassing traditional media filters. By 2013, he was personally composing tweets on his Android phone, closely tracking his follower count and engagement metrics. His provocative style—attacking critics, commenting on celebrities, and making outrageous claims—proved perfectly suited to a medium that rewarded emotional engagement over factual accuracy. Throughout this period, Trump was studying the political landscape and identifying openings. He watched as the Tea Party movement transformed the Republican Party, pushing it toward populism and away from its traditional establishment. He observed how figures like Sarah Palin could energize voters through cultural grievance and attacks on "elites." By early 2015, Trump had assembled a small team to explore a presidential run, including veteran operative Corey Lewandowski as campaign manager. Unlike his previous political flirtations, this effort involved serious preparation: polling, message testing, and strategic planning for what would become the most unconventional presidential campaign in modern American history.

Chapter 4: Breaking the Rules: The Unconventional Campaign (2015-2016)

Donald Trump's presidential campaign announcement on June 16, 2015, immediately broke with political convention. Rather than presenting a vision of American greatness or outlining policy proposals, Trump focused on grievances, particularly targeting Mexican immigrants. "They're bringing drugs. They're bringing crime. They're rapists," he declared, before adding, "And some, I assume, are good people." This inflammatory rhetoric, which would have ended most traditional campaigns, instead catapulted Trump to the top of Republican primary polls within weeks. The Trump campaign operated unlike any other in modern political history. It maintained a skeletal staff, relied heavily on earned media rather than paid advertising, and eschewed traditional campaign activities like detailed policy papers or extensive ground operations. Trump's rallies became the centerpiece of his strategy—part political event, part entertainment spectacle. At these gatherings, which regularly drew thousands of attendees, Trump would speak extemporaneously for over an hour, mixing policy pronouncements with personal grievances, attacks on opponents, and nostalgic appeals to "Make America Great Again." Trump's primary campaign was defined by his systematic dismantling of his Republican rivals. He assigned demeaning nicknames to opponents—"Low Energy Jeb" for Jeb Bush, "Little Marco" for Marco Rubio, "Lyin' Ted" for Ted Cruz—that stuck in voters' minds. He showed no deference to party elders like John McCain, whom he mocked for being captured during the Vietnam War. When Fox News host Megyn Kelly pressed him about his history of misogynistic comments during the first Republican debate, Trump later suggested she had "blood coming out of her wherever," yet suffered no consequences from conservative voters who would normally reject such vulgarity. The campaign's relationship with truth was unprecedented in American politics. Fact-checkers documented thousands of false or misleading claims, yet these had little impact on his support. When Trump proposed a "total and complete shutdown of Muslims entering the United States" following terrorist attacks in Paris and San Bernardino, critics called the idea unconstitutional and un-American. Yet polling showed the proposal was popular with Republican primary voters. Similarly, Trump's false claims about "thousands and thousands" of Muslims in New Jersey cheering the 9/11 attacks were widely debunked but reinforced his supporters' existing beliefs. After securing the Republican nomination, Trump faced Hillary Clinton in a general election campaign marked by unprecedented negativity. The October 2016 release of the "Access Hollywood" tape, in which Trump boasted about sexually assaulting women, would have ended any normal campaign. Instead, Trump survived by deflecting attention to Bill Clinton's past and by bringing women who had accused the former president of sexual misconduct to the second presidential debate. When WikiLeaks began releasing emails stolen from Clinton campaign chairman John Podesta, Trump enthusiastically highlighted their contents while dismissing concerns about Russian involvement in the hack. Trump's victory on November 8, 2016, shocked political observers who had dismissed his chances throughout the campaign. He lost the popular vote by nearly three million ballots but secured an Electoral College majority by narrowly winning Pennsylvania, Michigan, and Wisconsin. His success demonstrated the power of his populist message in former industrial regions and revealed the limitations of traditional polling and campaign tactics. More fundamentally, it showed that the political norms that had governed American presidential campaigns for decades—expectations about qualifications, temperament, truthfulness, and basic decency—no longer applied, at least not to a candidate who understood how to harness celebrity, grievance, and media attention into political power.

Chapter 5: Governing by Instinct: The Disruptive Presidency (2017-2020)

Donald Trump entered the White House on January 20, 2017, with no government experience and little interest in the traditional processes of governance. From his inaugural address, which painted a dark picture of "American carnage," to his final days in office, Trump approached the presidency as an extension of his personal brand rather than a constitutional office with defined powers and limitations. He governed largely by instinct, making major policy decisions based on gut feelings, television coverage, and conversations with a rotating cast of advisers, friends, and Fox News personalities. The early Trump administration was marked by unprecedented chaos and staff turnover. His first National Security Advisor, Michael Flynn, resigned after just 24 days amid revelations about his contacts with Russian officials. His first Chief of Staff, Reince Priebus, lasted only six months before being replaced by retired General John Kelly, who himself departed after a turbulent 17-month tenure. By the end of Trump's term, he had cycled through four chiefs of staff, five national security advisors, and four press secretaries. This constant churn reflected Trump's management style, which pitted advisers against each other and valued personal loyalty over expertise or experience. Trump's policy agenda was defined more by disruption than by coherent ideology. He withdrew from the Paris Climate Agreement and the Iran nuclear deal, imposed tariffs on allies and adversaries alike, separated migrant children from their parents at the southern border, and attempted to dismantle the Affordable Care Act. His signature legislative achievement, the 2017 Tax Cuts and Jobs Act, delivered significant benefits to corporations and wealthy Americans while adding an estimated $1.9 trillion to the national debt. His promised infrastructure plan never materialized, and his border wall remained largely unbuilt, with Mexico never paying for it as he had promised. The Russia investigation dominated much of Trump's first two years in office. After he fired FBI Director James Comey in May 2017, Deputy Attorney General Rod Rosenstein appointed Robert Mueller as special counsel to investigate Russian interference in the 2016 election and possible coordination with the Trump campaign. Trump repeatedly attacked the investigation as a "witch hunt" and attempted to undermine it through public statements and private pressure on Justice Department officials. Mueller's final report, released in April 2019, did not establish criminal conspiracy between the Trump campaign and Russia but detailed numerous instances of potential obstruction of justice by the president. Trump's first impeachment came in December 2019, after a whistleblower revealed that he had pressured Ukrainian President Volodymyr Zelensky to investigate Joe Biden and his son Hunter while withholding congressionally approved military aid. The House of Representatives impeached Trump on charges of abuse of power and obstruction of Congress, but the Republican-controlled Senate acquitted him in February 2020, with only one Republican senator, Mitt Romney, voting to convict. The COVID-19 pandemic, which reached American shores in early 2020, presented Trump with his greatest leadership challenge. His response was characterized by denial, misinformation, and an unwillingness to take responsibility. He downplayed the virus's severity, promoted unproven treatments like hydroxychloroquine, suggested injecting disinfectants as a potential cure, and undermined his own public health officials. By the time he left office, more than 400,000 Americans had died from the virus, and the economy had suffered its worst contraction since the Great Depression. Trump's handling of the pandemic, more than any other factor, likely cost him reelection, as voters concluded that his showmanship and instinct-driven approach to governance had failed them when it mattered most.

Chapter 6: Testing Democracy: Election Denial and January 6th (2020-2021)

The 2020 presidential election unfolded against the backdrop of a global pandemic that had killed hundreds of thousands of Americans and devastated the economy. Trump's campaign strategy centered on downplaying the virus while portraying his opponent, former Vice President Joe Biden, as mentally unfit and a puppet of the radical left. Despite trailing in polls throughout the race, Trump maintained that he would win easily and began laying the groundwork to contest any defeat by claiming that mail-in voting, which expanded dramatically due to COVID-19, was rife with fraud. Election night initially appeared promising for Trump as he built early leads in several key states. However, as mail-in ballots were counted in the days that followed, Biden pulled ahead in Pennsylvania, Michigan, Wisconsin, Georgia, and Arizona. Rather than conceding as is traditional when defeat becomes clear, Trump immediately declared victory and alleged a massive conspiracy to steal the election. "We were getting ready to win this election. Frankly, we did win this election," he falsely claimed in the early morning hours of November 4, adding, "This is a fraud on the American public." What followed was an unprecedented two-month campaign to overturn the election results. Trump's legal team, led by Rudy Giuliani and Sidney Powell, filed more than 60 lawsuits challenging the results in swing states. These suits were almost uniformly rejected by judges—many appointed by Trump himself—for lack of evidence. When legal challenges failed, Trump turned to pressure campaigns against state officials. In a recorded call with Georgia Secretary of State Brad Raffensperger, Trump urged him to "find 11,780 votes"—just enough to flip the state. Raffensperger, a Republican, refused. As Congress prepared to certify the Electoral College results on January 6, 2021, Trump focused on a last-ditch strategy centered on Vice President Mike Pence, who would preside over the joint session. Trump publicly and privately pressured Pence to reject electoral votes from contested states, a power Pence did not possess under the Constitution. When Pence refused, Trump turned his attention to the thousands of supporters gathering in Washington for a "Stop the Steal" rally he had promoted for weeks. On the morning of January 6, Trump addressed the crowd near the White House, telling them, "If you don't fight like hell, you're not going to have a country anymore," and directing them to march to the Capitol. What followed was the worst attack on the U.S. Capitol since the War of 1812. Thousands of Trump supporters overwhelmed police barricades, smashed windows, and forced their way into the building, sending lawmakers and staff fleeing for safety. For hours, Trump watched the violence unfold on television, reportedly pleased by what he saw, before finally issuing a tepid call for peace while telling the rioters, "We love you. You're very special." The insurrection resulted in five deaths, including one Capitol Police officer, and injuries to more than 140 police officers. It also led to Trump's unprecedented second impeachment, this time for "incitement of insurrection." Though he was again acquitted in the Senate, with seven Republicans joining all Democrats in voting to convict, the events of January 6 permanently altered Trump's legacy. What had begun with an escalator ride and inflammatory rhetoric about immigrants ended with a violent assault on American democracy itself—the logical conclusion of a political career built on grievance, division, and the relentless pursuit of power at any cost.

Summary

Donald Trump's rise to the presidency represents a unique convergence of personal ambition, media savvy, and societal change. From his early days learning the real estate business from his father in Queens to his reinvention as a Manhattan icon, television star, and ultimately president, Trump demonstrated a remarkable ability to adapt his personal brand to changing circumstances while maintaining consistent behavioral patterns. His presidency was defined by the same traits that characterized his business career: an obsession with loyalty, a transactional view of relationships, a preference for conflict over compromise, and an unshakable belief in his own instincts over expert advice. The Trump phenomenon reveals profound truths about American society in the early 21st century. His success exposed the weakening of traditional gatekeepers—political parties, mainstream media, and established norms—in favor of direct communication through social media and cable news. It highlighted deep cultural and economic anxieties among segments of the population who felt left behind by globalization and demographic change. Perhaps most importantly, it demonstrated how celebrity, combined with a willingness to break taboos and voice grievances others wouldn't, could be transformed into political power. Whether Trump's approach to politics represents a temporary aberration or a permanent shift in American democracy remains an open question, but his impact on our political landscape—from how campaigns are conducted to how presidents govern—will be felt for generations to come.

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Maggie Haberman

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