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Summary: Confidence Man: The Making of Donald Trump and the Breaking of America by Maggie Haberman

  • The book is a biography of Donald Trump that traces his life and career from his childhood in Queens, New York, to his presidency, his impeachment trials, his defeat in the 2020 election, his role in the January 6 insurrection, and his potential comeback in 2024.
  • The book reveals many aspects of Trump’s personality, motivations, and behavior that shaped his actions and decisions as president, such as his narcissism, drama-seeking, bullying, lying, cheating, suing, exploiting, undermining, attacking, inciting, mishandling, and attempting to overturn.
  • The book explores the impact of Trump’s presidency on American democracy, society, and culture, arguing that Trump reoriented an entire country to react to his moods and emotions, creating a polarized and divided nation.

Confidence Man (2022) is a full account of Trump’s life in the spotlight. It tracks his career from early New York real estate deals to his tumultuous tenure in the White House. It shows how his aggressive personality was molded early on and only intensified as the stage grew bigger.

Introduction: A rare look into Trump’s life in the spotlight.

In 1975, Donald Trump paid a visit to the offices of Richard Ravitch, the chairman of the New York State Urban Development Corporation. Trump wanted one thing, a tax exemption for his plans to renovate the Commodore Hotel on 42nd Street. But Ravitch was unmoved. Trump’s plan wasn’t well researched and he saw nothing in it that would qualify him for tax exemption. But Trump wouldn’t take no for an answer. Standing in his office, he told Ravitch, you either grant me tax exemption or I’ll have your job. To which Ravitch replied, you either get out of my office or I’ll have you arrested.

Remarkably, the way Trump dealt with that problem is how he’d continue to deal with problems throughout his life. Positioning himself as the victim, he’d throw out all kinds of threats and accusations – the more unexpectedly outlandish, the better. It was a style that ultimately got him into the White House and resulted in one of America’s most violent transitions of power.

In this summary to Maggie Haberman’s Confidence Man, we’ll cover how Trump’s bombastic personality was honed through his early years as a New York real-estate mogul, and how his signature chaotic leadership style only intensified as he ascended on to the world stage.

Book Summary: Confidence Man - The Making of Donald Trump and the Breaking of America

Early Influences

In 1980, Donald Trump spoke to a New York Times reporter about one of his most formative experiences. It was November 21, 1964, and an 18-year-old Trump accompanied his father to the ribbon-cutting ceremony of the newly completed Verrazano-Narrows Bridge, which connects Brooklyn and Staten Island. It was a “sad experience” for Trump. It rained all morning as politicians patted each other on the back, and everyone failed to recognize the real man of honor: the 85-year-old Swedish engineer who designed the bridge, Othmar Ammann. His name wasn’t even mentioned. That’s when Trump realized that people will walk all over you if you let them. The way he saw it, they made a fool out of Ammann. And Trump vowed, from that day forward, no one would ever make a fool out of him.

It’s a pretty strong origin story for a man like Trump. But the weird thing is that his account is full of inaccuracies. The record of the event shows that there wasn’t a cloud in the sky that day. Also, Ammann was one of the first people to be introduced, receiving a round of applause from the crowd. Plus, Ammann wasn’t Swedish, he was Swiss.

Ironically enough, in 1986, that story played out in a similar way after Trump was given a contract to renovate the Wollman Rink in New York City’s Central Park. When the job was complete, Trump took the stage and declined to acknowledge the work done by city officials, the contractors, or the construction firm. Trump claimed all the credit. Art Nusbaum, the head of the construction firm that completed the job, noted that Trump isn’t interested in winning gold if it means he has to share the stage with silver and bronze. He wants them all. Citing Trump’s narcissism, Nusbaum’s firm refused to work with him again.

Over time, Trump not only became the man who wanted all the attention and all the credit, but also the man who refused to leave the stage. The Trump presidency had many unexpected twists and turns, but looking back, it’s impressive just how consistent he’s been over the years. He was someone who was clearly influenced by a select number of people in his life, and he took those lessons and traits to create a personality and force of will that was ceaseless in its pursuit of recognition.

Naturally, at the top of the list of formidable influences was his father, Fred Trump. Fred’s father was a German immigrant who died in 1918 during a flu pandemic when Fred was just 12 years old. He left behind a small fortune (what would be half a million dollars today), thanks to small businesses he owned and land he’d purchased in Queens. It became the foundation for E. Trump & Son, named after Fred’s mom, Elizabeth. Fred was tasked with expanding the business and he eventually made valuable political connections in New York which helped him buy up land and create a real estate empire in the 1930s.

By the 1960s, Fred had five kids, two daughters and three boys. What Fred taught all his children was to push through – to keep going no matter what. If their mother was having emergency surgery in the hospital, the kids went to school anyway. The boys especially looked up to their father, and Donald never deviated from his father’s plans. He went to the New York Military Academy, then to Fordham University, and finally to the University of Pennsylvania’s Wharton School of business.

While Fred’s influence loomed large over his career, Trump soon found another major influence in legendary New York lawyer Roy Cohn. Cohn made a name for himself by being part of the team that helped Senator Joseph McCarthy root out Communists and gay people from positions of power during the 1950s. Cohn became acquainted with Trump in the 1970s when Trump Management, Inc. was accused of discriminatory rental practices by the federal housing authority. To Trump, Cohn’s fight-tooth-and-nail-for-everything approach was everything he wanted to hear.

Cohn was also a notoriously transactional individual. If you could be of use, he liked you. If he didn’t like you, well then, “he’d sell you down the tubes” is how Trump put it. It was like a Mafia don mentality. It was simple and it made total sense to Trump. As a pair of father figures, Fred laid out a path, while Cohn opened up new avenues of possibility.

The Comeback Kid

Donald Trump was always a politically minded businessman. To work in real estate, it just made sense to know which politician was in charge of zoning approvals and possible tax relief. But as the ’80s went on, Trump became more aggressive in getting his name associated with whatever issues were getting headlines.

In 1989, after a woman was beaten and raped while jogging through Central Park, Trump used the case to take out a full-page ad in all of the major New York papers. In it, he called for the death penalty to be reinstated, and to “Bring back our police!”

While Trump could reliably find a way to get his voice heard on any hot-button issue, he remained hesitant about entering politics in earnest. But it wasn’t for a lack of interest from other people. And no one was more interested than Roger Stone. A political consultant and lobbyist, Stone’s career dates back to the early ’70s, when he worked for President Richard Nixon, performing low-level “dirty tricks” against Nixon’s rivals.

Since they first met in 1980, Stone was a firm believer in Trump’s political potential. And after Trump’s first book The Art of the Deal was published in 1987 and became a best seller, Stone encouraged him to test the political waters. Trump considered running on a Republican ticket in the 1988 election, then on the Reform Party ticket in 2000, and then again as a Republican in 2012. But each time, he pulled the plug on his campaign before it really got going.

Throughout these years, Trumps experienced highs and lows. The 90s in particular had been rough. He’d gone through two high-profile divorces. Deals were falling through. His Taj Mahal casino was siphoning money. He was paying for things he couldn’t afford and borrowing money he couldn’t pay back. In August of 1990, the Wall Street Journal reported that he had a net worth of negative $294 million. In 1995 alone, he claimed $916 million in personal losses. Throughout it all, Trump blamed others for his problems.

But by the late ’90s, a comeback was underway. Shares of Trump Hotels and Casinos went public and traded well enough to ease some of his money problems. But more than anything else, Trump had mastered the art of controlling his own narrative. In 1997, he published another book, The Art of the Comeback. Those days, he was a billionaire simply because he said he was.

Then, in 2004, Trump stumbled upon an even better platform for brand recognition and expansion: The Apprentice.

The Rise of the Popularist

Trump was the star of The Apprentice for over a decade. It was a dominant show and it literally transformed the Trump brand. Soon everything – from bottled water and steaks to desk chairs and mattresses – was being officially branded with the Trump name.

Twitter also helped. At first, Trump used it as a way to promote his various products and he soon became hooked. By the time the 2012 elections came along, he was using it as a soapbox for his political aspirations.

The years leading up to that election were important for several reasons. During his short-lived campaign, he reconnected with Roger Stone and was introduced to Steve Bannon, a right-wing media mogul who used to work for Goldman Sachs. When Bannon talked about populism, he had Trump’s interest piqued. Still, at their first meeting, Bannon had to clarify that the term was populist, not “popularist,” which is what Trump saw himself as. More than anything else, his team worked hard at reframing Trump within the Republican party. He buried his playboy image and walked back many of his Reform Party claims, like being pro-choice and having progressive views on health care.

Trump also proved he could get a crowd going. At the 2011 Conservative Political Action Conference, Trump got a huge response. A lot had changed since the last election. The 2008 economic crisis got a lot of voters angry, and the Tea Party political movement had mobilized many of these voters by tapping into their anger and encouraging more outsider candidates to run for office. When Trump took the stage and told the audience that Republican candidate Ron Paul had “zero chance of winning” applause broke out. They ate it up and major Republican Party officials took notice. They began to see the broad appeal that Roger Stone had seen all along.

Though he ultimately decided against running in 2012, Trump was now a force to be reckoned with. With his Twitter account and his nationwide TV fame, media outlets never stopped reporting on his opinions, including his promotion of the debunked theory that Barack Obama wasn’t born in the US. His name stayed in the headlines. The more aggressive and outlandish his comments, the more press he could get.

By early 2015, there was talk again of a potential run for the presidency, and this time, it was serious. But despite support from some folks in the Republican Party, Trump’s campaign quickly became a headache for many establishment players. After his announcement speech, Washington-based party officials held a private meeting to try and figure out how to handle him as a candidate. But, as they soon found, trying to “handle” Trump is a losing game.

Throughout his career, whenever Trump got a whiff of someone trying to control him, he did the opposite of what they asked. Ask him to tone it down? He’d push further. The fact that the more negative things Trump said the more positively the voters responded , only made matters worse for the Republican leadership. It was like their hands were tied. For instance, there was his threat of banning Muslims from entering the country. Other Republican candidates condemned the remarks, but even bad press had a way of boosting Trump’s campaign.

When his aids and his daughter Ivanka tried to get him to use a press conference to change his stance on the proposed ban, he made it clear. “You think I’m going to change?” he asked them. “I’m not changing.”

What confused everybody was that Trump was right. He didn’t need to change. One of his advisors marveled, “I’ve never seen a situation before where someone fucks up and their numbers go up.”

No Way Out

It was an eventful election year, to say the least. Russian hackers broke into the email servers of the Democratic National Convention. A recording of Trump bragging about “grabbing” women by the genitals was leaked to the press. Even Trump was surprised when he ended up winning. He was already preparing to declare the election a farce and say that it had been stolen from him. Instead, he had to put together a White House cabinet quickly.

Ultimately, Trump ran the White House as he’d run his other businesses. He kept people siloed off from one another, he stoked rivalries and competition between staff, he pushed back whenever someone tried to control him. Bad news wasn’t appreciated. People threw each other under the bus to avoid being blamed for problems and they fought viciously for Trump’s approval. It was just as he always liked it: Chaotic. Never boring.

In fact, even before day one, there were problems. The FBI’s investigation into Russia’s efforts to influence the election plagued the administration’s first year. This problem wasn’t helped by Trump’s efforts to ask the FBI director, James Comey, for leniency and loyalty. But this is precisely how he dealt with problems in New York, and it’s how he intended to conduct business in the White House.

Throughout his presidency, there was always one thing missing: someone like Roy Cohn. Someone who’d tell his enemies to go to hell and fight every battle like it was the last. Comey wasn’t going to be that man. His first attorney general, Jeff Sessions, wasn’t going to be that man, either. Sessions infuriated Trump by recusing himself from all matters related to the Russian investigation.

Trump eventually fired Sessions, as well as many other cabinet members and White House staff, in his ongoing search for people who’d serve his specific needs. By mid-2019, Trump had lost more of his original cabinet than Reagan, Obama, and both Bushes. He’d already worked with three press secretaries, three chiefs of staff, and six communications directors. If they weren’t fired, they resigned.

While the workplace was certainly chaotic, there was also the problem of Trump’s refusal to listen to expert advice, especially when it went against his own opinions. Trump long believed that other countries were taking advantage of the US, with money and efforts being wasted by having a military presence in places like South Korea. In Trump’s worldview, everything could be simplified by one-on-one transactional relationships. The US was helping South Korea, but what were they doing to help the US? It was a bad deal, and it should stop.

By the time 2020 came around, Trump had endured an impeachment trial related to a conversation he had with the incoming president of Ukraine, Volodymyr Zelensky. The conversation sounded very much like the kind of transactional deal Trump was familiar with: withholding money in the hopes that Zelensky would investigate his enemies. But that year had a different challenge in store for the Trump administration: a pandemic.

Trump generally took the COVID-19 outbreak as a personal affront. “Can you believe this is happening to me?” he asked multiple White House visitors and callers during the crisis. Certainly, campaigning for reelection was difficult for Trump amid the pandemic. Trump needed big live rallies where he could run off his list of grievances to an appreciative audience. His opponent in the 2020 election, Joe Biden, could effectively communicate without in-person events. And when it came to election day, Biden won both the popular vote and the electoral votes – being the first Democrat to win the state of Arizona in decades.

Of course, Trump wasn’t going to admit defeat without a fight. While he didn’t have Roy Cohn in his corner, he had old friends like Roger Stone and his personal lawyer Rudy Giuliani. Giuliani helped Trump to litigate the election in every way possible and Stone promoted a “Stop the Steal” campaign online.

But neither predicted what would happen on January 6, 2021, when the electoral college votes were scheduled to be counted and confirmed in the Capitol Building. Trump had latched on to the idea that his vice president, Mike Pence, would be able to control the event and make sure the votes weren’t confirmed, theoretically keeping Trump in the White House. Despite Pence signaling that he wouldn’t go along with this plan, it nonetheless got plenty of attention online and Trump made sure his supporters turned out at the Capitol to put pressure on Pence to come through for him.

Instead, the event turned into a violent riot that saw over 2,000 Trump supporters break into the Capitol Building, resulting in at least five deaths. When the rioters were eventually dispersed, Pence completed his job and confirmed the votes.

It seemed this was what it took for Trump to finally consider leaving the White House, if not admitting defeat. In the coming days, nearly 150 pardons came pouring forth from the White House. But this time, there was no net to prevent Donald Trump’s fall. No family fund to withdraw money from. No bank willing to bail him out. But when he got into his presidential helicopter for the last time, a song was playing. Frank Sinatra’s rendition of My Way. Yes, this time Trump fell. But he went down doing it his way.


Trump’s personality was honed by his desire to seek approval from his domineering father, as well as through formative mentors like the aggressive lawyer Roy Cohn. Trump’s desire for praise and recognition was apparent in his years as a New York real estate mogul, as was his chaotic style of leadership. All of these traits were heightened while in the White House, leading to an administration that featured unprecedented personnel turnover and, ultimately, a disastrous finale that tested the limits of democracy.

About the Author

Maggie Haberman is a journalist who joined The New York Times in 2015 and was part of a team that won a Pulitzer Prize in 2018 for reporting on the investigations into Donald Trump’s, and his advisers’, connections to Russia. She has twice been a member of a team that was a finalist for a Pulitzer Prize, in 2021 for reporting on the Trump administration’s response to the coronavirus, and in 2022 for coverage related to the Jan. 6, 2021 riot at the Capitol. Before joining The New York Times as a campaign correspondent, she worked as a political reporter at Politico, from 2010 to 2015. She previously worked at The New York Post and The New York Daily News.


Politics, Biography, Memoir, History, Presidents, Writing, Journalism, Mystery, Crime, American History, Business, Social Sciences, Government, Federal Government, United States National Government, United States Executive Government, Political Leader Biographies

Table of Contents

Prologue 1
Chapter 1 The Power of Negative Thinking 17
Chapter 2 Welcome to Fear City 35
Chapter 3 Fifth Avenue Frieze-Out 47
Chapter 4 Blind to the Beautiful Mosaic 61
Chapter 5 On the Way Up 79
Chapter 6 On the Way Down 101
Chapter 7 Nice and Complicated 121
Chapter 8 The America We Deserve 135
Chapter 9 Asphalt Survivor 159
Chapter 10 140 Characters 171
Chapter 11 Rising on a Lie 181
Chapter 12 Make or Break 201
Chapter 13 Many People Are Saying 213
Chapter 14 Stop the Steal 225
Chapter 15 The Sci-Fi Campaign 245
Chapter 16 No One Smarter 259
Chapter 17 Why It’s Presidential 269
Chapter 18 Out Like FLynn 281
Chapter 19 Executive Time 293
Chapter 20 In the Tank 307
Chapter 21 The Greatest Showman 323
Chapter 22 Taking a Bullet 333
Chapter 23 Extreme Action 345
Chapter 24 Party Man 357
Chapter 25 Tougher Than the Rest 373
Chapter 26 One Strike and You’re Out 389
Chapter 27 Acquitted 403
Chapter 28 Get Healthy America 415
Chapter 29 Divide and Conquer 429
Chapter 30 Tulsa 441
Chapter 31 Not One of the Diers 453
Chapter 32 Trial by Combat 463
Epilogue 489
Acknowledgments 509
Notes 513
Illustration Credits 577
Index 579


The book is a biography of Donald Trump, the 45th president of the United States, written by Maggie Haberman, a Pulitzer-Prize-winning New York Times reporter who has covered him for years. The book traces Trump’s life and career from his childhood in Queens, New York, to his rise as a real estate mogul, media personality, and political leader in New York City and beyond. The book also examines his presidency, his impeachment trials, his defeat in the 2020 election, his role in the January 6 insurrection, and his potential comeback in 2024.

The book reveals many aspects of Trump’s personality, motivations, and behavior that shaped his actions and decisions as president. Haberman portrays Trump as a narcissistic drama-seeker who covered a fragile ego with a bullying impulse. She shows how he was influenced by his father Fred Trump, his mentor Roy Cohn, and other figures from the New York demimonde of hustlers, mobsters, political bosses, compliant prosecutors, and tabloid scandalmongers. She also describes how he exploited his fame and fortune to gain power and attention, often lying, cheating, or suing his way out of trouble.

The book also explores the impact of Trump’s presidency on American democracy, society, and culture. Haberman argues that Trump reoriented an entire country to react to his moods and emotions, creating a polarized and divided nation. She details how he undermined the norms and institutions of governance, challenged the rule of law and the constitution, attacked the media and his critics, incited violence and hatred among his supporters, mishandled the COVID-19 pandemic and other crises, and attempted to overturn the election results.

The book is a well-researched and well-written account of one of the most norms-shattering and consequential eras in American political history. Haberman draws on her extensive knowledge and experience as a journalist who has followed Trump for decades, as well as interviews with hundreds of sources and numerous interviews with Trump himself. She provides a comprehensive and authoritative portrait of Trump as a historical figure who transformed American politics and society.

The book is also a compelling and disturbing read that exposes the dark side of Trump’s personality and presidency. Haberman does not shy away from revealing the flaws, failures, scandals, and crimes that marred Trump’s career and administration. She also does not hesitate to criticize or challenge Trump’s actions and statements when they are false, misleading, or harmful. She offers a balanced and nuanced perspective that does not rely on simplistic caricature or partisan bias.

The book is a must-read for anyone who wants to understand Trump and his impact on America. It is not only a biography of a president but also a history of a nation that was shaped by him. It is a book that will inform, enlighten, and provoke readers who are interested in the past, present, and future of American democracy.

Summary: Confidence Man: The Making of Donald Trump and the Breaking of America by Maggie Haberman

Alex Lim is a certified book reviewer and editor with over 10 years of experience in the publishing industry. He has reviewed hundreds of books for reputable magazines and websites, such as The New York Times, The Guardian, and Goodreads. Alex has a master’s degree in comparative literature from Harvard University and a PhD in literary criticism from Oxford University. He is also the author of several acclaimed books on literary theory and analysis, such as The Art of Reading and How to Write a Book Review. Alex lives in London, England with his wife and two children. You can contact him at [email protected] or follow him on Website | Twitter | Facebook

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