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.
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
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
Illustration Credits 577
From the Pulitzer-Prize-winning New York Times reporter who has defined Donald J. Trump’s presidency like no other journalist, Confidence Man is a magnificent and disturbing reckoning that chronicles his life and its meaning from his rise in New York City to his tortured post-presidency.
Few journalists working today have covered Donald Trump more extensively than Maggie Haberman. And few understand him and his motivations better. Now, demonstrating her majestic command of this story, Haberman reveals in full the depth of her understanding of the 45th president himself, and of what the Trump phenomenon means.
Interviews with hundreds of sources and numerous interviews over the years with Trump himself portray a complicated and often contradictory historical figure. Capable of kindness but relying on casual cruelty as it suits his purposes. Pugnacious. Insecure. Lonely. Vindictive. Menacing. Smarter than his critics contend and colder and more calculating than his allies believe. A man who embedded himself in popular culture, galvanizing support for a run for high office that he began preliminary spadework for 30 years ago, to ultimately become a president who pushed American democracy to the brink.
The through-line of Trump’s life and his presidency is the enduring question of what is in it for him or what he needs to say to survive short increments of time in the pursuit of his own interests.
Confidence Man is also, inevitably, about the world thatproduced such a singular character, giving rise to his career and becoming his first stage. It is also about a series of relentlessly transactional relationships. The ones that shaped him most were with girlfriends and wives, with Roy Cohn, with George Steinbrenner, with Mike Tyson and Don King and Roger Stone, with city and state politicians like Robert Morgenthau and Rudy Giuliani, with business partners, with prosecutors, with the media, and with the employees who toiled inside what they commonly called amongst themselves the “Trump Disorganization.”
That world informed the one that Trump tried to recreate while in the White House. All of Trump’s behavior as President had echoes in what came before. In this revelatory and newsmaking book, Haberman brings together the events of his life into a single mesmerizing work. It is the definitive account of one of the most norms-shattering and consequential eras in American political history.
“This is the book Trump fears most.” – Axios
“Will be a primary source about the most vexing president in American history for years to come.” – Joe Klein, The New York Times
“A uniquely illuminating portrait.” – Sean Wilentz, The Washington Post
“[A] monumental look at Donald Trump and his presidency.” — David Shribman, Los Angeles Times
“Confidence Man [is] Maggie Haberman’s much anticipated biography of the president she followed more assiduously than any other journalist. No doubt, there are revelations aplenty here. But this is a book more notable for the quality of its observations about Trump’s character than for its newsbreaks. It will be a primary source about the most vexing president in American history for years to come.” —Joe Klein, The New York Times
“A uniquely illuminating portrait…Haberman’s contribution in Confidence Man [is] much larger than its arresting anecdotes. Later generations of historians will puzzle over Trump’s rise to national power. The best of them will have learned from Haberman’s book that none of it would have been possible but for a social, cultural, political, media and moral breakdown that overtook New York beginning in the 1970s, a fiasco of trusted institutions that, having allowed the Trumpian virus to grow, failed at every step to contain its spread, then profited from, aided and even cheered its devastation.” — Sean Wilentz, The Washington Post
“[A] monumental look at Donald Trump and his presidency . . . it may be first among equals.” — David Shribman, Los Angeles Times
“Haberman, the New York Times’ Trump whisperer, delivers. [Confidence Man] is much more than 600 pages of context, scoop and drama. It is a political epic, tracing Donald Trump’s journey from the streets of Queens to Manhattan’s Upper East Side, from the White House to Mar-a-Lago, his Elba.” —The Guardian
“Delivers eye-popping details about the Trump presidency.” —Terry Moran, Good Morning America
“Maggie Haberman has become the chronicler-in-chief of the Donald Trump era.” —John Dickerson, CBS Sunday Morning
“Haberman deploys a deep sense of Trump’s origins and career, including his relationships with New York’s mayors and powerful Democratic ward bosses such as Meade Esposito. Haberman helps us understand how his lifelong desire for stardom pushed him to bid for the presidency and how his unorthodox credentials and tactics enabled him to win. She has a witness’ eye for much that she relates.” —NPR.org
“An origin story plus an inside-the-room blow-by-blow—a book arguably only Haberman could have written. . . . It’s been called the book Trump fears the most—he’s ‘terrified,’ said one former aide—and that’s because Haberman is the reporter who knows him the best.” —Michael Kruse, POLITICO
“Chockablock with fresh anecdotes and insights.” —Frank Bruni, The New York Times
“Haberman stands out among journalists who have followed Mr. Trump . . . Haberman makes a particular contribution with [Confidence Man] by describing how the annealing interplay of politics and commerce in the New York of the 1970s and 1980s equipped Mr. Trump with the low expectations and cynical convictions that would carry him so far . . . Her devastating portrait of Mr. Trump’s failure should give his imitators pause.” —The Economist
“Maggie Haberman breaks more news than the rest of us.” —Jonathan Swan
“Maggie Haberman gets all the information”— Jimmy Kimmel
“No reporter has lived rent-free in Trump’s head longer than Haberman.” — POLITICO Playbook
“Haberman’s book is chockablock with scoops . . . but what singles it out from the competition is its perceptiveness about Trump’s character and the way his private vices became public menaces.” —Peter Conrad, The Guardian
“With a masterly command of her subject, Haberman carefully weighs her sources and composes a highly readable, believable account of Trump from childhood through his petulant Mar-a-Lago exile.” —Shepherd Express
“The most comprehensive portrait of the 45th president to date, one that correctly diagnoses him as a malignant, world-historical narcissist and that will be read long after he alights from the proverbial couch.” —Air Mail
“Deeply reported and immersively told, this is an essential contribution.” —Publishers Weekly, starred review
“A damning portrait of narcissism, megalomania, and abject failure—and the price the country is paying in the bargain.” —Kirkus Reviews
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“What do you need me to say?”
It was May 5, 2016, two days after the Republican primary in Indiana. I sat in the back of a yellow taxicab as it rolled down Fifth Avenue, my computer open on my lap and a phone held to my ear.
The likely Republican nominee for president was on the other end of the call. I had reached out to his staff for comment about a fresh round of support he had received from David Duke, a former Ku Klux Klan grand wizard and onetime Louisiana politician, who had recently alleged that opposition to the Trump campaign came from “Jewish extremists” and “Jewish supremacists.” The Anti- Defamation League, as it did at other points during that campaign, called on the candidate to “make unequivocally clear” that he rejected Duke’s statement.
Donald Trump greeted me and then cut quickly to his point. “I’m here with my two Jewish lawyers,” he said, appearing to refer to David Friedman and Jason Greenblatt, both of whom handled matters for his company, the Trump Organization.
“I have a statement. Are you ready?” he asked. I waited, my fingers hovering over the keyboard. “Antisemitism has no place in our society, which should be united, not divided,” he said, as I typed his words. Then a pause. A pause that went on a beat too long.
“That’s it?” I asked.
Another pause. Then Trump asked, “What do you need me to say?” Trump was notorious for seeking cues that would help him please his audience, but in this context, his uncertainty threw me. Knowing what to say to show you wanted to separate yourself from the nation’s most famous white supremacist should not be hard. I reiterated what I had told his campaignaides, that I was seeking a response or reaction to Duke’s antisemitic remarks about “Jewish extremists”; Trump seemed to realize why his initial statement was deficient, and added that he “totally disavows” what Duke said. A few seconds later, we hung up.
What do you need me to say?
In some ways, it was the question that informed all Trump had done as a businessman, where success had made him a recurring character in New York City’s tabloid newspapers. Young Donald Trump had been athletic as a teenager, and then aspired to a career in Hollywood. He ultimately fulfilled his father’s desire for a successor in the family business: real estate. But what the son really always wanted was to be a star.
So that question guided Trump to cast himself as he preferred to be seen—a take-charge billionaire in a leather-backed seat on the reality television show The Apprentice. He was usually selling, saying whatever he had to in order to survive life in ten-minute increments. He was also guided by a belief in repetition; over and over he would convey to employees and friends a version of the same idea: if you say something often enough, it becomes true. Together these instincts helped him to evade public and private danger over the course of nearly fifty years, and then became the foundation for his approach to politics, as a candidate and then a president and a former president.
Though some of his confidants held out hope that the weight of the presidency would change Trump, that was never a likely outcome. Over the years, those who got closest to him and chose to stay there often suggested they had been sucked in by a version best described as the “Good” Trump. The Good Trump was capable of generosity and kindness, throwing birthday parties for friends and checking on them repeatedly when they fell ill, calling the daughter of a political ally who was suffering from breast cancerfor a surprise chat from the White House. The Good Trump could be funny and fun to be around, solicitous and engaged, able to at least appear interested in the people in his company. The Good Trump could heed advice from aides hoping to curb his self-destructive impulses and could seem vulnerable. That version of Trump won the loyalty of many people over decades. Being close to Trump was like “being friends with a hurricane,” one long-time friend told me. “It was very exciting, but you kind of don’t know which way the wind was blowing.”
In the White House, those who met Trump for the first time were often disarmed, seeing someone not at all like the angry voice of his Twitter feed or the fuming boss portrayed in innumerable news accounts. In some respects, he benefited from that media coverage and social media persona; he was often calmer in person in initial interactions, leading people to question the veracity of what they had read. (The all-capitalized tweets that projected anger were sometimes sent while he was laughing about the same topic.) He is charismatic and can be charming, and in those initial encounters, he woulda sk people questions about themselves, zeroing in on them, giving them the sense that they were the only person in the room.
But even those who rationalized staying close to him acknowledged that a “Bad” Trump always revealed himself. That was the man who made racist comments and then insisted people had misunderstood him, giving his allies cover by which to defend him. He was interested primarily in money, dominance, power, bullying, and himself. He treated rules and regulations as unnecessary obstacles rather than constraints on his behavior. He lost his temper suddenly, and abusively, directing his ire at one aide in a roomful of others, before moving on from a burst of anger that instilled fear in everyone that they could be its next target. Occasionally, he would recognize that he had gone too far, but instead of apologizing, he would be effusive toward his target the next time they saw each other. He sought an endless stream of praise, prompting a range of aides to offer it in his presence or on television. He created an environment perpetually beset by rivalries, where those in his circle became fixated on tearing down whoever had begun to win his favor.
He disregarded the advice of long-serving government employees and business professionals and his own lawyers. He encouraged people to take risky actions in his name, and demanded they prove themselves to him over and over; many were so eager for his approval that they obliged. His thirst for fame seemed to grow each time he tasted more of it, and his anger at being wounded, which was often met only with an outsize reaction against the person he blamed for the injury, was always there. Trump almost always foreclosed few options until the last possible minute and modulated his behavior only when he had to; more often than not, he waited out people and institutions who posed resistance, ultimately bending them to his will through inertia. That version of Trump was the one who was most often seen in the eight weeks leading to the violent aftermath of his 2020 loss on January 6, 2021. After he left office, some of his closest aides and supporters privately described themselves and his political movement as having been held hostage to his refusal to cede the stage; independently, those people said the only thing that would change the situation was Trump’s passing.
Trump did not produce the intense polarization that has riven the country since at least the 1990s, when President Bill Clinton and Speaker Newt Gingrich were pitted in a zero-sumpartisan conflict amid increasingly virulent culture wars. A sequence of traumas followed: impeachment trial, close presidential election decided by the Supreme Court, catastrophic and world-altering terrorist attack, two seemingly endless and costly overseas conflicts, a devastating hurricane that lay bare racial disparities, a fiscal crisis that left millions in financial ruin with no one held accountable. But he did capitalize on the aftermath of those events, adding accelerant to existing trends and exploiting the cultural divide, defined in part by anger at government and financial elites, and by resentment among white voters at the country’s shifting demographics. In a celebrity-obsessed country that over many years treated politics as a wrestling match or a game, Trump found his moment, fueling and benefiting from the collapse of cultural and political identities into one another as the country cleaved along the lines of whom you hate, or who hates you back.
Trump had spent decades surviving one professional near-death experience after another, and after a lifetime of bluffing and charming and cajoling and strong-arming his way through challenging situations, he saw no need to change after winning the White House in 2016. By any objective measure, Trump had already led a remarkable life by the time he got there. He had been a famous figure for decades, defining an in‑your-face approach to wealth that helped enmesh him in the pop culture fabric of movies and television. He was unrivaled in his ability to reinvent himself just when he approached the brink of personal disaster, often owing to his own behavior.
By the end of his presidency, he had assembled a record of historicalc onsequence, changing the Republican Party’s policy orientation toward anti-interventionism, nativism, and confrontation with China. He had accumulated a list of legacy accomplishments, including a dramatic reshapingof the U.S. Supreme Court with conservative appointees, a revision of the tax code, peace accords in the Middle East, and an economy that his predecessor had rebuilt and which Trump grew, with record-low unemployment numbers. But none seemed as significant to him as the prize he lost—a second term.
When eighty-one million voters rejected him, revoking the job that brought the most sustained attention he had ever experienced, Trump attacked the democratic processes that brought him to power in the first place. For weeks, he insisted ballots cast against him were fraudulent without providing evidence, as his allies loaded up specious lawsuits. Trump, who routinely conflated legal and public relations problems, appeared to expect law-enforcement officers and judges to reflexively take his side. He wanted to promote a conspiracy theorist lawyer as a chief adviser in the White House and considered pushing the attorney general to appoint a special counsel to investigate her claims, while entertaining a suggestion that the government be dispatched to seize voting machines.
All was in the service of seeing how far he could take what he often called “the fight.” He pursued a scorched-earth strategy even as his private actions after the election conceded the bleak reality of his situation. In public he echoed the “Stop the Steal” rallying cry conceived years earlier by one of his oldest advisers. In private, Trump renovated his post-presidential home in Florida and at least acted as though he were debating whether to attend Joe Biden’s inauguration. Some allies discussed whether any lawyers would be willing to negotiate a global settlement to let him avoid criminal charges that loomed upon leaving office (the idea went nowhere).
When he ran out of other options, Trump encouraged his supporters to march to a branch of the federal government that was beyond his control and initially stood back, watching television while they launched a violent uprising, stormed through the Capitol building, and interrupted the certification of the election he had lost.
Trump possess [sic] a unique base of support among young people, executives, middle-leve lwhite collar workers and minorities,” read the executive summary of the Report to Donald Trump on Public Opinion in America, delivered to him in October 1988 by the research firm Penn and Schoen Associates, Inc.
“Regarding issues which detract from his support,” wrote the pollster who conducted the survey, Doug Schoen, “only one really impacts a large number of voters: Trump’s lack of experience in government. This, however, can be overcome, and we have outlined a plan in that regard later in this memo.”
The 95‑page report was completed eleven months after Trump published The Art of the Deal, the bestselling book that elevated a real estate developer largely unknown outside New York into the American standard of aspirational success. At that point in his life, Trump was getting his first taste of fame, the drug that would sustain him and of which he seemed to require increasing doses over time. A quarter century later, Trump experienced the ultimate high: in the White House, he received as much attention as the world can offer a single human being.
Before he sought office, the biographers Wayne Barrett, Tim O’Brien, Gwenda Blair, Harry Hurt, and Michael D’Antonio put significant work into chronicling Trump’s rise, his family, his business ties, and his fame. He became the subject of more books during and immediately after his presidency than almost certainly any other one-term president, with the possible exception of John F. Kennedy. These books, some written by my colleagues and competitors on the White House beat, have explored Trump’s moods, his dysfunctional management style, and how he reached decisions on critical policy matters. Their chapters have been filled with fly‑on‑the-wall anecdotes, insights from disaffected staffers, and scoops that often left me kicking myself for not having had them. But they almost always start sometime in the White House, or with the launch of his presidential campaign, when Trump presented himself as an ingenue to politics.
The reality is quite different. Trump had considered campaigns for the presidency, sometimes with more intensity than he let on in real time, throughout much of his adult life. It was partly an effort at brand enhancement, but the idea of becoming a celebrated national figure with immense power captured his imagination in the late 1980s. Even in the decades when he chose not to seek office, he was being shaped for it. He did not act in a way that most political strategists would have recognized as serious ahead of a campaign, but his interest level was.
But the work of the presidency itself rarely matched the thrill of standing in the center of an excited convention crowd as balloons dropped cinematically on him as a party’s nominee. As other presidents have, Trump discovered the limited powers of the office were not commensurate with the grand title. Most of the powers that come with the presidency did not actually interest him; he alternated between unfocused involvement in minutiae and appearing to pass the time. During one late-day session with aides to focus on the music played at his rallies, Trump had the group search through Spotify for specific songs from the Who’s rock opera Tommy for more than an hour because he was trying to find one that he insisted existed. (The aides couldn’t find it.)
This book is an effort to find the threads that weave those two worlds together. It is not intended as an exhaustive review of the White House years, or of matters related to the investigations into whether there was a conspiracy between Russians and the Trump campaign in 2016, or of the final ten weeks of the Trump presidency. It is an examination of the world that made Trump and the personality and character traits he possessed as he emerged from it, and how they shaped and defined his presidency.
My task became easier after January 6, 2021. The riot at the Capitol was, for a time, too much to take for a number of Trump aides, allies, advisers, and associates. Some declined to speak, either because they felt lingering gratitude toward him for professional or personal reasons or because they remained fearful of him. But, especially with Trump out of office, others were willing to offer a fuller portrait than they had been at any previous point. I spoke to more than 250 people specifically for this book. Conversations, information, and scenes described here are based on detailed notes and recordings, as well as contemporaneous observations and recollections. (Trump, responding to a lengthy list of questions about some of the reporting in the book, dismissed most as “fake news,” “false,” or “fantasyland.”) It became clear over the course of those interviews that much of what happened during the presidency was foretold by the earlier parts of Trump’s life.
The New York from which Trump emerged was its own morass of corruption and dysfunction, stretching from seats of executive power to portions of the media to the industry in which his family found its wealth. Late twentieth-century New York was a place in which tribal racial politics dominated aspects of public life, keeping Black officials locked out of city-wide government power until 1989, informing news coverage of crime and public services, and dictating what got built where and who paid for it. The world of New York developers was filled with shady figures and rife with backbiting and financial knife fighting; engaging with them was often the cost of doing business. But Trump nonetheless stood out to the journalists covering him as particularly brazen; they were hard-pressed to point to another developer who would do something like breezily admitting to using an alias while under oath in a lawsuit about the underpaid, undocumented workers who’d built his eponymous tower.
It was his desire to see how far he could take a presidential campaign that defined the later years of his life. For all the previous times he had toyed with running, and all the scut work he did to develop relationships in key primary states, aides conceded that he never gave much thought ahead of time about what the job itself entailed. Without understanding how the federal govern- ment worked, and with little interest in learning, he recreated around him the world that had shaped him.
During two campaigns and four years in office, he treated the country like a version of New York City’s five boroughs. Trump aides soon realized in 2017 that he had imagined a presidency that functioned like one of the once-powerful Democratic Party machines in those boroughs, where a single boss controlled everything in his kingdom and knew his support alone could ensure electoral success for others, and where “us” versus “them” defined a city where racial dynamics changed from one block to the next.
When he arrived in Washington, Trump defaulted to the accumulated wisdom gathered over decades of boom-and-bust cycles in his business and his personal life. In his earliest days, he had a handful of key advisers and mentors. Norman Vincent Peale, who preached the “power of positive thinking” and a proto-prosperity gospel, gave Trump a belief that he could will something into existence; when a situation worked out in his favor, Trump often attributed it to mental force. From the temperamental owner of the New York Yankees, George Steinbrenner, whose habit of theatrical firings mesmerized fans and made him as much a focal point of press attention as the team’s on-field doings, Trump found a display of hypermasculinity he often emulated during the fragile era when the AIDS virus terrified the country in the 1980s. From Ed Koch and Rudy Giuliani, he learned about showmanship in elected office. And from Meade Esposito, the ironfisted Brooklyn Democratic Party boss, he learned how he thought powerful political allies were supposed to behave. The provocateur and political flame thrower Roger Stone, who spent years helping to groom Trump for political office, starting with that first 1988 poll, was key to mapping Trump’s political rise. Other than his father, the most important influence on the future president was Roy Cohn, who taught him how to construct an entire life around proximity to power, avoiding responsibility, and creating artifice through the media. How much of Trump’s displays of brute personality have been a function of keeping people from seeing through the artifice is unknowable, perhaps even to him.
Just as he was guided by old models, he was motivated by dated rivalries and grudges. Those who had been around him awhile often recognized, in the many personalized feuds that occupied his time in office, threads of grievances related to the Trump Organization’s business. Two of his favorite targets, Senator John McCain and New York representative Jerry Nadler, had opposed Trump’s access to a federal loan program in the 1990s for construction on Manhattan’s West Side, while another, Representative Debbie Dingell, had been married to a late congressman who wanted one of Trump’s casino-related actions investigated.
Yet for all the intrigue that is part of the Trump mythos—the talk of his unpredictability or descriptions of him as an agent of chaos—the irony, say those who have known him for years, is that he has had only a handful of moves throughout his entire adult life. There is the counterattack, there is the quick lie, there is the shift of blame, there is the distraction or misdi- rection, there is the outburst of rage, there is the performative anger, there is the designed-just-for-headlines action or claim, there is the indecisiveness masked by a compensatory lunge, there is the backbiting about one adviser with another adviser, creating a wedge between them. The challenge is figuring out at any given moment which trick he is using.
When assessing others, Trump is usually focused above all else on whether something or someone has “the look,” reflecting his view of life as a show hewas casting. Obsessed with other people’s secrets, Trump is expert at finding their weaknesses and exerting pressure on those weak points, as well as encouraging people to try to please him by taking risks on his behalf so that he can claim to be at a remove from the fallout. For all the talk of how he values loyalty, he has been most abusive to those who readily offer it, and he enjoys watching people who had previously criticized him grovel in search of his forgiveness or approval. Yet people also describe him as lonely, and often a people pleaser as much as he is a fighter, frequently allergic to direct interpersonal conflict.
He is incredibly suggestable, skimming ideas and thoughts and statements from other people and repackaging them as his own; campaign aides once called him a “sophisticated parrot.” He has shown a willingness both to believe anything is true, and to say anything is true. He has a few core ideological impulses, but is often willing to suppress them when it’s useful for another purpose. He makes vague statements that allow people to project what they want onto his words, so two sides of the same issue could claim his support. More often than not, Trump is reacting to something instead of having an active plan, but because he so disorients people, they believe there must be a grander strategy or secret scheme at play. Whatever he’s up to is often part of what he sees as a game, whose rules and objectives make sense only to him.
His need to live in the eternal now usually outweighs any ability to think of the long term. But Trump also lives in the eternal past, constantly dragging a deep raft of old grievances—or impressions of better days lost—into the present, where he tries to force others to relive them along with him. His willingness to take a course of action that he knows will inflame critics and lead to him being seen as tough has guided him for decades.
Among his most consistent attributes are a desire to grind down his opponents; his refusal to be shamed, or to voluntarily step away from the fight; his projection that things will somehow always work out in his favor; and his refusal to accept the way life in business or politics has traditionally been conducted. These qualities have been his edge, as is wearing on his sleeve that which other people strive to keep hidden. He grew angrier over time, especially when he faced one investigation after another, from prosecutors but also from political opponents. Yet precisely what was causing that anger was often beside the point. A core tenet of the Trump political movement has been finding publicly acceptable targets to serve as receptacles for preexisting anger. That anger helped signal his supporters, who are bound to him more by common enemies—liberals, the media, tech companies, government regulators—than shared ideals. Employees and advisers who wrapped their identities in him felt more bonded to him when he was under attack. (In the White House, aides who had not known him previously were struck by the projection of confidence at all times, even when he seemed to be at low points.) His most ardent fans saw pieces of themselves in him, or something they wanted to be like.
His entire business career prior to the presidency was not a mirage. He built a giant tower on Fifth Avenue and owned three casinos in Atlantic City, convincing banks and government officials to help him do it. He bought up major properties and forced those in power to deal with him. He developed a portfolio of holdings. But he was never a businessman on the scale of titans of finance and real estate in New York that he tried to appear commensurate with. Executives in Trump’s hometown scoffed that he was playacting at having a bigger bank account and bigger real estate portfolio than he did, mocking his eventual willingness to lend his name to almost any licensing deal. And the matter of whether he inflated the value of his properties to deceive lenders was at the heart of a criminal investigation into his company after he left office. But outside the bubble of New York City, he had been synonymous with wealth for decades; across the country he was merely someone who’d built big towers branded with gold letters.
To fully reckon with Donald Trump, his presidency and political future, people need to know where he comes from.
I was born in New York City the same month that Donald Trump first tangled with the federal government, to parents who met while working at the New York Post, one of the tabloid newspapers that Trump came to identify with. At my public elementary school on Manhattan’s Upper West Side, one field trip was to see the public lobby of the new architectural marvel known as Trump Tower. I have lived for most of my adult life in the borough where Fred and Donald Trump learned how political power worked. My career has been spent at the news outlets Trump cared most about.
For much of the last decade, as Trump went from being a primarily local to a national and international story, reporting on him has been my full-time job as a correspondent for The New York Times. I have found myself on the receiving end of the two types of behavior he exhibits toward reporters— his relentless desire to hold the media’s gaze, and his poison-pen notes and angry statements in response to coverage. The opportunities that his rise presented to a journalist were manifold, in terms of both unending stories and increased interest level in my work. But so were the downsides of being forcibly cast as one of the characters in the movie he was forever scripting with his life.
Over time, Trump has had both the thickest skin and the thinnest skin of any public figure I have ever covered, sloughing off a barrage of negative coverage in one moment, while zeroing in on a perceived minor slight made against him by a talking head on television in the next. From his earliest days through the present, Trump has always had enforcers, informants, and people willing to spy on one another scattered throughout his orbit, to create a sense of menace and a threat of attacks to try to force people to engage with them on their terms. Many have been willing to use his inherent paranoia and thin interest in details to bend him for their own ends. Trump often encouraged their tactics.
Republicans’ rejection of the mainstream media intensified during the Obama presidency and then dovetailed with Trump’s anger, except for him it was all more personal than it was to his copartisans. He considered himself part of the media after ingratiating himself as a frequent television commentator and radio guest for years, and he treated coverage he did not like as a betrayal.
One of the most peculiar aspects of Trump over time has been his ability, not always intentional and often not stated explicitly, to get the people around him to adopt his behavior. Many in his world have started to practice qualities that only Trump has been able to get away with. As the head of what was ultimately a privately owned family business, the number of people subject to that pull had been limited. As a candidate for president, and then as commander in chief, the circle expanded dramatically, and came to include even some of his Republican critics who started to act like him.
But so did many critics who remained in opposition to him, adopting his habit of personal insults or making claims that exceeded what the facts demonstrated, or refusing to apologize for errors or believing the ends justify the means of their attacks. Over two decades, the political tide had lowered for what was considered acceptable public behavior, pulling down everyone in the process. Trump was very comfortable navigating the changing waters. Even if so much about Trump’s Washington years—the personalities, the style, the approach to power—was familiar to me, permanently examining his world left me often questioning whether even the most minute of facts were true, much as many of the people who worked for him in the White House found themselves doing.
Ultimately, as both a candidate and president, Trump spoke to me more often than he claimed, but nowhere near as much as some Democrats and some Trump aides convinced themselves was the case. In the White House, he tweeted about me repeatedly and mentioned my name, unprompted, in meetings with advisers. One time, it followed having seen me mention during a PBS interview that Trump watches several hours of television a day; he complained about my remark, ignoring the fact that he had learned of it only because he had been watching television. He derided my appearance to aides, saying to one, “Did you ever notice that her glasses are always smudged?”
Shortly after his election in 2016, someone who had known Trump for years, in shock at the result, told me, “The country’s elected Chauncey Gardiner and nobody realizes it,” referring to the protagonist of Being There. The book was adapted to a movie in which Peter Sellers plays a dim man named Chance, a gardener, who through a series of misunderstandings ends up being confused for an upper-crust genius named Chauncey Gardiner. But that missed the mark; Trump was not especially knowledgeable of much beyond real estate deals, building construction, sports, movies, and television, but he was shrewd and smarter than his critics gave him credit for, possessed of a survival instinct that was likely unmatched in American political history.
He also was not, as Chance the gardener was, harmless; Trump’s zero-sum mentality ensured someone else would often have to pay the price for his success.
A single fact in a story that I cowrote with three colleagues the weekend before the election in 2016 about the missteps by the Trump campaign had infuriated the candidate: we wrote that advisers had removed the Twitter app from his cell phone. Hours after the polls closed on November 8, 2016, and as a key state was being called for Trump, a Times colleague, Patrick Healy, tried his cell phone.
Mr. Trump, Patrick said, seeking a comment, you’re about to become the president of the United States. “Thank you, thank you—great honor. You tell Maggie,” he replied, “that nobody took my Twitter away.”
A different colleague—this one a veteran of the paper’s Washington bureau, Adam Nagourney—sent me a note about what Trump’s win meant for my career. “This is great for you,” he said, alluding to the typical route for a campaign reporter who follows a winning candidate to the White House, and the fact that I had covered Trump longer than other reporters.
I had just followed a slashing, often dysfunctional, retribution-minded campaign, shaped at every moment by the candidate’s impulse for control— of his news coverage, his supporters, and his aides—alongside an innate drive to test the limits of transgressive behavior and a dangerous disregard for democracy and civil rights. Now an entire government would be in his hands, his strongman impulse joined for the first time with expansive power over the lives of millions of people. I typed back my immediate reaction: You have no idea what is coming.