Donald Trump spent more than 15 years figuring out how to sell himself effectively in the political world. He studied long and hard and had a carefully thought-out plan before officially declaring his presidential candidacy in June 2015.
Many people do not believe Trump was so methodical. For a long time Trump created so much noise in other arenas that it drowned out his political machinations. As New Yorkers, we were well aware of his overblown image. From the hard-to-impress citizens of the money-obsessed metropolis, he had won the rare tribute of an instantly recognizable nickname: The Donald. He was the gossip-page fixture who blasted enemies, used every publicity opportunity to extol the gauche luxuries of his condo developments, and somehow drove his mistress to proclaim on a tabloid front page that with him she’d experienced the “Best Sex I’ve Ever Had.” He lived in the Fifth Avenue sky, firing and hiring on his reality show, surrounding himself with fashion models in his box at the U.S. Open tennis championships in Queens and with socialites at his Palm Beach club. He was always good for an attention-getting quote about anything—and both of us took him up on that in our newspaper work in the 1990s and 2000s.
We weren’t immune to believing the easy myth at first. It goes that Trump’s political dalliances over the decades were all stunts designed to satisfy his ego or create free publicity to promote a new product. Trump, savvy New Yorkers thought, was a political ignoramus, an Elmer J. Fudd fixated on his mansions and yachts who could not possibly have serious policy ideas or a realistic vision of himself occupying 1600 Pennsylvania Avenue. This groupthink was confirmed by his brutishness when he did share an opinion on charged events in full-page newspaper ads—most infamously his 1989 “Bring Back the Death Penalty! Bring Back Our Police” ad arguing that five African American teenagers suspected of raping a Central Park jogger be executed—followed by outlandish cable news interviews to reinforce his point.1 “Maybe hate is what we need if we’re gonna get something done,” Trump told CNN’s Larry King after publishing the jogger ad. His un-commenced runs for office—in 1988, with a New Hampshire primary season speech; in 2000, with talk of a third-party bid; and in 2011, when, during talk show appearances ostensibly to promote The Apprentice, he veered into speculation about challenging President Barack Obama—seemed to confirm a tiresome pattern: he would never fully declare his candidacy.
But now? Still? After he ran for the White House, spent $66 million of his own money, and won?2 Despite many books and documentaries painstakingly tracing the history of Trump and his family backward to Germany and the Klondike, and forward to the cheeseburgers and blaring televisions of the presidential living quarters, the myth that Trump was never serious about politics before 2015 holds on more stubbornly than the idea that you can get a good deal on a Rolex on Canal Street.
For us, the existing stories about Trump’s political rise didn’t add up. At best, other authors credited political advisers and campaign strategists like Steve Bannon, Kellyanne Conway, and David Bossie for formulating a viable Trump recipe in the years immediately leading up to 2016. We’d written enough about Trump over the years that we had strong sources to tap for a deeper understanding. When did he get serious about politics? Did he have a real plan when he declared his candidacy in 2015, or was it all seat-of-the-pants? Were there behind-the-scenes players we hadn’t heard of? Why all the apparent chaos around him?
What we found is that Trump prepared diligently over many years, learning and evolving. There are plenty of things he does not know. He may even be, as some psychologists argue, a classic narcissistic personality, insisting on a stilted version of reality, or a victim of the Dunning-Kruger effect, a cognitive bias that leads the afflicted to transform his lack of knowledge on certain subjects into a stubborn assertion of superior comprehension. But when it comes to honing and trusting his instincts, manipulating the media, branding, timing the political tides, collecting useful advisers, engaging in public takedowns, creating and thriving in chaos, adapting winning strategies from others, and dozens of other sometimes subtle methods of getting his way, he is a master.
Trump’s early presidential explorations presage what he is doing now and what he is likely to do next as president. Here we see how his years-long repetition of an anti-immigrant message culminated in the idea of a border wall with Mexico, and why he has unique reasons to believe that a lot of news reporting is inaccurate.
We narrowed our focus to 1999–2015, pivotal years that start with what we now see was Trump’s first serious exploration of a presidential run and end at the moment when he unfurled a fully baked strategy and declared his intention to run and win.
Other books spend only a few paragraphs on Trump’s exploration of a presidential run on the Reform Party ticket in 2000 and his near run for New York governor in 2014. Our sources show convincingly that these were pursuits on which Trump spent copious time and mental energy. They were major moments in the political education of a future president—dramatic episodes that well deserve a full unwinding.
Likewise, most Trump narratives tell a version of the birth of The Apprentice that makes him look lucky rather than strategic to have landed on TV. They only follow the first triumphant season of the NBC show closely. Here, we reveal new facts about the origin story, and then zoom in on a later, troubled season. With this additional light, some of Trump’s strengths and flaws can finally be fully displayed and considered, along with what the entertainment industry hid.
These firsthand accounts are evidence to annihilate myths. Trump had long said he wouldn’t run for president unless he thought he could win. No, he didn’t know in 2015 that he would win. But he thought he could. And with that he stood atop the brass-and-glass escalator in the public atrium of Trump Tower and rode down to his destiny, announcing on June 16, 2015: “So ladies and gentlemen, I am officially running for president of the United States, and we are going to make our country great again.”
We are not doing this to argue that one should support or not support President Trump’s policies. We are journalists who saw a part of the record that was incomplete, believed we were in a position to fill it, and passionately felt our duty was to do just that. We understand that if you take away FBI director James Comey announcing a new investigation of Hillary Clinton, foreign meddling in the election, hush money to former lovers, the fog around Trump’s net worth, strategic missteps by Democrats, the Electoral College system, and other unknown factors, Trump may not have won.
What we do ask is that you consider, as we started to, that Trump was diligently preparing for decades to take advantage of opportunities such as those this particular election presented.
Here is a quick but useful trip through Trump’s political prehistory. Donald J. Trump, the son of outer-borough real estate mogul Fred Trump, went into the family business full time after graduating from the Wharton School at the University of Pennsylvania in 1968. His father heavily subsidized his ambitions to become a force in Manhattan commercial development, a fact Trump successfully hid for years, building the myth that he was largely self-made.3
He’d become president of the Trump Organization in the 1970s, although his father still worked in the company. Trump’s first notable success was converting the derelict Commodore Hotel on 42nd Street in Manhattan into the flourishing 30-story Grand Hyatt. Then, starting in 1979, he bought and razed the Bonwit Teller building on Fifth Avenue to make way for his eponymous condo Xanadu, Trump Tower.
A month before the 1980 presidential election, with Trump Tower still under construction, the 34-year-old developer sat for his first in-depth television interview with Rona Barrett, a well-known celebrity reporter. Barrett became interested in him because of New York gossip-page mentions of his youth and wealth, and of his wife of three years, the Czech model Ivana Zelníčková. Barrett sensed something lurking behind his answers to questions about current events and asked if he’d ever want to run for president.4 He answered that he didn’t think he would.
Donald Trump: Because I think it’s a very mean life. I would love, and I would dedicate my life to this country, but I see it as being a mean life, and I also see it in somebody with strong views, and somebody with the kind of views that are maybe a little bit unpopular, which may be right, but may be unpopular, wouldn’t necessarily have a chance of getting elected against somebody with no great brain but a big smile.
He’d clearly thought about it. “One man,” he said, “could turn this country around.” On another topic, Trump told Barrett that the bad publicity he received for destroying Bonwit Teller’s signature 1929 limestone facade reliefs rather than preserving them as he’d promised was actually good for him. Those who cared little for historic preservation and wanted prime city views had seen the critiques and bought condos.
In his answers about politics, Trump grappled with a difficult problem: How does one become president if one is not a wholesome-seeming candidate type with a smile as disarming as Jimmy Carter’s or hair as thick as Ronald Reagan’s? It would take him more than three decades to perfect a formula.
Donating to the campaigns of political officials in regions where he had real estate interests over the years was business to Trump, not politics. When he dove into the political fray more directly for the first time in 1987, the timing foreshadowed some of the Russia troubles he’d have as president. Two months after a six-day5 trip to Moscow in July 1987, paid for by the Soviets, to discuss building two luxury hotels in the communist nation,6 Trump spent about $95,000 to print a full-page open letter in the New York Times, Washington Post, and Boston Globe. It read: “There’s nothing wrong with America’s Foreign Defense Policy that a little backbone can’t cure,” adding that America “should stop paying to defend countries that can afford to defend themselves.”7 Trump is not known for spending money without hope of receiving something tangible in return, and the idea that American allies, including Japan, should be left to fend for their own self-defense was certainly a position Moscow would favor. Whatever his motivations for the ad buy, Trump went on CNN’s Larry King Live to criticize U.S. trade policies with Japan, Kuwait, and Saudi Arabia and tout that he would address a Republican luncheon in New Hampshire the following month.
Larry King:… You realize now, in just setting foot in that state, people are going to presume things.
Donald Trump: Well, they can presume whatever they want. I have no intention of running for president, but I’d like a point to get across that we have a great country, but it’s not going to be great for long, if we’re going to continue to lose $200 billion a year. You’re going to get into the early ’90s—1990, 1991—and the whole thing’s going to blow.
On October 22, 1987, a week before the publication of his canonical advice book The Art of the Deal, Trump flew to New Hampshire. He had been brought there by a mercurial political consultant named Roger Stone. Already advising former football player and Reagan housing secretary Jack Kemp on his presidential campaign, Stone saw a potential political star in Trump. The developer delivered a stem-winder about trade deficits, taxes, and his business skills, shouting to an audience of 500 people, “I’m tired of nice people already in Washington. I want someone who is tough and knows how to negotiate.”8
Thanks to the success of The Art of the Deal, which rose to number one on the New York Times bestseller list and held the spot for 13 weeks, Trump was invited to appear on The Oprah Winfrey Show in April 1988, shortly after he acquired the Plaza Hotel in Manhattan. Oprah asked Trump whether he wanted to run for president. He “probably wouldn’t do it,” he said. But he wouldn’t rule it out if Americans’ lives worsened.
Oprah Winfrey: You’ve said, though, that if you did run for president you believe you would win.
Donald Trump: Well, I don’t know, I think I’d win … I wouldn’t go in to lose. I’ve never gone in to lose in my life. And if I did decide to do it … I would say that I would have a hell of a chance of winning, because I think people … are tired of seeing the United States ripped off. And I can’t promise you everything, but I can tell you one thing, this country would make one hell of a lot of money from those people that for 25 years have taken advantage. It wouldn’t be the way it’s been, believe me.
He was both feeding America’s anxiety about itself and suggesting he had a solution. Also worth noting is that he said he had no interest in running in 1988, and he did not run. He said that if he ever did run, he would try to win.
His August 27, 1998, interview with CNBC’s Chris Matthews turned from a discussion of President Bill Clinton’s legal strategy amid investigations to Trump’s political ambitions.
Chris Matthews: Why don’t you run for president?…
Donald Trump: People want me to all the time.
Chris Matthews: What about you?
Donald Trump: I don’t like it. Can you imagine how controversial I’d be? You’re thinking about [Clinton] with the women? How about me with the women?9
Trump didn’t have a winning answer—yet. Here is where we pick up the story in the mid-1990s. At the end of this book, we will leave you at the Trump Tower escalator in June 2015. We trust you can find your way from there.
This story is told with every source named and on the record, with one slight exception: we paraphrase an MGM entertainment executive who works under Mark Burnett. That executive refused to allow their name to be used in responding to charges leveled against producers of The Apprentice by named sources.
This is not a criticism of other works that rely on anonymous sources: anonymous sources are an essential part of many of the best pieces of journalism. It’s just that in this case, we found we could tell the story we wanted to tell without them, which is always the goal.
Some of our interview subjects are household names, some not. Among them are behind-the-scenes assistants, off-camera TV producers, Apprentice contestants, obscure Albany political players, and spotlight-shunning New York nightclub fixtures. From those who served in the Trump White House or regularly appear on talk radio and TV we received new, revealing stories.
We repeatedly requested an interview with Donald Trump through various White House channels, including then White House deputy chief of staff for communications Bill Shine, Press Secretary Sarah Huckabee Sanders, and innovations director and Trump son-in-law Jared Kushner, but did not land a fresh interview.10 Because Trump has given so many interviews over the years, we were often able to include his comments already on the record from the eras we examine.
We recorded nearly every one of our more than 100 interviews and worked from transcripts. To make reading easier, we fixed some grammar and condensed some quotes. Our comments are meant to provide context and fill in relevant history. The quotes are arranged in a way to move the narrative forward clearly. None of our interview subjects were in a room or on the phone together speaking directly to one another.
For decades, Donald Trump was preparing to run for president. It wasn’t the only thing he was doing. There were casinos, relationships, deals, golf, a “university,” out-of-court settlements, and big-time wrestling matches throughout his energetic life. But the evidence here shows he was puzzling out politics all along.
Some who criticize his political persona will allow that Trump possesses a preternaturally sharp intuition for what some audiences want to hear. Few consider—Steve Bannon told us during an interview at the Loews Regency hotel in New York—that Trump’s approach to gut instinct is studied. According to Trump’s co-authored 2004 book How to Get Rich, he briefly studied the groundbreaking psychoanalyst Carl Jung’s book Memories, Dreams, Reflections. Trump noted that even with a quick reading, Jung’s philosophy can help in “fine-tuning your intuition and instincts.”
Some of what Trump brought to politics is already becoming the new normal, evident in the fierce social media rhetoric deployed by his rivals. More of his techniques, once understood, are sure to be adopted. Others are unique to the forty-fifth president.
Here’s the news: there is a method to the madness.