Biographer Charts Donald Trump's Ambition, Fame And Candidacy

With his victory in the South Carolina primary, Donald Trump has solidified his position as the front-runner for the Republican presidential nomination. Former Newsday reporter Michael D’Antonio, author of "Never Enough: Donald Trump and the Pursuit of Success" (excerpt below), joins Here & Now's Jeremy Hobson to take a closer look at Donald Trump’s life and career.

What do you make of Trump not mentioning Jeb Bush in his victory speech?

“Well, it’s typical Donald Trump. Gracious is not on his list of traits. This is a fellow who has enemies, and he might have friends, but really what he has are allies. Jeb was an enemy, he was vanquished, on to the next enemy.”

On the history of the Trump name, dating back to his grandfather

“It started out as Drumpf, with a ‘D’ and an ‘F’ on the end, and he’s a fascinating character himself. He actually, pretty much, stole real estate in the mining country of the Pacific Northwest, squatted on it, erected businesses and traded with miners, and then when it was time to move on to the next site, he went and captured another piece of land and squatted on that and exploited it.”

That’s where the Trump fortune began?

“It is, and his father almost lost it all in the Great Depression, and this is Fred Trump, who was quite different from Donald in that he had to be forced to put his name on something. In fact I think only one of his apartment complexes in Brooklyn and Queens, which was his territory, actually had his name on it.”

How was Donald Trump different from his father?

“You know, Donald’s first interest was film. Before he left college, he played with the idea of being a film producer or an actor, so he was a showman from the start. Very outgoing, whereas Fred was kind of stiff in his social interactions, and he had incredible ambition to be at the top in New York’s most challenging borough, Manhattan.”

On his experience at New York Military Academy and how it affected him

“He was sent there at age 12 and had to adhere to the discipline there, but he took to it. NYMA rewarded aggression, it rewarded competitiveness, it rewarded any instinct you might have to prevail over another boy, and Donald had all of this and then some. So he thrived there.”

He has been married three times. What kind of family man is he?

“I would say that he’s a less-than-devoted family man. By that I don’t mean that he doesn’t love his kids or his grandchildren, but he’s really obsessed with his business and with his competitive drive. I’ve heard from the members of his family that he’d get bored rather quickly and want to leave family engagements. The kids could come and visit and play around him, but he was gonna take calls and he was gonna do business and he learned that from his father. His father would work all day and come home and at night, he would place calls using a fake identity in order to feel out real estate prices in areas where he was hoping to fill out property. Later on, Donald did the same thing, faking identities in order to spread, in his case, news of how great Donald Trump is.”

You write that when Trump is making deals, he assumes the deal is done from the start, and that helps him make the deal.

“It does. I think he has, in his mind, the shape of things as they will be at the end, and he pursues that goal against all other factors. He also doesn’t leave anything on the table. I know one other billionaire real estate man and he told me that he always leaves something on the table and he always makes sure the other party does as well as he does. That’s not Donald Trump. He wants to beat you and then he wants to grind you into the ground, which is why he wasn’t gracious about Jeb’s withdrawal from the race.”

What happened in the cases where deals did not go his way, or when he had to file for bankruptcy?

“I think Donald is a great deal maker, but he is not a great operator. The businesses that went bankrupt, the casinos and the ones that he was forced to sell like Trump Airways, all employed thousands of people and required real attention to detail when it came to operating them, and that’s not what Trump is about. In fact, if you go to his offices, there are about two to three floors of Trump Tower not populated by very many people at all. There might be 40 or 50 people and that’s it. Things that need to be run are operated on location and by managers he hires. He’s not very much interested in those day-to-day details.”

Have you caught him saying something untrue or exaggerated and admitting to it?

“Well sure, there was the whole case of his draft status during the Vietnam War. He often said that because of the draft lottery and the high number he got, he was never drafted and never had to serve. Well, that wasn’t the reason he didn’t have to serve. He actually had a series of medical deferments before the draft lottery even started. When we talked about this he sort of sheepishly said ‘you know, well yeah you’re right. I wasn’t intentionally misleading people,’ and then he whipped off his shoes and pointed to these two little bumps and said ‘see, I have heal spurs and that’s why I couldn’t be in the Army. I couldn’t march.’ I didn’t really see anything protruding from his elegant feet, and their beautiful socks, but you know that was the true story, he did have medical deferments and that’s why he didn’t serve.”

Has he ever apologized for anything, as far as you have observed?

“You know, I’ve never found that he has. It’s sort of like him saying that he’s never confessed a sin to God. This is not a man who says ‘I’m sorry’ very readily. Barbara Walters once challenged him, I think on the air, to say that he was sorry about something and he just couldn’t do it.”

On Trump's ability to read an audience being compared to cracking a safe

“It’s classic Donald, and he does perform beautifully. What’s funny is, he goes around his house turning off the lights. He is obsessed with cost and electricity, and he’s just - it’s so hard to fathom that people are buying into this, but you know he’s like a character on TV. I was thinking about Joe McGinniss’ 'The Selling of the President [1968],' in '69 and there was a great quote in it with one of Nixon’s ad men saying ‘I don’t like it, but this is the way the world is going. I’m not like most people, they all buy this,’ and I think we’re now at the point where we almost have like an ironic post-advertising candidate. People are dying to think that he’s in on the joke, but he’ll never break character. He’s always going to hold onto that pose, that ‘no I’m really serious and I’m as crazy as I seem.’ It’s - wow, what a creature.”

By Michael D’Antonio

In profile, which was how TV viewers saw him that night, Donald Trump resembled nothing as much as a rooster in a tuxedo. His posture, developed in military school, was firmly erect. His eyes were focused, with narrowed intensity, on a distant challenger. And arcing from his forehead back to his neck, his famous helmet of golden hair evoked the cockscomb of a Rhode Island Red. For the rooster, this beacon is meant to attract female attention and warn off enemies. For Trump, who sat among admirers and detractors at the 2011 White House Correspondents’ Dinner, it drew the television camera that caught his reaction to the public ridicule heaped on him in the name of entertainment, by both comedian Seth Meyers and the president of the United States.

The only hint that Trump was suffering came as Meyers mocked him for a full two and a half minutes. As the people laughed and strained to catch a glimpse of Trump, he leveled a look that could kill at the comedian. His face remained unmoving, and glowering, as even the diners at his own table found themselves unable to resist the tide of laughter. Meyers revealed the reason for all the derision when he spoke of a poll that found that only 38 percent of Americans were certain the president had been born in the United States. Since the Constitution requires that presidents be native born, the issue, which had been manufactured by conspiracy theorists, was a blatant attempt to paint Obama as an “other” whose claim to office was illegitimate.

Through his long, strenuous effort to promote this “birtherism,” Trump had made himself a target of those who believed this talk was divisive, destructive, and perhaps a veiled form of racism. He objected to this criticism, insisting that he was not prejudiced and that he was posing important questions. “When it comes to racism and racists,” Trump said, “I am the least racist person there is.”

When it was his turn to address the White House correspondents and their guests, the president confronted the birthers head-on, but with remarkable humor, even presenting a video clip borrowed from the animated movie The Lion King as “my official birth video.” Obama then mentioned Trump by name, praising the leadership he had demonstrated while performing as host of a reality TV show and making the “kinds of decisions that would keep me up at night.” Obama added that with the birther issue resolved, Trump could “get back to focusing on the issues that matter—like, did we fake the moon landing?”

Confronted by a critic who stood rungs above him in the status hierarchy, Trump did not offer the killer stare. Instead he allowed the corners of his mouth to turn up, ever so slightly, which deepened the crow’s-feet that framed his eyes. He then offered a wave to the president. Trump could take a joke. Afterward he took pains to seem unperturbed and spoke as if he had achieved something by gaining the president’s notice. “I was actually very honored by the way I was treated,” said Trump. “They treated me with great respect. They joked and they clowned, but I was the topic of conversation and that’s perhaps not so bad.”¹

In one way or another, Donald Trump has been a topic of conversation in America for almost forty years. No one in the world of business—not Bill Gates, Steve Jobs, or Warren Buffett—has been as famous as Trump for as long. First associated with high-profile real estate development in 1970s Manhattan, his name soon became synonymous with success defined by wealth and luxury. Placed on skyscrapers, casinos, and commercial airliners, the name TRUMP (usually spelled in gold-colored, capital letters) became a true personal brand that connected one man to a seemingly endless number of offerings. In time it would be stamped on hotel rooms, furniture, neckties, meat; almost anything that might be sold as high quality, high cost, and high-class.

The kind of class Trump sought to deliver was defined not by social standing but by cash. Eagerly catering to the nouveau riches and the aspiring, he dismissed those who belonged to what he called “the lucky sperm club” while glossing over that he had been born into one of the wealthiest families in the country. Trump cast himself as the everyman’s rich friend, who shunned high society, except when it was helpful to sell expensive apartments. In such cases he dropped the role of the anti-snob and readily referenced the Astors, Whitneys, Vanderbilts, and other blue bloods of a bygone age. It was understood, however, that he brandished these names out of commercial interest and that his heart was really aligned with Middle America. These were the people who followed him on TV, bought his products, and might even give him their votes should he ever get off the fence and actually run for office.

Today, according to the best available data, 96 percent of Americans recognize the name Donald Trump, but most don’t like him. Henry Schafer of the firm that defines celebrities with its Q Score ratings called Trump the “quasi-celebrity people love to hate.” In 2014, 61 percent of those polled in Trump’s hometown of New York City viewed him unfavorably. Comedians find him an irresistible target. Jon Stewart, the former host of the long-running satirical news program The Daily Show, routinely jabbed Trump, calling him, among other things, Fuckface von Clownstick. The television host and comedian Bill Maher famously offered Trump $5 million if he could prove he wasn’t “the spawn of his mother having sex with an orangutan.”²

The level of commentary offered by Stewart and Maher says much about the rancor of our age. It’s hard to imagine Mark Twain requiring the censor’s bleeps that accompanied Stewart’s rants. Of course Twain may never have met anyone quite like Trump. Gleefully aggressive, Trump looks for opportunities to take offense and then wrestle a supposed enemy into the gutter. When Stewart offered a generic juvenile taunt, Trump replied in a deeply personal way, asking, “If he is so above it all & legit, why did he change his name from Jonathan Liebowitz? He should be proud of his heritage! Jon Stewart @The DailyShow is a total phony. He should cherish his past, not run from it.” After Maher’s comment, Trump filed a $5 million lawsuit. Although he eventually dropped it, the filing required a court’s attention, at taxpayer expense, and a defense by Maher.³

But even as he appeared appeased his critics, Trump’s views and bully persona made him exceedingly popular with people who believed he represented important ideals, especially the American promise of success represented by great wealth. His image was amplified as he hosted a TV game show—The Apprentice—and maintained a constant presence on the social media site Twitter, where millions followed his commentary and many implored him to seek the presidency.⁴

Ever provocative, Trump gained attention by expressing raw and unrefined thoughts rather than nuanced reflections. In his calculation, honesty comes from the corner of his heart that is willing to fling insults and divide the world into enemies and friends. As veteran gossip columnist Liz Smith sees it, Trump is often ruled by the needy child who resides in his psyche and would rather get negative attention than be ignored. Of course Trump does profit financially as he gives this part of himself free rein, and he has little patience for reflection or analysis. He just presses on, defying science with his criticism of immunizations for children and battling against the facts on climate change.

Trump has denied facts others accept and pushed the limits of propriety throughout his long and hyperactive life. In his parents’ home, at school, and in the worlds of business and politics, he has continually asserted his superiority with only the barest hint of doubt. Perhaps nothing in nature is more voracious than this man’s hunger for wealth, fame, and power. And it is this force that has allowed him to endure considerable mockery and substantial setbacks in business and still come back for more. Indeed, in the time after his humiliation at the correspondent’s dinner, Trump nurtured an ambition to mount his own campaign for the American presidency—a real campaign and not another of his flirtations—and thereby claim the greatest accomplishment available to a mere mortal in the twenty-first century.

The Trump candidacy would be planned and plotted for 2016 when he would make it official in an address to well-wishers and journalists gathered in the lobby of his Trump Tower skyscraper in Manhattan. The most unconventional kick-off speech in many election cycles, the announcement—particularly his claim that Mexico is “sending” criminals across the U.S. border—would launch Trump on a rapid ascent to the top of the Republican field. For many weeks to come, Trump would outrage his critics and baffle his opponents as he held the nation’s attention with one outrageous statement after another. As some Republicans speculated that he was a Democratic Party plant, many liberals said Trump’s popularity reflected the irrational fears of the GOP base. All could agree that his ability to disrupt the status quo was breathtaking in its power and efficiency. Trump was unrivaled, it seemed, in his ability to capture and hold the attention of the American public.

Excerpted from Never Enough: Donald Trump and the Pursuit of Success by Michael D’Antonio. Copyright © 2015 by Michael D’Antonio. Reprinted by permission of Thomas Dunne Books, an imprint of St. Martin’s Press, LLC.