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Trump Seriously: On the Trail With the GOP’s Tough Guy

“I’m owned by the people. I’m no angel, but I’m going to do right by them.”

Donald TrumpDonald Trump

Donald Trump

Photograph by Mark Seliger

Hey, ya made it, great to see ya!” says Donald Trump, having just stepped aboard his throne room of a plane and stopping by my seat to extend his hand. “You get the big tour yet? No? What the hell? C’mon, I’ll show you myself.” 

I follow him into the stateroom of the 757, past three rows of sleeper seats wrapped in eggshell calfskin, with seat-belt buckles of plated gold and the family crest stitched in every headrest; past the conference center, with its mahogany table and a dozen executive high-backs snugged around it; past the in-plane theater, with its oyster-shape couches and the 57-inch flatscreen tuned to Fox; past the bumped-out bulkhead and the first of two bedrooms, this one fitted with mohair couches that convert to a full-size bed; and then the master bedroom, with its silk-spun walls and bathroom fixtures finished in rosy gold.

“Not bad, you agree?” calls Trump over his shoulder, leading me down the corridor to the cockpit. “I bought this from Paul Allen and gutted it top to bottom. It’s bigger than Air Force One, which is a step down from this in every way. Rolls-Royce engines; seats 43. Didja know it was featured on the Discovery Channel as the world’s most luxurious jetliner?” (Fact-check: It isn’t bigger than Air Force One, and it was featured on the Smithsonian Channel. But in this, as in much of what Trump says, it’s more about the broad strokes than the details.)

After takeoff, I find him in the stateroom, reading notes. “Gotta concentrate,” he says. “I’m speaking in front of thousands. After the rally, we’ll have plenty of time to talk.”

This seems fair, though we’ve spent hours in his office and haven’t gotten around yet to a single policy question, beyond his assurance that we’d touch on “all that stuff” later. I buckle in to watch the campaign coverage when he asks me if I know what inversions are. “Uh, no,” I say, thinking I’m in for a tutorial about wind patterns at 30,000 feet. “It’s when companies leave America and take thousands of good jobs with ’em. What do ya think of that, does that sound fair?” he says.

“Well, no, it doesn’t. But what would you do about it in your first hundred days?”

“Yeah, I gotta remind myself to talk about that tonight. But I’m busy now! I really gotta prep!” He burrows into his notes, marking a section in ballpoint. Not 60 seconds pass before he looks at me again. “You know New Hampshire has a huge problem with heroin? Why do ya s’pose that is?”

I tell him that it probably has to do with OxyContin and school kids raiding their parents’ medicine chests. They run out of pills, then find that bags of heroin are cheaper. “Yeah? Well, which is worse for you, the heroin or the pills?” I explain that they’re both derivatives of opium, which is dicey however it’s delivered. “Hunh!” he says. “Interesting. I didn’t know that. But I gotta get back to my notes!” (At a press conference, an hour later, he’ll respond to a question about heroin in New Hampshire by saying that “it starts probably with OxyContin, from what I’m hearing.”) Sixty seconds pass. “Hey, you believe this goddamn ISIS? Chopping people’s heads off, putting people in cages and drowning ’em. We gotta waterboard ’em, don’t you agree?”

I tell him I’m not in favor of chopping people’s heads off, and ask if he’d sanction waterboarding as president. He begins a rambling answer, then asks the woman across from me if she believes in the practice of waterboarding. And so it goes for the 26 minutes it takes us to fly from New York to Hampton, New Hampshire, where tonight he’ll go on in front of 2,500 people, a crowd to thoroughly dwarf the several hundred people who’ve turned out to watch Jeb Bush and Rand Paul speak in the state. In those 26 minutes, he’ll devote some 90 seconds to his typewritten notes, diverted instead by the mentions of him on Fox and the crowd of whims and tangents in his head. To sit alone with Trump is to be whipsawed and head-snapped by his sentences that start and stop, his thoughts that take hard detours or suddenly become questions in midstream. But as I learn in Hampton, exactly none of this will matter once Donald Trump takes the stage. The second those klieg lights hit him, he’ll find his maestro voice, that nimble and knowing schoolyard brogue that doesn’t miss a trick or a chance to pounce. Besides, he’ll say the exact same unscripted things he said in Michigan days earlier and will say again tomorrow at the Iowa State Fair, all of it word for word from memory. You may lament Trump’s message, but you can’t move him off it. It’s like trying to stop a 757.

This past June, Donald John Trump rode down the escalator in the five-story, pink-marble atrium of Manhattan’s Trump Tower to declare his candidacy for president of the United States. Since then, he has been mocked and reviled, worshipped and courted, and, till very lately, dismissed as a fever dream of the torch-and-pitchfork segment of the Republican Party. Entering stage far-right with wing-nut invective — the people coming across our border are “rapists” and “killers” who routinely commit “great amounts of crime” — he has dominated the race since the day he got in it and posted a large and durable lead ever since. The caveat: His negatives are through the roof. About a third of registered Republicans likely to vote next year say they’d never pull the lever for him. 

Donald Trump

In all the hysteria, however, what’s often missed are the qualities that brought Trump here. You don’t do a fraction of what he’s done in life — dominate New York real estate for decades, build the next grand Xanadus for the super-rich on the far shores of Dubai and Istanbul, run the prime-time ratings table for more than 10 years and earn a third (or sixth) fortune at it – without being immensely cunning and deft, a top-of-the-food-chain killer. Over the course of 10 days and several close-in encounters, I got to peer behind the scrim of his bluster and self-mythos and get a very good look at the man. What I saw was enough to make me take him dead serious. If you’re waiting for Trump to blow himself up in a Hindenburg of gaffes or hate speech, you’re in for a long, cold fall and winter. Donald Trump is here for the duration — and gaining strength and traction by the hour.

Begin with his message and mode of delivery. Standing over his shoulder, I watched Trump use the press to speak directly to his base, talking past the cameras and microphone banks to that furious demographic of working and out-of-work factory-town families who saw their wages set like Quikrete in the 1980s and watched the spoils and tax breaks swim upstream. When we landed in New Hampshire and pulled in to a Hampton high school in his motorcade of stretch SUVs, Trump was mobbed by reporters with the pushy fervor of kids seeking autographs at spring training. He batted aside their questions — Iraq, Russia, immigrants — to buttonhole the hundreds of people milling outside, unable to get in but listening on speakers, and the thousands more seated down the hall.

“I built a net worth of more than $10 billion. I’ve been a world-class businessman. . . . That’s the thinking that our country needs. Take our jobs back from China and Japan and Mexico. . . . Take a look at China. . . . We owe them $1.4 trillion . . . because we’re led by people who don’t have a clue. Honestly, I think we’re led by stupid people.”

There, in those words, is his campaign. I am strong; politicians are weak. I speak truth and never retreat; they lie and wave the white flag to our foes. They have stripped us bare; I will build us back, make this country feared the whole world over. Everything he utters is a version of this, dressed in different raiment or reference — and he’s saying it to people, his “silent majority,” who have longed to hear these words since Richard Nixon. “He’s delivering a message of power and courage without any proof points called policy,” says Steve Schmidt, the Republican wise man and campaign warhorse who’s been watching Trump with mounting fascination. “A huge chunk of conservatives are unmoored from the issues. What moves them is his tone and attack on Republicans who they hold in complete contempt.”

In the airless auditorium, the faithful are packed so tight that it feels like a breeding barn with a PA system. They are the young and the old, the blue- and white-collar, the white and, well, white-haired. He has a pitch-perfect ear for their curdled resentment and a ventriloquist’s gift for reading it back to them in words that they think but cannot utter at work, or anywhere else but their kitchen tables. Canvassing the crowd before he comes on, I hear the same phrases over and over. “Finally, someone’s saying what we’ve all wanted to say — we’ve been pushed too far for years,” says Tina, a gym-toned mom in a sleeveless top. “I like that he’s not politically correct — we don’t have time for that here,” says Lise, a frost-tipped blonde in the row behind her, calling Trump “another Ronald Reagan.” “He means what he says, and says what he means,” says a converted Democrat named Dino. “The other guys, they got marbles in their mouth — you don’t even know what they’re saying.”

Trump takes the stage to a standing ovation. His speech goes the way it always goes. “They had 24 million people [at the debate the other night]. . . . Do you think they were there for . . . Rand Paul? Rand, I’ve had you up to here!” He touches his armpit, zinging the vertically challenged Paul: “He didn’t like it when I said you have to pass an IQ test to get up on the stage.” Then he pivoted to Carly Fiorina. “Carly was a little nasty to me — be careful, Carly! Be careful! But I can’t say anything to her because she’s a woman. . . . I promised that I wouldn’t say that she ran Hewlett-Packard into the ground. I said I wouldn’t say it! That her stock value tanked. That she laid off tens of thousands of people, and she got viciously fired. I said I will not say that. And that she then went out and ran against Barbara Boxer, and . . . lost in a landslide. And I said, ‘I. Will. Not. Say. That!’ ”

The enormous audience leaps to its feet in eruptive, rocking laughter. And for 58 minutes, he goes on like this, playing the crowd like a Telecaster. Mexico’s taking your jobs. Ford and Nabisco are fleeing there. No more Oreos for Trump! What’s most striking is the ease with which Trump does it — no note cards, no teleprompter, no prep in the car. Running his first race for office at 69, an age when other men are seeking help for bladder conditions, he gives every impression of being born for this — and of having the time of his life.

A week or so earlier, I’d been summoned to Trump’s office at his glitter-bomb cathedral, Trump Tower. It is hard to overstate the effect of the building on your sense of dimension and place. You walk into a lobby that is half-Vegas, half-Vatican, a vaulting altar of brass and obsidian that soars halfway to heaven, where they serve dark-roast. There’s a Starbucks somewhere up in the sky-high atrium, not far from the 60-foot waterfall. You fight the urge to dunk your head in the pool where it collects, and try, instead, to regain your wits on the whooshing ride up to the 26th floor.

There, you are met by the first in a series of dazzling young female assistants. Trump also likes the theatrics of beauty. Many of his close aides are women in their twenties not very long removed from college. Hope Hicks, Trump’s communications director who, several years ago, was studying at Southern Methodist University, leads me into the boss’s office, which is as much Trump’s trophy room as workspace. Every flat surface is adorned by his image: framed magazine glossies from Important Publications, none more so, at least per Trump, than the 1990 Playboy where “I was one of the only men to ever get on the cover.”

Trump offers me a seat by his mahogany desk. Over his shoulder looms a bust of Ronald Reagan. (There is also a bald eagle, the stuffed-animal version, for any preschool patriot who wanders in.) In an earlier sit-down, Trump had fought me to a standstill when I tried to draw him out about his past. As countless writers before me have discovered to their sorrow, there’s no such thing as question-and–answer with Trump. Instead, you frame a query, then stand back and watch him go, hoping that in the monologue that follows, he touches at least obliquely on your topic. This time, he did divulge about his father, going on at length and with real feeling. Fred Trump, the second in a line of self-made magnates (his father, Friedrich, had earned his fortune in the Klondike gold rush, selling lodging, food, booze and possibly women to hordes of miners), was possessed of the singular family gift: He could see the future and beat everyone else to it.

“When the car was just coming out, houses had no garages,” says Trump. “Dad went all over Queens, building garages in the Thirties, and he could throw ’em up like nothing. He had great energy and vision, worked seven days a week and liked it, and was happy in his life. I watched people take vacations, and they’re miserable. Him, two hours at the beach with us on Sundays, and he was back to work.”

Fred was among the first of the great wartime developers to figure out the import of Federal Housing Authority programs, vast new pots of government loans to build housing for the working- and middle-class. Trump doesn’t volunteer that much of the family fortune derived from taxpayer funds, or that his father was a master manipulator of the Democratic machine in Brooklyn. Fred’s real money was made erecting outer-borough housing for the returning vets of World War II, brick behemoths that he delivered on schedule and hundreds of thousands of dollars under budget.

Though Fred lived and died a very rich man, he made his kids work like peasants. The three boys spent summers pulling weeds and pouring cement, learning the building trade from the subfloor up, while the two girls toiled in his real estate office in the bowels of Coney Island. Trump tells the story of being dragged by the nose to join Fred on his rounds collecting rents. “We’d go on jobs where you needed tough guys to knock on doors,” he says. “You’d see ’em ring the bell and stand way over here. I’d say, ‘Why’re you over there?’ and he’d say, ‘ ’Cause these motherfuckers shoot! They shoot right through the door!'”

Trump has raised his own kids in comparable fashion, disabusing them of any notions of unearned grandeur. “I was a dock attendant for a couple of summers, then went into landscaping,” says Don Jr., a company vice president running international projects, with an office directly below his father’s. “My brother and I are probably the only sons of billionaires who can operate a D-10 Caterpillar.” “I did less-than-glamorous internships in sweltering New York — the South of France wasn’t an option,” says Ivanka in her immaculate office next door to Don Jr. Together with Eric, the third of Trump’s kids by his first wife, Ivana Trump (he has two younger children by subsequent wives), his three grown offspring handle his vast portfolio of luxury hotels and resorts. Polished and restrained where their father is flamboyant, they’ve nonetheless paid him the highest praise by enlisting in the family trade. No less telling, none of them are train wrecks like so many children of billionaires. “We grew up with a lot of those kids and know them well,” says Don Jr. “But I guess we were pushed and motivated differently.” 

It’s worth noting that Trump was nearly a train wreck himself as the son of wealth in Jamaica Estates, Queens. An indifferent student who was “mouthing off to everybody” and carrying around a switchblade in his pocket, he was yanked out of prep school by his disappointed parents and sent to the New York Military Academy upstate. “He thought he was Mr. America and the world revolved around him,” says Col. Ted Dobias, his former instructor and baseball coach, a barrel-chested man who’s now nearing 90 but whose memory is diamond-drill sharp. “I had a lot of one-on-ones” with the 14-year-old Trump, adds Dobias, some of which got physical, both men say. Whatever it took to seize the eighth-grader’s attention, Dobias seemed to turn him around. By ninth grade, Trump was a model cadet; as a senior, he made cadet captain, says Dobias, and was the star first baseman for Dobias’ varsity squad. “He was good-hit and good-field: We had scouts from the Phillies to watch him, but he wanted to go to college and make real money.”

After graduating from Wharton, where his academic laurels have been grossly overstated through the years (he didn’t finish first in his class or anywhere near it, and went altogether missing from the list of honors for the class of 1968), Trump began working for his old man in Brooklyn, but had little sustaining interest in low-rent units. What he wanted was to have his name writ large on the next iconic towers of Manhattan. It was the mid-1970s, when the city was swirling the drain of insolvency and structural collapse, but even from the boroughs, Trump could look ahead a decade to the gilded age of the 1980s. Seizing upon the collapse of the Penn Central railroad, the largest corporate bankruptcy in history at the time, he scooped up an option to redo the Commodore Hotel, a Beaux Arts colossus gone badly to seed as one of the troubled railroad’s minor holdings. 

Donald Trump

“The area was dying, people were leaving the city, but I went to Bowery Bank across the street and said, ‘If you lend me the money, 42nd Street is gonna be great again,’ ” Trump says. Bowery and a second firm, Equitable Life, staked tens of millions of dollars on the reconstruction. Trump strong-armed City Hall to give him an unheard-of break – full tax abatement for 40 years — and stripped the old girl of her limestone vestments, dressing her in dazzling skirts of glass. Reborn as the Grand Hyatt in 1980, the building — a great mirrored beacon to investors eager to pounce on midtown projects — came along just as the stock market soared, minting a brash generation of new millionaires.

Those young-money turks burned to tweak their stodgy fathers by flashing their sudden wealth on shiny objects. Trump built them the gold-dust condos of their dreams, converting the dowdy Gulf and Western in Columbus Circle into a brass-and-glass playpen for Wall Street flyboys, after setting his style template with Trump Tower. That building helped revive Fifth Avenue, which, like many of New York’s former talismans, had fallen into sad decline. It was also a benchmark moment for Trump: the accomplishment with which he officially eclipsed Fred as the signature builder of his age.

“So here’s a story I’ve never told,” he says, warming to the memory of that triumph. “When I was building Trump Tower, my father stood across the street and said, ‘Don’t use glass and bronze, use brick. It’s better, less expensive, and no one cares about the outside. All they care about is the size of the closets!’ ” Trump laughs and shakes his head in mordant wonder, as if to say, Oh, the humanity. By the way, Trump has told this story many times, according to Gwenda Blair, the author of Donald Trump: Master Apprentice, which will be reissued as an e-book this fall. “It’s all part of what he does,” she says, “the bragging and the repetition: It’s called branding, and he’s relentless at it.”

Trump springs from his desk chair and summons me over to the floor-to-ceiling windows facing north. Below us, beyond the Tiffany Building and the Plaza Hotel, spreads the splendid sine qua non of Central Park, lush in its summer coat of greens and golds. “I mean, who has this location? I own this,” says Trump, marveling at his great good fortune. “I’m at the point in my life — tremendous cash flow, very little debt — where I could do anything I want. I said, ‘Now, I’m gonna take the risk of running for president. We need that kinda mind to make great deals.’ ”

As we stand there, hundreds of feet above New York, gazing on the Lilliputian tourists, it occurs to me to wonder: How on Earth, from this vantage, did Trump see into the hearts of underemployed white folk? How did he know that they stewed and simmered over free trade, immigrants and fat-cat Republicans who’d sold them down the river for decades? How did he guess that they’d conflated those things to explain the flight of factory jobs, and that all they really cared about, besides the return of those jobs, was that someone beat the hell out of the party hacks — the Jeb Bushes and Scott Walkers and Karl Roves? 

“What you’ve tapped into,” I say, “is that people see those guys and say, ‘This one’s owned by David Koch, that one’s owned by Sheldon Adelson, and so on, and then they look at you . . .”

“I’m owned by the people!” Trump says. “I mean, I’m telling you, I’m no angel, but I’m gonna do right by them!”

But the answer to my question is ringing in the air — specifically, in the echo of Trump’s accent. He was raised around lunch-pail guys in Queens and learned to talk like them trailing his father to building sites. He shares the syntax and sympathies of meat-and-potatoes types, and has crafted his message for their ears expressly, calling out the enemies on their list. In New Hampshire, I watched that huge crowd come to a boil as he took dead aim at corporate greed. “When the head of Ford calls me up and he says, ‘Mr. President, we really want to build this plant in Mexico,’ I’ll say, ‘Congratulations . . . we’re gonna charge you a 35 percent tax on every car and truck and part that comes in!’ ‘But you can’t dooo that, Mr. President!’ Trust me, I can do it — and what happens is, they probably fold by 5 p.m.”

Never mind the pipe-dream scenario being spun, which omits that only Congress can set new taxes: The whole room shakes as if on skates. That mind-meld is what lets him flaunt his wealth and sell it as proof he’s on their side. He bragged in New Hampshire about his great relations with China and Saudi Arabia: “They all buy apartments from me. They pay millions and millions of dollars. Am I supposed to hate them? I love them! I sell apartments for $50 million, $30 million, $25 million, $18 million, some of the cheap ones, like $10 million, OK? Those are the cheap ones. I don’t even sign those contracts.” Why would he run the jewels in the faces of people who’re largely living from check to check? To pound home the point that there are good tycoons, patriotic wise men like himself and his friends (Carl Icahn and Henry Kravis, to name just two) who are itching to step in and save the country’s bacon by rewriting its woeful trade deals with China and Japan. “Do we want nice people? Or do we want these horrible human beings negotiating for us? I want horrible. . . . We will make great trade deals. We will make Social Security without cuts. . . . You’ll have phenomenal plans — you’ll have them for much less money. The insurance companies will not be happy, but, see, they don’t give me money. They give to Jeb, and they give to Hillary. . . . I don’t want their money!”

That assault on the bad rich, the takers and job exporters, is the second masterstroke of his campaign. He’s not just spurning their money, he’s spilling the beans on them, outing the ways in which they’ve gamed the system to enrich themselves and co-opt the Republican Party. “Because he knows Wall Street and because he doesn’t need its money to campaign, it seems like he could actually fight his fellow elites and win,” wrote Ross Douthat in an op-ed piece for The New York Times titled “Donald Trump, Traitor to His Class.”

“I have senators flying in from Washington to New York, and I gave to everybody,” says Trump in his office. “Why? Because that was business: When I went to see them, they were always nice. If I’d said no, then went back to them and said I needed help on a tax code — zero chance; they’d say, ‘Fuck him!’ That’s not a good thing for our country, but that’s the system, and the public understands it better than anybody.”

Nor do his conservative heresies stop there. He’s called for immediate tax hikes on hedge-fund profits; tax hikes for the ultrawealthy like himself to pay for sweeping cuts for the middle class; vast spending increases on health care in general and for veterans and women in particular; huge capital investments in the country’s infrastructure, beginning with roads and bridges; and a wartime-era ramp-up of the Defense Department budget to “make our military so strong that nobody would mess with us.” How would he plow such mandates through a Congress that is run by the very party he’s betraying? And where does he find the money to do these things when he himself says we’re nearing the point of no return on a deficit of $19 trillion? His answer on this and all matters fiscal is the canard about capital clawbacks: “I’d renegotiate trade deals so that our country becomes rich again,” he says, “and end deals where car manufacturers go to other countries. I’m gonna have them built right here.” For the moment, though, the “how” is beside the point. What counts is that he’s hijacked the party’s base out from under the noses of its bosses, taken it clean away from Jeb Bush and Karl Rove and stashed it in a place they’ll never find it. If nothing else comes of his remarkable run, he’ll have done us all a priceless favor, showing the angry right that the Republican Party is run by, for and about the very rich.

To this point, at least, it’s been an asymmetrical war: Trump carpet-bombs his rivals each and every day without much in the way of artillery coming back. But sooner rather than later, the counterinsurgency will start, a coordinated effort by the party’s elites to trash him and his scary ideas. “Trump’s challenge is, he’s got an unusual coalition — Tea Party Republicans, non-Tea Party Republicans and even some Democrats,” says Nate Cohn, the standout data journalist for The New York Times. “What happens when he starts getting attacked on all the issues? Will he be able to hold his supporters together under the brunt of attack ads from the Super PACs?”

Cohn isn’t convinced that Trump’s constituency will see him through that thresher and beyond. “He’s had total command of the media so far, and much of his strength is based on that. But popularity derived from public attention is generally thin, as we saw with Herman Cain and Sarah Palin.”

Steve Schmidt, the Republican strategist, puts it somewhat more crudely: “Trump’s starring in a reality show of his own making, and treats every appearance like an episode,” chasing ratings in the form of fresh votes. But how do you turn appointment TV into a lasting candidacy? “You need a huge team on the ground doing the nuts-and-bolts work — collecting signatures to be on the ballot in certain states, bringing voters to the polls — and Trump is very late to the party,” says Cohn. “Most of his rivals have been at this over a year, and have those seasoned operatives locked up. And even if they’re available, is he really prepared to pay them a premium now?” 

Donald Trump

The first time we met, Trump led me to understand that his run had cost him peanuts thus far. A little outlay for jet fuel and salary to staff events, but not a dime dropped on advertising or charters. “I thought I’d have spent $10 million on ads, when so far I’ve spent zero,” he says. “I’m on TV so much, it’d be stupid to advertise. Besides, the shows are more effective than ads.” But with a commanding national lead at the end of August and runaway margins in the early primary states of New Hampshire and South Carolina, he’s had to staff up aggressively on the fly. To that end, he’s dispatched his campaign manager, Corey Lewandowski, to speed-hire ground troops across the country, pros who’ll try to turn his rock-star crowds into follow-through voters in six months. He’s brought on Chuck Laudner, an old hand in Iowa politics, to run his operation in that state, and had ramped up months ago in South Carolina and New Hampshire, putting strong, seasoned crews to work.

“We’re up to 60 people now, including 14 in Iowa,” Trump tells me, “and building huge, phenomenal teams in the first seven states. I know that costs money, but I’ve got this, believe me. Remember: The two biggest costs in a presidential run are ads and transportation. Well, I own two planes and a Sikorsky chopper, so I’d say I’m pretty well covered there, wouldn’t you?”

Still: Trump, for all his billions, has far less sitting in liquid assets. Bloomberg ran the numbers on his FEC filing and pegged his cash on hand at $70 million; Politico had it closer to $250 million. Either way, it sounds like a lot of money till you factor the per-diem costs of the past couple of presidential cycles. Barack Obama spent about $1.6 million a day at this stage of his first run, in 2007. The price tag may have doubled in the eight years since, though Trump has the cost breaks noted above, so perhaps it’ll only run him the million per. But Obama was raising money as fast as he spent it, while Trump is barely bothering to lift a finger. (At last report, he’d taken in $100,000, or about five percent of what he’s spent already.) Is he really prepared to shell out $30 million a month, and more when the primaries roll around?

Absolutely,” he tells me. “I’m prepared to underwrite this! I make $400 to $600 million a year.”

Last year, per the figures he himself released, he had $362 million in income, some of that a one-time sale of stocks. This year figures to be a slimmer one: He was summarily dropped by seven business partners when he entered the race raging against “illegals.” Per media estimates, he lost as much as $50 million in those canceled deals, the bulk of it from NBC, his golden goose. It’s been a very pricey couple of months indeed for him, and that goes against the flow of his business model. Since the bad old days of the early Nineties, when the real estate market tanked and his company filed for Chapter 11, owing the banks nearly $1 billion, he’s been much more reluctant to invest hard cash. He owns very little of what gets built now bearing his name, earning many tens of millions by leasing his logo to high-end hotels and resorts. He also reaps license fees from retail products that pretty much cover the spectrum from clothes to liquor, though he’s lost the great buzz machine that was The Apprentice, and with it, the multi-million-dollar salary that earned him $213 million over 14 years.

But politics isn’t like selling vodka that someone else makes and mass-distributes. It’s the ultimate high-risk, low-return endeavor, in which $5 billion will be spent, in total, this cycle, most of it by candidates with slim hopes. Will Trump go all-in on his bet with himself, selling off assets as he goes? Or will he turn at some point to the people he denounces – the hedge-fund guys and influence-peddlers who fund the Super PACs of his rivals – and quietly make his terms with them? If so, what becomes of the clenched-fist crowds he’s been drawing in record numbers at every stop? Here
is the bind Trump finds himself in as he buckles down to a long and arduous run. He has carved his mark as the exception to every rule: the teller of dark truths; the man too rich to bribe. Any deviation, any hint of half-stepping, will cost him far more than it would, say, Bush or Ted Cruz. Why? Because Trump’s central claim is he’s not them. The day his backers doubt that is the day he starts unraveling. They’ve been burned too many times to grant second chances.

After the Hampton rally, Trump is so exultant he practically floats the 10 miles back to his plane. On the tarmac, he hands out $100 bills to the drivers of his motorcade, and profusely shakes the hands of his advance-team members, some of whom, he says, will return to the school to collect names and cellphone numbers of folks still there. “You’d be amazed,” Trump tells me. “These people get so excited that they stick around for hours afterward.”

He parks himself at the dining table in the center of the big plane’s cabin, turns on the massive flat-panel unit that is preset to Fox News and watches reports of the speech he’s just given, while wolfing down a takeout dinner. Onscreen, it is wall-to-wall coverage of Trump, though none of it is mediated by Megyn Kelly, the network’s golden girl and homegrown star. A week after the Republican debate, in which she’d taken on Trump and tried to gore him over his caddish remarks about women, she’d gone missing from the conversation, vanishing to her beach house till late August. In the sweet but too-brief battle between Trump and the network that followed his ugly dust-up with Kelly, Trump had emerged from it the walk-off winner after staring down Roger Ailes, the Fox News chief. During his four-day boycott of the station, he pumped up the ratings of its rival networks by appearing on their shows and savaging Fox, and escalated his all-out war on Kelly with the crack about her bloody “wherever.” Ultimately, peace broke out, and Ailes brought him back on. Trump’s return, on Sean Hannity’s show, drove ratings back up, beating out the competition several times over. It devolved into a victory lap for Trump, but even in triumph, he couldn’t keep the truce. In his office, Trump slipped me a printout of a story titled “How Roger Ailes Picked Trump, and Fox News’ Audience, Over Megyn Kelly.” “I don’t start these fights, but I sure as hell win them,” he told me.

And that is Trump all over: He can’t-stop-won’t-stop whaling away at anyone who dares to bait him. The day after Kelly returned from exile, Trump trashed her afresh with snarks and retweets, refusing to give Kelly peace. This is the other thing he learned from his father, who taught his sons to “attack, attack, attack,” says Blair, the biographer. “He’s constantly on offense, picking massive fights, and it always results in polling spikes,” says Matt Boyle, a correspondent for Breitbart News, the only other writer on Trump’s plane. Riding the campaign trail since the middle of last year with Ben Carson, Cruz and others, Boyle marveled at Trump’s skill for fomenting fights, which kept him atop the news cycle every day. “And Fox, John McCain, they always respond to him,” which brings the media back a second day and sucks up all the inches on Page One. How do Bush et al. fight back against a puncher whose arms never seem to get tired? “They haven’t figured it out yet, and they’re blowing up in front of us,” says Boyle. “This guy here, he’s just at a different level.”

Donald Trump

With his blue tie loosened and slung over his shoulder, Trump sits back to digest his meal and provide a running byplay to the news. Onscreen, they’ve cut away to a spot with Scott Walker, the creaky-robot governor of Wisconsin. Praised by the anchor for his “slow but steady” style, Walker is about to respond when Trump chimes in, “Yeah, he’s slow, all right! That’s what we got already: slowwww.” His staffers at the conference table howl and hoot; their man, though, is just getting warm. When the anchor throws to Carly Fiorina for her reaction to Trump’s momentum, Trump’s expression sours in schoolboy disgust as the camera bores in on Fiorina. “Look at that face!” he cries. “Would anyone vote for that? Can you imagine that, the face of our next president?!” The laughter grows halting and faint behind him. “I mean, she’s a woman, and I’m not s’posedta say bad things, but really, folks, come on. Are we serious?”  

And there, in a nutshell, is Trump’s blessing and his curse: He can’t seem to quit while he’s ahead. The instincts that carried him out to a lead and have kept him far above the captious field are the same ones that landed him in ugly stews with ex-wives, business partners, networks, supermodels and many, many other famous women. At 69, he can still carry on like the teen who was yanked out of prep school and delivered to Col. Dobias, the take-no-shit instructor at the military academy. After I met Ivanka and praised her to her father, he said, “Yeah, she’s really something, and what a beauty, that one. If I weren’t happily married and, ya know, her father . . . ”

He’d made essentially the same crack nine years ago on a talk show while promoting Season Three of The Apprentice — but now he’s running for president, not an Emmy. “Does the guy have the wisdom to grow his base, what Kennedy called ‘greatness and fitness?’ ” says Schmidt, the GOP strategist. “Can his range and tone expand to meet that criteria?” Maybe what Trump needs is another Dobias, someone to tell him enough is enough and to get back on his game already. But if he had a consigliere, how likely is it that he would even listen? He’s gotten this far largely taking only his own instruction, acting on his gut and nose for blood. Attack, attack, attack, said his old man at the wheel, driving around Brooklyn on summer Sundays to spring surprise inspections on lazy supers. Trump paid attention and learned another lesson beside it: Take plenty of muscle with you when you go.

Meantime, you can say this for the man: He keeps a campaign promise, at least through dessert. After dinner on the plane, Trump gets up to stretch his legs, wandering to the galley for something sweet. He rummages through the cupboard, where his beloved Oreos live. Trump grabs the pack of cookies, eyes them fondly a moment, then replaces them on the shelf, uneaten. Returning to his seat with a couple of Vienna Fingers (made by Keebler, not treasonous Nabisco), he catches me looking at them and grunts. “I meant what I said: No more Oreos for Trump! And you can quote me on that if you want.”

In This Article: Donald Trump, Election 2016


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