Donald Trump Lets His Hair Down

A conversation with the host of The Celebrity Apprentice

Photograph by Peter Yang
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Like you, we've always wondered what's inside Donald Trump's wallet. So, on a recent visit to his office at the top of Trump Tower in Manhattan, the epicenter of his vast real estate empire and putative presidential ambitions, we ask him if we can take a look. He pulls it out, dips it down and hides it behind his huge desk, peers inside, saying, "Let me just see if there's anything ... ," and then holds it out, fanning through it, revealing his Winged Foot Golf Club membership card and his very own gun permit, neither of which he apparently ever leaves home without.

"It's a Donald J. Trump wallet," he says, happily. He's still a fairly big, fairly imposing guy at age 64, has hair that's the patriotic shade of amber waves of grain, dresses like men of the world used to dress, in a dark suit, with a crisp, white shirt and a tie that's the subtlest pink ever. "We sell them at Macy's. They sell great. Hey — I have the number-one-selling tie in the country. What color tie do you like? Your tie looks like shit. Do you want a tie? It's not a bribe. They're nothing. I sell shirts, PVH, Phillips-Van Heusen. Cuff links." He waves his arms around, shoots his cuffs to show off glittering cuff links. "Trump cuff links!" he shouts. "They're magnificent! Everybody's buying them! If I said I got them at Harry Winston, for $100,000, you'd believe it! Forty-nine dollars at Macy's! Macy's doesn't even want to carry other brands! We blow them out!"

This article appears in the May 26, 2011 issue of Rolling Stone. The issue is available now on newsstands and will appear in the online archive May 13.

That's pure Trump-speak — loud, over-the-top, just the kind of Ronco Veg-o-Matic, everyone's-a-mark, carny-barker, hard-sell ballyhoo that he hopes will also blow out the other presidential hopefuls, should he decide to run. But will he run? He says the world will know his answer by June — at which time, if he announces in the affirmative, he will also reveal the true size of his financials, which, he says, will shock the world, being around $7 billion, if not more, and make Mitt Romney, with his measly hundred millions, look like a floppy little fish indeed and certainly not the kind of guy who, for instance, could spin the roulette wheel on ties and cuff links and make gazillions.

Photo Gallery: The Many Business Failures of Donald Trump

"We need a businessman," Trump says, working himself into a lather of self-congratulation, "and I've been successful. Right now, I have the greatest properties in the country. I have great stuff. The point is, I'm running for office in a country that's essentially bankrupt, and it needs a successful businessman, and, by the way, let me explain about one thing, might as well get that clear: I never went bankrupt."

He's drawing a distinction here, which is that while various of his businesses may have sought Chapter 11 bankruptcy protection over the past two decades, Trump the person never has. In the early 1990s, for instance, after a decade of profligate spending — $3.8 billion worth, mainly financed by junk bonds and Trump-snookered banks — he came face to face with an economic downturn that forced four Trump properties — the Plaza Hotel and his three Atlantic City casinos — into bankruptcy. It happened again in 2004, and also in 2009, when Trump Entertainment found itself $1.7 billion in debt. Trump's way is to dismiss these financial catastrophes with a snarl and a shrug. As he said in his 2007 book, Think BIG and Kick Ass in Business and Life, "I figured it was the bank's problem, not mine. What the hell did I care? I actually told one bank, 'I told you you shouldn't have loaned me that money. I told you the goddamn deal was no good.'" Or, as he casually says today, "I play with the bankruptcy." Which is kind of a sad, dispiriting advertisement for his genius as a businessman. Do we really want that kind of guy in office? At least some people seem to think so.

"Look," Trump chuckles, "I'm number one in the polls already, and I haven't even done anything!"

Which is no longer true, since it was largely Trump's bellyaching that prompted the White House to release President Obama's so-called long-form birth certificate, proving once again that Obama was born in the U.S. (unless you're a birther, in which case it proves nothing). "I'm very proud of myself," Trump crowed the day it happened. Naturally, he made no mention of what his "investigators" in Hawaii discovered poking around about Obama's birth — "They cannot believe what they're finding!" he had said in early April — probably because they either didn't exist or they found nothing. Instead, in his quest for ever-bigger headlines and even more attention, he stooped to new lows, by bringing up Obama's college education and playing the race card. "How does a bad student go to Columbia and then to Harvard?" Trump said, the clear implication being that it was only thanks to affirmative action and never would have happened had Obama been white. It's despicable stuff, and yet, coming from Trump, not all that surprising. If nothing else, he's a master of smoke and mirrors, and so far has managed to keep anyone from focusing too tightly on his own past. Those bankruptcies. His marriage-wrecking affair and two divorces. His garish casinos that may or may not have had mob ties. The time he referred to his current wife, Melania, as "a young and beautiful piece of ass" (which he now denies ever having said). And let's not forget the whole abortion thing, where Trump has recently flipped to pro-life; the whole let's-invade-the-Middle-East-and-just-like-take-all-the-oil thing; and all the rest of those kooky things he spouts on a daily basis, keeping his name in the news in an effort, no doubt, to boost the ratings of his Celebrity Apprentice reality-TV show while appearing to be testing the presidential waters. He's one top-notch novelty act and a Barnum-type showman with an unerring instinct for what to say to appeal to the loonier segment of the electorate. He's good at catering to the lowest common denominator like that, decorum be damned.

But what about some Trump constants, some things that are unwavering in his character and nature?

For one thing, he goes to bed late, gets up early, usually wearing only "the undies," as he calls them, never "the formality" of pajamas, brushes his teeth first, takes a leak second, and only then steps into the shower, his hand reaching out through the steam to grab the shampoo and lather up that hair of his that has received so much attention over the years. How does he do it?

He steeples his fingers, purses his lips and launches right into it like it was some kind of major policy issue. "OK, what I do is, wash it with Head and Shoulders. I don't dry it, though. I let it dry by itself. It takes about an hour. Then I read papers and things. This morning I read in the New York Post about Jerry Seinfeld backing out of his commitment to do a benefit for my son Eric's charity. I've never been a big fan of Jerry Seinfeld — never dug him, in the true sense — but when I did The Marriage Ref, which was his show and a total disaster, I did him a big favor. Then he did this. It's a disgrace." He goes on, "I also watch TV. I love Fox, I like Morning Joe, I like that the Today show did a beautiful piece on me yesterday — I mean, relatively speaking. OK, so I've done all that. I then comb my hair. Yes, I do use a comb." He pauses, frowning, casting his mind back to capture the details of the event. "Do I comb it forward? No, I don't comb it forward." He pushes the leading edge of the flying wing of his hair back, to show where the hairline is. "I actually don't have a bad hairline. When you think about it, it's not bad. I mean, I get a lot of credit for comb-overs. But it's not really a comb-over. It's sort of a little bit forward and back. I've combed it the same way for years. Same thing, every time."

After that, he spends some time not saying what he doesn't want to say, in a very mulish, deeply parsed, Republican-president sort of way.

Does he have a Bible by his bed?

"I do," he says. Then: "I have a Bible near my bed."

Where near?

"It's up in my apartment." Silence.

When was the last time he went to church?

"Two weeks ago. A church in Palm Beach, Florida. What was the sermon about? I'd rather not get into it, frankly."

Where does he stand on gun control?

"I'm against gun control for the reason, it doesn't affect the bad guys, because they're going to have guns. What kind of gun do I have? I'd rather not say. I have a gun. It's a handgun, OK?"

Is it Trump-sized?

"It's a gun. I have a gun. It's a handgun." Silence.

All this talk seems to be making him thirsty. He calls for a Coke, and a hot number in spike heels arrives with a Coke in a glass of ice. Trump sips, smacks his lips.

"I've never smoked a cigarette in my life," he goes on. "I've never had a drink, never had a joint, never had any drugs, never even had a cup of coffee. So, those are some good things about me. I probably have some bad things about me, too." He pauses, as if waiting for some bad things to materialize out of thin air, but when a miracle occurs and they don't, he starts up again. "I will say, though, that I like a little caffeine. People assume I'm a boiler ready to explode, but I actually have very low blood pressure, which is shocking to people. I'll drink water. Sometimes tomato juice, which I like. Sometimes orange juice, which I like. I'll drink different things. But the Coke or Pepsi boosts you up a little."

And then he goes on about the ratings of Celebrity Apprentice and the ratings of himself in presidential polls, both of which are "very, very" high. This is all well and good, but it's incredibly boring, and eventually you are forced to cut him off, with, like, is there one orgasm in his life that he would consider the most memorable?

He leans back in his chair, tilts his head up, takes a long time to think this over, his cherubic cheeks reddening either with the effort of recollection or the maintenance of a boiler about to explode. At last, very smoothly, he says, "Well, always the children. And this building. Trump Tower." A duller answer one cannot imagine. Maybe he'll take a shine to something larger, like naming the central problem of existence.

"Conflict," he says, snapping forward. "Conflict, if it's not resolved, leads to lots of bad things, and that's where this country is right now. We're in many, many conflicts that ultimately could end up in calamity."

But, seriously, has anyone ever loved conflict more than him?

He smiles. "Look, sometimes you need conflict in order to come up with a solution. Through weakness, oftentimes, you can't make the right sort of settlement, so I'm aggressive, but I also get things done, and in the end, everybody likes me."

Well, maybe not everyone. He's been called some pretty terrible things recently, like "farcical," "an unpolished and graceless blowhard" and "a monstrous parody of entitled American wealth masquerading as skillful entrepreneurship." Just days ago, Republican strategist Karl Rove pronounced him "a joke." Trump shrugs most of these things off. They come with the territory, and, in fact, by shrugging them off, he is able to once again demonstrate the insane, over-the-top self-confidence and self-regard that seem to have caught the fancy of a certain segment of the population — probably the same folks who believe it when Charlie Sheen claims he is somehow "winning." Trump didn't do so well at the White House Correspondents' Dinner last month, however. While President Obama and host Seth Meyers poked fun at him and his hair, all Trump could do was stare straight ahead, with no expression whatsoever, betraying how utterly humorless he is about himself. Trump doesn't like Rove's "joke" comment, either. "That was a very nasty thing for him to say," he mutters darkly. "He shouldn't have said that. We'll have it out with Karl Rove. I don't lose too often."

So, Rove might want to look out. And so might Jerry Seinfeld, for that matter.

"I don't want to ruin my image by saying this, but I'm a much nicer person than people understand," Trump says. "I like to do the right thing and help people. But when people are disloyal to me — I have a couple of instances of well-known people, where I'd help them out, but when I needed a favor, not a big favor in this one case, this guy didn't want to do it. That's 15 years ago. I haven't spoken to him since. He died. He's dead mentally. In other words, for me, they don't exist. I hold a grudge. I have the longest memory. I always kick back. I believe in that."

It's kind of weird hearing Trump spit out his words with such rigid vehemence just like he does on his reality show, knowing how huge a constant that grudge-holding is with him and that you yourself might one day be on the receiving end of just such a grudge. You can always hope that age will lay him low first, but it's not likely, given how healthy he is. "I had a father who was 94," he says, "a mother who was 90, so, you know, I'm genetically lucky that way, too."

Also, he's got a big thing about germs, so he's a frequent hand-washer and goes everywhere with packets of hand sanitizer stuffed into his suit jacket. He pulls one out now, dangling it in the air. It's a Super Sani-Cloth Germicidal Disposable Wipe ("The two-minute germicidal wipe") — which isn't exactly the kind of market-share leader you might expect Trump to favor. He rubs his palms together. "I don't use Purell, Purell is too sticky, but this other stuff is great. I always carry a couple of them."

Leaning back, he goes on, "The question has come out, 'How can Donald Trump campaign if he doesn't shake hands?' Well, over the years, I've shaken many hands, and I have no problem shaking hands. But it's not a healthy thing. With the germs, it's not a question of 'maybe' — they have been proven, you catch colds. You catch problems. Frankly, the Japanese custom is a lot smarter."

One can just imagine Trump, then, his first big time out on the hustings, massively ambivalent, surrounded by his fellow man, the crush closing in on him, the panic that must arise as he finally confronts the great unwashed them, that hideous, germ-ridden, infection-spreading other that he has for so long tried to avoid in the flesh but that his attention-craving ego (not to mention his TV show) so needs. It would have to be unbearable. After an event like that, he probably couldn't get to his Super Sani-Cloths fast enough. So that's another thing we would maybe have to look forward to in a Trump presidency: less handshaking, more bowing, fewer colds, fewer "problems." And if it were just that, what's not to like?

From The Archives Issue 1131: May 26, 2011