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Donald Trump's books reveal his obsession with women — and himself

Playboy's 50th Anniversary Party in New York
Donald Trump at the Playboy 50th Anniversary celebration in 2003
Photo by Peter Kramer/Getty Images

Donald Trump's treatment of women has come under sharp scrutiny after leaked audio showed him bragging about sexual assault.

We know Trump regularly insults women who criticize him. We know he has been accused of sexual harassment, sexual assault, and rape.

But a look back at the many books Trump has written over the years reveals a lot about how Trump thinks about women, and about the often-regressive attitudes that may well inform his behavior.

It's clear that Donald Trump is obsessed with women’s physical beauty. In his books, as in his other public remarks, mentioning it is practically a verbal tic. It’s often the first, or only, quality that Trump mentions when describing people. When he talks about someone he admires, he’s likely to use the word "attractive" — for men and women alike, but especially women.

In his 1997 book Trump: The Art of the Comeback, Trump says he decided to buy the Miss Universe pageant because "it’s about fun; and it’s about beauty, the ultimate beauty — that of a woman."

In Think Like a Billionaire: Everything You Need to Know About Success, Real Estate, and Life (2004), he quips that if he’d been in charge of casting the first season of The Apprentice, he would have chosen "sixteen supermodels."

But when it comes to women, the only thing more important to Trump than their looks is often how they make him look by association. And their value, or lack thereof, as sexual objects is never far behind.

"All the women on The Apprentice flirted with me — consciously or unconsciously," Trump wrote in his 2004 book How to Get Rich. "That’s to be expected. A sexual dynamic is always present between people, unless you are asexual."

For Trump, it seems, there is no woman who is not potentially sexually available to him, and no woman he doesn’t evaluate based on whether he’d sleep with her or date her.

In The Art of the Comeback, Trump briefly eulogizes the recently departed Princess Diana by remarking wistfully that he has "only one regret in the women department," which is that he never got to "court" Diana. "She was a genuine princess — a dream lady," he wrote. "She’ll truly be missed."

Trump on "brains" versus "beauty"

Trump’s compulsive beauty rating doesn’t stop when it comes to his female employees. His executive assistants, he writes, are "not only efficient and fast, but also very pleasant and beautiful young women. You don’t have to be beautiful to work for me — just be good at your job. I’ve been accused of admiring beautiful women. I plead guilty."

But, he adds, "when it comes to the workplace, anyone who is beautiful had better have brains, too."

He tells a cautionary tale about the time he hired a "breathtaking European beauty" as a receptionist "who could easily rival Ingrid Bergman in her heyday." She didn’t do so well at her job because she didn’t recognize the names of American celebrities, Trump said, and so never put their calls through to him. "But you should have seen her. What a knockout," he added.

In Surviving at the Top (1990), Trump wrote that he was drawn to his first wife, Ivana, because she was "different." Before her, he said, good looks had been "my top — and sometimes, to be honest, my only — priority in my man-about-town days." (In those days, he said, he was "out four or five nights a week, usually with a different woman each time.")

"Ivana was gorgeous, but was also ambitious and intelligent," Trump said. "I think everyone sensed that I found the combination of beauty and brains almost unbelievable. I suppose I was a little naive, and perhaps, like a lot of men, I had been taught by Hollywood that one woman couldn't have both."

But the supposed tension between "beauty" and "brains" didn’t go away for Trump as he got older, and the two concepts ended up colliding in ugly ways toward the end of his marriage to Ivana. His "big mistake" in his marriage, he wrote in The Art of the Comeback, was "taking her out of the role of wife and allowing her to run one of my casinos in Atlantic City, then the Plaza Hotel."

The mistake in "allowing" this wasn’t that Ivana was bad at the work; to the contrary, he said, "she did an excellent job." The problem, it seemed, was that Ivana was too good at the job — in the sense that she was too invested in the work and presumably not invested enough in her "role of wife."

"The problem was, work was all she wanted to talk about," Trump said. "When I got home at night, rather than talking about the softer subjects of life, she wanted to tell me how well the Plaza was doing, or what a great day the casino had. ... I work from six o’clock in the morning until seven or eight o’clock at night; to come home and hear more was just not tolerable. And Ivana just wouldn’t stop. She had so much energy, and it wasn’t simply, ‘We had a good day today’; she had to relate everything that happened during the day in detail, and then everything that was planned for the following days and weeks."

He started to realize, he said, that he was "married to a businessperson rather than a wife."

But if what Trump wanted was a more domestic home life with less chatter about work from his spouse, that apparently wasn’t enough for him with his second wife, Marla Maples: "We wanted different things," he said. "Marla was content when it was just her, Tiffany [their daughter], and me. I, on the other hand, realized that business needed to be taken care of constantly."

Trump on getting attention from women

Trump actually had some moments of introspection in 1990’s Surviving at the Top about the dissolution of his relationship with Ivana. "I’m not comfortable discussing my feelings," he admitted. He said he wanted to make it work — that his marriage "was the only area of my life in which I was willing to accept something less than perfection," and how the "American Dream of sharing life with a wife and children" wasn’t something he could "just toss aside easily."

But in that same chapter, he couldn’t help not-so-humblebragging about the attention he was getting from women:

At the very time my marriage was going bad, I was starting to get attention from an unbelievable array of women.

Some of it was downright ridiculous. After I made an appearance on the Phil Donahue show to promote my first book, for example, I got mailbags full of flirtatious letters and outright propositions from women, many of whom included nude Polaroids of themselves in various poses. Somehow I didn't see myself going arm-in-arm in public with ladies of that ilk.

Yet it wasn't just gold diggers and would-be groupies who were showing interest in me. Some of the attention was coming from women who were quite interesting and even, in certain instances, great beauties — and often well known.

Trump’s attempts to act like he’s above it all are familiar, and are just as unconvincing as his claims that he wasn’t really calling Megyn Kelly a "bimbo."

Trump is a master, if you can call it that, of paralipsis: the rhetorical device of emphasizing something by claiming you aren’t going to talk about it.

He does this all the time. Elsewhere in the chapter, Trump says: "I’ve never had any trouble in bed, but if I’d had affairs with half the starlets and female athletes the newspaper had linked me with, I’d have had no time to breathe."

All told, Trump probably spends more time talking about the women he didn’t sleep with than the women he did. Like most things he says, it’s a tool of self-aggrandizement. He’s allegedly so desirable that women come out of the woodwork to throw themselves at him — but he’s too classy to bother with those tramps who send him nude Polaroids.

Trump’s brags about his sexual conquests, or the times he nobly declines potential conquests, often includes more than a hint of slut shaming. He takes special care to brag about the women who are married to important people who throw themselves at him: "If I told my real experiences with women, often seemingly very happily married and important women, this book would be a guaranteed best-seller (which it will be anyway!)," he wrote in The Art of the Comeback.

In that book, he also discusses how he grew up believing that "aggression, sex drive, and everything that goes along with it was on the man’s part of the table, not the woman’s." How wrong he was, he said he learned:

As I grew older and witnessed life firsthand from a front-row seat at the great clubs, social events, and parties of the world — I have seen just about everything — I began to realize that women are far stronger than men. Their sex drive makes us look like babies. Some women try to portray themselves as being of the weaker sex, but don’t believe it for a minute.

"I don’t know why I bring out this craziness in women, but somehow I do, and it’s not always pretty," he said. Sometimes, he said, this "craziness" makes women lie about romantic involvement with him just to get attention.

"It got to the point where any women I was seen with in public became the subject of rumors," he said. "To be honest, some of the rumors had some truth in them, but the stories usually went too far. ... To make matters worse, some people took advantage of the hype just to get their names in the papers. Even Madonna, a master of hype in her own right, got in on the act."

Trump complains that bad journalism about his alleged affairs devastated his family, especially his children. But he spends most of his time talking about this coverage in ways that soothe his own ego. He claims that it wasn’t Madonna or Olympic figure skater Katarina Witt who spurned his romantic advances — he was the one who spurned them, and they were so upset about it that they had their publicists spread lies about him.

It’s worth being skeptical of these accounts. Trump denies ever going on a date with model Kim Alley, and claims that she tearfully admitted to lying about it on Geraldo — when she actually said she wished she’d never socialized with Trump in the first place.

The story about Madonna is the same one told by Trump’s "publicist," who sounded an awful lot like Trump himself.

And right after Trump describes hanging out with Witt — and making her angry by insulting her choice of music to skate to — he claims it was his romantic "disinterest" in her that made her turn rude toward him.

Trump on marriage and prenups

Trump’s obsession with female attention is almost matched by his disregard for monogamy — either his own or that of others.

This isn’t necessarily a bad thing in and of itself; monogamy isn’t for everybody, and some advocates argue that we’d all be better off just being honest about that. It’s almost a breath of fresh air when Trump candidly admits in The America We Deserve (2000) that he doesn’t think monogamy in marriage is the most important "family value" out there, especially compared with "your relationship with your parents, your sisters and brothers. ... A lot of people want to say that being monogamous is the only family value. They don't understand that family values means having a context, having a place where you belong, having people who really know you and to whom you're accountable."

But where Trump’s candor turns truly distasteful, as with so many topics he discusses, is when he uses it as a weapon to show his contempt of others, or as a tool to make himself look sexy and great, or both.

He brags in The America We Deserve about how various conservative "moralists" who expressed outrage over Bill Clinton’s affairs had used Trump’s hotels to sleep with their mistresses.

He brags about anonymous women married to important men who allegedly threw themselves at him, like one "lady of great social pedigree and wealth" who came on to him "at a magnificent dinner being given by one of the most admired people in the world" while her husband was sitting nearby.

He brags in Surviving at the Top about hooking up a friend of his with the unnamed wife of a man "who was then the prime minister of a major country."

Yet it’s also clear that Trump is worried about women abusing the institution of marriage — about "gold diggers," whether or not they’re the kind of women who send nude Polaroids as a come-on.

Trump talks at considerable lengths about prenuptial agreements, which he calls a "modern-day necessity." He discusses multiple times how they came in handy with both Ivana and Marla, even though it was awkward to ask for them initially.

In Think Big and Kick Ass in Business and Life (2007), Trump tells a story about a buddy of his who is the "toughest guy" Trump knows but a "schmuck when it comes to women." After hearing that this friend was about to marry a Las Vegas showgirl, Trump says he told him, "‘You have zero chance of this marriage lasting.’ I was even more sure of it after I met the woman and she came after me. ... What a joke! She found me more attractive than him, and he is telling me what a great marriage he will have. He is in for trouble because he does not have a prenup." (Even in his cautionary tales, Trump can’t resist adding an anecdote about women throwing themselves at him.)

Despite claiming in The Art of the Comeback that he doesn’t want to speak ill of Ivana, he spends an entire chapter going on about how she allegedly used dirty legal tricks in an unsuccessful bid to get more money. (He doesn’t mention the allegation of marital rape that Ivana made at the time, although Ivana herself walked that back a few years later and said she had merely felt "violated" by the incident.)

Trump grouses about Ivana’s ingratitude after the settlement was finalized: "In the worst financial period of my life I gave her a big check, a beautiful house, and total financial security. I didn’t have to do it."

He scoffs at her attempts to make something of herself after the divorce: "Before the settlement and documents were even dry, Ivana built a small cottage industry on my back. ... I would laugh as I watched Ivana on Larry King and other shows, telling other women the how-to’s of getting divorced and living life afterward."

The multimillion-dollar heir also mocks his ex-wife’s "little business" and how she "would talk about herself as a businesswoman and not as someone who received a large settlement from her husband."

"Despite all of this, I still think of Ivana as a very kind and good woman," Trump finally adds. "Without a doubt, Ivana is a great mother and an okay businesswoman."

Even Donald Trump is aware that there are rules of social decorum. Sometimes you have to say nice things about people who have upset you. You shouldn’t brag too much about your sexual conquests, even if you’re a rich and successful man. You can’t just go around ogling women’s bodies all the time — you have to acknowledge that they are people with brains, too.

He gives lip service to these sorts of things. He tries to make concessions. He tries to convince the world that he is a great, classy guy. But it’s usually pretty easy to see what lies beneath.

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