Politics & Policy

In The Art of the Deal, Trump Shows His Soft Side

(Trump: Tom Pennington/Getty)

When asked to introduce himself at the most recent Republican presidential debate, the front-runner began, “I’m Donald Trump. I wrote The Art of the Deal.”

Trump mentions his book quite frequently on the campaign trail, and ranks it among his proudest accomplishments. It debuted atop the New York Times best-seller list in 1987 and remained on the list for 51 weeks. Trump is fond of boasting that it’s sold more copies than any other business book in history, a claim that’s disputed.

Whatever its place in Trump’s personal mythology, The Art of the Deal is a fascinating time capsule, a long look at a 40-year-old mogul on his way to becoming the country’s most famous businessman. Looked at today, the book reveals that Trump’s current portrait of himself as a 1980s Reagan-booster is a convenient half-truth at best. But it also makes it easy to see why the first boomlet of “Trump for President” talk began in 1988, and why such talk was always short-lived until now.  

The Trump that emerges from The Art of the Deal is a much softer, warmer, and probably happier figure than the man dominating the airwaves today. He comes across as a garrulous uncle, reverent to his father and mother, still wildly enamored with his wife Ivana, and taking delight in his growing children. He writes about Ivana with fondness, heaping praise on her skill at managing the Trump Castle casino. He chuckles that he never expected to spend parts of his mornings examining kindergarten classrooms at private schools for Ivanka and Eric.

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The man now famous for never apologizing is shockingly vulnerable in describing his regrets about his late brother Freddy:

I can remember saying to him, “Come on Freddy, what are you doing? You’re wasting your time.” I regret now that I ever said that.

Perhaps I was just too young to realize that it was irrelevant what my father or I thought about what Freddy was doing. What mattered was that he enjoyed it. Along the way, I think Freddy became discouraged, and he started to drink, and that led to a downward spiral. At the age of forty-three, he died. It’s very sad, because he was a wonderful guy who never quite found himself. In many ways, he had it all, but the pressures of our particular family were not for him. I only wish I had realized this sooner.

Earlier this year, Trump seemed flippant, even sacrilegious, when discussing his faith and referring to the Eucharist as “my little cracker.” But back in 1987, he wrote of being awed at a dinner with then-Cardinal John Joseph O’Connor:

No matter whom you’ve met over the years, there is something incredible about sitting down to dinner with the cardinal and a half dozen of his top bishops and priests in a private dining room at St. Patrick’s Cathedral. It’s hard not to be a little awed.

Then again, Trump has his own unique measure of a spiritual leader. “As we leave, I tell Ivana how impressed I am with the cardinal,” he writes. “He’s not only a man of great warmth, he’s also a businessman with great political instincts.”

#share#Honest as the book is, it includes plenty of the brashness one associates with Trump today. He sets up a trip to Moscow to meet with Soviet officials about “building a large luxury hotel, across the street from the Kremlin.” Cadillac goes into production on two limousines — “the most opulent stretch limousines ever made” — to be called the Trump Executive Series. An unnamed modern artist friend throws paint on a canvas and laughs with Trump that collectors will pay top-dollar for it.

The Trump that emerges from The Art of the Deal is a much softer, warmer, and probably happier figure than the man dominating the airwaves today.

Trump seems to realize he lives an absurd life. He remarks that pouring concrete in a photo op is “a little ridiculous” and that “contrary to what people think, I don’t enjoy doing press. . . . I don’t particularly like talking about my personal life.”

In short, the Donald Trump of 1987 seems quite different from the Trump who’s stormed national politics over the last few months: In addition to the now-familiar penchant for egotistical overstatement, he displays a surprising self-awareness and introspection.

He is also light years away from becoming a conservative Republican.

1987 Trump takes subtle jabs at Reagan:

He is so smooth and so effective a performer that he completely won over the American people. Only now, nearly seven years later, are people beginning to question whether there’s anything beneath that smile.

He hates the “new federal tax law” — the Tax Reform Act of 1986, which included Reagan’s second round of tax cuts — declaring it will be “a disaster for the country, since it eliminates incentives to invest and build.” He calls up Senator John Danforth to congratulate him for voting against the bill. (Today, most conservatives see the 1986 reforms as a positive step toward lower taxes and a simpler tax code.)

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He raves about the joys and high profit margins of the casino industry — “It’s a very good business being the house” — without spending much time dwelling on the fact that it is one of the economy’s most highly regulated sectors. (This is an industry where opening up a competing facility without a license is literally criminal and any new entrant to the market has to jump through considerable regulatory hoops.)

Then, there’s his lengthy portrait of a fight with City-zoning authorities during the planning and construction of Manhattan’s Trump Tower. The protracted negotiations Trump describes would be enough to make most conservatives rail against a micromanaging nanny state. But in the end, he accepts it as the price of doing business in New York. His decisive move turns out to be schmoozing the New York Times architecture critic, Ada Louise Huxtable. Trump concludes that the resulting column, ‘A New York Blockbuster of Superior Design,’ likely “did more for my zoning than any single thing I ever said or did. . . . The power of the New York Times is just awesome. It is certainly one of the most influential institutions in the world.”

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Today Trump is the populist crusader, but back in 1987, he was perfectly fine with using a Times columnist to sway the minds of city officials, as long as he got what he wanted.

The years following the publication of The Art of the Deal would be tumultuous ones for Trump. His marriage to Ivana ended about as messily and publicly as can be imagined, followed by a six-year marriage to his mistress, Marla Maples. He avoided personal bankruptcy but it took four Chapter Eleven filings to keep his companies afloat. In 1991, he sold his yacht, the Trump Princess, to Saudi Royal Al-Waleed bin Talal; Trump Airlines ceased operations in 1992.

#related#And yet, Trump managed to rebound. His celebrity status became one of his most important assets. He licensed his name and image for the development of real estate projects in which he had no personal stake. He popped up in ads for Pizza Hut, McDonald’s, Nike, Oreo’s, and even a signature line of mattresses. In 2004, he debuted his reality television series, The Apprentice, and it too enhanced the Trump brand and proved wildly profitable — to the tune of $213 million in personal profits over 13 years, according to Trump.

The past 25 years made the current GOP presidential front-runner sharper, harder, somehow even more flamboyant and ubiquitous, and indisputably angrier. Perhaps Trump’s rise to fame is so associated with the 1980s that he’s become a walking caricature of that decade: brash, successful, loud, and proud. We’re told voters want a candidate who makes them think of the future, and not the past. But if we must think about the past, we could do a lot worse than the glory days of the Reagan administration. It’s just not clear Trump could get us back there — or that he’d even really want to.

— Jim Geraghty is the senior political correspondent of National Review.


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