What Donald Trump’s “The Art of the Deal” Reveals About His Surprising Sustained Success in the 2016 Presidential Race

“I play to people’s fantasies...

Image via: https://www.youtube.com/watch?v=81yRpZXZdKk

Donald Trump’s The Art of the Deal is a popular book. It has sold somewhere between hundreds of thousands and millions of copies since it was first published in 1987. Trump considers it not nearly as good as the Bible, but a distant 2nd for best book ever. Like most of what Trump has talked about on the 2016 presidential trail, he has mentioned The Art of the Deal over and over and over again.

I decided to read it and see if anything can be gleaned related to how Trump has seen such incredible and surprising success in this election cycle. Far exceeding most pundit predictions, Trump jumped into the race in June, quickly took the lead and, for the most part, hasn’t looked back. Now we’re less than a month away from the Iowa caucus, and a potential Trump presidency is inching closer. How is this possible? Looking for an explanation for his success, and an idea of what might come should he win, from the pages of The Art of the Deal:

[pages correspond to the paperback version]

“We had one major advantage: the fact that we are not a bureaucracy…In our organization, anyone with a question could bring it directly to me and get an answer immediately.” (pg. 2o9) - A handyman recently came to my house and we got to talking politics. He said he’s planning to vote for Trump, and I asked him why. “I might vote for Trump just to piss off the Democrats and the Republicans at the same time,” he said. “Is Trump an asshole? Sure, but I know a lot of assholes.” I think people underestimate how much a Trump vote may just be a vote of no confidence in our two-party system, an extreme vote against the status quo. There is a palpable feel that, while Trump may have his flaws, he will get rid of red tape, and at least he’s not lying to me. Trump’s brashness may not be a strength or a weakness to some voters — it may just be a side issue they easily dismiss for what they feel is the greater good.

Image via: http://afflictor.com/2015/10/25/trump-launched-a-political-campaign-that-tore-into-reagans-record/

“My style of deal-making is quite simple and straightforward. I aim very high, and then I just keep pushing and pushing and pushing to get what I’m after.” (pg. 45) - Trump details several specific deals he worked on in great detail in The Art of the Deal. Some were successful, some weren’t, but he always puts a positive spin on them, and more importantly, they all evolved from the starting point - from the initial offer. There’s reason to believe that his bluster, his hardline stances, are simply the start of the negotiation for what he ultimately will consider a successful deal in the end. Take immigration (a big wall, Mexico will pay for it, deport all illegal immigrants, pause on all Muslims entering the U.S.) — what if it’s all a negotiating tactic? A way to haggle and compromise and eventually land at a pretty good spot for what he wants? This also translates to what might happen should he somehow make it through the GOP primary and face Hillary Clinton in the general election. It’s conceivable Trump may swing back to the middle, and do so convincingly.

“I play to people’s fantasies. People may not always think big themselves, but they can still get very excited by those who do. That’s why a little hyperbole never hurts. People want to believe that something is the biggest and the greatest and the most spectacular. I call it truthful hyperbole.” (pg. 58) - Perhaps my favorite quote in the entire book, Trump’s “truthful hyperbole” line is largely what gives him so many Pinocchios and Pants on Fires from the fact checkers, but what allows him to claim he’s basically telling the truth. But more interesting is the idea that he’s setting out to play to people’s fantasies. He can be their cipher, voters can live and affect change vicariously through him. It’s what most politicians aim to convey, and the most effective ones — like “hope and change” Barack Obama in 2008 — are quite successful using that method.

You can’t con people, at least not for long…If you don’t deliver the goods, people will eventually catch on.

On the press:

“I like to be accommodating. As long as they want to shoot, I’ll shovel.” (pg. 23) - The first of several interesting quotes about the press that I’ll touch on. Here, he’s referring to his work on the Wollman Rink in Central Park, where he says he was surprised so much of the press wanted to come up and take pictures after a press conference. He claims he didn’t understand the press fascination, but if they wanted to take pictures, he’d pretend to shovel some cement onto the rink. It’s this exercise with the press that has extended nearly 30 years later during this election cycle — if the press is going to follow his every move, Trump will give them a show.

“Contrary to what a lot of people think, I don’t enjoy doing press…Nonetheless, I understand that getting press can be very helpful in making deals.” (pg. 33)

“If there’s one thing I’ve learned from dealing with politicians over the years, it’s that the only thing guaranteed to force them into action is the press — or, more specifically, fear of the press.” (pg. 305)

“Most reporters, I find, have very little interest in exploring the substance of a detailed proposal for a development. They look instead for the sensational angle.” (pg. 340) - Think the press have changed much, either in reality or in Trump’s mind? He knows minutia doesn’t drive ratings, and detailed policy isn’t easy for the reporter or the viewer/reader. They want the “sensational angle” — and with Trump’s campaign for the last 6 months, they have it.

Perception is reality:

“I…told him to make it appear that we’d spent a huge sum of money on the drawings. A good-looking presentation goes a long way.” (pg. 124) - Trump said this to his architect on an early hotel project he was working on. You could say this sentiment is the crux of a successful politician — the wrapping is even more important than the present, the packaging more important than the product. With Trump, his packaging is that of an anti-politician, making for an even more attractive starting point, and an even less important, for many voters, product.

“If most malls succeed in part because they’re so homogenous and safe, I’m convinced that the Trump Tower atrium succeeds for just the opposite reasons. It’s larger than life, and walking through it is a transporting experience, almost as if you’re in a wonderland.” (pg. 178)

“What the bulldozers and dump trucks did wasn’t important, I said, so long as they did a lot of it.” (pg. 214) - When Trump was trying to secure a partner for his Atlantic City casino, he wanted to appear like it was a lot further along in construction than it actually was. So he instructed his site supervisor to bring in equipment from all over the state to simply appear busy, even if that meant digging a hole and filling it in again. This method worked, and the master persuader got what he wanted. Scott Adams’ (the Dilbert creator) has written some incredible pieces about Trump’s persuasion techniques. This anecdote shows Trump has been working at a high level for a long time.

Who Trump really is:

“I have an almost perverse attraction to complicated deals, partly because they tend to be more interesting.” (pg. 200) - I’m not sure what these four quotes tell us about his run, other than they give an insight into who Trump, the person, is — and also convey elements of a personality that would very attractive to a voter. He describes an attraction he has as “perverse,” but the attraction is to complication.

“I fight when I feel I’m getting screwed, even if it’s costly and difficult and highly risky.” (pg. 236) - He fights on principle, even if it’s smarter not to.

“If there’s one thing I’ve learned about the rich, it’s that they have a very low threshold for even the mildest discomfort.” (pg. 261) - He is rich, but he holds his fellow rich people in fairly low regard.

“Committees are what insecure people create to put off making hard decisions.” (pg. 281) - He is decisive, secure in his decision-making. (I should note these character traits are not what I necessarily believe about Donald Trump. But they are what he portrays of himself in his 1987 autobiography, and they are traits he continues to portray on the trail in 2016.)

In conclusion:

“What I admire most are people who put themselves directly on the line.” (pg. 367) - Trump concludes The Art of the Deal wondering what he might do next. Politics doesn’t enter the fray, but he makes a distinction between rich people giving away their own money — being philanthropic — which he says should be a given, and something greater. It’s not enough, he posits, to simply give — you should give back. Put yourself on the line. And this election, whichever way it ends up, he has.

“You can’t con people, at least not for long. You can create excitement, you can do wonderful promotion, you can get all kinds of press…but if you don’t deliver the goods, people will eventually catch on.” (pg. 60) - Finally, to those who say this Trump election is just a facade for some other secret purpose, people like me who jokingly suggest he might be a Manchurian candidate for Hillary Clinton or Vladimir Putin…the Trump in The Art of the Deal would agree. You can’t con people for long. You must deliver the goods, or they will catch on. We’re a month away from votes being cast. It seems more and more like Trump views the presidency as his biggest deal ever, and he’s looking to close.