The Art of the Trump: A Deal for All Seasons

“I don’t do it for the money. I’ve got enough, much more than I’ll ever need. I do it to do it. Deals are my art form. Other people paint beautifully on canvas or write wonderful poetry. I like making deals, preferably big deals. That’s how I get my kicks.”

Just as Ronald Reagan once plundered the toolkit of his former career – namely his screen presence and charisma – to power the presidency, so too has Donald Trump been plundering his toolkit, bringing to bear on the Oval Office a mixed bag of dirty tricks gleaned in the convergent worlds of the boardroom and the red carpet. Trump is renowned for – whether or not some or indeed all of it justifies the renown  – his business acumen, his big-balled risk taking, his chaotic and quixotic sex life, and especially for being a merciless, sociopathic, bullying ball-bag of a man; all of which made him a compelling TV star, precisely none of which qualifies him to safeguard the health, happiness and financial well-being of 327 million souls.

Trump may have been an entrepreneur, but he made his gambles knowing he had a multi-million dollar safety net behind him. Trump may have generated vast profits, but much of his success was built upon his aversion to paying tax and contractors – the real truth of his assets buried and obscured behind bank loans, off-shore accounts and IOUs.

I’ve read a lot of books about Donald Trump, but until recently I’d never read a book by Donald Trump. I plumped for the most famous and influential of them, the New York Times’ Best-selling The Art of the Deal, first published in 1987. However, it’s perhaps something of a stretch to say that it was written by Donald Trump. Anyone who’s ever read Trump’s Twitter feed or listened to his speeches knows that eloquence and coherence aren’t his strong points. Any book written by Trump and Trump alone would probably scan like a version of Jack Kerouak’s On The Road as penned by Narcissus after a massive head injury.

The Art of the Deal was ghost-written – aka simply written – by journalist Tony Schwartz. In 2016 Schwartz publicly lamented his part in helping to cement Trump in the public consciousness as some sort of munificent emperor, an image that, in concert with Trump’s appearances on The Apprentice, somehow convinced the American public that a dead-eyed orange cabbage was the best choice for Commander-in-Chief. I can well imagine the quantity of Prozak Schwartz would’ve needed to ingest to keep calm during those long months with Trump translating his grandiose, slogan-centric puffery into something palatable.

Trump’s distinct lack of empathy and rampant sense of self-righteousness and entitlement blinds him to the fact that he’s more redolent of Mr Burns and Biff Tannen than Andrew Carnegie and Henry Ford. Let’s see if we can divine in his writing the man we see at work on the world-stage today, be it on the golf course, or tapping away on Twitter as he takes a shit.

I’ve tried to group my selected quotes into categories, with catty asides where appropriate.

The White House as boardroom and battlefield

“I’m the first to admit that I am very competitive and that I’ll do nearly anything within legal bounds to win. Sometimes, part of making a deal is denigrating your competition.”

Trump’s certainly taken that insight with him to the White House, only remove the bit that says ‘within legal bounds’.

“I fight when I feel I’m getting screwed, even if it’s costly and difficult and highly risky.”

And doesn’t America know it.

“Most people are surprised by the way I work. I play it very loose. I don’t carry a briefcase. I try not to schedule too many meetings. I leave my door open. You can’t be imaginative or entrepreneurial if you’ve got too much structure. I prefer to come to work each day and just see what develops.”

Yep. Still seems to be his signature style as president. A sort of nonchalant dictatorship.

On the Trump Organisation: “With so many regulators and regulations to satisfy, we had one major advantage: the fact that we are not a bureaucracy. In most large public corporations, getting an answer to a question requires going through seven layers of executives, most of whom are superfluous in the first place. In our organisation, anyone with a question could bring it directly to me and get an answer immediately. That’s precisely why I’ve been able to act so much faster than my competitors on so many deals.”

“I’ve never had any great moral problems with gambling because most of the objections seem hypocritical to me. The New York Stock Exchange happens to be the biggest casino in the world. The only thing that makes it different from the average casino is that the players dress in blue pinstripe suits and carry leather briefcases. If you allow people to gamble in the stock market, where more money is made and lost than in all the casinos in the world put together, I see nothing terribly different about permitting people to bet on blackjack or craps or roulette.”

The NYSE is a casino, except for when Trump wants to claim he’s directly responsible for its robust performance.

Man of the People

Because he really is just like one of us, right?

“And while I can’t honestly say I need an eighty-foot living room, I do get a kick out of having one.”

“In the middle of 1985, I got an invitation from Adnan Khashoggi, a Saudi Arabian and a billionaire at the time, to come to his apartment in Olympic Tower. I went, and while I didn’t particularly go for the apartment, I was impressed by the huge size of its rooms.”

Yes, that Khashoggi family. That dude was the uncle of the Saudi journalist, Jamal Khashoggi, who was butchered in the Saudi embassy in Turkey. Interesting connection there.

“I rarely go out, because mostly, it’s a waste of time.”

I guess when your house is the size of a city park, and you own scores of buildings, you don’t need to.

“For me the relevant issue isn’t what I report on the bottom line, it’s what I get to keep.”

Trump and the press

Trump knows the press, and has learned how to wield it as a weapon. It helps that he has Fox News and the Murdoch press on-side.

“First, the press thrives on confrontation. They also love stories about extremes, whether they’re great successes or terrible failures.”

“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. You can apply all kinds of pressure, make all sorts of pleas and threats, contribute large sums of money to their campaigns, and generally it gets you nothing. But raise the possibility of bad press, even in an obscure publication, and most politicians will jump. Bad press translates into potential lost votes, and if a politician loses enough votes, he won’t get reelected. If that happens, he might have to go out and take a 9 to 5 job. That’s the last thing most politicians want to do.”

“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. In this case, that may have worked to my advantage. I was prepared for questions about density and traffic and the mix of housing on the site, but, instead, all the reporters wanted to talk about was the world’s tallest building. It gave the project an instant mystique. When I got home that night, I switched on the CBS Evening News, expecting to hear news from the opening of the summit between Ronald Reagan and Mikhail Gorbachev. Dan Rather was in Geneva anchoring the program, but after summarising the day’s developments, suddenly he was saying: ‘In New York City, developer Donald Trump announced plans to build the world’s tallest building.’ It demonstrated how powerful and intoxicating a symbol I’d found for my project.”

Prescience with a dash of irony and a sprinkling of ‘Oooo, bet you regret saying that now, Trumpy’.

“I discovered, for the first time but not the last, that politicians don’t care too much what things cost. It’s not their money.”

On Mitterand: “It wasn’t just that he was a socialist, and that he began nationalising companies, it was also that he turned out to be a dangerous man. What can you say about a guy who goes around selling nuclear technology to the highest bidder?”

Yeah, Trump would never do anything like that. Too much integrity.

“Atlantic City’s reputation had also been hurt by corruption charges growing out of the FBI’s Abscam sting operation. In 1980, the vice-chairman of the Casino Control Commission, Kenneth MacDonald, resigned after admitting that he’d been in the room when a $100,000 bribe was passed to a local politician by potential investors looking for help in getting a casino license.”

Imagine being in a room when some dodgy deal, bribe or attempted extortion was going down. Trump would NEVER do anything like that.

On Conrad Hilton: “His son Barron joined the company in the 1950s, and of course it was only a matter of time before he took over. It had nothing to do with merit; it’s called birthright.”

Remind me just how many of your children are prominent figures in your administration?

“But Conrad believed very strongly this inherited wealth destroys moral character and motivation. I happen to agree that it often does.”

(cough cough)

“You can probably guess how much stock I put in polls.”

Yes. It very much depends upon how favourable they are to you.

“There is nothing to compare with family if they happen to be competent, because you can trust family in a way you can never trust anyone else.”

(cough cough, IRONIC, cough cough, MAFIA)

On Ed Koch: “He’s presided over an administration that is both pervasively corrupt and totally incompetent.”

(sound of someone taking a machine gun to a barrel of fish)

“Meanwhile, no fewer than a dozen Koch appointees and cohorts have been indicted on charges of bribery, perjury, and accepting kickbacks, or have been forced to resign in disgrace after admitting various ethical transgressions.”

Imagine that…

“The irony is that Koch made his reputation by boasting about his integrity and incorruptibility. It doesn’t seem to occur to him that if the people he appoints prove to be corrupt, then in the end he must take the responsibility.”

That sort of thing doesn’t occur to a lot of people, to be fair. Wouldn’t you agree, Donald?


Simply put: guy from the big house and the guy from the book? Same crook, different deal.