Trump’s ‘Art of the Deal’ goes to Washington


“You can’t con people, at least not for long,” wrote the president-elect in his best-selling business book. And when the honeymoon period expires, Trump will have to start delivering the goods.

A version of this post was published on Medium.


The president-elect has honed his deal-making skills over decades. He made some good deals and well-documented bad deals. When Trump claims that he is one of the world’s greatest businessman and worth $10 billion  —  it’s laughable based on his bankruptcies, lawsuits and near-total lack of transparency about his assets. But it’s hard to argue with the fact that he pulled off one of the great deals in history in becoming the 45th president of the United States.

Serving as president of the U.S. is many orders of magnitude more daunting, complicated and serious than negotiating to put your name on a hotel or building a luxury golf course property. Experience as the CEO of a company with a few billion in assets, a handful of direct reports and legion of lawyers is quite different from managing an $18 trillion economy, 538 term-limitless members of Congress and 325 million citizens.

But then, the junior senator from Illinois Barack Obama didn’t come into office with extensive experience in military, economic and domestic affairs on a global scale, either. However, Obama did come into office having served in government for a decade, with deep experience in the rule of law, a disciplined approach to problem solving and an intellectual curiosity that made him less vulnerable to the opinion of whoever last had his ear.

President-elect Trump, on the other hand, seems to get his information from watching TV (and complaining about how unfair the coverage is, and claiming he didn’t say what he said), his Twitter feed and a small circle of advisers chosen based on loyalty. And as we have seen, his positions on issues tend to be fluid, a moving target, and not just because he likes to keep people guessing. Trump has proven to be impulsive and to play very loose with the truth.



What can we expect from President Trump now that he will occupy the White House and all the responsibility that will come with the job of leader of the free world?

Much can be learned from the lessons shared in Trump’s best-selling book, “Trump: The Art of the Deal“ (co-written with Tony Schwartz). Four principles from the book capture the techniques Trump applies to accomplishing his business goals, and now his political ambitions:

Get the word out: “One thing I’ve learned about the press is that they’re always hungry for a good story, and the more sensational the better … The point is that if you are a little different, a little outrageous, or if you do things that are bold or controversial, the press is going to write about you.”

Play to people’s fantasies: The final key to the way I promote is bravado. 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.

Fight Back: “In most cases I’m very easy to get along with. I’m very good to people who are good to me. But when people treat me badly or unfairly or try to take advantage of me, my general attitude, all my life, has been to fight back very hard.”

Deliver the goods: “You can’t con people, at least not for long. You can create excitement, you can do wonderful promotion and get all kinds of press, and you can throw in a little hyperbole. But if you don’t deliver the goods, people will eventually catch on.”

Trump’s interactions with the press, in particular what he often refers to as the “failing New York Times,” is a good example of Trump’s principle of promotion. For his entire campaign, and after his unexpected election, Trump has been getting the word out with bombastic, outrageous and controversial speeches, tweets and TV and radio appearances, adding up to more than a billion dollars of free media. Trump also plugged into what he learned becoming a reality show TV personality on “The Apprentice,” this time creating a 24/7 reality show that played to people’s fantasies about a more aggressive and whiter America.

He energized his base with hyperbole, insults and epithets such as “Crooked Hillary,” chiming in with his fans at rallies with calls to “lock her up.” And the media could not resist covering the show 24/7, and the audience, no matter what political persuasion, could not turn it off.

When the mainstream press came to the realization that the outlaw creator of fantasies Donald Trump wasn’t going to flame out, despite his bullying, lying and barrage of sexist, ethnic and religious taunts, it got more serious and aggressive in covering the candidate.

Exercising his principle of fighting back very hard, Trump found the perfect foil for advancing his cause in the mainstream media. It further energized his base and diverted attention from facts about his checkered business past, associations with the alt-right, sketchy Trump Foundation and history of sexism (locker-room talk), undisclosed tax returns and more. People in the Trump camp didn’t trust the insitutions and people who promised them change over the last decade, and the brash New York billionaire was promising change in a spectacular, bizarre and visceral fashion.

Trump’s battle with the New York Times is a perfect illustration of his get-the-word-out and fight-back tactics.

Just prior to meeting with the NYT on Tuesday, with the hope of a more tempered and “presidential” president-elect emerging from his cocoon, Trump threw a flurry of tweet jabs at the beacon of mainstream media:


This is the president-elect trying to bring an adversary to heel, staying in Trump classic bully, hyperbolic character, continuously antagonizing the opponent, hoping to get into their head and give him a better negotiating position. Then, when he shows up with his softer, “we should all be friends” side, he expects that the adversary will soften up, feeling relief and surprise that the egomaniacal flame-thrower is really a reasonable human being who didn’t mean all those unkind words.


True to his negotiating playbook, when Trump met with the NYT, he softened the edges and called for everyone to “get along.”

Putting on his magnanimous self, Trump called the paper “a world jewel,” and said he had “great” and “tremendous” respect for it. He noted that the Times had treated him “very rough” and that he’d “like to turn it around.” He concluded that having a better relationship with the NYT would make his job much easier, as if the job of the press is not to ask hard questions about what he says or does and make it easier for him to push through his agenda. Trump is applying his negotiating tactics to move the New York Times closer to an American version of the People’s Daily in China. And if the NYT doesn’t go easier on him, Trump will be back to threatening First Amendment protections, as he did during the campaign when he promised to open up federal libel laws to make it easier to sue the Washington Post, NYT and other news outlets.

NYT op-ed columnist Charles Blow wasn’t buying into the softer version of Trump:

I will say proudly and happily that I was not present at this meeting. The very idea of sitting across the table from a demagogue who preyed on racial, ethnic and religious hostilities and treating him with decorum and social grace fills me with disgust, to the point of overflowing. Let me tell you here where I stand on your “I hope we can all get along” plea: Never.

You are an aberration and abomination who is willing to do and say anything  —  no matter whom it aligns you with and whom it hurts  —  to satisfy your ambitions.

This brings us to another lesson cited in “The Art of the Deal.” Ultimately, all the bombast, birtherism, self-promotion and brow-beating of opponents won’t win the deal. “If you don’t deliver the goods, people will catch on,” Trump wrote.

Trump hasn’t yet fully switched gears from becoming the most powerful man in the world and understanding the job requirements, with help from his new “friend,” President Obama, to focusing more on delivering the goods he promised during his campaign.

It turns out that a lot of what he promised he doesn’t fully intend to deliver. For Trump the negotiator, everything is negotiable. He has created his own reality-distortion field that ignores facts and inflates his ego, with no clear ideology or detailed plan for addressing the challenges he laid out in the campaign  —  build a wall, kill Obamacare, bomb the shit out of ISIS. Trump may find that the reality-distortion field surrounding him during the campaign won’t protect him from his new reality  —  the actual job of being president and delivering the goods.

It’s difficult to understand exactly what Trump stands for or his values, which makes him unpredictable and his ideas subject to whatever scraps of information are floating in the air. It also keeps billions of viewers watching the show across the globe tuned into to see what the next episode will bring. He wants the world to believe that he is “crazy like a fox,” and uses Twitter to keep his adversaries, and even his transition team, off balance.

His conservative supporters, who helped get him elected, aren’t sure if he will support their platform, and liberals are hoping that the Donald J. Trump who used to be a Democrat will miraculously resurface.

As demonstrated during his on-the-record interview with the New York Times, the platform Trump campaigned on has become a malleable mashup of positions. For example, to all his supporters who he promised that he would lock up Hillary Clinton, Trump told the NYT that he was not inclined to pursue that path:

I think it’s time, I think it’s time for people to say let’s go and solve some of the problems that we have, which are massive problems and, you know, I do think that they’ve gone through a lot. I think losing is going through a lot. It was a tough, it was a very tough evening for her. I think losing is going through a lot. So, for whatever it’s worth, my, my attitude is strongly we have to go forward, we have so many different problems to solve, I don’t think we have to delve back in the past. I also think that would be a very divisive, well I think it would be very divisive, you know I’m talking about bringing together, and then they go into all sorts of stuff, I think it would be very, very divisive for the country.

Trump also now might take waterboarding off the table. After speaking with retired Marine Corps General James N. Mattis, a favorite for Secretary of Defense in the new administration, Trump rambled to the NYT:

I met with General Mattis, who is a very respected guy. In fact, I met with a number of other generals, they say he’s the finest there is. He is being seriously, seriously considered for secretary of defense, which is  —  I think it’s time maybe, it’s time for a general. Look at what’s going on. We don’t win, we can’t beat anybody, we don’t win anymore. At anything. We don’t win on the border, we don’t win with trade, we certainly don’t win with the military. General Mattis is a strong, highly dignified man. I met with him at length and I asked him that question. I said, what do you think of waterboarding? He said  —  I was surprised  —  he said, ‘I’ve never found it to be useful.’ He said, ‘I’ve always found, give me a pack of cigarettes and a couple of beers and I do better with that than I do with torture.’ And I was very impressed by that answer. I was surprised, because he’s known as being like the toughest guy. And when he said that, I’m not saying it changed my mind. Look, we have people that are chopping off heads and drowning people in steel cages and we’re not allowed to waterboard. But I’ll tell you what, I was impressed by that answer. It certainly does not  —  it’s not going to make the kind of a difference that maybe a lot of people think. If it’s so important to the American people, I would go for it. I would be guided by that. But General Mattis found it to be very less important, much less important than I thought he would say. I thought he would say  —  you know he’s known as Mad Dog Mattis, right? Mad Dog for a reason. I thought he’d say ‘It’s phenomenal, don’t lose it.’ He actually said, ‘No, give me some cigarettes and some drinks, and we’ll do better.’

Trump also declined to repeat his campaign promise to abandon the Paris Agreement that addresses climate change, stating, “I’m looking at it very closely,” and had an “open mind.”

I have some great, great, very successful golf courses. I’ve received so many environmental awards for the way I’ve done, you know. I’ve done a tremendous amount of work where I’ve received tremendous numbers. Sometimes I’ll say I’m actually an environmentalist and people will smile in some cases and other people that know me understand that’s true. Open mind.

The NYT Editorial Board welcomed Trump’s moderated views expressed during his visit, but questioned his sincerity:

We would applaud any sensible change of position, however arrived at. Mr. Trump’s apparent flexibility, combined with his lack of depth on policy, might be grounds to hope he will steer a wiser course than the one plotted by his campaign. But so far he is surrounding himself with officials eager to enact only the most extreme positions. His flexibility would be their springboard.

Trump brings a level of narcissism, abrasiveness and lack of government experience that will rewrite the book on presidential mien. He will walk an extremely fine line running the country and looking after his businesses at the same time. No one is expecting that Trump can completely separate himself from his business interests and entanglements, or that he will share his tax returns with the American people. After all, he told the NYT that “the president of the United States is allowed to have whatever conflicts he wants,” but noted that he didn’t care about his business any more, his kids (who spend a lot of time advising the president-elect) were running it and he cares only about America. At the same time he acknowledged that his new Trump hotel in the nation’s capital might see more business, and that his brand is “hotter than it was before.”

No doubt, Trump’s blurring of business and national interests will be heavily scrutinized and add to the controversy surrounding his administration.


In winning the election, Trump vanquished his opponents, slapped the elites in the face, and is now dealing with the immensity of the job he won. He is parading potential cabinet members in and out of Trump Tower like a beauty pageant. Proposed cabinet members include fellow billionaires, the “king of bankruptcy” to run Treasury, an advocate for privatizing K-12 schools, a climate-change skeptic, a fiercely anti-immigration attorney general, a HUD secretary who has said he is not qualified to run federal beauracracy and a U.N. ambassador with little foreign policy experience  —  as well as a vice president who advocated for anti-LGBTQ laws, believes being gay is a choice and that preventing gay marriage is not discrimination, but enforcement of “God’s idea.”

The team Trump is assembling doesn’t appear to align with the hints of moderation he displayed with NYT editors. In claiming the throne, Trump has an enormous weight on his shoulders. He is hiring people who he instinctively likes and for the optics, not based on resumes. As the host and star of the show, he will play them off against one another, hiring and firing them like on an episode of “The Apprentice.”

When he started his campaign, Trump said, “I will be the greatest jobs president that God ever created.” Now he needs to create those good paying jobs he promised for those who helped catapault him into the White House, as well as those who didn’t. That includes the coal-mining jobs and factory jobs, mostly lost to automation, that he said he would bring back. He needs to offer a replacement for Obamacare and explain how he will create a more secure America that doesn’t take away constitutional freedoms and discriminate against Muslims or those who disagree with his policies.

Given his lack of interest about the affairs of state exhibited during the campaign, it’s not expected that President Trump will immerse himself in briefing books, lengthy policy debates and the incredibly complex and nuanced issues that demand difficult decisions multiple times a day. He will gravitate toward what he knows best  —  building projects, such as a wall (or fence) with Mexico and rebuilding U.S. infrastructure, and rewriting those trade deals he despises. He’ll authorize drone strikes and watch the large-screen TV in the Situation Room as missiles obliterate their targets. As Trump told “Fox and Friends,” “When you get these terrorists, you have to take out their families. They care about their lives, don’t kid yourself. When they say they don’t care about their lives, you have to take out their families,” as if there were no Geneva Convention.

It may be that Trump delegates the daily running of the country to his ambitious favorite progeny and experienced pols like Vice President Pence, and spends his time hosting dignitaries, building walls, redecorating the White House with gold faucets and pictures of himself, and promoting his real estate holdings around the world and his newfound prowess as a statesman.

Hopefully, that will not be the case, and President Trump will surprise us once again, this time not just winning the election but winning the respect of all Americans and the world. Given the signals emanating so far from Trump Tower, the Trump presidency doesn’t appear to be moving in that direction.


Dan Farber is the senior vice president for strategic communications at Salesforce; he has also been an editor at CBS Interactive, CNET and Ziff-Davis. Reach him @dbfarber.

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