The Best Donald Trump Books

You are the man that made the myth. Before we discuss your book choices, what was it like writing Donald Trump’s autobiography?

Tony Schwartz: I wrote The Art of the Deal because my second child was about to be born. We were under financial pressure, and this was an opportunity to make a significant sum of money in a short amount of time. I had great misgivings about Trump, whom I’d just written an article about for New York magazine in February 1985, called “The Cold War on Central Park South”. It was about how Trump had harassed tenants living under rent control in a building he owned. He wanted to get them out so he could convert it into a luxury condominium. And the tactics he used were pretty awful, like breaking the elevators so people had to walk up many flights of stairs and not replacing the lights in the hallways and threatening to put homeless people in empty apartments.

So, I had a sense of who Trump was and I knew this was a compromising decision. But, still, I rationalized; I told myself, he’s a real estate developer who just wants to promote himself, so this is harmless, and it can set me up financially to do good work. In simple terms, it was a decision to sell out.

Over the year that I spent on The Art of the Deal, I felt a growing sense of despair and discomfort. I was creating a character for this book that I knew was more appealing than he really was, a version of Trump that exaggerated his wins and never mentioned his shady methods. As a ghost writer, it was my job to paint him in the best possible light, but as I came to know the person I was portraying better and better, I felt worse and worse about what I was doing.

“Trump invents reality every day, without constraints, bumpers, borders or limits”

The book became an enormous success. I didn’t talk about it much for 30 years. I have joked that Trump inadvertently led me to the Dharma, but it’s sort of true. By counterexample, he prompted me to rethink my life. The next book I wrote was called What Really Matters: Searching for Wisdom in America. Writing The Art of the Deal pushed me to fully embrace a set of values very different than Trump’s. What I didn’t anticipate was that Trump would one day use the vastly idealized version I created of him to run for political office. “America needs a leader who wrote The Art of the Deal,” he said in announcing his run for the presidency. That person was me. America didn’t need me as president, and it definitely didn’t need Trump.

Trump seems to have been uncharacteristically generous in this treatment of you. Although he seems to hoard credit and prides himself on his skills as a negotiator, he gave you a “with,” allowing your name to appear on the cover, and he gave you fifty percent of royalties. He must’ve really loved you. What was it like to be loved by Donald Trump? What insight did you get into his personal magnetism?

Trump doesn’t love anyone, and he didn’t love me. I was a means to an end, like everyone else in his life.  I do believe he felt that I understood him. We never talked about any of this, and certainly not about our relationship. He’s not a reflective man in any way. On the face of it, we could not have been more different. But he felt a certain comfort with me, perhaps because he sensed the part of me that had some of the same primitive drive he did. I understood that in him, and was able to create a voice from it that made him more self-aware and appealing than he was.

So why haven’t you chosen Art of the Deal among your titles?

Because I don’t think it’s that revealing about Trump. It’s a piece of fiction and relative to what’s been written about him, including some of the stuff I’ve written, I don’t think The Art of the Deal offers the deepest insight about who he is.

We asked you to name five books to demystify Donald Trump the man. Let’s begin with a book by arguably the most eminent American sociologist of this century, Arlie Russell Hochschild. Tell us about Strangers in Their Own Land.

I chose Strangers in Their Own Land—and put it first on my list—because Arlie Hochschild is a brilliant writer and a sociologist of great empathy and insight. Although the book was written before Trump was elected president, it goes a long way toward explaining him, and more specifically toward explaining why people embraced him.

Explain.

Hochschild writes about people who live in the bayous of Louisiana. They’re conservative, despite the likelihood that their lives are arguably worse because of the Republican policies that Trump has embraced and advanced. Specifically, she talks about the fact that these folks live in an area deeply threatened by dumping, pollution, poisoned fish, undrinkable water and skyrocketing incidences of cancer. It’s the opposite of self-interest for the people Hochschild writes about to support politicians whose environmental policies have created the crisis they’re facing.

“Over the year that I spent on The Art of the Deal, I felt a growing sense of despair and discomfort”

Ultimately, this book is about the power of emotion over reason, which is why I chose it. Trump may be the most aggrieved person on the planet. There are many millions of Americans who feel aggrieved. They believe that minorities and immigrants are skipping to the front of the line, to use Hochschild’s phrase, unfairly and at their expense. Hochschild’s understanding of the inner experience of people who represent Trump’s base is what makes this such an important book.

Donald Trump’s intuitive understanding of aggrieved white men seems to be one of the keys to his success.

Absolutely. Even though he inherited something like $400 million in his 20s, he feels aggrieved every day, all day long. So, he taps into that feeling among voters.

I should warn our readers that your titles keep getting more dire. Next on your list of Trump books we have American Carnage: On the Front Lines of the Republican Civil War and the Rise of President Trump. Please tell us about it.

American Carnage is also a precursor book; it describes what happened to the Republican Party in the period before Trump was elected that made it possible for Trump to co-opt the party. It focuses on the leadership of John Boehner and Paul Ryan. And then it’s the description of the campaign Trump ran.

American Carnage was written by a journalist who identifies as conservative and who had great access to people who I don’t think would’ve spoken so openly to mainstream reporters. The book helps you understand, from the inside, how Trump took over the Republican Party. It’s weird and it’s fascinating. And it’s a perspective that I haven’t seen represented anywhere else.

Tim Alberta, the author, is the chief political correspondent for Politico, which is as inside-the-Beltway as magazines get. Although Trump is known for his attacks on the media, he has often observed that he’s scoring hits, selling papers and gaining ratings for those who cover him. I wonder whether, as someone who knew Trump when he was engaged in a mutually beneficial relationship with the New York tabloids in the eighties, you think he has established a similarly symbiotic relationship with the Washington media?

Without question. Trump is addictive. We all know that to be true because we’re all preoccupied with him, whether we’re supporters or reporters or critics. Journalists are always looking for an exciting story and Trump can always create drama. As a politician, he creates drama by being utterly odious, but he remains a subject of fascination.

Fire and Fury: Inside the Trump White House is the next title you’ve chosen.

A lot of journalists hate Michael Wolff and his book. Readers liked it; it sold hugely. There is a legitimate quarrel with some of his facts and sourcing. If you’re looking for the most sober and rigorous account of what happened in the first many months of the Trump White House, this is not your book.

But from my experience of Trump, this is the most deeply accurate book that’s been written about him—the chaos he creates and which has enveloped all of us since he took office. Michael Wolff has a remarkable capacity to get inside the heads of people. He does it in this book just as he did it in his book about Rupert Murdoch.

Let’s move on to the next book on your list, Gaslighting America: Why We Love It When Trump Lies to US.

The author, Amanda Carpenter, is the former press secretary to Ted Cruz and a die-hard, right-wing Republican. The very fact that she chose to write a critical book is interesting in itself.

She does an incredibly good and persuasive job of deconstructing the secret to Trump’s success. She unfolds how over and over again, he takes control of any given news cycle by doing things that would cause the end of other politicians’ careers. She sees the paradox of Trump’s appeal. Like Strangers In Their Own Land, this book helps you to understand the incomprehensible—that voters like Trump not despite his lies, but in some way because of them.

You’ve said that since Trump is not constrained by a conscience regarding telling untruths, he has a strategic advantage over more honest politicians.

Trump invents reality every day, without constraints, bumpers, borders or limits. As he gets into more and more trouble, and faces the prospect of impeachment, he doubles down on convincing people that things that aren’t true are true. Most people are constrained by conscience. That’s the part of you which says, “I couldn’t do that because it’s wrong,” or “I couldn’t do that because people would think poorly of me,” or “I couldn’t do that because it doesn’t feel right.” Freud called that superego and Trump doesn’t have one.

The Dangerous Case of Donald Trump is next up.

This is a book of essays, mostly by psychiatrists. The majority of books about Trump focus on his actions. This is a book about why he does what he does. It presents a range of interpretations about what Trump’s underlying personality disorder is, but there is consensus that he suffers from one.

There’s a little bit of self-interest in this choice, because I wrote one of the book’s essays based on my own experience with Trump. My own belief is that the person Trump became is deeply attributable to having a brutal father and a neglectful mother.

When pressed to suggest a new name for Trump’s autobiography, you suggested ‘The Sociopath’. What firsthand experiences did you have that supports this diagnosis?

The characteristics that define a sociopath are callousness, hostility, impulsivity. Is there any reasonable person who would say that doesn’t define Donald Trump?

You’ve been called, by your former editor at New York magazine, the Dr. Frankenstein of Donald Trump. In Shelley’s ending, the monster outlives all efforts to destroy him. Forgive me for mixing metaphors, but can you identify any silver stakes for Trumpism?

Trump isn’t a vampire; he can’t live forever. The silver stake for Trumpism is changing our culture. We need a developmental leap. We need a renewed focus on human development, not just child development but also adult development. That’s what I spent the last thirty years of my life doing—figuring out how to motivate people to take a more embracing view of the world—less selfish and more empathic.

That’s what you wrote about after The Art of the Deal in What Really Matters.

What Really Matters was my response to—and my first attempt to do penance for—writing The Art of the Deal. My experience with Trump had left me feeling that the world he represented and the way he lived was the opposite of the way I wanted to live. I set out to learn from people who were more focused on wiser ways of living. What Really Matters is the story of my own search, and that search continues to this day.