An essential reading list for understanding Donald Trump

February 14, 2017
Photo by Pete Vernon

At times it feels like Donald Trump has always been with us. Nearly four decades of coverage have made him a ubiquitous presence in the gossip pages and on magazine covers. With journalists understandably focused on the daily deluge of news from the Trump White House, we thought it might be helpful to put together a list of readings that provide windows into the life and times of the man in the Oval Office.

Unsurprisingly, given his testy relationship with the press, the profiles and investigative pieces on the list range from skeptical to outright hostile. But despite being burned time and again, Trump seems addicted to the limelight that comes with attention from the media. From Wayne Barrett’s early investigations into a little-known, Queens-born developer to Maggie Haberman’s look at Trump’s life in the White House, the president has welcomed journalists into his life in ways few politicians ever have.

The profiles reveal an enduring interest in politics—by the late 1980s, Trump was floating the idea of running for president—and a fixation on a few issues, namely trade and crime, that would later become centerpieces of his campaign. With up to 204 weeks left in his term, you should have plenty of time to get through the 22 readings listed below. So pop open a browser tab or head to your local book store. Here is CJR’s recommended reading on Donald Trump:



Trump: The Greatest Show on Earth: The Deals, The Downfall, The Reinvention by Wayne Barrett

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In 1978, the legendary investigative reporter Barrett first began covering “a 32-year-old, little known developer who had yet to build his first project.” Barrett’s cover story for The Village Voice launched an obsession that cast him as the dean of Trump-watchers until his death on January 19, one day before his long-time subject was sworn in as the nation’s 45th president. Originally published in 1992 as Trump: The Deals and the Downfall, the book was updated and reissued in August 2016.

The Making of Donald Trump by David Cay Johnston

Johnston, a Pulitzer Prize winning investigative journalist, first met Trump in Atlantic City during the summer of 1988. He described the future president as “a modern P.T. Barnum,” and, over the course of nearly three decades, chronicled Trump’s business dealings and personal proclivities for The Philadelphia Inquirer and The New York Times. Also published in August 2016, The Making of Donald Trump offers a scathing look at the president’s “lifelong entanglements with a major cocaine trafficker, with mobsters and many mob associates, with con artists and swindlers.”



The Trumps: Three Generations of Builders and a President by Gwenda Blair

Author and journalist Gwenda Blair traces the history of Trump’s forebears, from grandfather Friedrich Drumpf’s immigration from Germany, to father Fred’s creation of a real estate empire, to The Donald’s romantic entanglements and financial rises and falls. First published in 2000, Blair has added a new preface attempting to tie the characteristics she observed in Trump in the 20th century to the unexpected political success he’s achieved over the past 20 months.

Trump: The Art of the Deal by Donald J. Trump and Tony Schwartz

Trump’s 1987 best-seller combines standard autobiography with business advice. On the campaign trail, he called it his second-favorite book (after the Bible). Credited co-author Tony Schwartz emerged as a fierce critic of Trump the candidate, and claimed that Trump did no writing at all on the project. It’s in this book that Trump coined the phrase “truthful hyperbole,” which he defines as “an innocent form of exaggeration—and a very effective form of promotion.”


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The Expanding Empire of Donald Trump by William Geist, The New York Times Magazine, April 8, 1984

“Donald J. Trump is the man of the hour,” writes Geist in this profile that follows Trump from architectural meetings to hotel ballrooms, where he is hailed by the likes of late Yankees owner George Steinbrenner and then-NYC Mayor Ed Koch. “Spending a day with Donald Trump is like driving a Ferrari without the windshield,” Geist says. “It’s exhilarating; he gets a few bugs in his teeth.”

Donald Trump Gets What He Wants by Graydon Carter, GQ, May 1, 1984

The seeds of future battles are planted throughout the first story that Graydon Carter wrote on Trump. “Hands small and neatly groomed;” “striver from an outer borough;” “a half-block-long Cadillac stretch limo with ‘DJT’ vanity plates.” Many of the insults that would come to mark Carter’s running feud with Trump—now the stuff of New York media legend—appear, in veiled form, in this article.


Citizen Trump by Bill Powell and Peter McKillop, Newsweek, September 28, 1987

“Donald John Trump—real-estate developer, casino operator, corporate raider and perhaps future politician—is a symbol of an era,” Powell and McKillop write. “For better or worse, in the 1980s it is OK to be fiercely ambitious, staggeringly rich and utterly at ease in bragging about it.” The Newsweek cover story catches Trump near the height of his 1980s celebrity status, riding in helicopters with boxing promoter Don King, taking out full-page ads criticizing US foreign policy, and feuding publicly with Mayor Koch.

Playboy Interview: Donald Trump by Glenn Plaskin, Playboy, March 1990

In perhaps the most revealing interview he’s ever given, Playboy finds Trump just before his fall, “young, blond and a billionaire.” After nodding to rumors that Trump will buy Tiffany’s, NBC, the New York Daily News or the Waldorf Hotel, Plaskin writes (jokingly), “And the Presidency? No, that takes an election, and it is clear that Trump is not that patient. Too much to do!” As for the interview itself, here’s an answer that wouldn’t look out of place on the campaign trail 26 years later: “I hate seeing this country go to hell. We’re laughed at by the rest of the world. In order to bring law and order back into our cities, we need the death penalty and authority given back to the police.”



Trump: The Fall by Newsweek Staff, Newsweek, June 17, 1990

“For a high-rolling decade, Donald Trump was the King of Glitz…Like a modern-day Gatsby, he lived as lavishly as he spent,” Newsweek reporters write in this profile of Trump’s financial downfall. The piece catches Trump in the midst of his attempts to negotiate his reported $3.2 billion debt load, all while his marriage to first wife Ivana was falling apart. Even if he succeeded in holding onto his empire, they wrote, “the Trump ‘mystique’ may never recover.”

Trump Solo by Mark Singer, New Yorker, May 19, 1997

Singer visited Trump as the real estate mogul’s second marriage was dissolving, but whose financial comeback was already underway. He found a man defiant and boastful, happy to engage in the sort of “truthful hyperbole” (or, in some cases, outright fantasy) that Trump had described in Art of the Deal. Towards the end of the article, Singer judges Trump as having “aspired to and achieved the ultimate luxury, an existence unmolested by the rumbling of a soul.”

The Art of the Donald: The Trumpster Stages the Comeback of a Lifetime by Mark Bowden, Playboy, May 1997

Bowden finds Trump in the midst of his comeback, but brings readers to that redemption only after explaining how it all went wrong in the early 1990s. By the time of the article, “Donald has discovered what all celebrities eventually find. If you’re doing well, there’s nothing written about you that can hurt you. And if you’re doing poorly, there’s nothing written about you that can help.”

Donald Trump: How I’d Run the Country (Better) as told to Cal Fussman, Esquire, August 2004

Back in the public eye as host of The Apprentice, Trump got an Esquire cover story. Though the Iraq war began more than a year before this interview ran, Trump has often pointed to it as evidence that he had been against the war from the start. “My life is seeing everything in terms of ‘How would I handle that?’” Trump told Fussman. “Look at the war in Iraq and the mess that we’re in. I would never have handled it that way.”

36 Hours on the Fake Campaign Trail with Donald Trump by McKay Coppins, BuzzFeed, February 13, 2014

Three years ago, McKay Coppins spent a couple days riding in chauffeured SUVs, on a private flight, and sleeping at Mar-a-Lago as Trump toyed with the idea of running for governor of New York. Coppins, who Trump would later call “a dishonest slob” and a “slimebag reporter,” got the sort of access journalists today can only dream of. In hindsight, his conclusions read like a dare: “Trump very badly wants to be taken seriously as a potential political candidate and not be written off as a man-boy who cried wolf. But, at the same time, he plainly has no interest in actually running for office.”

Donald Trump and the Central Park Five by Amy Davidson, New Yorker, June 23, 2014

In one of the darkest moments of Trump’s early forays into politics, he took out a full-page ad in The New York Daily News calling for the state to bring back the death penalty for the teenagers known as the Central Park Five. The boys were convicted after providing coerced confessions, and were finally exonerated in 2002 when DNA evidence proved that another man had been responsible for the attack and rape at the center of the case. That wasn’t enough for Trump, who called the city’s 2014 settlement with the Central Park Five “a disgrace.”

Trump’s War on “Losers”: The Early Years by Bruce Feirstein, Vanity Fair, August 12, 2015

In the late 1980s and early 1990s, Spy magazine delighted in sticking pins in the ballooning image of Donald Trump. Editors Graydon Carter and Kurt Andersen coined the moniker “short-fingered vulgarian,” which reappeared on the campaign trail in memorable fashion. Feirstein, a contributing editor at Spy, remembers, “we fact-checked his books and his finances (with predictable results), trolled him by sending miniscule checks—as low as 13 cents—to see if he’d cash them (he did), and wrote up his all-but-forgotten business debacles…And yet, none of it stuck.”

Donald Trump Is Not Going Anywhere by Mark Leibovich, The New York Times Magazine, September 29, 2015

‘‘I’ve had much more than 15 minutes of fame, that’s for sure,’’ Trump tells Leibovich in this profile, written in the early fall of 2015, as Trump stubbornly held to his lead in the crowded Republican primary field. In one revealing passage, Leibovitch writes: “I asked whether he had ever experienced self-doubt. The question seemed to catch Trump off guard, and he flashed a split second of, if not vulnerability, maybe non­swagger. ‘Yes, I think more than people would think,’ he told me. When? ‘I don’t want to talk about it.’”



Trumpology: A Master Class, Politico Magazine, May/June 2016

Susan Glaser and Michael Kruse brought together five Trump biographers for a roundtable discussion of precious source material for those eager to explain Trump’s surge toward the GOP nomination. It’s vital reading for those interested in background on the man who would be president. Politico reconvened the panel several times, most recently in the days before Trump’s inauguration.

Donald Trump’s Ghostwriter Tells All by Jane Mayer, New Yorker, July 25, 2016

In the mid-1980s journalist Tony Schwartz spent 18 months with Donald Trump, getting to know the man and his ideas in order to ghostwrite what would become the international best-selling Art of the Deal. After Trump announced his candidacy and emerged as a front-runner, Schwartz emerged as a fierce critic of his former subject, telling Mayer, “I genuinely believe that if Trump wins and gets the nuclear codes there is an excellent possibility it will lead to the end of civilization.”



The Choice 2016, Frontline, September 27, 2016

Frontline’s excellent look at the shaping of candidates Trump and Clinton examines the experiences that brought each of them to the verge of the White House. The documentary looks at Trump’s difficult, if privileged, childhood, meteoric rise to the heights of New York celebrity, and flirtations with running for office. It theorizes that, ultimately, Trump was spurred on by an uncomfortable evening at the White House Correspondents Association dinner.

Trump boasts about his philanthropy. But his giving falls short of his words. By David Fahrenthold, The Washington Post, October 29, 2016

David Fahrenthold and his trusty notepad were the media darlings of the 2016 campaign. Starting with a simple question about whether Trump had actually donated the money he promised to veterans’ groups, Fahrenthold embarked on a reportorial odyssey in search of evidence of Trump’s giving. In this piece, published just before the election, he explains his process and his findings regarding the “ardent philanthropist.”

Donald Trump: The Ugly American by Graydon Carter, Vanity Fair, November 2016

No one does imperious disdain quite like Carter. The Vanity Fair editor traces his relationship with the man who was days away from being elected president from their first meeting in 1983 through encounters at the White House Correspondents Association dinner to the insult that appears on the menus of Carter’s Greenwich Village restaurant (“Waverly Inn—worst food in city.”)

A Homebody Finds the Ultimate Home Office by Maggie Haberman, The New York Times, January 25, 2017

Cable television, Lay’s potato chips, and “beautiful phones.” These are a few of the things Donald Trump enjoyed during his first week in the White House. Despite an oft-repeated aversion to the “failing” New York Times, Trump got on the phone with Maggie Haberman to discuss his adjustments to the new digs.

Pete Vernon is a former CJR staff writer. Follow him on Twitter @ByPeteVernon.