Tim O’Brien did not set out to write a conclusive assessment of Donald Trump’s wealth. But it was those three pages in a 275-page book that occasioned what is, even in the annals of frivolous Trump lawsuits, a special display of petty, thin-skinned litigiousness.
In October 2005, O’Brien, then a business reporter for the New York Times, published a book about Donald Trump, TrumpNation: The Art of Being the Donald. The book was not a hatchet job. Not only did O’Brien interview friends and employees and business associates and political rivals and much of the rest of the Who’s Who of the World of Donald, he also chatted with the man himself — repeatedly. They met for formal interviews in Trump’s various homes and offices. Trump drove O’Brien around in his Ferrari and in his Mercedes. They watched Pulp Fiction together on Trump’s gold-laden private jet. It all went into the book, from which emerges a portrait of a complex, fickle, charming, self-obsessed, cinematic American original.
Of course, no book about Trump can avoid the quasi-impenetrable question of his wealth. In 2004, O’Brien had co-authored a piece for the Times detailing Trump’s financial woes — he had recently filed for the third of what would be four Chapter 11 bankruptcies — and quoted anonymous sources who reported that Trump’s wealth was not nearly what he claimed; in fact, it was in the hundreds of millions, they said. (Contemporaneous reports in the Washington Post and Time magazine suggested the same.) Trump, meanwhile, notoriously unreliable in his own estimates, offered figures ranging from $1.7 billion to $9.5 billion. In TrumpNation, O’Brien cited those numbers, alongside “three people with direct knowledge of Donald’s finances” who estimated his wealth was “somewhere between $150 million and $250 million.” Trump denied it, in his usual colorful fashion: “You can go ahead and speak to guys who have four-hundred-pound wives at home who are jealous of me, but the guys who really know me know I’m a great builder.”
Despite his having included all of this information, including Trump’s denial, Trump accused O’Brien of cherry-picking his information to hurt Trump’s reputation. He sued him for $5 billion in damages.