In 2005, Tim O’Brien, then a financial reporter at The New York Times, published the book “TrumpNation: The Art of Being the Donald.” O’Brien talked to sources with an up-close view of Donald J. Trump’s finances, who concluded that the real-estate developer’s net worth was $150 million to $250 million, rather than the $2 billion to $5 billion Trump had variously claimed. Trump, who had courted O’Brien by taking him for rides in his Ferrari and private jet, sued O’Brien for libel in New Jersey in 2006. Trump called O’Brien a “wack job” on the “Today” show — while, O’Brien says, continuing to curry favor with him privately. O’Brien’s publisher, Warner Books, was also named in the suit and hired top lawyers who put Trump through an unsparing two-day deposition. Asked about his finances, Trump was caught lying or exaggerating 30 times. “He thought he’d get a friendly judge, and we would roll over,” says O’Brien, who is now the executive editor of Bloomberg View. “We didn’t.” The case went through four judges and was dismissed in 2009.
Trump’s suit against O’Brien is one of seven forays President-elect Trump and his companies have made as libel plaintiffs. He won only once, when a defendant failed to appear. But the standard measure — defending his reputation and achieving victory in court — isn’t how Trump says he thinks about his investment. “I spent a couple of bucks on legal fees, and they spent a whole lot more,” he told The Washington Post in March about the hefty sum he spent on the case against O’Brien. “I did it to make his life miserable, which I’m happy about.”
Trump was wrong: Warner Books spent less than he did, and O’Brien paid nothing. But that doesn’t make Trump’s central idea any less jarring: that libel law can be a tool of revenge. It’s disconcerting for a superrich (if maybe not as rich as he says) plaintiff to treat the legal system as a weapon to be deployed against critics. Once installed in the White House, Trump will have a wider array of tools at his disposal, and his record suggests that, more than his predecessors, he will try to use the press — and also control and subdue it.
As a candidate, Trump blustered vaguely that he wanted to “open up our libel laws.” I asked his spokeswoman, Hope Hicks, by email what he meant by that, but she didn’t answer the question (or others I posed). It’s not within the president’s direct powers to change the rules for libel suits. But our legal safeguards for writers and publishers aren’t foolproof. In the last few years, Trump has been joined by at least two billionaires who are determined to exploit cracks in the wall of defense around the press. The members of this club are innovators. They have sued or funded suits to defend reputations or protect privacy. But an underlying aim appears to be to punish critics like O’Brien or even destroy entire media outlets.