Lucky Loser: How Donald Trump Squandered His Father's Fortune and Created the Illusion of Success

by Russ Buettner

But Fred, so determined to find immortality in his son’s accomplishments, never seemed to question why Donald lied about him to elevate his own stature. He never wavered in his support, even as Donald broke the fundamental rules of business that had been central to Fred’s success. Careful planning and financial forecasting. A hesitancy to take on large debts, and never with a personal guarantee. Fred’s eternal and unquestioning support came to define Donald’s idea of loyalty, his baseline expectation for anyone wishing to remain in his good graces. It also became a level of grace he extended to no one.

He ran the risk, a tremendous risk in this case, of feeding the most ravenous money-eating predator in real estate: time. Though he often dismissed his father’s expertise, he might have taken to heart a lesson Fred said he had tried to impart to his favorite son: “I always told Donald, ‘If you dawdle, you lose your shirt. You pay interest 365 days a year.’ ”

Schwartz, who had earned a reputation as a substantial and careful journalist, wrote a note to himself that a truthful rendition of his subject could make Trump seem “just hateful or, worse yet, a one-dimensional blowhard.” But he recognized that crafting Trump into a “sympathetic character—even weirdly sympathetic,” would be vital to the book’s success.

The truth was that Trump was hemorrhaging cash, largely from massive interest payments. But it was all other people’s cash. His entire operation, and his lifestyle, was a float. He was living, and creating a phony image, on borrowed money. And he was only warming up.

Roffman had posited that Trump must have been bluffing about being willing not to build the Taj Mahal because he would not want to find himself with a white elephant, a term for a business asset that does not produce enough revenue to cover its costs. Now, Donald Trump had a circus tent full of white elephants.

Trump expressed condolences for the families and complimented their contributions to his company. He then made their deaths about himself, saying he had intended to be on the helicopter but changed plans at the last minute. But for him, the real import of the crash would be the loss of leadership at a crucial moment. With one of the biggest casinos in the nation under construction, costs approaching $1 billion, and almost $50 million in interest payments coming due every six months on just that one project, Trump had no one he trusted leading his casinos.

Years later, Michael D. Cohen, one of Trump’s lawyers from that era, recalled Trump beaming with delight at a massive refund check he had just received from the IRS and saying, “He could not believe how stupid the government was for giving someone like him that much money back.”

Though he was under no obligation to do so, Roth passed along more than $100 million of that cash to Trump. Despite Trump’s efforts, much of his losses on businesses he ran would be covered by a windfall from a business that was not subject to his judgment.

On his way to defeating Clinton that November, Trump often repeated a line on the campaign trail—“I’m really rich”—to argue that his experiences in business made him uniquely suited to be president. He certainly appeared rich. That he had received the equivalent of a half billion dollars from his father, another half billion as a reality television star, and lost much of that money creating an illusion of success, never came up.

Here’s the part that may sting most in a country that sees itself as history’s greatest meritocracy: Good things happened to Donald Trump. He did not earn most of those good things. He was born. He was discovered by a revolutionary television producer. And he was pushed into an investment against his will. And from those three bits of good luck came the equivalent today of more than $1.5 billion. That sort of tailwind could paper over a litany of failure and still fund a lavish life. And there is no evidence that in fifty years of labor Donald Trump added to his lucky fortunes. He would have been better off betting on the stock market than on himself.

Either way, the rise of that ecosystem was perhaps the final lucky stroke of Trump’s very lucky life. The man who became famous thanks to the rise of celebrity business journalism and “wealth porn” in the 1980s, the man who was discovered as a midlife ingenue at the birth of reality television, now enters any dispute with an unquestioning megaphone at his disposal. Nixon should have been so lucky.

He began his campaign seeking to undermine all journalism beyond Fox News. He told the television journalist Lesley Stahl, as she recalled, that he had made attacking the media a centerpiece of his campaign—calling reporters “enemies of the state”—to “discredit you all and demean you all so that when you write negative stories about me no one will believe you.”

It is too soon to tell whether Trump’s rise has been singular to him or has revealed a shift in America’s culture and politics that will last. But this version of America—a place with no agreed-upon facts, where being a person of one’s word no longer matters, where one man’s self-created problems serve as a proxy for a nation under attack—this is the world as Donald Trump wants it to be.

American voters now face a third chance to decide whether it is the world they want.