As Donald Trump stood on the debate stage last week, sweat shining through his make-up, he made his hard sell to the American people: if he wins the presidential election in November, he will make the country great again. If he loses, the US is fated to doom and decline under Kamala Harris.
What he didn’t mention is that losing at the ballot box will also come at huge personal cost, leaving him staring down the sights of half a billion dollars in legal debts — not to mention possible jail time — that would threaten what remains of his business and property holdings. Indeed, his personal finances were one of the barbs Harris picked to rile Trump in last week’s debate. The man who ascended to the presidency portraying himself as a savvy billionaire could be facing enormous pressure on his finances. And it wouldn’t be the first time.
To millions of his supporters across the US, Trump is the Platonic ideal of the American Dream: a self-made property magnate who cast aside a life of leisure to run for president and fix his country.
But a new book, Lucky Loser, by New York Times journalists Russ Buettner and Susanne Craig, shows that this popular caricature of Trump as a canny real estate titan — one painstakingly crafted by him, and by television producers — is more fiction than fact.
With scalpel-like precision, they investigate decades of business records and tax returns — Mary Trump, the former president’s niece, shared the family tax records and financial information with them in 2017, later winning them and David Barstow, another colleague, a Pulitzer Prize — to paint a detailed portrait of just how much Trump was given to set him up for success in business, and the hundreds of millions of his father’s money he squandered on bad deals.
“There were no guardrails placed on him,” Buettner told me last week, when I met him and Craig in the New York Times offices. Trump has tried, and failed, to sue them over their reporting and has had to pay nearly $400,000 (£305,000) to cover the newspaper’s legal expenses.
The book arrives at a moment when Trump’s finances are under considerable stress. Next year, New York appeals courts will likely decide whether he has to pay $464 million for fraudulently inflating his net worth to qualify for favorable loans and other benefits, and $83 million to the writer E Jean Carroll, whom a New York jury found he sexually assaulted in 1996 — something he later denied — for defaming her. A long-standing audit by the tax authorities could cost him more than $100 million. He could also face jail time on a number of other charges.
It wasn’t always like this. When Buettner was working at the New York Daily News, a tabloid, back in the late 1990s, Donald Trump was a figure of fun. Dressed in a three-piece burgundy suit, his hair bouffant, he would call press conferences to announce bold new projects that, often, turned out not to exist. A plan to build the tallest tower in the world. Another to buy the World Trade Center.
Yet Trump was always backed and bailed out by his father, Fred Sr, who had worked carefully throughout to build a property portfolio that would be worth a billion dollars in his lifetime. Famously frugal, he would pick up unbent nails from the ground on his building sites and give them to his carpenters to use.
By combing through business records, Buettner and Craig estimate that Trump Sr gave his favorite son over $400 million, much of it through dubious tax schemes that at times, they say, amounted to fraud. It was a tap that Fred Sr kept turned on throughout his son’s life, at one point even sending one of his bookkeepers round to Donald’s ailing Taj Mahal casino in Atlantic City to buy $3.35 million worth of chips, bailing him out of another financial bind.
Yet at nearly 80 years old, the former president still bristles at the idea that he was given a huge helping hand by his father. At the debate last week, he blustered when Harris brought up the $400 million given to him by Fred Trump Sr and claimed that he had been “given a fraction of that, a tiny fraction” and “built it into many, many billions of dollars”.
Craig and Buettner watched, fascinated.
“He wants that hardscrabble story, and by birth he didn’t have it,” said Craig. “He’s 78 years old, and he still just can’t thank his father and acknowledge his contributions to his wealth.”
Even Trump’s myth-making couldn’t fully obscure some of his more disastrous business decisions. Companies he owned have, to date, declared bankruptcy six times. He doesn’t own many of the buildings that bear his name. He was, Buettner and Craig write, mostly a salesman, not a builder.
“He wants that hardscrabble story, and by birth he didn’t have it.”
Their work has not been well received in Trumpworld. “This ‘book’ has already been thoroughly debunked and is a desperate attempt to interfere in an election that President Trump will win,” said Steven Cheung, the campaign spokesman for Trump. “These fabricated lies are nothing more than incoherent bullshit, and should be repurposed as toilet paper.”
The book is damning of Trump’s financial management, but his talent for self-promotion and ability to walk away from the wreckage of failed plans shines through on every page.
“He’s an exceptional promoter,” said Buettner. “He’s doing that from a very young age, he’s calling places and describing these astronomical [projects] he’s going to build. I think there were several times when he said he was going to build the tallest building in the world, and it didn’t happen.”
First aired in early 2004, The Apprentice transformed Trump from a gaudy caricature into a vision of success, selling the story of his glamorous life to audiences of millions. The show — and in particular, product placement payments — was bringing in real money. In 2011, he made more than $50 million, but due to his losses on his businesses, he paid no income tax on this.
Some of those licensing deals, said Craig, were “very damaging to his reputation. But it was just all about getting a check. He would put his name on anything”.
One of his great business failings, Buettner told me, was Trump’s belief that any product which bore his name would be worth whatever he spent on it. Bottled water (Trump Ice), clothing (Trump suits) and perfume (Donald Trump — The Fragrance, RRP $60) all failed. As his fame from The Apprentice waned, hotels and buildings began dropping his name from their facades. He started selling off some of his assets.
By the time he was running for president in the 2016 election, Deutsche Bank noted that Trump had reported negative cashflow for four of the last five years. His last two big developments, including golf courses in the UK, had been “financial failures that required constant infusions of cash”, Buettner and Craig write.
Then Trump won the 2016 election, promising to hand over control of his businesses to his two oldest sons Donald Jr and Eric. The latter, his second son, has been running what remains of his business interests in recent years.
Today, that largely consists of golf courses, fees to his private clubs, his social media network, Truth Social, and a number of properties including two office buildings he owns with a property company in the US. He also has a few licensing agreements overseas, including for a tower in Jeddah, Saudi Arabia, and golf resort in Oman.
He hasn’t built anything in more than 15 years, since finishing the Trump International Hotel and Tower in Chicago (he later completed a renovation and redeveopment of the Old Post Office building in Washington, which was a money-losing venture that he sold). Buettner and Craig say that they don’t have access to his post-2018 tax information, and that it isn’t possible to know his net worth. But, they add, his properties would have been very exposed during the pandemic.
As the former president campaigns to return as the leader of the free world, he is still selling products bearing the Trump name. This summer, he advertised gold trainers for $399, and a “God Bless the USA” Bible that takes a “patriotic” angle on God’s word and costs $59.99.
Should he win, Trump has promised to stuff the Department of Justice with his allies, purging his enemies. The restrictions to doing business while in office that he gestured at in his first term would, the authors said, probably be removed.
“I think there are so many moments where he has taken advantage of the opportunity that was there. Where he’s met the moment so many times,” said Craig. “And this is just another one of them.”
Louise Callaghan is the U.S. correspondent for The Times and The Sunday Times of London
