Forget "The Apprentice" — Trump's taxes show he was really "The Biggest Loser"

Between Poppa Trump and Mark Burnett, Trump was gifted $840 million — but he may still owe as much as $1 billion

By Amanda Marcotte

Senior Writer

Published September 28, 2020 12:10PM (EDT)

Donald Trump (Drew Angerer/Getty Images)
Donald Trump (Drew Angerer/Getty Images)

Donald Trump's seemingly immovable approval numbers are a testament, above all other things, to the power of racism, and the way that 40 to 42% of Americans will stand by their man, no matter how bad things get, so long as he keeps hating the same people they hate. But that legendary floor of his — he has almost never dropped below 40%, or risen above 45% — is also a testament to the power of narrative fiction, especially of the televised variety.

During the 2016 Republican primary, polling showed that Trump supporters were bamboozled by "The Apprentice," mistaking the fictional Trump of the "reality" TV show for the real Trump, a repeated business failure with a series of bankruptcies under his belt. To this day, about half of Americans still believe that Trump is a competent steward of the American economy, despite the worst downturn since the Great Depression, because they mistook a character he played on TV for the real thing. Trump has boosted this lie about his business acumen by concealing decades of his tax returns so that he could claim to be a successful billionaire without being fact-checked by his own accountants. 

But now, after years of trying, the New York Times has successfully harpooned the white whale that journalists, prosecutors, activists and Democrats have been hunting for years: Donald Trump's tax returns.

Unsurprisingly, the documents suggest Trump cheats on his taxes, as he cheats in every other aspect of life, from marriages to presidential elections. Perhaps more importantly, the documents show that Trump's entire persona as a successful businessman isn't just a lie, but the inverse of reality. If we're going strictly on profit and loss, Donald Trump is the worst living businessman in America. 


Trump has twice been basically gifted half a billion dollars by benefactors — twice! — first by his father and then by reality-show producer Mark Burnett for "The Apprentice." In both cases, tax documents suggest he took more money than most people can even dream of, and flushed it straight down the toilet. Trump isn't a successful businessman. He's the photographic negative of a successful businessman. If "The Apprentice" had been honestly named, it would have been called "The Biggest Loser."

As the Times reports, Trump's work on "The Apprentice," for which he did very little beyond showing up to perform before the cameras, earned him "a total of $427.4 million." Instead of investing this cash bonanza, which he received through no skill or effort beyond letting makeup artists and editors make him look as good as possible, Trump turned around and dumped that money into businesses "that in the years since have steadily devoured cash," such as $315 million in reported losses for his golf clubs and $55 million in losses for his Washington hotel. He does make money off Trump Tower, but the massive losses are part of the reason Trump has avoided paying income taxes for so many years. 

Not only did Trump blow all the money that Burnett basically handed to him, he also appears deeply in the hole. He owes an eye-popping $421 million to various banks, most of which is coming due in the next four years. On top of that, he may owe another $100 million to the federal government, due to his shady tax practices. As Forbes journalist Dan Alexander calculated on Sunday, Trump's debts may total more than a billion dollars

Trump isn't the "stable genius" he claims to be, but no doubt the man has a gift for losing money. 

What makes this even more outrageous is this is the second time Trump was given nearly half a billion dollars that he proceeded to set on fire. As the New York Times pieced together in 2018 from documents provided by Trump's niece, his father, Fred Trump, funneled $413 million to his profligate son (often illegally), only to watch The Donald waste it all on vanity projects. 

In fact, as with the "Apprentice" money, Trump not only lost the cash Daddy gave him, but kept spending. Trump's tax documents from 1985 to 1994 obtained by the New York Times show that he lost a billion dollars during that time. In 1990, in fact, Trump was so strapped for cash, despite his father's largess, that he pressured Fred, who was then 85 and suffering from dementia, to change his will in order to bail his wildly and unimaginably irresponsible son out of debt. 

Trump was likely only saved from ruin in the last decade or so by the infusion of Burnett cash — but then he went deeply into debt yet again. 

How does Trump keep up his lavish lifestyle? Well, no doubt a huge reason he loses money hand over fist is because he burns through it to keep up his lifestyle. He also appears to use accounting tricks to put taxpayers on the hook for his lifestyle. The Times found that by claiming all personal luxuries as business expenses, Trump "can still live a life of wealth and write it off."

Why does this matter? Trump voters already know the man is a liar and a cheat, and have clearly decided they don't care. During a 2016 presidential debate, Hillary Clinton accused Trump (correctly, it turns out) of not paying federal income taxes. He declared that made him "smart." For Trump voters, his tax cheating only adds to his mystique, and enhances his claim that, as a "successful" businessman, he knows how to run the economy, so people should set aside their concerns about his rancid personality and vote for him anyway. 

As Greg Sargent of the Washington Post argues, Trump campaigned on the idea that "he enriched himself off a system rigged to enable such elite gaming" and that he could somehow "unlock its spoils for supporters." In reality, however, these tax returns show that Trump's epic cheating wasn't shrewd so much as a desperate effort to "compensate for truly epic levels of incompetence and failure."

Trump is incapable of handling a checking account, much less running the economy. He cheats, without question. But he does so in no small part because he's too stupid to make money honestly. 

The deadly combination of Trump's ego and incompetence is such that he cannot help but destroy everything he touches. If Trump had simply put the money he'd been gifted into a mutual fund or other such investments, he'd be insanely rich. Hell, if he'd stuck it inside a mattress, he'd be rich beyond the imagination of the vast majority of Americans.

But Trump can't help but screw things up. He's a narcissist who wanted to show he was good at business — even though he's desperately bad at it — and kept on buying up vanity projects like golf courses that lose lots of money. 

Unfortunately for the health of our nation, we can see the same tendencies playing out with the coronavirus pandemic. If Trump had simply left well enough alone, letting public health officials do their job, the pandemic would still be bad, but would now be much better contained. But Trump can't help but get in his own way. He kept interfering with the response, insisting on treating the pandemic as a PR crisis and a political issue, rather than a health crisis. In the process, he undermined testing, mask-wearing, social distancing and other measures that could have greatly reduced viral transmissions. The result, as of Monday morning, is more than 7.1 million cases and nearly 205,000 deaths

Trump's entire campaign pitch has been that he may be an asshole, but at least he's a smart, tough asshole. His daughter, Ivanka, hit this theme hard at the Republican National Convention, joking that "my dad's communication style is not to everyone's taste" but that "the results speak for themselves."

Yeah, First Daughter: They do. It was was preposterous at face value to claim that Trump was an effective leader, in light of the rapidly escalating death toll from the pandemic and a national unemployment rate 8.4% — down from the worst months of 2020 but still more than double what it was in February. But as these tax documents prove, it's a lie that goes back decades. Trump is both an asshole and a terrible businessman, quite possibly the worst on planet Earth. He surrounds himself in gold-plated cheese, but his real Midas talent is his ability to turn anything he touches to ashes. He did it to his endlessly fake and failed business enterprises, and now he's doing it to our country. 

By Amanda Marcotte

Amanda Marcotte is a senior politics writer at Salon and the author of "Troll Nation: How The Right Became Trump-Worshipping Monsters Set On Rat-F*cking Liberals, America, and Truth Itself." Follow her on Twitter @AmandaMarcotte and sign up for her biweekly politics newsletter, Standing Room Only.

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