The revelations about Donald Trump’s finances obtained by the New York Times have produced two distinct reactions. One is that he’s a terrible, failing businessman, and the other is that he’s a tax cheat. Seen in one light, the two interpretations are in tension. “The reporters can’t seem to decide if Mr. Trump is a shark exploiting the White House for personal gain or a sap who is bleeding cash while in office,” argues a Wall Street Journal editorial. “Brilliant or bumpkin? Make up your mind.”
But there is a different way to think about Trump’s career, which is that he is a brilliant con man, who has, throughout his career in business and politics alike, honed the singular skill of identifying marks and exploiting them with spectacular lies.
The new Times scoops merely flesh out the story that emerged in its revelatory 2018 report, which we now know came about with the cooperation of his niece, Mary Trump. That story reconstructs the creation of Trump’s image from the beginning. It is one of the most successful cons — and almost surely the most historically significant — in American history. For reasons I’ve never understood, its implications have not been absorbed.
In the mid-1970s, the Trump family set out to sell the world on a character of its own creation: Donald J. Trump, dashing and brilliant business genius. The story’s protagonist was the child of multimillionaire developer Fred Trump, a son who had accomplished almost nothing in business, and whose taxable income was under $25,000. The trick was quite simple: young Donald would squire reporters around his father’s business empire and claim he had built it himself.
In 1976, the Times produced a profile ushering the young star onto the stage. “He rides around town in a chauffeured silver Cadillac with his initials, DJT, on the plates,” gushed a profile. “He dates slinky fashion models, belongs to the most elegant clubs and, at only 30 years of age, estimates that he is worth ‘more than $200 million.’”
In reality, Donald Trump was in the money-inheriting business. In 2018, the Times revealed to its readers that this entire profile was a “spectacular con.” Forty-two years earlier, Trump had carefully taken the Times reporter through a Potemkin village of his father’s wealth:
In the chauffeured Cadillac, Donald Trump took the Times reporter on a tour of what he called his “jobs.” He told her about the Manhattan hotel he planned to convert into a Grand Hyatt (his father guaranteed the construction loan), and the Hudson River railroad yards he planned to develop (the rights were purchased by his father’s company). He showed her “our philanthropic endeavor,” the high-rise for the elderly in East Orange (bankrolled by his father); an apartment complex on Staten Island (owned by his father); their “flagship,” Trump Village, in Brooklyn (owned by his father); and finally, Beach Haven Apartments (owned by his father). Even the Cadillac was leased by his father.
The strategy was to convert Fred Trump’s fortune into publicity, which Donald could then monetize. The lies used to construct Trump’s image were massive. In 1984, Donald concocted a series of lies to persuade Forbes he was worth $900 million. Its reporter, Jonathan Greenberg, diligently unraveled every exaggeration and reduced the published sum to $100 million, only to discover decades later that the actual amount was a mere $5 million. The power of the lie was its scale. Greenberg could imagine Trump was exaggerating his wealth tenfold, but the idea he was exaggerating it 180-fold beggared imagination.
Trump’s career as a real-estate magnate failed, and he fell into bankruptcy as his father’s inheritance eventually ran dry. But as the second installment of the Times reports on his taxes shows, he revived his career by monetizing the publicity he had so carefully seeded. He developed a brand as a television star portraying a business genius. He lent his name to a dizzying array of products, from detergent to double-stuff Oreos. The image had become the business itself.
While Donald was never able to equal his father’s prowess as a builder and landlord, his talent as a confidence man far surpassed it. Trump leveraged his fame into a series of scams: “Trump University” (a fake real-estate-training seminar designed to bleed its victims dry); the “Trump Network” (selling its targets urine-testing systems, which would be used to direct them to buy overpriced vitamins); using the “Trump Foundation” as a racket to funnel supposedly charitable funds into his pocket, and so on.
At times, these scams have edged close to outright criminality. At other times, they have crossed over the line. Trump is currently under investigation for tax fraud. And, as law professor and tax expert Daniel Shaviro argues, the information in Trump’s recent returns strongly suggests more outright fraud — deductions like hairstyling and a country estate seem to violate black-letter rules governing tax deductions.
The arc of Trump’s career has been to exploit a series of victims, pocket his winnings, and use them to find new ones. He lied to a series of reporters, built and sold an image as a brilliant deal-maker, scammed his fans out of their money, and lied to the government about his income.
Trump’s political career is a natural step in the progression, one he had been contemplating for decades. The Republican Party was a perfect vehicle for a character like Trump. The mainstream media had grown steadily more resistant to his lies, but the conservative media ecosystem was fertile terrain, a propaganda machine so attuned to his needs that he didn’t even need to try to fool them. Whatever lies other Republicans would spout about Barack Obama or climate change or the wonder-working powers of tax cuts, Trump would exceed them. From Fox News to Hugh Hewitt to the anti-anti-Trumpers, his acolytes simply did not care whether anything he said was true.
Trump (or, more precisely, his ghostwriter) once claimed, “Deals are my art form. Other people paint beautifully or write poetry. I like making deals, preferably big deals.” The last four years have made it apparent Trump is bad at striking deals, despite being free of the burden of having principles. Deals are not his art form.
Lying is. Lying is how he rebuilt his fortune after he ran through his inheritance, and how he kept his head above water financially. Lying may or may not be enough to get him a second term, or even to keep him out of prison. But if you are betting that Trump’s lies will stop working, you are betting against the evidence of his entire adult life.