Chapter 3: The Mask of Success

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Chapter 3: The Mask of Success

We are what we pretend to be, so we must be careful about what
we pretend to be. —Kurt Vonnegut, Mother Night

What if the most powerful man in the world built his empire not on success, but on pretending he had it?

I remember September 11, 2023. It wasn’t just the anniversary of 9/11; there was also a grim (but, frankly, satisfying) show going on in Manhattan that had the nation (and Louise, me, and the listeners to my radio program) glued to their TV screens.

In a crowded federal courthouse in New York City, former president Donald Trump sat stone-faced as his former accountant testified under oath about the Trump Organization’s financial statements. For decades, Allen Weisselberg explained, the company routinely inflated Trump’s assets—sometimes by billions of dollars—to secure loans, insurance, and business opportunities. Properties were suddenly worth double on paper. Apartment buildings grew fictional floors. Golf courses sprouted imaginary mansions ready for sale.

It was, the accountant admitted, a systematic campaign of deception designed to make Trump appear far wealthier and more successful than he actually was.1

Just days earlier, Trump had launched his campaign to recapture the presidency in 2024, once again promising voters that only he—the self-proclaimed business genius—could fix America’s economy. “I’m the only president in modern history who left office with a smaller national debt than when I came into office,” he declared at a rally, a claim so brazenly false that even Fox News felt compelled to correct it. During Trump’s presidency, the national debt had actually increased by $7.8 trillion, nearly 40 percent and more than any other president in history.2

These courthouse revelations surprised no one who’d been paying attention. They were merely the latest documented evidence of what had been apparent throughout Trump’s career: his business empire was never built on success. It was built on the appearance of success, a golden façade carefully constructed through media manipulation, aggressive self-­promotion, and outright fraud.

It’s a façade that didn’t just make Trump wealthy and famous, it made him president. And it’s a façade that continues to threaten American democracy itself as he has again returned to power.

Born on Third Base, Claimed He Hit a Home Run

In American mythology, few archetypes are more powerful than the self-made man. I was so entranced with the idea that I started my first business—fixing TVs in my neighborhood in Lansing—when I was thirteen years old and had just gotten my amateur radio license . . . and went on to being a serial entrepreneur through my entire life. (I haven’t had a “job” since I was a DJ and later news reporter for WITL AM-FM when I was sixteen and living on my own.)

From Benjamin Franklin to Andrew Carnegie to Steve Jobs, we celebrate those who, through determination and ingenuity, rise from modest beginnings to extraordinary success. It’s the story that makes America itself possible, that here, unlike the aristocracies of the Old World, merit matters more than bloodline.

Like me and my wannabe entrepreneur father, Donald Trump understood the power of this narrative, although he played it out on a much larger (and less ethical) stage.

Throughout his career, Trump positioned himself as a self-made billionaire, a bootstrapper who, with a “small loan of a million dollars” from his father, built a global empire through his own brilliance and hustle. The origin story he told the world—and himself—was one of overcoming obstacles, conquering New York’s brutal real estate market through grit, vision, and unparalleled deal-making skill.

It was, like so much about Trump, a performance masking a very different reality.

According to a New York Times Pulitzer Prize–winning investigation in 2018, Trump received at least $413 million in today’s dollars from his father, Fred, not the $1 million “small loan” he repeatedly claimed. The investigation, based on more than one hundred thousand pages of financial documents, revealed that “the president has often sold himself as a self-made billionaire, but a Times investigation found that he received at least $413 million from his father’s real estate empire, much of it through tax dodges in the 1990s.”3

The mechanisms of this wealth transfer were elaborate and, in many cases, potentially fraudulent. The Times documented how Fred Trump created numerous shell companies to disguise gifts to his children. In one particularly brazen scheme, a company called “All County Building Supply & Maintenance” was established as a purchasing agent for Fred Trump’s properties. In reality, it was a vehicle for transferring wealth to Donald and his siblings while simultaneously defrauding tenants in rent-controlled buildings.4

As David Cay Johnston, who won a Pulitzer Prize for his reporting on tax loopholes for the wealthy, observed: “Donald Trump is not a self-made man. He is a self-made myth.”5

Trump didn’t earn his fortune. He inherited it. And then lied about it.

The Emperor of Bankruptcy

When I was seventeen, I started a small electronics business in East Lansing across the street from MSU, growing it to five employees (including Louise, who did the bookkeeping). It was called The Electronics Joint and our logo was a pot cigarette (a “joint”) with rabbit ears antenna on top. But I expanded the business too fast, and within three years had managed to drive it into bankruptcy.

It was one of the best lessons of my life, and while a few other businesses I started didn’t take off, I never repeated that mistake of borrowing money to grow a business faster than the market itself could provide. Donald Trump, by contrast, never learned the same lesson, even though he had multiple chances.

Between 1991 and 2009, Trump filed for corporate bankruptcy six times—an unprecedented record for a major American business figure. His failures included the Trump Taj Mahal (1991), Trump Plaza Hotel and Casino (1992), Trump Castle Casino Resort (1992), the Plaza Hotel in New York (1992), Trump Hotels & Casino Resorts (2004), and Trump Entertainment Resorts (2009).6

The pattern was consistent. Trump would secure financing for grandiose projects, often by personally guaranteeing portions of the loans. He would launch with enormous fanfare and self-celebration. Then reality—in the form of mismanagement, market downturns, or simple mathematical impossibility—­would set in. The businesses would collapse, investors would lose billions, but Trump himself would emerge remarkably unscathed (unlike my business crash in 1970; I eventually paid back all my creditors), protected by corporate structures that insulated his personal wealth from his business failures.

But Trump’s failures weren’t victimless. The real casualties were the small businesses caught in his wake. J. Michael Diehl, who sold Trump $100,000 worth of pianos for the Taj Mahal, was eventually forced to accept seventy cents on the dollar, a $30,000 loss that threatened his small business. “I feel like I’ve been taken by the best,” Diehl later told reporters. “He knew what he was doing, and he did it intentionally.”7

USA Today identified at least sixty lawsuits by ordinary Americans—carpenters, painters, glass companies, even a toilet manufacturer—who claimed Trump had refused to pay them for their work.8 For these contractors, it wasn’t just business. It was economic violence.

I’ve spent my entire life in an entrepreneurial space, and even cofounded a group for entrepreneurs in Atlanta that’s still around (the “Terminus Group”); we’d get together once a month in a private room in a nice restaurant and swap stories, share successes and failures, and mentor and support each other. Never in all those fifty-plus years in business (including my being profiled on the front page of the Wall Street Journal and in an editorial and book by the publisher/editor of Inc. Magazine) have I known a single businessperson who delighted in screwing vendors, contractors, or employees.

Frankly, I suspect most businesspeople would recoil from such a person, viewing him as a predator to be avoided. Which, it turns out, perfectly describes Donald Trump.

Trump Steaks, Trump Vodka, Trump University

As Trump’s ability to secure financing for major construction projects diminished following his multiple bankruptcies, he pivoted to a new business model: selling not buildings, but his name. By the 2000s, Trump had essentially transformed from a builder to a brand.

The results were a parade of failures that would have humbled a less narcissistic man:

· Trump Steaks were sold through Sharper Image, a store better known for massage chairs and electronic gadgets than quality meat. The venture lasted just two months in 2007. As Sharper Image CEO Jerry Levin later admitted: “We literally sold almost no steaks. If we sold $50,000 of steaks grand total, I’d be surprised.”9

· Trump Vodka, launched in 2006 with the ridiculous tagline “Success Distilled,” ceased production in 2011 after failing to gain traction in a competitive spirits market. Trump, a teetotaler, nonetheless proclaimed it would outsell Grey Goose. It didn’t come close.

· Trump University represented perhaps the most egregious of Trump’s failed ventures—not merely a business failure but an alleged criminal enterprise. Far from a university, it was an unaccredited series of seminars promising to teach Trump’s real estate “secrets” to ordinary Americans. Students, many of them elderly or financially vulnerable, paid up to $35,000 for courses that former employees would later describe as a “fraudulent scheme” designed to “separate people from their money.”10 This led to multiple lawsuits alleging fraud, culminating in a $25 million settlement in 2018 that provided refunds to over six thousand former students.11

Each failure was brushed aside or reframed as a success, because Trump’s business model wasn’t about performance, it was about projection. The appearance of success mattered more than actual success. The gold-plated name was more valuable than the substandard product behind it. The press conference announcing the venture generated more value than the venture itself.

This was not success. It was the simulation of success, a simulation so convincing that even Trump himself seemed unable to distinguish between his mythology and reality.

The Invention of a Titan

In 1987, The Art of the Deal was published, a book that would cement Trump’s image as a business genius in popular culture. The book was a runaway bestseller, spending forty-eight weeks on the New York Times bestseller list. Even Louise and I (then running an advertising agency in Atlanta with dozens of Fortune 500 companies as clients) read it at the time, and we both thought it was pretty good; everybody we knew in business was discussing it.

There was just one problem: Trump didn’t write it. And according to the man who did, much of it wasn’t true.

Tony Schwartz, the ghostwriter hired to craft Trump’s business “memoir,” spent eighteen months with Trump, attempting to extract something approaching a coherent philosophy from Trump’s rambling self-­aggrandizement. What he discovered was a man with “no attention span,” who was fundamentally “insecure” and obsessed with public perception.

In a remarkable 2016 interview with the New Yorker, Schwartz expressed profound regret for his role in creating the Trump mythology: “I put lipstick on a pig. I feel a deep sense of remorse that I contributed to presenting Trump in a way that brought him wider attention and made him more appealing than he is.”12

Schwartz revealed that the book’s depiction of Trump as a brilliant dealmaker was largely fictional. Trump’s supposed business philosophy—­“truthful hyperbole” being perhaps the most famous concept—was crafted by Schwartz to put a positive spin on what was, in reality, compulsive lying. “ ‘Truthful hyperbole’ was my euphemism for a lie,” Schwartz explained.13

Despite its questionable veracity, The Art of the Deal transformed Trump’s public image. He was everywhere: Oprah, Lifestyles of the Rich and Famous, tabloid covers. The media, desperate for the spectacle Trump reliably provided, largely played along. Few journalists investigated whether Trump’s claims about his wealth, his deals, or his business acumen were actually true.

By the early 2000s, Trump had pulled off a remarkable feat: his actual business record was one of repeated, spectacular failure, but his public image was that of the ultimate winner—the living embodiment of wealth, success, and the American dream.

The Apprentice: Image Becomes Identity

If The Art of the Deal laid the groundwork for Trump’s business mythology, it was his next venture into media that would seal it permanently in the American consciousness: The Apprentice.

Premiering on NBC in January 2004, The Apprentice was the brainchild of producer Mark Burnett, who saw in Trump the perfect central figure for a reality show about business competition. The show was an immediate hit, drawing as many as twenty-eight million viewers for its first season finale. I watched a few episodes and found it formulaic and hokey, but Louise—like most of America—was entranced.

In her defense, she redeemed herself when we attended the 2011 White House Correspondent’s Dinner where President Obama humorously peeled the bark off Trump. At the predinner party put on by the Washington Post, we were standing near the door to the ballroom when Trump, an attractive woman who may have been Melania (we didn’t recognize her at the time), and his two bodyguards walked in.

Louise was standing about four feet from Donald and stared at his forehead; he seemed to think he was being admired, as he gave her a half-smile. She then turned to me and, in a loud voice, said, “Bad plugs!” Trump turned red, spun around, and left the room as the people around us chuckled. It really wasn’t his night (although I’ve always thought it may have been his humiliation at the hands of Obama that night which spurred him to run for president).

But like The Art of the Deal before it, The Apprentice was a work of fiction. The boardroom where Trump rendered his famous verdicts wasn’t his actual office but a set constructed for the show. The helicopter and limousine were props. The “jobs” offered to winners were often ceremonial positions created for the show rather than actual executive roles.14

Most significantly, the show portrayed Trump as the head of a thriving, expanding business empire at precisely the time when his actual business was in dire straits. By 2004, Trump had already declared corporate bankruptcy three times. His casino company, Trump Hotels & Casino Resorts, would declare bankruptcy for a fourth time that very year, with Trump resigning as CEO.15

What The Apprentice accomplished was remarkable: it transformed Trump from a tabloid figure associated with gaudy excess and business failure into an authoritative symbol of American business acumen. For the millions of Americans who watched the show, Trump wasn’t the guy who stiffed contractors and bankrupted casinos. He was the billionaire boss who fired incompetence with flair.

It wasn’t just that viewers believed the fictional portrayal of Trump. The fiction became, for all practical purposes, the reality. As Ivanka Trump told a documentary filmmaker in 2010: “Every article from then on out referred to him as ‘billionaire Donald Trump.’ Everything was billion, billion, billion. And I think that that did a tremendous thing for his brand and for his properties.”16

Losing More Than Any American

If the mask of success Trump constructed through media manipulation was impressive, the reality it concealed was equally astonishing, but for very different reasons.

In May 2019, the New York Times published another bombshell investigation into Trump’s finances. After obtaining printouts from Trump’s official Internal Revenue Service tax transcripts from 1985 to 1994, journalists discovered a financial reality that completely contradicted Trump’s carefully crafted public image.

The headline was stunning in its simplicity: “Decade in the Red: Trump Tax Figures Show over $1 Billion in Business Losses.” The investigation revealed that “year after year, Mr. Trump appears to have lost more money than nearly any other individual American taxpayer.”17

The numbers were staggering:

· 1985: Trump reported losses of $46.1 million from his core businesses.

· 1990 and 1991: Trump’s losses exceeded $250 million each year.

· Total over ten years: $1.17 billion in losses.

These weren’t just business setbacks. They represented a level of financial mismanagement so profound that Trump was losing more money than almost any other American taxpayer during this period. And yet, throughout these disastrous years, Trump was appearing on television, in magazines, and in newspapers as the very personification of business success. Behind the gold-plated façade, the reality was a businessman whose ventures regularly failed, who was kept afloat by his father’s money, by banks too invested to let him fail, and eventually, by the licensing of his name to properties and products he neither built nor created.

The Brand That Became a Weapon

By 2015, when Trump descended the escalator in Trump Tower to announce his candidacy for president, he had transformed himself into a brand that millions trusted. Not for his policy knowledge. Not for his moral compass. But because he looked like a winner, and in an America increasingly disenchanted with political elites, looking like a winner was enough.

When mainstream journalists attempted to fact-check Trump’s claims about his business record, his supporters dismissed these reports as “fake news” or attacks from a biased media. The decades-long investment in creating the Trump mythology had paid off; no amount of factual reporting could penetrate the image now firmly established in the public consciousness.

As linguist George Lakoff explained: “Trump uses your brain against you. He keeps repeating the same thing over and over, and every time he repeats it, it gets strengthened in your brain.”18 By the time Trump ran for president, the neural pathways linking his name to concepts like “success,” “wealth,” and “winning” had been so deeply established in millions of American minds that contrary evidence simply couldn’t compete.

The Party That Knew and Followed Anyway

What’s perhaps most revealing about Trump’s rise to the presidency is that Republican insiders weren’t fooled by his schtick. Unlike many ordinary voters who knew Trump only through The Apprentice and his carefully cultivated media image, GOP operatives and donors had seen the bankruptcies, the failed ventures, the lawsuits, and the erratic behavior right in front of them in real time.

“How do you abandon deeply held beliefs about character, personal responsibility, foreign policy, and the national debt in a matter of months?” asked Stuart Stevens, a veteran Republican strategist who had worked on multiple presidential campaigns. “You don’t. The obvious answer is those beliefs weren’t deeply held.”19

Republican senators like Lindsey Graham called Trump a “kook,” “crazy,” and “unfit for office” during the 2016 primaries. Ted Cruz called him a “pathological liar.” Marco Rubio mocked the size of his hands and questioned his business acumen.20

And yet, when it became clear that Trump had captured the Republican base through his performative aggression and racist dog whistles, the party’s resistance collapsed with stunning speed. Once-fierce critics became sycophantic supporters. Principles that had defined conservatism for generations—free trade, fiscal responsibility, personal character, respect for the law, strong alliances—were abandoned overnight.

Why? Because Trump excited the base. He drew attention. He could dominate a news cycle without spending a dime. And, most importantly, he could win. For a party increasingly focused on power over principle, that was enough.

Mitch McConnell got judges. Paul Ryan got tax cuts. Evangelical leaders got Supreme Court justices who would overturn Roe v. Wade.

The bargain these Republican leaders made was cynical but straightforward: they would tolerate Trump’s corruption, his cruelty, his attacks on the norms and standards that had been respected by presidents since George Washington, and his Russian entanglements in exchange for policy wins they couldn’t achieve through democratic means. They pretended to believe the mask was real, knowing full well it wasn’t, because the mask was useful to them and their donors.

It was Roy Cohn’s final lesson—utility above truth in all cases—applied to governance itself.

They didn’t get a president who embodied conservative principles or Christian values. They got a con man in chief. And they handed him the keys to our republic.

Why It Matters

Donald Trump didn’t rise to power in spite of his failures; he rose because of how well he disguised them. He didn’t build an empire. He built a mask. And when that mask stepped into politics, neither our media nor many of our voters asked what was behind it. They asked, instead, the horse-race question of whether or not it could win.

This is how democracies are gutted from within—not just through violence, but through illusion. Through celebrity. Through spectacle. Through the elevation of brand over truth. When perception matters more than reality, when performance trumps competence, when the simulation of strength is more compelling than actual leadership, the conditions are ripe for democratic collapse.

Trump’s presidency would bring these assaults on decency to their logical conclusion. The same man who had pretended his way to business fame would now pretend his way through governance. The same tactics that allowed him to survive business failures would get him through political crises. The same indifference to truth that characterized his business career would now shape America’s relationship with reality itself.

The mask of success that Trump had spent decades constructing would become the face of America to the world. And behind it, just as in his businesses, lay impending disaster—a pandemic response bungled, alliances fractured, democratic norms shattered, and ultimately, an insurrection incited.

Trump’s mask is still on. But the damage it hides is all around us.