Seth Gitell is a former journalist at the New York Sun and gitell.com, where an early version of this article first appeared.

About eight years ago, on a weekend that saw Lehman Brothers spiraling towards bankruptcy, I attended Trump University—or, as it was known then, Trump Wealth Institute—at a hotel in a Boston suburb. It was the end of an era, in more ways than one: the financial system was in freefall, and I was writing a weekly politics column for the New York Sun, which would cease print publication within weeks. A couple years later, as complaints poured in from people who’d paid thousands of dollars to Trump Institute for real-estate “mentorship” that never materialized, Trump’s enterprise would change its name to the Trump Entrepreneur Initiative. A couple years after that, New York’s attorney general filed a civil suit accusing Trump of fraud and seeking $40 million in restitution. As recently as this Super Tuesday, a judge ruled that the suit can move forward, and Trump has vowed to fight it. Trump U, of course, has become a rancid refrain in the Republican presidential primary; it’s become a regular feature in Marco Rubio’s stump speech, and at last week’s CPAC, Ted Cruz’s team was distributing “Trump University” t-shirts and fake diplomas.

At the time, it seemed impossible that a weekend meetup in a local hotel conference room would hold any political significance whatsoever. I’d read Trump’s The Art of the Deal in college, so when I spotted an internet ad for the Trump “way to wealth” seminar, I thought it might be an interesting vantage point from which to capture the feelings of regular people at a terrible time. I was also intrigued by the idea of what strategies a figure as rich and famous as Trump could bring to the public, in the midst of a crisis to which few had any solutions.


The invitation called for me to arrive at the seminar 30 minutes prior to its 9 a.m. starting time. When I got to the Westin Waltham Hotel, about 20 minutes west of Boston, a number of people, most of them elderly, were already sitting in easy chairs outside of the ballroom that would house the program. I sat down while an older, semi-coherent man peppered me with questions about the size of my Dunkin’ Donuts coffee. After a while I left the foyer and came back and sat next to two men a few years younger than me, who were dressed in chinos and button down shirts. I asked them about their presence at the event. They weren’t in the mood to talk. Each muttered something about trying to learn about the real estate business, then cut the discussion short.

Although the seminar had been billed as a kind of on-ramp to Trump-style success, it was little more than a Trump-branded infomercial for real-estate-investment advice.

A diverse group of people were filling out registration cards outside the ballroom. There was a pair of young Central American women dressed as if they were going to church, and several other groups of non-English speaking people, as well as a number of women in their 60s who reminded me of my mother. Inside, I saw a few African American faces, some Asians, Latinos and whites. The only common thread, perhaps, was a desire to financially better themselves during a downturn. And it was that desire which the instructor, a self-described member of Donald Trump’s financial empire, had come to ignite.

In an almost two-hour routine, he played on the insecurities and fears, hopes and dreams, of his audience. Before the seminar got started, Trump appeared via a brief video, like a capitalist version of Chairman Mao in a Communist China reeducation camp. “You’re going to learn the Trump way to get cash back when you buy a property,” Trump bellowed on the hotel screen. “You’re going to learn the Trump way to build your real estate empire, property by property.”

Trump may have given his name and image to the event, but he was not the star of the show. That honor fell to the instructor, a slim man in his 50s who dramatically entered the ballroom, just after the Trump video ended, wearing a black suit and red tie. “You have to learn to take care of yourselves,” he told the attendees. “There’s no more job security in this country. … It’s financial security that counts.” Within a few moments, he exhorted the entire group to say aloud, “I have to stop working this hard.” Later, he prompted the crowd to repeat these words: “I need at least $3 million.”

Although the seminar had been billed as a kind of on-ramp to Trump-style success, it was little more than a Trump-branded infomercial for real-estate-investment advice. (Today, the instructor continues to dispense advice, via his own site, on investing in foreclosed properties. A LinkedIn post last fall, advertising one of his webinars, was titled, “Donald Trump Says I Am Great At Real Estate.” He is not involved in the Trump University lawsuit.) To the instructor’s credit, he announced at the beginning of the seminar what the game was about. He was there, he said, to sell a $4,000 tuition program at the Trump Institute, which, he added, was tax deductible—and which he was authorized to offer for the low, low price of $2,000.

Soon after he began to speak, the two younger men whom I’d spoken to earlier got up to leave. When I asked them why, one of them said sternly, “Thanks. We’re all set.”

Meanwhile, the instructor launched into a preamble relevant to the financial news we were witnessing. “This is a meltdown,” he said. “It’s historic, and this is just the tip of the iceberg. We have not seen the bottom yet.” He was just warming up. Soon he spoke with anger. “They took advantage of good hardworking Americans,” he said. “And they’re going to pay for it.”

I’m not a member of any of the Evangelical churches. But that’s what the instructor’s speaking style reminded me of. He was gripping, compelling, moving. At times he spoke sternly about the financial plight that many Americans had found themselves in. “You better watch out where you bank,” he hissed knowingly. At other points he was folksy, telling a story about how he, on a weekend clad in jeans and rugged jacket, approached a property owner to tell the man of some $500,000 in special loans and grants he was eligible for, only to find him arrogant and all-knowing.

I found myself fascinated by this character: He seemed ripe for a screenplay. He reminded me of Tom Cruise in Magnolia—or even Alec Baldwin in Glengarry Glen Ross. Like Trump himself, he appeared equal parts salesman, adviser, therapist, preacher and talk show host. He spoke quickly, but slowed at times. And his schtick was calibrated to play against elites: He said that he was not a college graduate—in contrast to his brother, whom he said had always doubted everything but couldn’t find a way to make money. His eyes twinkled and he laughed derisively. At one point, he described how he could use his computer—and Trump Institute tools—to find out almost everything about a given property. Then he paused and said, “But nobody can find that Bin Laden guy. Ha!”

The people I saw at the Trump seminar were looking for something that went beyond money. They were looking for an opportunity for a better life.

I made it through about an hour and forty-five minutes of the talk—which is saying something for someone who has no interest in real estate: I certainly didn’t fork over any money for the program. By that time in the 2008 campaign, I’d seen Barack Obama speak in person more than a dozen times, and there were moments in even his best speeches where I’ve drifted off. The instructor held the room rapt for the better part of a couple hours. He also made frequent use of Trump’s name and reputation. “One thing about us: Everything we touch turns to gold,” he boasted. “We make a lot of money in real estate.” First-person plural: We, us. My favorite was when he mentioned the Trump casino: It was as if he’d talked himself into an ownership stake. “Yeah. We own a casino. We don’t gamble in it,” he said, to hoots of laughter.

Count me as a skeptic when it comes to these money-making schemes: But hey, maybe I’m too much like his brother. One of his suggestions involved dividing a one-unit property into a property that could contain a number of lots, which required getting pre-approval from the county or municipal authority to change the zoning. In the instructor’s example, the zoning official was more than happy to make the change. His insider’s trick? He advised attendees to go in and ask the zoning authority for his or her “expert advice”—“expert advice” being a key phrase that would stroke the ego of the underappreciated zoning official. When he concluded the story by making a considerable profit, the older, semi-coherent man I had seen before the program exclaimed, “That’s a good idea!”

It’s entirely possible this idea might work somewhere in America; it certainly would not have worked in Waltham, Massachusetts. I don’t know of anywhere within Boston’s Route 128 belt where an investor could single-handedly sweet-talk his or her way into zoning-pre-approval—not without investing all sorts of money in lawyers and community relations firms. In this region—a complex ecosystem supporting many species of neighborhood activists, environmental and community groups, and various political officials and bureaucrats—such hasty changes are unheard of.

Which was really too bad. The people I saw at the Trump seminar were looking for something that went beyond money. They were looking for an opportunity for a better life. For hope during a difficult time. For all of the things, one imagines, that disenfranchised voters across the country are now drawn to in the tough-talking candidacy of Donald J. Trump. At the time, I remember thinking that maybe the specific advice wasn’t what was important. Maybe the instructor’s insistent enthusiasm would be enough of a confidence boost to the would-be entrepreneurs in the room to take control of their lives. Who knows? People presumably went into seminars like that with their eyes open, right?

Now, with Trump University ensnared in litigation, it’s clear that not every student of Trump University was as skeptical as I was. And yet, as Candidate Trump runs the table through the early part of the electoral calendar, I’m reminded of the immortal words of George W. Bush: “Fool me once, shame on you; fool me—uh … you can’t get fooled again.”