Fact-Checking All of the Mysteries Surrounding Donald Trump and Penn

Why is everything about Trump’s time at Wharton shrouded in secrecy? We set out to uncover the truth.

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It was, it can be said without fear of exaggeration, a day that will live in infamy. When President Donald Trump emerged from his mysterious one-on-one summit with Russian president Vladimir Putin in Helsinki in July of 2018, the respective visages and body language of the two world leaders could not have been further apart. The Russian president looked smug and sated, like a vampire with a bellyful of peasant blood; Trump looked like a man who’d just received a painful enema. Or, as grizzled, now-banished White House aide-de-camp Steve Bannon describes it in Siege, Michael Wolff’s decadent and depraved follow-up to 2018’s Trumpworld tell-all Fire And Fury, “like a beaten dog.”

Speculation within Trump’s inner circle was that Putin must have something on Trump. The pee tape? Evidence that Don Jr. tried to buy Hillary’s emails? His tax returns? Nah. As Bannon told Wolff, “nobody gives a fuck” about that stuff. But, he wondered, “What if they have his college transcript?”

Ahh, the college transcript. Trump famously graduated from Penn’s Wharton School in 1968 — a fact he reminds audiences of over and over again. (Per Penn’s student newspaper, the Daily Pennsylvanian, he publicly name-dropped Wharton 52 times between June 2015 and January 2018.) But despite all his humblebragging about that Wharton degree, Trump has never allowed his academic performance there to be made public.

“This was a major, major thing with Trump — that people might think he’s stupid,” Michael Wolff told me around the time of Siege’s publication earlier this summer. “The focus of that for Trump is the college transcripts, which are apparently terrible. I’ve spoken to friends of Trump from that time, and this was a guy that was obviously not interested in school and possibly never read a book in his life. For everyone that had known him then and years afterward, the assumption was that he had terrible grades, he was a lackluster student at best.”

In truth, Trump’s Wharton GPA is just one of many mysteries surrounding the 45th president’s relationship with Penn, Philadelphia’s most powerful private institution, which, unwittingly or not, helped unleash Trump on the world. Over the years, there have been rumors about how Trump might have gotten into Penn in the first place, and how much — or how little — he’s donated to the school as an alum. There are tales about Trump’s social life as a Penn undergrad — did he, in fact, have a fling with Candice Bergen? And there are stories — including one particularly juicy one — about the Penn careers of Trump kids Don Jr., Ivanka and Tiffany, all of whom followed in their old man’s red-and-blue footsteps.

Trump’s Wharton GPA is just one of many mysteries surrounding the 45th president’s relationship with Penn. Perhaps the biggest reason for this shroud of mystery is Penn itself; the school’s sphinx-like reticence about its most famous alumnus plays at times like a silent scream.

Perhaps the biggest reason for this shroud of mystery is Penn itself; the school’s sphinx-like reticence about its most famous alumnus plays at times like a silent scream. For instance, Penn has never had Trump deliver a commencement speech or conferred an honorary degree on him. In the wake of his election, Penn tour guides were discouraged from bringing up the T-word and issued simple instructions for handling questions about Trump’s tenure at Penn: Keep it short and sweet — “Yes, he graduated from Wharton in 1968” — and leave it at that. Tell Penn you’re writing an article about Donald Trump’s time there, and you’ll get the academic version of name, rank and serial number: “Donald J. Trump earned a B.S. in real estate, which was awarded on May 20, 1968,” says Ron Ozio, Penn’s director of media relations, declining my request for an interview. Which is peculiar, given that most universities make a lot of marketing hay out of an alumnus in the White House — and Trump is Penn’s first.

So what is the truth about Trump and Penn? What’s the reality behind all those rumors? Because Philadelphians deserve answers, and because I’ve made a career out of lost causes and thankless jobs, I went on a hunt for the facts.

Mystery #1: After two years at Fordham University, did Trump need special treatment to gain admission to Wharton?

The answer begins with James A. Nolan, the Penn admissions officer who interviewed Trump and ushered his application through the vetting process, which he says he did at the behest of Trump’s older brother, Fred Trump Jr. Nolan grew up in Queens and had been friends with Fred since high school in the mid-1950s. During an interview at his apartment on Washington Square, Nolan told me he spent a lot of time in those days at the Trump McMansion in Jamaica Estates, which he described as “very big, with lots of bedrooms” and blackface lawn jockeys lining the approach. Both friends planned to enroll at Penn, but only Nolan got accepted. Ten years later, Nolan was working in Penn’s admissions ­department — he would later become director of undergraduate admissions — when Fred called in a favor.

This was first revealed in Gwenda Blair’s book The Trumps: Three Generations That Built an Empire (Simon & Schuster, 2000). “Whether that was 100 percent why he got in, I don’t know, but clearly it was helpful,” Blair told me. Blair says that at Nolan’s request she kept his identity a secret until earlier this summer, when Nolan granted interviews to the Washington Post and this magazine.

Nolan is adamant: Trump wasn’t accepted to Wharton solely on his say-so. Both the head of transfer student admissions and the vice dean reviewed Trump’s application and Nolan’s interview notes before giving final approval.

Now 80, Nolan says he found “no evidence” of Trump’s alleged “super genius” at the time. Furthermore, he says, Wharton wasn’t nearly as difficult to get into in the mid-’60s as it is today. Back then, according to Nolan, Penn was accepting 40 percent of all applicants, as opposed to its current cutthroat acceptance rate of seven percent. Not surprisingly, Trump remembers it differently. “I got in quickly and easily,” he told the Boston Globe in 2015. “And it’s one of the hardest schools to get into in the country — always has been.”

Nolan says helping Trump is a big regret. “I wish I hadn’t interviewed him,” he says, breaking into the deep belly laugh of a man who knows that at his age, nothing he says can possibly hurt him. “In retrospect, I wish I hadn’t done that.”

Mystery #2: Did one of his Wharton professors repeatedly tell friends and associates that Donald Trump “was the dumbest goddamn student I ever had”?

It’s rare for a professor to disparage the intelligence of a student, but according to attorney Frank DiPrima, who was close friends with professor William T. Kelley for 47 years, the prof made an exception for Donald Trump, at least in private. “He must have told me that 100 times over the course of 30 years,” says DiPrima, who has been practicing law since 1963 and has served as in-house counsel for entities including the Federal Trade Commission and Playboy Enterprises. “I remember the inflection of his voice when he said it: ‘Donald Trump was the dumbest goddamn student I ever had!’” He would say that [Trump] came to Wharton thinking he already knew everything, that he was arrogant and he wasn’t there to learn.” Kelley, who passed away in 2011 at age 94, taught marketing at Wharton for 31 years, retiring in 1982.

As Trump admitted in The Art of the Deal, all he got out of Wharton was bragging rights: “In my opinion, that degree doesn’t prove very much, but a lot of people I do business with take it very seriously, and it’s considered very prestigious. So all things considered, I’m glad I went to Wharton.”

Mystery #3: Was Donald Trump the proverbial Big Man on Campus at Penn?

Despite his braggadocio, Trump appears to have left no substantive mark in the collective memory of his graduating class. Efforts by media outlets — including the Washington Post, the Boston Globe, the Daily Pennsylvanian and this magazine — to locate Penn classmates with vivid memories of Trump’s tenure proved largely fruitless. He was involved in no known extracurriculars, rarely socialized on campus, and didn’t even submit a yearbook photo. One classmate, Louis Calomaris, told the Boston Globe that he remembered Trump standing up in class and declaring, “I’m going to be the king of New York real estate.” prompting eye-rolls from his classmates. “Sit down, you [expletive],” Calomaris remembered thinking.

For an article titled “Many of Trump’s Wharton Classmates Don’t Remember Him,” the DP contacted 269 of his fellow matriculates. Seventy-four responded; 68 said they had “never encountered Trump at Penn.” “Wharton was a pretty small community back then … you knew everyone. Well, except him,” 1968 Wharton graduate Kenneth Kadish told the DP. “It wasn’t that [Trump] was just not prominent, it was like he was nonexistent.” Nolan, the admissions officer, recalls: “I never saw him with another student. Always by himself. Kind of a sad sack.”

I was able to locate one classmate with something nice to say about Trump. “I knew him and I liked him, and most of the people I went to school with didn’t know him and don’t like him,” says Ted Sachs, who sat next to the future president in corporate finance and went on to a prosperous career in the financial sector. After class they would go out for fried oyster sandwiches, a Trump favorite. Not surprisingly, Trump did most of the talking. “He talked about himself mostly,” says Sachs, who voted for Trump in 2016 and plans to do so again in 2020. “He was very focused on himself, like he is today. But in a nice way.”

Mystery #4: Did Trump attempt to “date” Penn student Candice Bergen and get shot down?

Prior to flunking out in 1965, Ms. Bergen was the It Girl at Penn, elected both Homecoming Queen and Miss University. Her proto-screen-siren star power was apparently visible in the night sky from as far away as New York, because one evening, the phone in her dorm rang, and on the other end was one Donald Trump, pre-Wharton. “I was 18,” Bergen told Harry Connick Jr. back in 2017. “He was a nice-looking guy, I mean, he was. And I was in college, and it’s where he was going to be going to college. … It was like a blind date. He called me in the dorm. And I was bored. So he picked me up. He was wearing a burgundy three-piece suit with burgundy patent leather boots, and he was in a burgundy limousine, so it was very color- coordinated.” It was a short date: “I was home by nine.” She expanded on her account a few days later on Watch What Happens Live With Andy Cohen: “He was a good-looking guy. And a douche. I was home very early. … ” She stressed that there was no kiss, “no physical contact whatsoever.” Within a year, Ms. Bergen, who politely declined to participate in this article, was a movie star on track for a storied career and never looked back.

Mystery #5: Did Donald Trump finish first in his class at Wharton, as he bragged to multiple journalists over the years?

This assertion appeared in a fawning New York Times profile of the Trump Organization published in 1973, the same year the Department of Justice sued Donald and his father Fred for housing discrimination for refusing to rent to people of color. Sample paragraph:

Donald, who was graduated first in his class from the Wharton School of Finance of the University of Pennsylvania in 1968, joined his father about five years ago. He has what his father calls “drive.” … “Donald is the smartest person I know,” he remarked admiringly.

The claim was repeated in another doting profile of Trump in the New York Times in 1976. Noting that practically every article ever written about Trump in the wake of the Times profiles parroted the “first in his class” claim, the Times finally corrected the record in yet another eye-roll-inducing profile published in 1984 (“Spending a day with Donald Trump is like driving a Ferrari without the windshield. It’s exhilarating; he gets a few bugs in his teeth”), declaring that the notion that Trump finished first in his class at Wharton was contradicted by the university’s commencement program.

The program for the commencement ceremony lists the names of students who graduated from Wharton with honors — cum laude, magna cum laude, summa cum laude — and Donald Trump isn’t among them. Nor is his name included on the Dean’s List published in 1968 by the Daily Pennsylvanian. Given that colleges and universities are prohibited by law from releasing transcripts to anyone other than the student in question, and that Trump has purportedly forbidden the school to do so, we’ll have to rely on proof by omission that Trump didn’t graduate with any academic distinction whatsoever.

Trump himself finally copped to this in a 1988 New York magazine story written by Julie Baumgold. “Okay, maybe not ‘first,’ as myth has it,” Baumgold wrote, “but he had ‘the highest grades possible.’”

Mystery #6: Did Trump donate $1.4 million to Penn over the years or merely pledge to do so? Did his pledges coincide with the enrollment applications of his children? Why doesn’t his name appear prominently anywhere on Penn’s campus?

Penn pleads the Fifth. “Thank you for your inquiry,” says John H. Zeller, vice president for development and alumni relations. “We have a policy to not disclose or comment on any donors’ history or support.”

However, in the run-up to the 2016 presidential election, the Daily Pennsylvanian’s Luis Ferré-Sadurní did a deep dive into all extant publicly available donor reports between 1968 and 2007 — there were presumably 39 annual-giving reports issued between those years, but he was only able to locate 32 of them. Also unavailable were annual reports from 2008 to 2016. Ferré-Sadurní determined that Trump had pledged at least $1,480,500 between 1968 and 2007. However, the reports only list money pledged, not how much, if any, Trump actually forked over. That information remains a closely guarded secret. Zeller told the DP that Penn “has an exceptionally high rate of fulfillment” for pledged gifts but declined to confirm or deny that Trump followed through on his pledged donations.

“We don’t know, and we may never know,” says Ferré-Sadurní, who now covers the housing beat for the New York Times. “But a lot of the pledged donations seem to be made right around the time each of his kids was going to Penn or trying to get in.”

The only physical evidence on campus of Trump donating anything to Penn is a plaque on the wall of the Class of 1968 Seminar Room — an aggressively unremarkable meeting room with a conference table, whiteboards, and an overhead projector — tucked into the bowels of Van Pelt library. Trump’s name is nearly lost in the crowd of 27 Class of ’68 donors who chipped in back in 2003. Pretty small beer for a billionaire twice over. Allegedly.

Mystery #7: Did Trump strike Don Jr. across the face in his freshman dorm room for attempting to wear a Yankees jersey to a baseball game with him?

That’s the story recounted in a November 3rd, 2016, Facebook post by Don Jr.’s former classmate Scott Melker:

I was hanging out in a freshman dorm with some friends, next door to Donald Jr.’s room. I walked out of the room to find Donald Trump at his son’s door, there to pick him up for a baseball game. There were quite a few students standing around watching, trying to catch a glimpse of the famed real estate magnate. Don Jr. opened the door, wearing a Yankee jersey. Without saying a word, his father slapped him across the face, knocking him to the floor in front of all of his classmates. He simply said, “Put on a suit and meet me outside,” and closed the door.

Melker’s post describes Donald Jr. as “a drunk in college,” a young man who “despised his father, and hated the attention that his last name afforded him.” It claims Don Jr.’s nickname was “Diaper Don” because he tended to “fall asleep drunk in other people’s beds and urinate.” (Melker’s account was denied by the Trumps.)

Melker, who resides in Miami Beach, where he’s a DJ/cryptocurrency trader, declined to comment for this story but acknowledges writing the post, which remains on his Facebook. “I was approached by Anderson Cooper, Bill Maher etc. around election time [and I declined],” he told me via Twitter message. “My personal FB post went viral when a Gawker writer screenshot it as news. I have nothing to add to it, and never intended for it to happen.” A request to connect me with others who were there that day was denied: “Been down that road before. Nobody is going to talk unfortunately.”

Mystery #8: What is known about Ivanka’s Penn stint beyond the fact that after two years at Georgetown, she transferred to Wharton, where, unlike her father, she graduated cum laude, in 2004?

Like her dad, Ivanka has been the subject of a DP story wherein nobody from her graduating class seems to have gotten to know her. Back in April of 2017, the DP reached out to 600 graduates from the class of 2004 and came up with … not that much. Most described her as “polished, hardworking and nice.” Roland Oliver told the DP: “She came to the school, and did her part, and left.”

What else? She lived in the Left Bank apartments, near 32nd and Walnut streets. Another 2004 Wharton graduate, Roman Galas, told the DP that he “saw her at Smokes’ once, sitting across from me at the bar, sipping her drink peacefully and gracefully.” She was occasionally spotted at White Dog Cafe and La Terrasse as well as in Rittenhouse Square.

A rumor made the rounds on campus that a breakup drove her from Georgetown to Penn midstream, but she denied it in a 2004 Philadelphia profile in which she described her life at Penn as “hermetic” and was characterized as more likely to binge-watch Law & Order than to trip the light fandango on the beer-sticky dance floors of the frat-party circuit. That job would be left to her half-sister, Tiffany.

Mystery #9: What do we know about Tiffany’s Penn years?

In 2012, Tiffany arrived at Penn on the heels of a brief but doomed bid at autotuned pop stardom (google “Tiffany Trump” and “Like A Bird” if you’re feeling sinister), as her father was waging his notoriously racist birther fake-news campaign. She double-majored in sociology and urban studies. According to unnamed sources interviewed by Vanity Fair, she was rebuffed in efforts to join Tabard, “a secret society that offers its members an exclusive social network,” out of fear that a scion of the toxic Trump family tree might drive away the swells.

But Kappa Alpha Theta was apparently happy to have her. Her alleged billionaire father reportedly kept her on a short leash, doling out a miserly $500-a-month allowance. Still, she managed to make the rounds of the elite-rich-kid party scene at Penn. One party boy who insisted on anonymity summed up the scene to me thusly: “You’re looking at Tiff Trump passing a joint to me, and I’m passing it to a kid who grabs it while wearing a $38,000 rose gold Patek Philippe watch and then, you know, accidentally drops the joint into his cheap red cup filled with Grey Goose. And that was a normal Tuesday night for them.”

Said party boy also noted that Joe Biden’s granddaughter Naomi, who attended Penn concurrently, was a scene fixture as well. “Tiff was even nicer than Naomi, which is kind of ironic given the parents,” he says. “Naomi thought she was hot shit. Tiff was really, really sweet. You never would’ve guessed from where she came.”

Mystery #10: Did Michael Cohen threaten to sue Penn back to the Stone Age if it released Trump’s grades?

Almost absolutely. In his televised testimony before the House Oversight & Reform Committee in February, Michael Cohen, who served as Trump’s personal attorney and fixer from 2006 to 2018, said the following about his former boss:

When I say con man, I’m talking about a man who declares himself brilliant but directed me to threaten his high school, his colleges, and the College Board to never release his grades or SAT scores. As I mentioned, I’m giving the Committee today copies of a letter I sent at Mr. Trump’s direction threatening these schools with civil and criminal actions if Mr. Trump’s grades or SAT scores were ever disclosed without his permission. These are Exhibit 6. The irony wasn’t lost on me at the time that Mr. Trump in 2011 had strongly criticized President Obama for not releasing his grades. As you can see in Exhibit 7, Mr. Trump declared “Let him show his records” after calling President Obama “a terrible student.”

For reasons that are unclear, the House Oversight Committee only made public the letter sent to the president of Fordham University. But given that Cohen referred in his testimony to “a letter” — ­singular, not plural — that he says he sent to all the schools Trump attended, along with the College Board, which administers the SAT, and the fact that in the third paragraph of the letter sent to Fordham, Cohen refers to “all of the College Board employees” (presumably having neglected to customize the missive before sending), we can safely assume that all of Trump’s academic institutions received the same letter. Amusingly, Cohen’s letter concludes four paragraphs of dire threats, including liability “to the fullest extent of the law including damages and criminality” for anyone who dares to reveal Trump’s grades, with the following:

P.S. Mr. Trump truly enjoyed his two years at Fordham and has great respect for the University.

•

There is another day that will live in infamy: On the morning of May 20th, 1968, a then-22-year-old Donald Trump — robed, slender, handsome, with a slicked-back coif of thick golden-brown locks — queued up with his classmates at the Civic Center for the University of Pennsylvania’s 212th Commencement for the Conferring of Degrees.

“The weather was beautiful, my parents were there, and it was a nice day,” Trump told the Boston Globe in 2015. “You graduate from a great school. I did well. That was the beginning, right? The real beginning was that day. … You know, I wasn’t Trump then, you understand? I was Trump but I wasn’t Trump.”

And so began his toxic glide path to the White House. First, he’d take Manhattan — armed with his Wharton degree, bottomless chutzpah, and his father’s deep pockets — and then, in due time, the world.

Published as “Trump University” in the September 2019 issue of Philadelphia magazine.