Oedipus Trump: Understanding Donald’s Dark Shadow

Unearthed 1980s Interviews Reveal How Trump’s Father and Roy Cohn Shaped the Insecure Man Behind the Billionaire’s Bluster

(This article also appears on the Huffington Post here)

It’s June 1, 1982, and a 35-year old Donald Trump is spending much of the afternoon in his palatial Fifth Avenue office trying to convince me that he is worth more money than any other real estate titan in New York. I’m there as Forbes magazine’s lead reporter, interviewing him for our first annual “Rich List” of wealthy Americans. Donald is in all-out promoter mode, arguing that his work, and not his father’s, was responsible for nearly all of the Trump family fortune.

I was only 23 at the time of the interview, but Donald Trump took me seriously. He knew that I was the gatekeeper between his ego and the millions of readers who would soon hear about the new Forbes 400 ranking of the wealthiest Americans.

As we discussed the largest asset in the Trump family portfolio, Donald claimed that the value of the family’s 23,000 apartments in Brooklyn and Queens and Virginia should be calculated, after debt, at $40,000 each. When he saw I wasn’t biting, he revised his assessment to $20,000 each. In an obsessive effort to prove that he, not his father, deserved credit for amassing this real estate portfolio, Trump claimed that “80%” of the apartments had been purchased by him.

All of these claims were clearly false. I knew that the rent-stabilized apartments were worth less than $10,000 each at the time, and that Fred had built them over many years. (When I did extensive research on this claim a few years later, I also learned that there were never more than 10,000 of them, and that the 23,000 number was a deliberate fabrication by Donald).

Donald must have known that I knew that both his valuation and his claim to have acquired 80% of them were outrageous. After all, the centerpiece of the Trump holdings was Brooklyn’s working class “Trump Village,” which was built in 1963. Donald would have been only 17 at the time. And he was far from home, spending his fifth year at the heavy-on-discipline military academy boarding school that his emotionally distant, dominating father had shipped his unruly, fight-prone son off to.

I thought, He can’t expect me to believe these lies, so why is he telling me them? And why is he lying so obsessively to compete with his own father?

Of all the endless ink that the media has lavished upon attention-starved Donald Trump, only one article has ever dealt extensively with his relationship with Fred Trump that included a comment from his father— a 1983 New York Times profile. Nearly all media attempts to interview Fred Trump (who died in 1999), including mine, were turned down. Back then, one top real estate developer explained the disappearance of Donald’s father by saying that Fred Trump “loves a crook and he loves a showman.” Speaking for himself on that rare occasion in 1983, Fred Trump told the Times, “Donald has a competitive spirit and I don’t want to compete with him. He amazes me. He’s gone way beyond me, absolutely.”

But these admiring words from a distant, hard-pushing father have done nothing to satisfy Donald Trump’s mean-spirited competitiveness, compulsive lying and neurotic need to impress.

Harry Levinson, a business psychologist specializing in family businesses was also quoted in that 1983 Times profile. He explained that, “The core problem of the entrepreneur in the family business is the unresolved Oedipal problem, trying to beat the old man.” This is felt most acutely, Levinson noted, when the father, like Fred Trump, has been very successful.

”The son feels so inadequate and unable to compete with the father that he works out compensatory behavior,” Dr. Levinson said. ”He goes to the opposite and blows himself up to deny his feeling of helplessness.”

A few weeks ago, Deepak Chopra appeared on the “Tonight Show” and provided a similar assessment. Donald Trump’s behavior, Chopra said, reflects “resentment, grievances, fear, hostility, guilt, shame …and very poor self-esteem.”

The driving need for Donald Trump to prove himself better than his father became abundantly clear during my first of three annual interviews with him that day in 1982. About a half hour into our interview, we were interrupted by the strangest phone call I had ever witnessed.

Donald’s secretary, Norma, stepped in and announced that she was sorry to bother him, “but your father needs to speak with you and says it’s important.”

Trump nobly informed me that, “I’ve gotta take this,” ordered Norma to “put him through,” and picked up his desk phone.

I stood up and motioned that I could step outside while they talked, but Trump waved at me to stay. I remained standing and observing, pretending to admire the degrees and awards and news clippings that lined his walls.

A few seconds into the call, Donald started reeling off instructions about which Treasury bills and CDs to buy, at which yields, and for how many millions of dollars. The conversation went on for a while, as Trump instructed his father, impatiently at times, about how to invest what purportedly was their entire portfolio of hundreds of millions of dollars.

The conversation struck me as a charade, because it was clearly way too much activity to have on a random day of the year, particularly a conversation timed with Donald’s interview for the Forbes 400.

I leaned a little closer, ostensibly to check out a few items on his desk, but really honing my ears upon the phone headset Trump was holding. During the short intervals when his father was seemingly asking questions, I realized that there was no voice on the other end. Trump was fabricating the whole conversation to drive home that he was the boss of his family empire. And that their cash position was huge!

Donald clutched the phone tighter to his ear and quickly finished the call. Then, with a sense of noblesse oblige for his patience with a father who had never attended college, explained, “He asks me on such things. I went to Wharton.”

Our wealth assessment interview continued, as I showed Donald my working list of more than a dozen other Rich List “candidates,” ranking the estimated net worth of the largest private real estate families in New York. On behalf of Forbes, I was interviewing most of them not only about their own holdings, but also about their knowledge of the holdings of the other names on the list.

There were a dozen real estate families that I had estimated were worth far more than the $200 million I had established for the Trump family. Looking at my ranked listing, Donald was visibly upset and frustrated by my stupidity in not appreciating what he regarded as the true value of his portfolio. When he saw that my top category for New York real estate wealth was $500 million, he instantly assured me, “Our net worth is substantially over $500 million. We’re worth more than any of these guys on your list!”

Trump then trash talked the holdings of some of the most successful builders in New York, especially the LeFrak’s family’s $500 million net worth, derived from New York’s largest apartment empire.

Trump fixated on how much higher up LeFrak and others were on the list from he and his father. “LeFrak—he’s got a lot of junk,” Trump warned, with a scowl.

Our afternoon-long meeting was interrupted a few more times. First, by his head of design and ex-model wife, Ivana Trump, dropping in to show him a sample of a lavish piece of marble for his approval. “Isn’t she great!” he cooed, as she sashayed out like a model on a catwalk. “She doesn’t need my approval, but she asks it anyway.”

The final interruption came toward the end of our interview. It happened, quite conveniently, just 10 minutes after Trump had told me about the great deal he had gotten on the Barbizon Plaza Hotel on Central Park South, which he had purchased in 1981 for $13 million. Within a few seconds of being interrupted by his secretary for another “important call,” he announced to the imaginary person on the other end of the phone, “I would only sell the Barbizon for $100 million.”

Donald Trump looked at me like the cat that ate the canary, confident that I could do the math, and add $80 million more to his estimate.

As I rode the Fifth Avenue bus downtown to the Forbes building on 12th Street, my head was swimming by the surreal quality of the afternoon. Donald would soon complain to my editor and eventually to Malcolm Forbes that I underestimated his net worth because I was, though a “good kid,” clearly an idiot when it came to real estate. My editor, Harold Seneker, carefully reviewed my calculations and stood by them.

Later that summer, after a researcher fact-checked my Trump entry and its $200 million family fortune estimate (divided between Fred and Donald), I received two calls at my desk. The first was Donald, chagrined and irate that I had “totally failed” at the task of estimating net worth. He admonished me to jack his number up to the highest net worth that we had estimated for New York real estate tycoons, which, in 1982, was Harry Helmsley and Sam LeFrak’s over-$500 million level. ‘There’s just no contest between me and the other names you mentioned,” he shouted. “No contest!”

The second call was entirely unexpected. My desk phone rang and the Forbes receptionist announced, “Roy Cohn calling for Donald Trump.”

“Jon Greenberg,” a scrappy voice bellowed in rapid fire Brooklynese. “This is Roy. Roy Cohn!”

He skipped a beat to let the name sunk in. Cohn, ostensibly a lawyer, rarely appeared in a courtroom until his notorious disbarment hearing a few years later. Instead, Cohn spent most of his time threatening lawsuits, schmoozing with mobster clients and New York’s politically connected influentials, and calling the media with favorable stories about his clients and damaging gossip about those who defied them. On the phone, I recognized Cohn’s voice and thought of TV clips of his 1950s career as a Rosenberg prosecutor and Senator Joe McCarthy’s dishonest commie-hunting pit bull.

I later learned that Cohn had become a surrogate father, mentor and best friend to Donald Trump. A revealing portrait of their close relationship was published in the New York Times this year, titled, “What Donald Trump Learned From Joseph McCarthy’s Right-Hand Man.” The story noted that the two men spoke as much as five times every day for their many business deals and hosted one another’s birthday parties in the cocaine-laden backrooms of Studio 54, during the wild and crazy days of the late 1970s and early ‘80s.

Roy Cohn was the man who taught Donald that not only could you stiff your creditors and force them to sue you and then settle for pennies on the dollar, but you could also fight federal housing discrimination charges by destroying evidence and filing intimidating counter-suits, as Trump did after Cohn started representing the Trump family in 1973. As recently revealed in this Washington Post expose titled, “The man who showed Donald Trump how to exploit power and instill fear,” Roy Cohn “agreed to represent the Trumps — his way. That meant hitting back hard while shaping public opinion. On Dec. 12, 1973, Donald Trump, his father and Cohn called a news conference at the New York Hilton hotel. They said they were suing the government for $100 million in damages relating to the Justice Department’s “irresponsible and baseless” allegations”.

Roy Cohn taught Trump that he could even tie up IRS audits with continual litigation. It was Cohn’s “hit back harder when prosecuted” strategy that underpinned what may be the most notorious public tax dodge in American history. Trump has not only evaded paying income taxes on up to $50 million of income a year for almost 20 years, but he seems to have done so on a reported 1995 loss of $916 million of someone else’s money (the unfortunate shareholders and bond holders of his bankrupt casinos).

As real estate specialist Charles Bagli reported in the Times recently, in a story titled, A Trump Empire Built on Inside Connections and $885 Million in Tax Breaks, with Cohn’s backing and his family’s political clout, the Trump family could even force city hall to provide unprecedented tax benefits through relentless court appeals and threats to fire officials who refused to comply.

Thankfully, on that summer afternoon in 1982, Roy Cohn was not calling me at Forbes to sue me, but to go to bat for his most famous client.

“What can I do for you, Mr. Cohn,” I said, grabbing my notepad and a pen.

“I’m Donny’s lawyer, Donny Trump.”

“Yes, Mr. Cohn.”

“You can’t quote me,” Roy Cohn instructed me. “But Donny tells me you’re putting together this list of rich people. He says you’ve got him down for just $200 million!”

“That’s right.”

“That’s way too low, way too low! Listen, I’m Donny’s personal lawyer, but he said I could talk to you about this. I am sitting here looking at his current bank statement. It shows he’s got more than $500 million in liquid assets, just cash. That’s just Donald, nothing to do with Fred, and its just cash. And you’ve got him down for what, for $200 million? That’s way too low, that’s crazy. He’s worth more than any of those other guys in this town!”

“Well, Mr. Cohn,” I said enthusiastically, “I would certainly be glad to review that document and take those numbers into consideration provided that they show what you say they do. I can grab a cab and be there in a few minutes.”

“I’m a busy man and I gotta head out!” Cohn retorted angrily, like a power broker who had already done me enough favors.

“Or you can have someone make a copy and just put the statement in an envelope. I can have a messenger pick it up within the hour.”

“You know I can’t do that, Greenberg!” Cohn snarled. “These are confidential statements. Just trust me: I’m looking at this statement, right in front of me. More than $500 million, just cash. You got my word on it.”

I thought of Cohn standing next to Senator McCarthy as he evoked his fictitious list of Communists in government, and did my best not to laugh into the phone.

Here was the world’s most notoriously crooked attorney asking me to toss aside extensive research and take his word about Donald Trump’s net worth.

I smiled and in my most professional voice replied, “Mr. Cohn, we really are going to need to have that statement if Forbes is going to make any changes.”

“It’s confidential!” Cohn yelled, shocked at my stupidity. “But I’ll ask Donny and get back to you. Meanwhile, just put him down at $500 million … $500 million at least.”

“I can’t…”

Cohn hung up the phone and of course, I never heard from his again.

Donald Trump’s insatiable need to impress and his sociopathic willingness to deceive and crassly diminish others made him a running joke among the fast growing Forbes Rich List team. (Internally one editor admonished a researcher to check every fact and not take anything for granted from a “notorious self-promoter and liar”).

Unlike some of the highly successful people that we interviewed whose wealth was accompanied by inner confidence and a modicum of class, Trump was then known to Forbes staffers—and is now known to all of us—as America’s poster child for the boastful, crass, greedy, attention-starved millionaire.

In 1984, after two more years of Forbes 400 interviews with Donald Trump and many others, I did research for an article that sought to shed light on the insecurity and low self-esteem that was Donald Trump’s dark shadow, entitled, “The Not So Mysterious Disappearance of Fred Trump.”

In what turned out to be an unpublished work, I explored Trump’s obsessive diminishment of his father’s accomplishments, as well as his sense of embarrassment at the un-classy outer borough (non-Manhattan) sensibility of Fred Trump and his empire of cheap working-class brown brick rental apartment buildings in Brooklyn and Queens. For the story, I interviewed nearly a dozen of the most successful men in New York real estate, talking about Fred Trump, the builder of Donald’s shadow.

Donald Trump’s close friend and fellow real estate mogul Peter Kalikow, who was also expanding a family real estate dynasty, said, “Fred was a tough, tough guy. Tough on his competition, his contractors, his family. Today Donald and he are both very tough, and may well be engaged in a personality test of wills. This may be Fred’s way to make sure Donald has intestinal fortitude.”

That same year, Donald Trump’s secretary told me that Donald did not want to be interviewed for an article about his father, but that she would set up a phone interview for me with John Baron, who was referred to as a Trump organization vice president. Baron talked to me at length about the family’s assets, and about Donald Trump’s competitive relationship with his father.

During recent years, I have learned that John Baron was actually Donald Trump. Baron was the name he used in phone calls to the media to provide information, often fictitious, that Trump did not want attributed to him but wanted to see appear in print (such as Madonna wanting to date him).

And so it was Donald Trump, disguising his voice, who provided what might be the most unguarded public self-reflection that he ever made about his father. “Fred might be having a hard time reconciling the fact that his son is selling apartments for so much,” Donald Trump as John Baron told me. “Perhaps it doesn’t make sense to Fred that he should sell when the same-sized apartments in Queens are selling for nearly 1/100the price of the places in Trump Tower.”

As for the son-father rivalry between the two men, Trump-as-Baron explained, “It was not an easy thing, initially. Fred Trump is a very strong man, and breaking through that mold and surpassing it was a struggle. Donald has a good deal of respect for his father and it was a friendly struggle—but a very strong struggle, too.”
A struggle to win, it seems, that continues to this day, 17 years after the death of his father.

The kind of struggle that will never end.


The founder and Editor of the Sonoma County Independent, Greenberg is an investigative financial journalist with 35 years of experience with national publications. Greenberg writes a political blog that appears in the Huffington Post In 2015, he won two first prizes from the Greater Bay Journalism Awards for his coverage of the closing of Palm Drive Hospital. In 2014, he won first prize for analysis from Award competition for his coverage of the Monday closings of Sonoma County's libraries. He has been an investigative financial and political journalist for such publications as The New York Times, The Washington Post, Mother Jones, Forbes, New York, Money, The Bohemian, The Santa Rosa Press Democrat, Playboy, Self, Inc., GQ, The New Republic, and Alternet. He is also the author of several well-reviewed books. As a new media innovator who has developed a half dozen interactive web platforms and dozens of content-focused web sites, Greenberg is committed to enhancing responsive government and expanding media democracy. Greenberg is founder of Progressive Source Communications, a Sebastopol-based public interest communications company. In the past, he founded and managed two other online companies, TV1.com, and Gist.com. Greenberg’s political work included serving as Policy Director for the New York City Council’s Select Committee on Lower Manhattan Redevelopment in the years following 9-11. His work resulted in more than $250 million of federal funds being re-directed to needy businesses and constituents in the impacted area. Greenberg has been Vice President of Fenton Communication’s New York office. His work on behalf of non-profit organizations has included communications consulting for Save Darfur, Stonyfield Farm, the ACLU, and the Lakota People’s Law Project. Greenberg holds a B.A. in writing from the State University of New York at Binghamton, and a Masters Degree in Law from Yale Law School, where he graduated with honors in First Amendment Law.
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