Complicated as his life had become by the 1980s, overall, that decade was a time of seemingly boundless material abundance for Donald Trump. If he saw something he wanted, he could almost always get it. And the list of items that Donald grew to desire knew no limits.
In 1987, Newsweek reported that Donald “owns three homes…110 rooms at Mar-a-Lago in Palm Beach…a huge triplex apartment in Trump Tower…and a 10-acre, 45-room weekend estate in Greenwich, Connecticut.”(133)
But that wasn’t all. Donald “also owns a Boeing 727, the Darth Vader helicopter, and now he's negotiating to buy a yacht owned by Saudi arms broker Adnan Khashoggi that's about six times the size of the average Manhattan apartment.”(133)
Now who exactly is this Adnan Khashoggi figure that Donald was doing yacht business with? Mainly, Khashoggi was an illegal trafficker of weapons of war. Most famously, Khashoggi was implicated for his participation in the Iran-Contra scandal of 1986. Turns out, Khashoggi was a key player in facilitating the illicit sale of US-made missiles to Iran, with the intention of using the dark money earned on this transaction to illegally fund paramilitary groups attempting to overthrow the government of Nicaragua.(134)
"Not many people live a life like Khashoggi," Donald boasted in the 1987 Newsweek article. Then, he “adds with a grin, ‘but I'm coming damn close.’”(133)
Newsweek continued, “Such ambition leaves little time for friendships. ‘I hate to have to rely on friends,’ [Donald] says. ‘I'm not a trusting guy. I want to rely on myself.’”(133)
The unusually callous mindset Donald publicly admits to holding with respect to the very concept of “having friends” is in complete alignment with what we already know about Donald’s mental health. Remember, due to a combination of his genetics and the neglectful and toxic familial environment in which Donald was raised as a child, Donald developed serious mental pathologies which, to the best of our public knowledge, were never so much as acknowledged, much less professionally treated.
Most saliently, like his father Fred, Donald Trump is a sociopath.
In the 1970s, 1980s and 1990s, Donald’s sociopathy was not a liability in his line of work. It was an asset.
As Donald once put it himself, one of his biggest strengths, "lies in my unpredictability."(133)
In 1990, Vanity Fair wrote that Donald’s “real skill has always been his ability to convince others of his possibilities.” But even still, “The line between a con man and an entrepreneur is often fuzzy…They say the Plaza is worth $400 million? Trump says it's worth $800 million. Who the hell knows what it is worth?”(135)
Donald’s lawyer at the time explained further, “Donald is a believer in the big-lie theory…you say something again and again, people will believe you."(135)
Simple and crude a strategy as this may have been, in truth, Donald’s faith in the “big-lie theory” was in fact quite effective for him, and for quite a long period of time.
Remember how back in the early 1980s, Donald Trump, Roy Cohn, and “John Baron” conspired to get Donald’s name on the Forbes 400 list? Eventually, Jonathan Greenberg, the journalist who wrote the Forbes piece, discovered he and the high-profile magazine had been duped all along.
In 2018, Greenberg wrote a follow up piece on the matter for the Washington Post. He explained, “It took decades to unwind the elaborate farce Trump had enacted to project an image as one of the richest people in America. Nearly every assertion supporting that claim was untrue. Trump wasn’t just poorer than he said he was. Over time, I have learned that he should not have been on the first three Forbes 400 lists at all. In our first-ever list, in 1982, we included him at $100 million, but Trump was actually worth roughly $5 million.”(136)
Greenberg now sees just how far Donald’s “big-lie theory” advanced his business prospects in stunningly successful ways. “This was a model Trump would use for the rest of his career, telling a lie so cosmic that people believed that some kernel of it had to be real. The tactic landed him a place he hadn’t earned on the Forbes list — and led to future accolades, press coverage and deals.”(136)
Donald’s lies about his own wealth led him places he would never have been capable of going, had he been the type of man who operated with honesty and integrity.
The lies Donald told to get and keep himself on the Forbes list proved absolutely crucial to him. Greenberg writes, “In the absence of a functioning balance sheet, the list didn’t just make Trump feel like a winner…it may have provided some of the documentation he needed to borrow reckless sums of money — vast loans that he used, for years, to actually make him a winner.”(136)
Greenberg references a biography on Donald, published in 2005 by Tim O’Brien. O’Brien wrote, “The more often Forbes mentioned [Donald], the more credible Donald’s claim to vast wealth became…The more credible his claim to vast wealth became, the easier it was for him to get on the Forbes 400 — which became the standard that other media, and apparently some of the country’s biggest banks, used when judging Donald’s riches.”(136)
Jonathan Greenberg was among the first known people to have been manipulated by Donald over phone calls in which Donald pretended to be someone who did not exist: “John Baron.”
Incredibly, Donald was at least at one point pressed into admitting to using this embarrassing strategy in a quite formal setting. A Washington Post article revealed that, “In a 1990 court case, Trump testified that he had used false names in phone calls to reporters.”(136)
And as it happens, Baron was not Donald’s only alias.
Donald had named his first imaginary friend “John.” “John Baron.”
Ingeniously, Donald’s came up with another stumper for his second imaginary friend.
This man would also be named, “John.” “John Miller,” to be exact.
For the record, we’re talking about Donald J. Trump here. Donald’s own middle name is…ugh.
In 1991, Sue Carswell was a reporter for People Magazine. She reached out to the Trump Organization to get in touch with the man in charge for a piece she was writing. She soon received a call back from John Miller, who presented himself as a media spokesman for Donald Trump.(137)
To be clear, John Miller, just like John Baron, is simply a false identity Donald Trump used for many years to manipulate people.
But apparently, John Miller and John Baron had different areas of interest. Baron was mostly concerned with tricking people into believing that Donald Trump was far wealthier than he actually was. Miller, on the other hand, was mostly concerned with tricking people into believing that Donald Trump was far more sexually desirable than he actually was.
In 1991, John Miller hopped on the line with People magazine journalist Sue Carswell. Without her so much as asking a single question, Miller launched into a description of the day-to-day erotic fantasy world that Donald Trump allegedly inhabited.(137)
“Actresses…just call to see if they can go out with him.” Miller claimed.(137) Ah, really? Actresses are just cold calling a real-estate corporation to ask if they can date its owner?
It gets better. John Miller goes on to tell Carswell that Madonna herself “wanted to go out with [Donald].”(137)
This was 1991 after all, the year that Donald’s marriage with Ivana finally ended in a very public and bitter divorce. Donald had been openly cheating on Ivana for years with Marla Maples.
But the fact that he was now with Maples, apparently wasn’t any reason for Donald to exert any modicum of self-control over his basest impulses.
As Miller told it to Carswell, in addition to Marla, Donald had “three other girlfriends.”(137)
One of them, Miller stated, was Carla Bruni. At the time, Bruni was a young model from Italy. She had dated Eric Clapton, and later Mick Jagger.(137)
On the phone with Sue Carswell, John Miller boldly declared that Carla Bruni chose to leave Mick Jagger for Donald Trump!(137) This was presented as fact to an established journalist at People Magazine.
In reality, Carla Bruni married Nicolas Sarkozy (making her the First Lady of France during his administration). To this day, she emphatically denies Donald Trump’s tall tales about any sort of romantic connection between them. She has exhaustively clarified that she never dated Donald, not once.(138)
Following her extraordinarily bizarre conversation with John Miller, Carswell played a recording of her phone call with some of her colleges. A quick consensus emerged that Donald Trump himself was the voice on the line, pretending to be someone he was not. Carswell then reached out to Marla Maples directly. Carswell played the John Miller tape to her, and Marla confirmed that the voice did in fact belong to Donald. In fact, Marla was soon in tears after hearing how coldly Donald spoke of their relationship, and how unabashedly he bragged about his alleged sexual exploits with multiple other women.(137)
But why? Why would Donald make such obviously untrue claims about himself?
In 1987, Donald Trump published a book under his own name that he did not write, titled The Art of the Deal.
Speaking in an echo of Donald Trump’s voice, the ghostwriter stated, “One thing I’ve learned about the press is that they’re always hungry for a good story, and the more sensational the better…The point is that if you are a little different, or a little outrageous, or if you do things that are bold or controversial, the press is going to write about you…I play to people’s fantasies.”(137)
Remember that the very same year Donald lied to journalist Sue Carswell about his allegedly extravagant sex life (over the phone under a false identity: John Miller), he had just finalized his divorce with his first wife, Ivana. It appears that Donald was perhaps overcompensating in this moment, trying to convince the world that he was still the most eligible bachelor in the universe. Regardless of the fact that by 1991, Donald was 45-years-old, balding, and had been a husband and father of three young children for fourteen years.
The psychologically unstable and traumatic environment in which Donald was raised as a child appears to have permanently handicapped his capacity to share and receive genuine love and affection. Remember, this is the man who publicly boasted about having no friends, and of trusting no one. How many people do you know (and trust) who have this same philosophy on life?
As the National Child Traumatic Stress Network puts it, people “Who have experienced complex trauma often have difficulty identifying, expressing, and managing emotions, and may have limited language for feeling states…Their emotional responses may be unpredictable or explosive.”(139)
These toxic relationship dynamics played out for all the world to see during the exceedingly vindictive and public divorce between Ivana and Donald in the early 1990s.
Let’s establish a couple key points here.
First, as a New York Times article from 1990 explained, the basis for the divorce was simple. Ivana was pursuing separation from her husband, under grounds of “Cruel and inhuman treatment by Mr. Trump.”(140)
Speaking under a deposition during the divorce proceedings in 1990, Ivana revealed something explosive.
Under deposition, Ivana detailed a recent occasion upon which Donald Trump had violently raped her.(141)
At the time, then in his mid-40s, Donald was just starting to go bald. Ivana, already having a plastic surgeon she had personally used, recommended that her husband make an appointment there himself.(141)
Soon, Donald found himself undergoing a “painful scalp surgery” operation. Returning home to Ivana that night, Donald was livid with her. He “lashed out at her…ripping out hair from her scalp.”(141)
Then, Ivana declared, “He raped me.”(141)
For reasons which remain publicly uncertain, Ivana soon afterwards changed her story. She claimed that during the incident she described in the deposition, “As a woman, I felt violated…I referred to this as a ‘rape,’ but I do not want my words to be interpreted in a literal or criminal sense.”(141)
25 years later, when her ex-husband decided to pursue his biggest job yet, Donald’s then lawyer Michael Cohen muddied the rape accusation waters even further. “Understand that by the very definition, you can’t rape your spouse.” Cohen claimed.(142)
This is 100% morally and legally inaccurate. Time Magazine explains, “Prohibitions against spousal rape were actually enacted in the 1970s, and it was illegal in all 50 states by the early 1990s.”(142)
At the time of Michael Cohen’s public defense of a man’s “right” to rape his wife, The Daily Beast had gotten wind of the decades old marital rape story, and was investigating the matter for further reporting.
This is what Michael Cohen, Donald Trump’s personal lawyer, had to say to this particular American journalistic publication, “I will make sure that you and I meet one day…And I will take you for every penny you still don’t have. And I will come after your Daily Beast and everybody else that you possibly know. So I’m warning you, tread very fucking lightly, because what I’m going to do to you is going to be fucking disgusting. You understand me?”(142)
This is how Donald Trump operates.
But even after the divorce was finalized, Donald continually sought to control and publicly intimidate the mother of his three young children.
In 1991, Ivana went on TV and was interviewed by Barbara Walters on the program 20/20.(143)
Donald sued his ex-wife immediately. He also directed his alimony payments to her to stop. Donald was able to do this because Ivana had allegedly broken a “non-discloser” agreement she had signed as part of the terms of their divorce.(143)
Non-discloser agreements are one of Donald’s favorite tools for silencing women he’d abused and discarded.
As such, Ivana was legally barred from speaking in public about her ex-husband of 14 years. “Without obtaining Donald's written consent in advance, Ivana shall not directly or indirectly publish, or cause to be published, any diary, memoir, letter, story, photograph, interview, article, essay, account or description or depiction of any kind whatsoever...concerning her marriage to Donald or any other aspect of Donald's personal business or financial affairs...As used in the preceding sentence, the term 'publish' and 'publication' shall be deemed to include...television.”(143)
While Ivana was married to Donald, he controlled her and sought to keep her in what he perceived to be her place. Donald flatly told his first wife and mother of three of his own children that he expected her to “Never look a day over 28 (years-old).”(144)
Back in 1988, Donald and Ivana had appeared on the Oprah Winfrey Show together. From this venue, one of the most successful television shows of modern America, Donald creepily proclaimed that he got along with his wife because, “Ultimately Ivana does exactly as I tell her to do.”(144)
A few years after their divorce, Ivana returned to Oprah’s show “with a new message: ‘I will not let men dominate me anymore.’”(144)
Much like his first casino, in the early 1990s, Donald Trump’s first marriage had ended in spectacular, public failure.
But as we’ve seen an abundance of evidence proving up to this point, Donald Trump is someone who is either incapable of or unwilling to learn from his own mistakes.
When Donald fails at something, his strategy is consistent and predictable. Step 1: Deny that the failure ever occurred. Step 2: Quickly do the same thing that got you into trouble the first time around, and pretend that no one else involved will notice.
After his first casino was an immediate financial failure, Donald decided to build a second casino in the same location, using the same lack of an actual business model.
After his first marriage crashed and burned for the whole world to follow in the New York tabloids, Donald decided to marry Marla Maples, the woman he’d been cheating on his first wife with for many years.
Interviewed on ABC Primetime Live in 1994, Donald nostalgically mused about how much simpler his life had been just a few short years ago, when he was married to Ivana, and cheating on her on the side with Marla Maples.
Again, on live TV, Donald Trump stated that in the late 1980s, “The business was so great…[I had] a beautiful girlfriend [Marla], a beautiful wife [Ivana], a beautiful everything."(145)
To be fair, Donald made it clear that he didn’t actually want to marry Marla Maples, but several circumstances aligned in a way that forced his hand.
In 1993, Donald once again opened up to People Magazine. He stated, “I didn’t want to get married [to Marla] before. But now there’s a new wrinkle.”(146)
That new wrinkle was the news that Donald had gotten Marla pregnant with what would become his fourth child, Tiffany Trump.
In 2004, when Tiffany was then 11-years-old, Donald publicly admitted how upset he was upon learning that Marla was pregnant with his fourth daughter back in 1993. On the Howard Stern show, Donald flatly stated, “I have a great little daughter, Tiffany…But, you know, at the time it was like, 'Excuse me, what happened?' And then I said [to Marla], 'Well, what are we going to do about this?’”(147)
“Well, what are we going to do about this?”
It’s obvious what Donald is implying in this moment. Donald saw the coming birth of his fourth child as a wholly unwelcome piece of news. In that initial conversation, Marla responded to him, “Are you serious? It's the most beautiful day of our lives.” On the Howard Stern show in 2004, Donald Trump noted his response to Marla, “I said, 'Oh, great.'"(147)
As Donald himself made quite clear, he did not want to marry Marla Maples, even after learning that he had gotten her pregnant. But at the time, multiple forces were converging to force Donald’s hand.
For one, Donald’s parents were embarrassed that he was fathering a child out of wedlock.(148) His father in particular pressured him to buckle down and put a ring on it.
Furthermore, by 1993, as Vanity Fair reports, Donald “was clawing out of the rubble of a cratering business career. Three of his [three] Atlantic City casinos had gone bankrupt. He’d nearly defaulted on $3.4 billion in debt, and, humiliatingly, his creditors had put him on a living allowance: $450,000 a month. Bankers forced him to sell his 282-foot yacht, the Trump Princess, as well as the Trump Shuttle airline and stake in the Plaza hotel.”(148)
At the exact same time Donald was trying to pressure Marla into having an abortion, Donald “was preparing to take his casinos public to raise cash to pay down his debts. His tabloid domestic life spooked Wall Street and diminished his chances for an IPO. Marrying Maples would calm investors.”(148)
Keep in mind, Donald Trump’s “tabloid domestic life” went far deeper than merely cheating on his wife Ivana in public with Marla for several years.
In 1994, the year after Donald did in fact acquiesce to circumstance and marry Marla Maples, he directly told Vanity Fair, “I had been in Europe fucking every model in the world. My life was wild.”(148)
Perhaps even a bit too wild, at least in one specific aspect. Vanity Fair explains that Donald, “a famous germophobe, also found monogamy reassuring as the AIDS crisis raged.”(148)
“Being [sexually active] out there is a little bit scary, to put it mildly,” Donald told Vanity Fair, “[Having promiscuous sex is] like being in Vietnam, in the forests, and knowing there are guns pointed at your head.”(148)
As always, Donald Trump can deeply relate to the experience of America’s men in uniform.
In any case, Donald reluctantly agreed to marry the Georgia beauty queen. But before Donald would consent to pull the marital trigger, he wanted to handle some business logistics with his glowing bride to be.
For his second marriage, Donald insisted on a fairly ruthless prenuptial agreement. In his own words, Donald acknowledged that the purpose of the prenuptial was, “When we get divorced, this is the way we’ll split things up.” But Marla wasn’t comfortable with the terms Donald was trying to force her into signing.
“This was the big battle all along,” Marla told Vanity Fair. The magazine noted that Marla “tried to hold out for better terms, but Trump utterly refused to budge…He held the line up their wedding day…’Marla was under duress. Donald’s position was: without the prenup he wasn’t going to get married.’ With 24 hours to go before a thousand guests arrived, Maples caved.”(148)
Tiffany Trump was born in October of 1993, her biological parents were married two months later.
True to form, Donald Trump’s second wedding was transactional, and highly theatrical. No fewer than seventeen separate TV crews were there to show the world how happy and fabulous Donald and Marla’s relationship was. Accompanying the TV cameras were throngs of NYC gossip columnists, and no less than the flashing cameras of nearly one hundred paparazzi.(149)
At his second wedding, Donald welcomed power players from across the nation who swarmed in to kiss the ring.
As the NYT reported at the time, “Among the 1,000 guests were faces from the worlds of politics, sports, business and show business. [New York City] Mayor David Dinkins was there to toast the bridal couple along with Senator Alfonse D'Amato…Representative Charles Rangel; Manhattan District Attorney Robert Morgenthau...Soap opera queen Susan Lucci…Rosie O'Donnell…Joe Frazier and O.J. Simpson…[the] chairman of Bear, Stearns & Company.” Also in the house, Saudi Arabian illegal weapons trafficker implicated in the Iran-Contra scandal and personal friend of Donald Trump, Adnan Khashoggi.(149)
Donald’s locker-room-banter-buddy Howard Stern was there to celebrate true love as well. Asked for comment on Donald and Marla’s life-long commitment to each other, Stern pretty much hit the nail on the head, commenting, "It's probably in bad taste, but I give it four months."(149)
We can learn a lot about Donald Trump by the people he selected to be in attendance at his second wedding. But guess who wasn’t there?
Recall that when Donald’s first child, Donald Trump Jr. was in middle school, he was mercilessly taunted by his classmates after his father’s scandalous affair with Marla Maples was front page tabloid news? DT Jr. was in fact so distraught over his father’s shameless infidelity and disregard for the well-being of his own family, that after Donald and Ivana’s divorce, DT Jr. refused to so much as speak to his father for a full year.
A young teenager at the time, DT Jr. flat out refused to even attend his father’s second wedding.(150)
For high school, DT Jr. was shipped off to boarding school in Pennsylvania, almost completely shut off from his family in Manhattan. As an adult, DT Jr. would describe being sent away to boarding school as a “relief from his home life.”(150)
In 1994, Donald and Marla Trump were newlyweds and parents of a baby girl, Tiffany. That year, the couple appeared on a television program called Lifestyles of the Rich and Famous. It was on this program that Donald made one of the most bizarre, creepy, and gallingly inappropriate remarks of his public life, up until that point.
Asked to speak about his daughter, who at that point was a literal baby who had not yet reached her first birthday, Donald Trump, her own father, had this to say about Tiffany:
“She’s a really beautiful baby, and she’s got Marla’s legs. We don’t know whether she’s got this part yet [he gestures with his hands over his chest, as if he’s cupping an adult women’s breasts], but time will tell…”(151)(152)
This is on film. Feel free to watch it with your own eyes on the link provided in the Sources Cited.(151)(152)
At Donald and Marla Trump’s gigantic photo-op of a wedding in 1993, Howard Stern predicted the marriage would last four months. In the end, their imminent divorce arrived in four years, after Marla had finally endured enough of the consequences of her decision to marry and have a child with a prodigious sociopath.
Donald and Marla Trump split up in 1997. Asked by reporters for comment on the situation, Marla “said her marriage was ‘built on an illusion’ and that she and Trump were never good together as a couple.”(153)
Marla described Donald Trump as "ego-driven" and "obsessive.” After years of pain and anguish, she finally admitted, "Donald was never the man I wanted to marry…He and his world were alien to me.”(153)
For Donald Trump, the birth of his daughter Tiffany was a highly unwelcome development. Donald’s immediate reaction to the news of Marla being pregnant with his child, was to encourage her to have an abortion.
For Marla Trump, the birth of her daughter Tiffany was highly energizing. It changed her entire outlook on her own life, and gave her a sense of purpose she’d never felt before. Marla stated, "After I became a mother, I was less willing to put up with [Donald’s] behavior."(153)
By the late 1990s, Marla was ready for a new life for herself and her daughter, “I’m so happy to be away from Donald, and I’m just trying to move as far away as I can."(153)
And she did. After divorcing Donald, Marla moved to California to raise Tiffany as a single mother. Outside of his money, Donald was not involved in his daughter Tiffany’s life throughout the overwhelming majority of her childhood and adolescence.
In 2016, 23-year-old Tiffany Trump explained that throughout her childhood, she only saw her father sporadically, “on spring breaks or for Easter.”(154)
Ok. We’re now going to take a step back and explore another aspect of Donald Trump’s life in the 1990s which had been humming along in the background amidst all the relationship drama just covered that he’d created for himself.
Remember that the final years of Donald’s first marriage with Ivana Trump were highly acrimonious and mean-spirited. But even in the midst of all this personal chaos, don’t forget that the watchful eyes of foreign adversaries remained laser-focused on Donald Trump all the same.
In 1990, Ivana’s father passed away. Still married at the time, Donald accompanied Ivana to Czechoslovakia to attend her father’s funeral.(155)
Recall that Ivana’s father was forced into collaborating with the local Communist intelligence services after his daughter married a super-rich and moderately famous American. The Czechoslovakian StB had been spying on Ivana and Donald Trump since they were married back in 1977. The surveillance never stopped.
Even at the funeral of Ivana’s father, StB agents were present to monitor the Trumps. One of the agents at Ivana’s father’s funeral was Jansa, one of the men who’d been on the Trump trail from the very beginning. During the service, unbeknownst to the family in attendance, Jansa stood just “100 metres away from the Trumps.”(155)
Also recall that the Cold War between the Soviet Union and America commenced almost immediately after the end of WWII in 1945. In the decades to come, the major power players in the East and West existed in a state of near constant tension, animosity and competition for global influence. But by the late 1980s and early 1990s, the dominos started to fall for the Soviet Union.
From 1985-1990, a young man from Leningrad was in charge of a KGB post in Dresden, East Germany. Among his principle responsibilities were, “Stealing technological secrets (from the West)…entrapping, compromising, and recruiting Westerners (to become KGB assets) who happened to be in Dresden studying and doing business.”(156)
But then, one fine day in late 1989, Dresden’s KGB post was faced with an enormous problem.
Massive throngs of protesters appeared outside the KGB’s gates.
The Berlin Wall was falling.
The KGB officer in charge reached out to Moscow to clarify his orders, but Moscow was silent.
Afraid that the protesters might storm the building, he ordered his staff to commence burning their intelligence documents immediately. Then, the officer walked outside and approached the protestors. He bluffed, threatening that anyone attempting to breach the gates of the facility would be shot. It worked. The protesters held off, and the KGB was successfully able to destroy its most sensitive documents in Dresden.(157)
But while the narrow worst-case scenario had been avoided for their unit, Dresden’s KGB officer in charge was shaken greatly by this moment. As put by the Center for American Progress, “Where America and the West saw the fall of the Berlin Wall and the collapse of the Soviet Union as democratizing moments, to [the young Dresden KGB officer], it humiliated the once mighty Soviet Union, ended his career, and introduced chaos into a previously stable system.(157)
The Dresden KGB officer’s name was Vladimir Putin.
The humiliation he felt when the Soviet Union collapsed would go on to shape his political worldview for the rest of his life.
And at the very same time that a cornerstone of Vladimir Putin’s life collapsed before his eyes, in the early 1990s, Donald Trump experienced a frightening collapse of his own.
The fall of the Soviet Union in 1991 marked the official end of decades of overt aggression between Communism and Capitalism. Perhaps ironically, at the very moment the Soviet’s centralized economy had failed spectacularly, Donald Trump’s free market real estate and casino empire found itself embroiled in imminent financial disaster as well.
While the tabloids focused on Donald’s messy personal life, behind the scenes, things were even darker. With respect to Donald Trump’s financial situation, chickens were finally coming home to roost.
Remember that against the advice of his own father, in the 1980s, Donald impulsively opened a casino in New Jersey. Once in operation, the casino quickly failed.
Then, Donald opened a second casino in New Jersey. Once in operation, this casino also quickly failed.
Never one to be discouraged by evidence, Donald soon opened a third casino in New Jersey. Once in operation, this casino was also a near immediate failure.
By 1990, Donald’s business empire was “on the verge of collapse.”(158)
Well, for starters, “the Trump Organization was reportedly $3.4 billion in debt, with Trump himself liable for more than $800 million.”(158)
In 1991, Donald Trump was so far in debt that “the New Jersey Casino Control Commission concluded, ‘Mr. Trump cannot be considered financially stable.’”(158)
As the NYT reported, “Casino regulators in New Jersey warned that ‘the possibility of a complete financial collapse of the Trump Organization is not out of the question.’”(159)
Why? Because “Decisions Mr. Trump made at the helm of his business empire during the 1980s…led to its nearly imploding (in the 1990s).”(159)
Although Donald was definitely playing with enormous sums of cash, the litany of evidence over the course of his many decades in business illuminate an obvious conclusion: Donald Trump is bad at math.
We’re not talking about anything overly technical or fancy right now. Forget advanced, college or professional level math skills. We’re just talking about the basics that all American children are presented with throughout their K-12 public school education.
Here is an elementary school math lesson that Donald Trump never learned: in order to be successful in business, you have to make more money than you spend.
In the 1980s, Donald threw enormous sums of money around with reckless, ADHD abandon. “He had bought a yacht for $29 million, the Plaza Hotel in Manhattan for $407 million and a failing airline for $365 million. All were losing money.”(159)
“In 1992, Trump defaulted on the debt of his airline, Trump Shuttle, turning it over to U.S. Airways.”(158)
Ah yes, back in 1988, Donald randomly decided to buy an airline, Eastern AIR Shuttle.
“It’s a diamond, it’s an absolute diamond.” He boasted.(160)
To be fair, Donald did in fact try to make his airplanes look like diamonds. After all, that is what Donald Trump does best, he finds something cheap, buys it with his father’s money, then he makes superficial, surface level changes to the product on an almost exclusively aesthetic level, then he sells it back to the demographic of people who are unable or unwilling to notice the difference.
Suddenly the owner of an airline, The Daily Beast explains, Donald “spent more than $1 million on each jet, going well beyond the normal cabin upgrades to add thick maroon carpeting, maple-veneer paneling, beige leather seats, and even faux marble sinks and gold-colored fixtures in the lavatories.”(160)
As appealing as such renovations may have been to Donald himself, turns out there was a bit of a problem.
“Older jets in particular (like those Donald had just bought) guzzle fuel and airline executives are obsessed with saving even a few ounces of weight.” All told, Donald’s stylish upgrades to his fleet of airplanes attempted to “add 20 to 30 pounds to each plane.”(160) Donald wanted to install heavy ceramic sinks in the bathroom. Donald wanted to change the standard emergency exit handles to heavy brass ones.
The problem was that these trivial upgrades were simply not mathematically possible, safe, or even legal.
In addition to having zero knowledge or experience in the highly technical airline industry, Donald’s decision to buy his own airline was also accompanied by visibly poor timing. As The Daily Beast reports, “Airlines have been notoriously poor investments…with high fixed costs and a vulnerability to unpredictable forces like gyrating fuel prices and economic downturns…In fact, although the economy in general was in decent shape in 1988, the airline business Trump was entering was in turmoil—dozens of airlines had shut down…and many major airlines had either merged or gone into bankruptcy court protection.”(160)
Now the proud owner of a sizeable, terrible investment, Donald did what Donald does. Incapable of self-oriented focus, discipline, or learning, Donald just starts swinging a baseball bat at his perceived enemies.
“I wouldn’t fly them; they’re losing money and their planes are old.” Donald publicly declared about an airline rival.
This comment sent shockwaves through the international airline industry. “Trump’s seasoned airline hands were horrified; even in the combative airline business, such talk was regarded as out of bounds, as it would only stoke more general fears of flying.”(160)
Also, for the record, Donald’s own fleet of twenty-one Boeing 727 jets were just as old as those of the rival he slandered in public.(160)(161)
The delusional demands Donald was making with respect to his airline became so severe, that the man in charge of spearheading the Trump Shuttle changes soon offered to resign. “’He insisted I fly the planes with only two pilots in the cockpit,’…instead of the required trio at the controls…it spoke volumes about Trump’s lack of understanding of the airlines—and of his very own fleet. The 727s Trump owned could not be flown with two pilots; it was designed for three and ‘would have been unflyable’ otherwise.” Plus, “the FAA would have never permitted it.”(160)
18 months after Trump Shuttle opened for business, the company fell straight on its face. Trump Shuttle had swiftly squandered $128 million.
By 1992, Donald was forced to sell off his failed airline.(161)
Throughout his long career, Donald had always had a talent for spending enormous sums of money. But remember, math. The trick is you actually have make more money than you spend, if you seek to be considered a successful businessman.
By the early 1990s, the vultures had begun to circle over Donald Trump. He was massively in debt, and his litany of unsuccessful businesses simply weren’t making anywhere close to the money Donald needed to just keep his head above water.
In 1993, Donald asked his siblings “if he could borrow $10 million from their respective shares of the family trust. Mr. Trump received the loan…and went back for another $20 million the following year.”(162)
Desperate, in 1995, “Trump Hotels & Casino Resorts, the company through which he owned and operated many of his properties in Atlantic City and elsewhere, held an initial public offering.”(158)
Yet, “contrary to Trump’s own lofty predictions—he mused toVanity Fair’s Edward Klein that the IPO might raise $4 billion—he only managed to raise $140 million.”(158)
That very same year, 1995, Donald “declared a loss of nearly $916 million” on his tax return. “His businesses continued to struggle, with his casinos posting $66 million in losses by the end of 1996 and another $42 million in 1997.”(158)
At this moment, Donald had been a major public player in the New York real-estate market for well over two decades. Year after year, starting in the early 1970s, Donald had been able to get loan after loan after loan with little to no rational scrutiny over what he’d actually do with the money. But by the mid to late 1990s, the Donald spell finally began to break for some of Donald’s largest financial enablers.
As the American Center for Progress explains, “Compounding Trump’s financial problems was the Wall Street stigma his business failures attracted. The Guardian has reported that, in the 1990s, ‘Wall Street banks, which had previously extended him credit, turned off the tap.’”(158)
In the 1990s, Donald Trump was recognized as being so profoundly incompetent, dishonest, and erratic that one New York banker stated, “If a major institution in New York—whether it was a Chase or a Goldman or a law firm or something—wanted to have a building built…I can give you almost 100 percent assurance that Donald would not be on the list (of potential builders).”(158)
For perhaps the first time in his life, by the mid 1990s, now 50-years-old, Donald Trump was unable to get what Donald Trump wanted. He had burned so many bridges, over so many years, told so many lies, and broken so many promises that even many of his longtime allies no longer wanted anything to do with him.
But just before the exorbitant debt hammer fell on Donald, another long-term actor in his life swooped in to bail him out. This time, it was not his father, whose health was now failing. This time, while his friends in New York had at long last turned their backs on him, Donald’s friends in Moscow stepped in and embraced him with open arms.
The Communist intelligence services in Czechoslovakia, the StB, began surveilling Donald Trump in 1977, the year he married Ivana. The StB tapped into phone conversations between Ivana and her father, to learn more about her husband, who appeared to be on an upward economic, and potentially even political trajectory. From the late 1970s through the entire 1980s, the StB secretly read the Trump’s mail. They even sent StB agents to New York City to spy on the Trumps from up close.
While the Czechoslovakian StB initiated the long-term espionage program on Donald Trump, their partners at the Soviet Union’s KGB would dramatically expand these efforts. In the final years of the Soviet Union, the KGB began to see Donald as an asset who’d become far more valuable to their geopolitical interests than they possibly could have hoped for when he was first brought to their attention back in 1977.
In 1987, David Bogatin, a Soviet living in America, pled guilty to “evading millions of dollars in state fuel taxes in what state officials called one of the largest gasoline bootlegging operations in the nation.”(163 31) As it happens, David Bogatin had done a face-to-face deal with Donald Trump not long before, in 1984, when he purchased five separate luxury condos for himself in Trump Tower.
Donald Trump accepted $6 million in cash from David Bogatin for the transaction.(164)
Bogatin then escaped US law enforcement, fleeing the country. The US government seized Bogatin’s five condos in Trump Tower, as they had determined “he had purchased them to ‘launder money, to shelter and hide assets.’”
Bogatin was big enough of a player that the United States Senate conducted an investigation into the man’s criminal history. Following the money, the Senate “revealed that Bogatin was a leading figure in the Russian mob.”(163)
According to the FBI, in 1991, another Russian mobster named Semion Mogilevich, “paid a Russian judge to spring a fellow mob boss, Vyachelsav Kirillovich Ivankov, from a Siberian gulag.”(163)
Mogilevich, the FBI learned, was “involved in weapons trafficking, contract murders, extortion, drug trafficking, and prostitution on an international scale.”(165)
Mogilevich got Ivankov out of prison because he needed his professional skill set. As the New Republic reports, “If Mogilevich was the brains, Ivankov was the enforcer…infamous for torturing his victims and boasting about the murders he had arranged.”(163)
Once out of prison, Ivankov used an illegal business visa to travel to New York City. From there, “According to the FBI, he recruited two ‘combat brigades’ of Special Forces veterans from the Soviet war in Afghanistan to run the mafia’s protection racket and kill his enemies.”(163)
Ivankov was a known, high-value target for the FBI in the 1990s. But the man was hard to find, even for the FBI on their home turf. FBI agents “spotted him meeting with other Russian crime figures in Miami, Los Angeles, Boston, and Toronto.”(163)
But it would be in the greater New York area where Ivankov apparently conducted the majority of his illegal business. The FBI eventually learned that Ivankov “made frequent visits to Trump Taj Mahal in Atlantic City, which mobsters routinely used to launder huge sums of money.”(163)
Even still, the FBI was having trouble locating where Ivankov actually lived. James Moody, then Chief of the FBI’s Organized Crime department, noted, “We were looking around, looking around, looking around…We had to go out and really beat the bushes. And then we found out that he was living in a luxury condo in Trump Tower.”(163)
David Bogatin was a Russian mob boss, and Donald Trump accepted millions in illicit cash from him in exchange for luxury housing in Trump Tower.
Vyachelsav Kirillovich Ivankov was also a Russian mob boss, and Donald Trump accepted millions in illicit cash from him in exchange for luxury housing in Trump Tower.
Let’s see if we begin to notice any patterns moving forward.
Eventually, the FBI arrested Ivankov. He was extradited back to Russia on murder charges. Then, as frequently happens to those who live by the sword, “Ivankov was gunned down in a sniper attack on the streets of Moscow.”(163)
When the Soviet Union collapsed in 1991, basic and necessary functions of civil society almost evaporated. Public safety and public order were no longer being maintained by the government.
Violent crime exploded. As Zarina Zabrisky, a Russian author explains, “[in] 1993, in Moscow[,] 5,000 organized crime-related murders were recorded. Assassination became a problem.”(165)
David Bogatin. Semion Mogilevich. Vyachelsav Kirillovich Ivankov.
In the 1990s, these Russian mob bosses were major players in orchestrating a culture of criminal intimidation of civilians and violent death of one’s black market rivals in major cities like Moscow.
As Zabrisky explains, “Murder evolved into a business strategy, and high-profile killings were an early part of Russia’s post-Communist collective memory. Vladislav Listyev, the popular television journalist, was shot dead outside his apartment in a crime linked to control of the lucrative TV advertising market. Ivan Kivelidi, chairman of the Russian Business Round Table, was killed by a nerve toxin, applied, it was said, to his telephone receiver.”(165)
David Bogatin. Semion Mogilevich. Vyachelsav Kirillovich Ivankov.
In the 1980s and 1990s, these Russian mob bosses poured vast waves of dark money into Donald Trump’s businesses.
But why would they do that?
As the New Republic explains, “At the time, Russian mobsters were beginning to invest in high-end real estate, which offered an ideal vehicle to launder money from their criminal enterprises. ‘During the ’80s and ’90s, we in the U.S. government repeatedly saw a pattern by which criminals would use condos and high-rises to launder money,’ says Jonathan Winer” a top official in Bill Clinton’s State Department.(163)
The New Republic continues, “Throughout the 1990s, untold millions from the former Soviet Union flowed into Trump’s luxury developments and Atlantic City casinos…the public record makes clear that Trump built his business empire in no small part with a lot of dirty money from a lot of dirty Russians.”(163)
The context in which this flow of illicit Soviet money was pouring into Trump properties in the 1980s and 1990s is key. The Center for American Progress explains, “With the collapse of the Russian economy…Russian oligarchs who had made their fortunes buying up formerly state-held assets now sought to stash their money in international real estate. The Trump Organization offered an appealing haven for several reasons, ranging from its ostentatious gold-plated aesthetic to its reputation for lax reporting standards.”(158)
To be clear, none of this is to say that Donald Trump was necessarily in on the joke. He was billions of dollars in debt, and he is profoundly amoral, so when this highly questionable Russian money became available to him, he took it. It is possible that Donald was in fact completely oblivious to what the Russians were actually up to.
Throughout the height of the Cold War, both the United States and the Soviet Union invested heavily in espionage. There were undercover Americans in Moscow and St. Petersburg, and there were undercover Soviets in DC and New York City. Yet, when the Soviet Union collapsed in 1991, a largely overlooked imbalance quickly emerged.
In 1991, George H.W. Bush was President. Under Bush, William Barr served his first term as Attorney General. In American Kompromat, Craig Unger explains that from this powerful perch, Barr “transferred three hundred FBI agents, many of them Russian-speaking, from counterintelligence work on the Russian Mafia to investigations of gang violence growing out of the crack cocaine epidemic…the New York Times characterized it as ‘the largest single manpower shift in the bureau’s history.’”(166)
But at the same time that America was packing up its vast network of covert intelligence operators, Russia was doing the exact opposite. As the US drew down, Russia ramped up. Unger references a former CIA intelligence officer who stated, “there were more Russian intelligence officers active in the United States after the fall” of the Berlin Wall and Soviet Union, than there were before so.(166)
In the 1990s especially, swiftly and systematically, Russia injected a staggering amount of illicit cash into Donald Trump’s businesses. As Craig Unger detailed in American Kompromat, “One-third of the units on [Trump] tower’s priciest floors had been snatched up by individual buyers or limited-liability companies tied to Russia.” But at this point, Trump had started to branch outside of New York. He now held a considerable amount of real estate in Florida, as well.(166)
Russia pounced on Trump’s Florida properties. In total, “more than 1,300 Trump-branded condos in the United States were sold ‘in secretive, all-cash transactions that enable buyers to avoid legal scrutiny by shielding their finances and identities…the average price of the condos was $1.2 million.”(166)
Remember that the Soviets, who became the Russians, had already for many years been surveilling and influencing Donald Trump. The fact that Donald was a super-rich, NYC businessman was enough of a reason to consider him as a potentially valuable target for covert influence. But remember that in the 1980s, Donald also began publicly flirting with the idea of running for President. Donald’s sudden interest in politics became something he openly spoke about in public after he was flown on a luxury, all expenses paid trip to Moscow on July 4th, 1987.
Central to the KGB’s strategy towards men like Donald Trump was gathering and constructing as many different lines of kompromat (blackmailable material) as proved possible. Again, much speculation has been made with respect to the possibility of the Soviets having recorded some salacious sex-tape of Donald during his first visit to do business with his own country’s greatest enemy during the Cold War in 1987.
The sex-tape might exist, and it might not. But either way, by the 1990s, the KGB had firmly sunk their hooks into Donald Trump from multiple other angles which were ultimately just as, or even more effective in gaining leverage over him than any sex tape might have been.
Tape or no tape, from at least the 1990s onward, when the Russians called a play, Donald Trump dutifully followed the plan.
Former KGB officer Yuri Shvets observes, “the real kompromat was the money trail that connected [Donald] to Russian intelligence through massive money laundering…Everybody has weaknesses. But with Trump it wasn’t just weakness. Everything was excessive. His vanity, excessive. Narcissism, excessive. Greed, excessive. Ignorance, excessive.”(166)
In 1995, there were 560 reported contract killings in Moscow.(165)
The following year, in 1996, Donald made his second seekers journey to Moscow. At home, Donald was bleeding money, friends, and business partners by the day. His financial foundation was crumbling before the public’s eyes. Back in 1987, Donald was flown to Moscow on a private jet, compliments of the Soviet Union. But by 1996, both Donald’s and the Russian’s finances were such that he had to get himself to Moscow on his own dime. This time, flying commercial.(165)
Yet, just like that, Donald announced he’d be building two major new luxury apartment complexes in Moscow. He’d personally be investing $250 million in the project. As the Moscow Project details, “Trump files his first trademark application, for ‘Trump Tower,’ in Russia. Between 1996 and 2008, he files at least seven more trademark applications.”(167) Donald’s Moscow ambitions, however, never actually materialized.
As we’ve learned by this point, over the course of several decades, Donald would never have been able to build his business empire without the support and backing of a wide and fairly diverse network of unethical and blatantly criminal individuals and organizations. In the 1970s and 1980s, Donald relied on the Italian Mafia to build Trump Tower and his Atlantic City casinos. In the 1980s and 1990s, when Donald had gotten himself into near-crippling debt, he relied on suitcase after suitcase of dirty money from Russian mobsters to sell off about a third of the vacant units in his line of luxury condos and apartments.
In the 1980s, law enforcement agencies in Canada and the US noticed an uptick in organized crime groups from Asia operating in North America. These groups were predominantly ethnic Chinese in origin, many based in Hong Kong and Taiwan.(168)
14K Triad of Hong Kong was one of the major players. The activity this criminal organization was involved in was ranged from, “heroin smuggling, alien smuggling [human trafficking] and counterfeit credit card manufacturing.”(168)
In the early 1980s, Canadian police commenced surveillance of a network of illegal gambling dens that 14K Triad was operating in Toronto. They learned that a man from 14K Triad named Danny Leung was a “major player in Toronto organized crime.”(169)
Fast forward a few years to the early 1990s. By then, Danny Leung had relocated to the US. He found a new job opportunity, one that would prove highly advantageous to the organized crime ring he was a member of.
Asian organized crime groups had in fact become so much more powerful in the US, that in 1992, the United States Senate Committee on Governmental Affairs released a 200+ page report on the matter. In that report, we learn something incredible.(168)
The US Senate confirmed, “Danny Leung is an associate of the 14K Triad.”(168)
But there’s more.
The US Senate also revealed, “Danny Leung...is a Vice President for Marketing of the [Trump Taj Mahal] casino.”(168)
That’s right, as a 1995 article in the NY Daily News reports, “Donald Trump has employed a known Asian organized crime figure at his Taj Mahal casino for five years and is defending him against attempts to yank his license, law enforcement officials say.”(169)
Let’s give Donald the benefit of the doubt here, and assume that he had no idea who Danny Leung really was upon hiring him for a high-level position in Donald’s largest casino.
But, not too long into Leung’s high-profile tenure working for Donald Trump, the New Jersey Casino Control Commission called an entire multi-day hearing, “on the background and character of Danny Leung.”(169)
The obvious move for Donald to make in this situation would have been to simply throw Leung under the bus. Donald could have claimed, like he often does, that he’s never met a specific person now causing him trouble whom he’d at one point hired, worked with, or cheated on his wives with.
But of course, Donald doesn’t make the obvious, risk-minimizing move. Instead, he doubles down.
Incredibly, after learning that the Canadian police had been tracking Danny Leung for years as a “major player” in organized crime, and after learning that the New Jersey regulatory agency entrusted with local casino regulation was actively investigating Leung’s criminal activity in America, and after learning the US Senate itself had directly named Leung as a high-ranking member of the violent 14K Triad, which specializes largely in both human and heroin trafficking, Donald Trump decided that he had the 14K Triad’s back.
The NY Daily News revealed, “Trump is not himself scheduled to testify on Leung's behalf at the hearing, but he is sending Taj President Dennis Gomes to do that.”(169)
Instead of cutting the tie and moving on, Donald Trump chose to go to the mat for someone he knew full well was an internationally significant, violent criminal.
What exactly Donald got out of this arrangement remains unclear.
Especially since we now know that Danny Leung, while working for Donald Trump in the Taj Mahal, was caught at least once stealing from the casino. “According to evidence filed by the commission's Division of Gaming Enforcement, [Danny Leung] flew in…organized crime figures from Canada who stole more than $1 million from the [Taj Mahal] in a credit scam. The incident was never reported because Trump never filed charges.”(169)
As we’ve learned by this point, over the course of decades, Donald Trump knowingly and actively worked with an impressive litany of professional criminals and internationally operational organized crime rings from multiple nationalities. These relationships were essential to Donald’s “success” over the course of many decades.
The relationships Donald Trump cultivated with the Italian Mafia, the Russian Mafia, and the Hong Kong Mafia have now been covered in depth.
But Donald Trump made other notorious friendships as well, ones that focused more on pleasure than on business.
133. Donald claims he’s coming close to the obscenely opulent lifestyle of a man he admires, Saudi Arabian illegal weapons of war trafficker, Adnan Khashoggi
134. Donald aspires to emulate lifestyle of international criminal trafficker, Adnan Khashoggi
135. How Donald strategically lies to create a false image of himself, and to generally get what he wants
136. Forbes 400 journalist realizes Donald, Cohn, and “John Baron” lied to him and offered false evidence to get Donald’s name on Forbes list of wealthiest individuals in America
137. “John Miller” proclaims actresses and models are calling into Trump Organization to book dates with Donald
138. “John Miller” claims Donald Trump was dating Carla Bruni (future first lady of France). This never happened.
139. National Child Traumatic Stress Network on how childhood trauma impacts behavior in adulthood
140. Ivana seeks divorce from Donald under grounds of “cruel and inhuman treatment”
141. 1990 divorce deposition, Ivana reveals she was violently raped by Donald Trump
142. Michael Cohen defends Donald’s right to rape his wife Ivana
143. Donald uses “non-discloser agreement” to publicly silence Ivana
144. On Oprah Winfrey Show in 1988, Donald declares, “ultimately Ivana does exactly as I tell her to do.”
145. On TV in 1994, Donald expresses nostalgia for his life a few years prior, when he had “a beautiful girlfriend, a beautiful wife, a beautiful everything.”
146. Donald reluctantly agrees to marry Marla Maples after getting her pregnant with his daughter Tiffany
147. When Marla tells Donald that they’re pregnant, he responds, “What are we going to do about this?”
148. Donald strong-arms Marla Maples into prenuptial agreement 24 hours before their wedding
149. Politicians, celebrities, international weapons-traffickers come to be seen at Donald and Marla’s wedding
150. Donald Trump Jr. traumatized by his father’s public infidelity to his mother, refuses to speak to his father for a year and is sent off to a boarding school
151. On TV, Donald comments on his baby daughter’s legs and future breasts. “Who is Donald J. Trump?” NowThis News, Oct 2020.
152. On TV, Donald comments on his baby daughter’s legs and future breasts.
153. Marla states that her marriage to Donald was “built on an illusion”
154. Tiffany, raised by Marla alone in California, rarely saw or spoke with her father throughout her childhood
155. Czechoslovakian StB surveilled Donald Trump even at funeral of Ivana’s father
156. Young Soviet official in charge of KGB post in Dresden, East Germany in late 1980s
157. KGB post in Dresden nearly overrun during the fall of the Berlin Wall
158. Early 1990s, Donald at least $3.4 Billion in debt, his businesses are “on the verge of collapse”
159. Why Donald’s businesses and finances collapsed in the 1990s
160. Donald insists on adding unnecessary, heavy ornamentation to his airplanes, rendering them unsafe to fly
161. The 18-month rise and fall of Trump Shuttle, Donald’s airline
162. Broke and desperate, Donald asks his siblings for money to bail him out in 1993. They do, twice.
163. Sadistic killer for the Russian mafia, Vyachelsav Kirillovich Ivankov, found by FBI to have been laundering money in Trump Tower and in Trump Taj Mahal casino
164. 1984, Soviet mobster David Bogatin kicks off Soviet money laundering operation in Trump Tower
165. Out of control violence envelops Russia after fall of Soviet Union in 1991
166. American Kompromat. Craig Unger. 2021. (pg 47-48, 57-58, 163-164, 170, 175-176, 186-188, 201)
167. 1996: Donald returns to Moscow and announces plans to build two new luxury apartment complexes there
168. 1992 US Senate report on Asian organized crime in North America
169. Donald Trump hires 14K Triad Mafia leader, publicly defends him after learning that he is a member of a violent international organized crime ring