Donald Trump’s Long-Documented History of Being a Horrible Person

Don’t just take my word for it; there’s plenty of evidence. Here’s some of it.

Martie Sirois
Oct 6 · 16 min read
Image by gfk DSGN from Pixabay

When we were facing the last Presidential election, I often felt floored by the folks who not only defended, but also sang the praises of then-candidate Donald Trump. “Maybe it’s time that a non-politician ran this country,” they’d offer. “Look what he’s accomplished as a successful business man! Don’t you think our country would flourish if we were run the same way?”

In short, no. I didn’t think so.

I never thought so.

In my mind, musings like these were a gateway drug for the alternative facts Twilight Zone we now find ourselves occupying — a continuum of time and space where we somehow manage to coexist alongside others who represent our polar opposites on the scales of logic and morals. It’s remarkably bizarre; we all breathe the same air, yet there are many folks who can no longer objectively agree on what a fact is.

It was no secret that Donald Trump has always been a con artist — and not even a good one! By 2016, how did people not know this? How were folks still believing Trump was a “successful business man,” let alone, a man of great moral character and stable temperament — so great and stable as to deserve the highest office in American government?

For most of my forty five years on Earth, there has been no shortage of unsavory evidence, documented, on the horribleness of “45,” the man who would end up — despite the popular will of the people — becoming the 45th President of the United States. And now, as we’re staring down the inevitable barrel of impeachment hearings, it seems the right time to send out yet another warning flare. It seems necessary to at least try, anyway, because there are still people who believe (contrary to all evidence, logic, and reason), that Trump is not a horrible person who’s fully unfit for the job, much less, the title “leader of the free world.”

But really, can anyone’s best hot take on how awful Trump is have the ability to sway his supporters? No, of course not. In fact, these things somehow persuade them to double-down harder, support him more — even at their own expense. Regardless of harm that will eventually trickle down and affect their own lives, Trump supporters won’t change course.

It’s kind of like when you tell a young child or toddler not to get near something that could hurt them (like a hot eye on a stove), and they end up touching it anyway — often, while smiling at you… at least until the shock and scorching pain sets in… which happens because their frontal cortex isn’t fully developed yet, and they lack impulse control and the ability to project future consequences resulting from current actions.

I make no attempts at hiding my utter disapproval of Trump, and no apologies for my displeasure with him. But this piece isn’t about my opinion; it’s about what has already been proven true — and publicly documented — over the span of decades: Donald Trump’s long, documented history of being a horrible person.

Image by Eric Perlin from Pixabay

A History of Racism and Scamming

In the 1940s, Donald’s father, Fred, got his start in the real estate business by building a single-family home for a neighbor in Queens. In Norfolk, Virginia during World War II, Fred Trump constructed housing for shipyard workers and Navy personnel. Upon returning post-war to his native New York, he started developing a hunger for bigger, better, flashier projects. Fred Trump soon realized that with the help of federal government loans, he could get exactly what he wanted.

Though his company eventually became known as one of the city’s “biggest developers,” it was also notoriously rife with controversy. Fred’s scamming and swindling tactics had to have been absorbed and deeply ingrained in young Donald, who is said to have idolized his father at one point in time.

In 1954, when Donald was only eight years old, his father Fred was subpoenaed to testify before the Senate Banking Committee on allegations that he defrauded the government through his FHA-insured housing developments in New York, in order to illegally reap windfall profits. During the hearing, Trump Sr. was cited for improper use of federal government loans.

Under oath, he admitted that he’d “wildly overstated” development costs (by at least $3.7 million — pg. 123) of just one of these projects known as the Beach Haven apartment complex in Brooklyn. That wasn’t the first of the Trump family’s corruption and misdeeds, and it certainly wasn’t the last.

Racial housing discrimination

During the 1970s and 80s, a man named Stanley Leibowitz was well-established in the Trump family business and managed several Trump buildings. In the 60s, though, Leibowitz was just one of Fred Trump’s assorted rental agents. It was then that he first learned of the Trump family’s housing discrimination practices.

In 1963, Leibowitz had discovered a great prospective tenant for a unit in Trump’s newly constructed Queens property, the Wilshire Apartments. The prospective tenant was a 33 year old female named Maxine Brown. She had an established nursing career and impeccable credit. She was ready to move in. She didn’t even need to see the unit; she just wanted to move out of the Harlem YWCA.

Leibowitz thought Maxine Brown was the perfect fit for a tenant — at least on paper. In reality, she was a black woman, and her application sat untouched. She persisted in calling to learn the status of her application. Leibowitz didn’t know what to say, so he contacted his boss about it. Fred Trump responded with a racist epithet.

In the words of Mr. Leibowitz:

“Mr. Trump and his son Donald came into the office. I asked what I should do with this application because she’s calling constantly and his response to me was, ‘You know I don’t rent to the N-word. Put it in a drawer and forget about it.’”

Leibowitz also recounted Donald Trump was there beside his father, and was nodding in agreement with the statement, You know I don’t rent to niggers.

Donald Trump was 17 at the time. As a young, impressionable, power-hungry guy, he eagerly welcomed being groomed for his father’s real estate development world. Growing up in the family business, Donald would’ve had frequent and ample opportunities to witness his father’s racial bias and discriminatory practices in action, but Donald already seemed to understand that “white appeal” was all just part of the deal.


By 1967, New York state investigators found that out of some 3,700 Trump Village apartments, only seven were occupied by black families. Eventually, it became common knowledge that all Trump Management employees knew to mark any apartment rental applications received from black people with a big letter ‘C,’ for ‘colored.’

This should’ve been no surprise, especially considering that according to original records from 1927, Fred Trump was arrested at a Ku Klux Klan riot, as one of 1,000 white-robed Klansmen marching through the Jamaica neighborhood of Queens. The Klansmen parade erupted into riot, resulting in the arrest of seven men — Fred Trump being one of them. Trump was detained “on a charge of refusing to disperse from a parade when ordered to do so.”

In October, 1973, the Department of Justice brought suit in Federal court against the Trump Management Corporation in its operation of 14,000 apartments and 39 buildings in Brooklyn, Queens, and Staten Island, for violating the Fair Housing Act of 1968. Specifically, for racial bias against black people in apartment rentals. Trump Management had refused to rent or negotiate rentals “because of race and color.”

It was also charged that Trump Management had required different rental terms and conditions because of race, and that it had misrepresented to blacks that apartments were not available.

A 1974 interview with a former doorman at a Trump building in Brooklyn revealed that he was instructed the following by a supervisor:

“if a black person came to 2650 Ocean Parkway and inquired about an apartment for rent, and he, that is [redacted] was not there at the time, that I should tell him that the rent was twice as much as it really was, in order that he could not afford the apartment.”

This part of the lawsuit was based on evidence gathered by testers for the New York City Human Rights Division, which alleged that black people who went to Trump buildings were told there were no apartments available, while white people were offered units.

Trump has been fond of saying that his family’s company was just one of numerous other companies around the country that were also faced with similar federal lawsuits at the time, and that his case was settled with “no admission of guilt.”

But that’s quite the spin.

Image by WikiImages from Pixabay

The Justice Department considered the case “one of the most significant race bias cases” at the time. In his usual fashion, Donald Trump acted irritated and inconvenienced over having to be in court, and of the charges, said, “They are absolutely ridiculous. We have never discriminated, and we never would.”

Trump also fought the case for two years — it wasn’t the simple, common ordeal he’d like others to believe it was — and, in taking the first settlement offer the federal government offered, the Trumps did not have to admit guilt or wrongdoing in settling the suit. Additionally, the Trump family had to make great efforts in settlement. They had to sign a consent decree which mandated the adoption of safeguarding measures, by “thoroughly acquainting themselves, their principal assistants and officers with the obligations of the Fair Housing Act of 1968.

Furthermore, they had to implement an educational training program on the Fair Housing Act of 1968 for all employees with rental or employment responsibilities, who had contact with prospective tenants, provided information to the public about rental, or accepted or processed applications for rentals, or who were engaged in any manner in the employment process.

This was only one part of the consent decree. And it wasn’t the end of the Trump family’s housing discrimination.

In 1978, the Justice Department alleged that Trump Management was in breach of the 1973 agreement. The new case dragged on until 1982, when the original consent decree expired and the case was closed.

The Central Park Five

This led to the wrongful conviction of a group of teens — four black and one Latino — Antron McCray, Kevin Richardson, Yusef Salaam, Raymond Santana and Korey Wise. They were only between the ages of 14 and 16, and collectively became known as “The Central Park Five.” After their arrest, the young men were violently interrogated and deprived of food and sleep, all contributing factors that helped coerce their confessions.

There was no DNA evidence linking the five young men to Meili’s attack. In 2002 they were finally exonerated, despite having already served most of their sentences. The actual perpetrator of the crime, Matias Reyes — a convicted sex offender and murderer already serving prison time — confessed. And his DNA matched that of the semen found at the crime scene.

In 2014, the Central Park Five settled their civil lawsuit case with Mayor Bill de Blasio and New York City for a sum of $41 million.

What does this have to do with Donald Trump? In May of 1989, shortly before the trial that wrongfully convicted these five teens, Trump paid approximately $85,000 to take out full-page ads in four different New York City newspapers that were worded to strongly call for the execution of these young boys of color. Though he didn’t use their names in the ad, he made it clear on Larry King that he was talking about the Central Park Five:

“I had some woman the other day stick a microphone in my face — from one of the major networks — and ask, ‘but don’t you have compassion for these young men that raped, beat, mugged, and everything else, this wonderful woman?’ …“Of course I hate these people, and let’s all hate these people, because maybe hate is what we need if we’re gonna get something done… I’m strongly in favor of the death penalty; I’m also in favor of bringing back police forces that can do something instead of just turning their back.” Donald Trump on Larry King, 1989

His discriminatory statements are always reflected in his behavior.

In typical fashion, Trump recklessly perpetuated the casual dehumanization of black and brown people with the release of this 1989 ad. And as recently as June 2019, Trump still refused to accept the fact that these boys were finally exonerated, found innocent. He also refused to apologize to them for the fact that he publicly called for their executions.

June of 2019 was also when we heard Donald Trump say something we’ve heard him say before — where he attempts to draw a false equivalency between two polar opposite sides. “You have people on both sides of that,” he said when asked about the Central Park Five during a Florida rally. “They admitted their guilt. If you look at Linda Fairstein” (the discredited prosecutor who oversaw their case), and if you look at some of the prosecutors, they think the city should have never settled that case,” he said.

Donald Trump has always been a con man — and a bad one

Image by gfk DSGN from Pixabay

If only there were a way to reduce Donald Trump’s plentiful crimes against humanity into a handy-dandy pamphlet, we’d really be in business. His many business failures and con jobs could be neatly compacted into bulleted lists. Maybe there could even be a summary from the numerous, unremarkable (non)memories from his fellow Wharton peers and professors. At least then, perhaps a portion of his voters could’ve gone to the 2016 ballot box as more informed voters.

Instead, it seems like many of his supporters were simply voting for who they perceived as being a “brilliant tycoon,” or “successful, wealthy businessman.” The people who based their votes on that reason, however, seemed to either not understand, or conveniently forget, that it was a carefully crafted character he played on The Apprentice — which happened to be nothing like him in real life. Full-grown adults (myself included) often need reminding of things like this — that “reality TV” is nothing like reality. In fact, it’s scripted.

These mammoth failures of every possible kind are each topics that are long and sordid stories of their own — stories for another day.

We now inhabit a world where people are more and more welcoming of the opportunity to argue with logic, science, and reason. In full defense of Trump, the same people who excoriated Barack Obama for daring to have a middle name like “Hussein” will argue, “Of course Trump had some business failures; all successful businessmen do!” But I’d argue that in Donald Trump’s case, it has been one massive failure, after another, after another. I’d argue that any business person would have to try really, really hard to fail as often and as hard as Donald Trump failed.

Again, there is quite a long documented history — public and freely available — of Trump’s abundant failures. There are enterprises, businesses, and organizations that all collapsed and failed. Not to mention, billions of dollars in lost revenues from his core businesses — you know, the one thing he was supposed to be so good at — apartment buildings, hotels, and casinos, i.e., real estate?

In just one ten-year period, his core businesses racked up losses of more than a billion dollars. Of that period, four years accounted for the loss of $359.1 million in revenue, and later, over a two-year period, his core businesses racked up losses of $517.5 million. Between 1992 — ’94, even as the economy was recovering, Trump’s core businesses managed to lose another $286.9 million.

There are equal accounts of his other failures, like the many, many times he cheated, duped, conned, swindled, coerced, or fleeced innocent people. Jonathan Greenberg, investigative financial and legal journalist and author, openly wrote of the time in 1984 when Donald Trump — posing under the fictitious Trump executive, ‘John Barron’ — lied to him about his wealth in order to have his name appear on the Forbes 400 (the magazine’s annual ranking of America’s richest people.)

Greenberg even has the tapes to prove it. (Lordy, are there tapes. Tapes for days. Tapes and tapes.)

Greenberg goes into great detail, explaining how, when Trump applied for an Atlantic City casino license, a 1981 New Jersey Casino Control Commission report revealed that Trump had an income of about $100,000 a year, while his 1979 tax returns showed a $3.4 million taxable loss; his personal assets consisted of a $1 million trust fund that Fred Trump provided to his children and grandchildren, a few checking accounts and a 1977 Mercedes 450SL; he possessed a few parcels of valuable but highly leveraged real estate, financed with $22.5 million in debt, all of it secured by his father’s assets. Donald himself did not own a safe deposit box or stocks in publicly traded companies.

In another New Jersey Casino Commission report from 1991, it was revealed that by the end of 1990, Trump’s entire cash position — in both his business and personal accounts — was just $19 million; an insufficient amount to pay the debt on his over-leveraged casino and real estate holdings while still covering his personal expenses of $1 million per month.

Image by David Bruyland from Pixabay

The bottom line is, everything about this guy is a smoke-and-mirrors show. His fans argue that’s exactly the point — the fact that we’re even talking about him right now is their “proof” that he’s good at his job, i.e., dominating the media. But I’d argue no, he’s not good at it, not any more than I’d consider Ted Bundy “good at” being a serial killer.

According to Greenberg, “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.”

In the domain of intelligence, unless you consider “scammer” a legitimate, ethical job, he’s grossly lacking. And honestly, he’s not even good at being a scammer. If he were, none of us would be the wiser. All it takes is a little Psychology 101 to understand this. His shameless plugs boasting of his enormous “wealth” should be enough of a red flag for the average Joe to see through — he’s not anywhere near as wealthy as he’d like to be.

He’s more of a throw-it-at-the-wall-and-see-what-sticks kind of guy. He seeks and finds the suckers who buy his snake oil, and then he panders to them. As Greenberg states, He sells average everyday Americans “chances to lose money at his casinos’ slot machines; he grants them admission to real estate society through the scam that was Trump University; he offers them armchair viewing of crass demonstrations of cruel power in ‘The Apprentice.’”

That about sums up the gist of it, though there’s still so much more.


If recent history has taught us anything, it’s that Donald Trump is a guy of profuse refusal. He refuses to acknowledge obvious mistakes and verbal gaffes. He refuses to admit guilt. He refuses to hold himself accountable. He refuses to correct lies. He refuses to apologize.

Instead, he relies on various unhealthy coping mechanisms to deal with cognitive dissonance — behaviors likely learned and adopted during his childhood. One example is how he doubles down on lies, even in the face of evidence. Another is how he uses psychological projection, meaning, he regularly accuses others of the offenses he’s guilty of committing.

But perhaps most troubling is his use of various psychological manipulation tactics in order to control others. We see this whenever he attempts to gaslight the country, like when he denies he said something that everyone clearly heard him say. While it might seem like a person capable of doing these things is clever and powerful, these are actually not hard behaviors to learn; it’s simple schoolyard bully behavior.

Image by Tibor Janosi Mozes from Pixabay

Of course, also added to the conglomeration that results in Donald Trump is a big splash of toxic masculinity, and a compelling case of several psychological phenomena occuring all together, from the very likely narcissistic personality disorder, to .

Donald Trump was born into economic privilege — albeit money largely obtained by fraud. He’s also had a lot of dumb luck so far, and there’s no shortage of high friends in low places. Otherwise, he’s pretty much an imbecile in everything, only he doesn’t know he’s an imbecile. In other words, he’s the Dunning-Kruger Effect, personified.


For more pieces like this that explore self, culture, equality, and politics follow The Evolver, a new publication on Medium for thinking, doing, and living — but better.


Martie Sirois (pronounced “sir-ROY”) is a top writer in Culture, Politics, and LGBTQIA for Medium, editor-in-chief of Gender From the Trenches, and has been a featured contributor for HuffPost, Scary Mommy, NPR affiliates, and SiriusXM Insight, among others. Martie is the founder of S.E.A.R.CH., a program of her local LGBT Center, for trans youth and their parents. Connect with Martie on Twitter, Facebook, or Instagram.

The Evolver

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Martie Sirois

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social/political commentary; heard on NPR affiliates; SiriusXM w/John Fugelsang; TIFO Podcast; featured contributor HuffPost & others. Mom of 3, trans advocate.

The Evolver

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