The Troubling History Of The Republican’s Frankenstein, Donald Trump

Published September 8, 2015
Updated September 29, 2025

From buying political favors to dodging the draft, we look inside the hypocritical and scandal-ridden history of Donald Trump.

Donald Trump History

Every four years, the United States gives the world one hell of a show in the form of the seemingly endless presidential campaign season.

While the last few months of this spectacle are usually characterized by cautious maneuvering between two very serious candidates, the first nine months of every campaign season are marked by cranks, eccentrics, and clowns from both parties elbowing each other aside to get to the microphone and bark comically extreme remarks at the base in order to secure the all-important unhinged-lunatic vote in the primaries.

Nobody is better at this game than Donald Trump.

The rough early period in presidential politics seems tailored to egomaniacal blowhards – imagine kicking off your run for the White House by accusing the entire country of Mexico of infiltrating the United States with rapists – and Trump has flourished in the scrum. As of this writing, Donald Trump leads in the polls and has emerged as the presumptive Republican frontrunner.

So, what’s his actual story? Trump has been a public figure for decades now, but as befits any natural disaster, he’s still full of surprises.

He Dodged The Vietnam-Era Draft

Donald Trump In A Cadet Uniform

A young Donald Trump. Image Source: March Matron

A standard operating procedure exists for vetting presidential candidates who were born between 1945 and 1956, and yes, Donald Trump did dodge the draft during the Vietnam War. He dodged it good, as only a rich kid could, first by getting student deferments, then – when being a college student wasn’t good enough anymore – by suffering from a terrible decline in health that saw his former A-1 designation plummet to 4-F: totally unfit for service.

Trump was born in 1946, which made him just the right age to serve in Vietnam sometime around 1964. Unfortunately for the nation’s glory, young Donald received four student deferments from ’64 to ’68, before a crippling injury left him with a bone spur in his foot, dashing his dreams of leading men in combat against the Viet Cong. Fortunately, Trump has the strength of an ox, and he recovered a few short years later – just after the war ended, in fact – in time to do heavy labor rehabbing his father’s multimillion-dollar real estate holdings.

He’s Prone to Making Wild Claims

The Troubling History Of Donald Trump

Speaking of his father’s business, Trump has consistently painted his rise to the top as the result of his own brilliance and scrappiness. Smart deals, big risks, and huge payoffs are apparently par for the course at the heart of the Trump empire.

This narrative is almost entirely an exaggeration.

Trump’s first big job for his father was to manage the Swifton Village apartment complex in Cincinnati, Ohio, which his father’s company bought at a foreclosure auction in 1964. Writing about Swifton years later in his book, Trump claimed it was his “first multimillion-dollar deal.”

The truth is that Donald was put in charge of the 800-unit complex by his dad, and his duties consisted of flying in every week or so and helping with the landscaping. Fred Trump’s company had acquired the property at a steep discount, partly by being the only bidder on the foreclosed property, invested $500,000 in renovations, then sold the place in 1972 for $1 million more than it had cost eight years before.

Trump is also fond of inventing numbers to describe how rich he is. Virtually every number he’s ever quoted for his personal wealth is inaccurate by several billion dollars.

During the 2012 circus, in which Trump used his presidential bid to promote that year’s season of “The Apprentice,” his financial disclosure forms claimed a net worth of over $7 billion. Bloomberg, however, went over Trump’s FEC filings and pegged his net worth at $2.9 billion.

These figures fluctuate with the Donald’s moods. In June 2015, Trump claimed to be worth $8.7 billion. Then federal elections officials certified his fortune at $1.4 billion. Less than a month later, Trump publicly boasted that he’s worth “over $10 billion.”

In order for these statements to be consistent, it’s necessary to believe that federal auditors mistakenly understated Trump’s wealth by over 600 percent, then that the Trump empire turned (at least) a $1.3 billion profit in three weeks.

Donald Trump

“Park the limo over there, the other limo over there, and the wish dragon on the roof.” Image Source: Seth Wenig/AP

Trump’s unreal statements don’t stop at financial disclosures. Take Trump’s birtherism, for example. Beginning in 2011, he publicly expressed doubts about President Obama’s citizenship status, urging him to release his long-form birth certificate. Obliquely referring to Trump as a “carnival barker,” the President of the United States of America was finally reduced to releasing the document in April 2011.

In a stunning demonstration of why you should never cave in to pressure from Donald Trump, Trump held a press conference in which he mused that the document might be a fake, then he called on the president to release his college transcripts.

Trump’s erratic behavior doesn’t stop with stalking the president. He’s also not above lashing out at critics who offend him. Trump sued the author of a 2006 book over the author’s estimate that Trump had a net worth of “only” around $200 million. The $5 million defamation suit was eventually dismissed, but only after the author had been dragged through several years of court proceedings.

In 2013, Trump filed another $5 million suit against late-night comedian Bill Maher for a joke Maher told about Donald Trump possibly being the son of an orange-haired orangutan. The suit was dropped after two months.

Bill Maher Joke About Donald Trump

Bill Maher doesn’t owe any damages, but he should consider paying a finder’s fee for all the jokes he got out of this. Image Source: YouTube

This litigiousness isn’t limited to people who write books and tell jokes for a living; Trump is not above using the legal system to bully legitimate, business-based criticism of his terrible investments, either. In 1990, a financial analyst published his professional opinion that the Trump Taj Mahal deal would initially turn over record-setting revenues, but go into receivership by the end of the year.

Trump went bananas and threatened to sue if the firm responsible didn’t either retract the assessment or fire the analyst. In the event, the analyst stuck to his guns, got fired, and (successfully) sued Trump for defamation after the Taj Mahal went into Chapter 11 in November 1990. The case was settled out of court for an undisclosed sum.

In 2008, Trump sued the California town of Rancho Palos Verdes, claiming that his civil rights had been violated, because the city refused to let him build a luxury development in a known landslide zone. Trump, showing his trademark sobriety and decency, sued Rancho Palos Verdes for $100 million, which was approximately five times the city’s total operating budget. After years of fruitless legal wrangling, Trump settled for a permanent environmental-impact deferment for property he already owned. . . in a place prone to landslides.

He’s a Terrible Businessman

Donald Trump Eating

Image Source: Business Insider

This all points to something fundamental about Trump’s character: he’s a lousy businessman. Over and over during his career, Trump has taken on real estate that looked (to him alone) like a good investment, only to run it into the ground almost immediately. The Taj Mahal fiasco was just the first of Trump’s five bankruptcy actions. Each time, Trump’s company, whichever one he’s using as a shell for investments, has gone under and taken outside investors with it.

The standard pattern Trump has fallen into, beginning with the Taj Mahal and continuing to his 2009 bankruptcy for the struggling Trump Entertainment Resorts (which went under again in 2014), has been to fail upwards with staggering audacity. Basically, Trump’s business model is a kind of legal fraud, in which he takes out huge loans to buy overhyped properties, then declares bankruptcy and forces his investors to claw back partial ownership in exchange for debt forgiveness and favorable repayment terms.

Speaking on the subject of his venal business practices, Trump is on record saying: “I’ve used the laws of this country to pare debt. … We’ll have the company. We’ll throw it into a chapter. We’ll negotiate with the banks. We’ll make a fantastic deal.” Most normal people would consider this dishonest, but Trump insists that lots of rich people do it, so it’s totally okay.

He’s A Hypocrite on Almost Every Subject Imaginable

Donald Trump With Beauty Pageant Contestants

Image Source: Dailymotion

This brings us to Donald Trump’s moral character, a phrase so full of contradictions that speaking it might cause an event horizon to form around your head to protect the rest of the universe from an unshielded paradox.

As far back as 1969, Trump’s management of the Swifton Village complex generated a civil rights lawsuit when a black prospective tenant was told there were no vacancies, after which the Justice Department found that in fact there were several open units. The case was eventually settled for an undisclosed sum.

Donald Trump has gone on record opposing the automatic granting of citizenship for people born in the United States, which history students will recognize as being one of the anti-discrimination measures adopted after the Dredd Scott case ruled that blacks aren’t automatically citizens by virtue of being born in America.

Apart from a depressingly popular nativism, it would be hard to name a principle Donald Trump takes seriously enough to apply to his own actions. Speaking on the subject of same-sex marriage, the current Republican frontrunner expressed his support for what he calls traditional marriage. Reminded that he’s on his fourth such marriage, and asked whether his multiple high-profile divorces render him unfit to comment on the sanctity of marriage, Trump reiterated his support for the sanctity of marriage.

Trump has consistently posed as a strict law-and-order candidate, even accepting a leadership award from the Marine Corps–Law Enforcement Foundation.

Unlike most public figures who accept leadership awards from police-affiliated organizations, however, Trump has been the target of multiple federal and state-level investigations, from the aforementioned fair-housing case to bribery and racketeering probes stemming from real estate deals with Philadelphia- and New York-based mafia crime families.

In 1986, for example, Trump bought the property that would become Trump Plaza in Atlantic City for double its assessed market value from Salvatore Testa, a gangster from Philadelphia. Construction on Trump properties, sometimes done by illegal immigrants getting as little as $4 an hour for 12-hour shifts, used contractors from the Gambino crime family as well as one deal with – no kidding – Fat Tony Salerno of the Genovese Family.

Mafia Boss Anthony Salerno

Mafia Boss Anthony Salerno.

The story of Donald Trump’s many sins can hardly be contained in a single article.

From his early efforts to skip the then-mandatory military service that less-privileged boys took on as a matter of course, to a lucrative career made with shockingly unsuccessful investments made on-margin and with other people’s money, to his comical presidential bid, perhaps the most frightening thing is that Donald Trump really is the candidate to beat this time around.

author
Richard Stockton
author
Richard Stockton is a freelance science and technology writer from Sacramento, California.
editor
Savannah Cox
editor
Savannah Cox holds a Master's in International Affairs from The New School as well as a PhD from the University of California, Berkeley, and now serves as an Assistant Professor at the University of Sheffield. Her work as a writer has also appeared on DNAinfo.
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Stockton, Richard. "The Troubling History Of The Republican’s Frankenstein, Donald Trump." AllThatsInteresting.com, September 8, 2015, https://allthatsinteresting.com/donald-trump-history. Accessed October 9, 2025.