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Donald Trump is the most public asshole since Goatse and has done even more degrading things for fame. He's aligned himself with Birthers and turned the Presidency of the United States into an ad for reality TV, and that's just so far this year. The terrifying thing is that Trump is winning. He's made such a joke of himself in the process that it's easy to miss the immense balls required to do what he does in public, and get away with it. At a certain point, you have to take a step back and marvel at the rap-sheet of dick-headed insanity he's managed to put together.

Building Flying Golden Toilets (On Bad Credit)

In 1988 Eastern Air Lines routes were about as profitable as Indian buffalo hunting grounds, and dying out faster. Trump's cunning plan was to buy them and make them more expensive. He justified the increased fares with the sort of pointless bling typically reserved for silver-plated watermelons. The Trump Shuttles featured maple wood veneer floors, chrome seat belt latches, and gold-plated toilet fittings so that the passengers could know how it felt to value money as much as Trump does.

His idea of the Mile High Club is to screw investors up there

The purchase was financed by a $380 million loan from 22 banks and not one of them ever saw a cent. As we'll soon find out, Trump has knocked over more banks than the Joker, who at least leaves once he's taken the money. Trump tends not to be satisfied with ruining mere days. For instance, after he defaulted on the loans the banks were forced to repossess the airline's assets, which it turns out were worth approximately as much as the Hindenburg's spare gas tank. They couldn't sell them, they couldn't use them, and they had to negotiate a settlement to force the company to even try to turn a profit. Since then it's been repeatedly re-merged with other divisions in the world's only financial application of homeopathy. They seem to be attempting to dilute it with enough other companies that Trump's presence will stop mattering quite as much.

Telling People They're Lucky (That He Didn't Rip Them Off Harder)

Trump Ocean Resort Baja: those four words contain the entirety of Trump's contribution to the project. None of this stopped the Trumps (multiple, him and his and daughter Ivanka) from pushing the Mexican resort like the Lost City of Gold. The project collected 32 million dollars from investors, and then promptly sent them a letter saying that loan negotiations had collapsed. It also informed them that the buildings that were supposed to be built with the money didn't exist, then closed by quoting the part of the contract that said the company was allowed to spend the deposits anyway. Mission accomplished, Trump removed his name from the project the next month. He then told interviewers that investors were "lucky" because they'd have lost even more money if anything had been built.

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Customers give us money for goods. "Customers" just give us the money.

How? Would the laborers have stolen bricks from their houses to build the resort? Rather than asking such questions, several victims sued Trump and developer Irongate to recover their $32 million, and his response was to sue Irongate as well - for $40 million. This is a man who charges eight million dollars for even being reminded that he screwed people over. Unfortunately, Irongate were bankrupt before either suit started.
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Suing People For Saying He's Rich

New York Times author Timothy O'Brien wrote that Trump "only" had 250 million dollars, so Trump sued him for five billion. Suing a writer for five billion dollars takes more piss out the legal system than the Supreme Court's plumbing.

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He also objected to legal documents from Deutsche bank valuing him at three quarters of a billion, and argued with Forbes magazine when they valued him at three billion. He pits his own delusions against every legal and financial fact available, but in his defense that is his only job skill. We're not sure how insecure in your manhood you have to be to argue with ten-digit wealth, but we're guessing Trump's penis is a socket.

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Trump distracted by the phallic microphone, imagining the joys of such (or any) size.

In March 1990 he threatened to sue a stock brokerage over an analyst who said the Taj Mahal casino hotel wouldn't work out. The company proceeded to fire the broker and deny being influenced by Trump. Within a year the analyst was proven right and got three quarters of a million from the brokerage (and an undisclosed sum from Trump), making him the only person the casino made money for. As of 2011 Forbes values Trump at 200 million, while Trump claims fifteen times that much. We're not going to take sides since we'd rather not be sued, so we'll just point out that Forbes has not filed for Chapter 11 bankruptcy four times.

Managing to Turn the 9/11 Mosque Debate Into Even More of a Circus

The Ground Zero mosque debate mocked every single word in that phrase: it wasn't at ground zero, it wasn't a mosque, and if it was a debate then shit-flinging monkeys are trade envoys. CNN, Fox, and thousands of Americans spent the middle of 2010 whipping each other into a racist lather, and Trump offered to pay 7.5 million dollars for the oppurtunity to appear on TV shouting "ME TOO!" There were so many insanities in his offer that he had to mix lithium into the printer ink to stop it from becoming pictures of screaming bat-children.

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In the written offer to the owners of the property, Trump stated that he respected freedom of religion so much that he was prepared to pay 7.5 million dollars to prevent a community center with a prayer room from being built on their property. It also stipulated that the mosque should be built "at least five blocks further from the World Trade Center site," essentially asking the owners of the property to magically force-field other sellers hundreds of meters away. Apparently the zoning radius of insane racism is between 2 and 7 blocks. It's probably safe to assume Trump knows the exact radius of stupidity because he has to buy belts. The landowner replied via lawyer to say he found the offer both laughable and insulting, to which Trump replied, "Classic Trump!"
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Personally Owing Almost A Billion Dollars.

In the early 90s, Trump found himself the owner of a personal debt of $900 million. That's not the companies he owns. At the time, his companies were in $3.5 billion of corporate debt. No, he himself owed almost a billion dollars personally after somehow convincing the world he was worth more than NASA's 30-year Voyager missions to Jupiter, Saturn, Neptune and Uranus.

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Though he also qualifies as a gas giant.

You could offer to buy everyone in the United States a drink and not owe as much money as he did. He could have personally cancelled out the Seychelles' economy by moving there.

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En route to the Reel Jeenyusses Conference

While sane men with jobs can't borrow a few grand, a man who's filed more 11's than a fantasy soccer manager was allowed to spend the lifetime income of over five hundred of them before anyone noticed he didn't actually have it. The corporate debts equal the entire education budget of two states, meaning society would actually have seen the exact same fiscal return if they'd invested the money in educating millions of children. And people still lend him money today. Enjoy that thought as you chew dry macaroni to pay off your student loans.

Suing Deutsche Bank (For Mentioning How He Ripped Them Off)

Trump burrowed $640 million from Deutsche Bank to finance the Chicago Trump Tower and hotel. He pulled it off by personally guaranteeing $40 million, and ensuring that nobody who knew how little that meant talked to anyone at Deutsche Bank. When they asked him to pay it back he instead sued them for three billion dollars. That's not a typo, though the bankers probably thought so when the lawsuit arrived. Instead of making a token good faith payment towards over three hundred million owed at the time, he took them to court, claiming a yearly interest of negative 1250 percent. While we don't know lots about finance, we're told that he might as well have claimed that he was trading Energon crystals to Skeletor.

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"Banks want loan money back now? What a country!"

Trump claims that the "force majeure" clause in the loan contract -- the one that protects borrowers from forces beyond anyone's control like lightning strikes and earthquakes -- should apply to the real estate market. He was claiming that the housing market crash was a literal Act of God. His argument was essentially that he should only have to pay back his loan if he made money. When Deutsche Bank noted in court that "Trump is no stranger to overdue debt," he sued them for damaging his reputation. He publicly turned his own "personal guarantee" into a threat of ten digit legal hassle. No one has turned their word into that much pain since the Cruciatus curse. Both sides eventually dropped their cases, which pretty much sums up his business plan: successfully make things so stupid the people who are actually trying to make money would rather lose forty million dollars than continue to be involved with you.
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Making Kids Play With Him

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"Hi kids, grab my Ts and we'll start playing together!"

In 1989 Trump decided to put his face on the fifty million dollar bill, and realized that children were the only people stupid enough to buy that. This was particularly pathetic because he actually had that much real money at the time and apparently couldn't think of anything better to do with it. The Trump board-game was the most childishly annoying waste of wealth since Richie Rich. He's on the notes, the board, the cards -- people have family albums with less pictures of themselves.

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Ego incarnate

The game is an Olympically special version of Monopoly. All the squares were Trump properties that have mostly gone bankrupt since then. The children's board game market was especially appropriate for Trump since his financial strategy resembles a younger sister playing Snakes & Ladders -- keep rolling the dice, hope you move forward, and when you lose too much knock over the board and start yelling at people.

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The original pieces were all T's, which made it impossible to tell them apart, as well as taking T in vain (a pitiable offense in the late 80's.) The game was relaunched with the words "You're fired!" added for the Apprentice audience, because two extra words is about their maximum capacity.

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The reality TV version of the game also had simpler rules, but we didn't need to tell you that.

Demanding A 25% Tariff On Chinese Goods

During his recent live-action satire of American politics and media he proposed a 25 percent tariff on Chinese goods, a move that would detonate the US economy faster than minting quarters out of plutonium .He then went on the Today show to demonstrate why anyone who ever lent him money was an idiot, summing up the US's relationship with China by saying: "They have some of our debt. Big deal. They don't have the cards. We have the cards." This is a man who considers owing someone almost a trillion dollars as the time to start playing tough. If Trump was flushed out of an airliner and you tried to sell him a parachute on the way down, he'd sue you for implying he could fly.

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Brewster has invested money better than Trump.

This turned even the Club for Growth (aka "The John Galt Fan Club") against him, and their four favorite things are "The government getting money from somewhere other than taxes" and "U-S-A! U-S-A!"
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Fencing A Married Couple Into Their Own Home (And Sending Them The Bill)

A golf course owner sent his hired henchmen to fence off a house he didn't like the look of, so we're already halfway into a movie teaching children the value of teamwork. By now you probably recognize such cartoonish assholery as the work of Trump. That's free Cracked investment advice. Trump engaged Disney-movie levels of villainy by applying for planning permission on land he didn't own, and trying to bully a married couple out of their home of 20 years once he realized he didn't own it.

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"I bet you ten million I can hit an orphan from here."

He sent workers to fencing off of the whole house from the outside then sent Mr & Mrs Milne a four thousand dollar bill for the work. Trump has apparently realized that it's everyone else's fault for letting him act like this, so he's decided they should pay for it too. It's such an over-the-top dick move we're expecting him to be foiled by a talking computer-animated animal.

Having The Balls To Pretend He's a Good Businessman

In The Apprentice Trump casts himself as a high-powered executive, in the same way a teenage boy might cast himself as James Bond infiltrating a Cheerleader Dorm. Total fantasy. Trump has been replaced in more businesses than toner cartridges, and has cost the business world more money in the process. He's had 19 failed businesses in 17 years and many of Trump's floundering companies were given debt relief on the specific grounds that Trump no longer be in charge of them. In 1991 the Taj Mahal hotel casino escaped bankruptcy when he gave up 50 percent of his ownership. In 1992 the Trump Plaza Hotel filed Chapter 11 and was forgiven some of its debt when Trump gave up 49 percent of his stock and was demoted to an unpaid "chief executive," forbidden from being involved in the day to day running of the company. That's the corporate version of being told to go do "free reading" in the corner while the class gets on with math.

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The Chief Executive hat.

In 2004 Trump Hotels and Casinos filed for bankruptcy, forcing Trump to step down as CEO and cut his share of stock from 56 percent (in charge) to 27 percent (hell no). Losing money in a casino when you own it is financial failure the likes of which hasn't been seen in Atlantic City in years, and they're in the financial failure business. Trump Entertainment Chapter 11-ed in 2009, forcing Trump to leave the board of executives. GoTrump.com entirely folded in 2006. If Trump went on a cocaine binge in a cloning factory there still wouldn't be so many Trumps losing money so quickly. He has publicly admitted "I do play with the bankruptcy laws--they're very good for me."

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"And people still give me money!"

Despite all this, Trump still believes he deserves to pick his own nickname, "The Donald", which is why we haven't used that name in this article. Screw you, Trump, The Duck is "The Donald" around here. Hell, we'll take financial advice from Howard the Duck before you. At least he only massively publicly failed once. Fans of incredibly rich adventurers in legality should read The 5 Craziest Exploits Of The World's Shadiest Politician, or 6 Objective Reasons The US Army Should Invade BP.

Luke McKinney also tumbles and has a website.

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