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.
"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.
Making Kids Play With Him
"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.
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.
"I DON'T WANNA PLAY ANY MORE!"
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.
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.
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!"
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.
"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.
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."
"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.