"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.
"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.
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!"
"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.
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.