Anyone who followed the tabloids in New York, or followed Losin' Donnie's career looked at Trump as a clown. He inherited a pile of money upon the death of his father (who padded his real estate empire's bottom line with fraud) and immediately set about to crowd out his siblings. It's been said that if Donnie had simply placed all of his inheritance into mutual funds he would be far richer today than he actually is. Despite being handed the world on a golden platter, Trump wasn't satisfied with being an under-the-radar lord of apartment complexes in Queens, no, he wanted to swim in the exclusive waters of Manhattan's moneyed elite. Not satisfied to be anonymously well-off, not only did he want to operate in the high rent environs of Manhattan, but he wanted to be recognized and lauded for his real estate ability. The problem was that he was utterly incompetent at it. He had inherited his father's facility at fraud, but none of his ability to create wealth. What he was good at, was self promotion.
Any objective analysis of Losin' Donnie's career would reveal failure after failure in real estate and most notably, casinos. Despite his demonstrated ability to lose money and run his businesses into the ground, he managed to time after time convince banks to keep loaning him money and for investors to continue to sink funds into his ill-fated projects. The seemingly endless stream of cash continues to prop him up to this day. While one might think that a serial screw-up would eventually fade from view and be unable to fund his lavish lifestyle, Trump seems to have defied common sense (and the rules of accounting). After the first few failures, Trump learned how to structure (or hire lawyers who knew how) business arrangements so that if things went well, he benefitted, but if they didn't, he was shielded by the use of limited liability companies (LLCs).
An LLC on one hand will shield its owners from liability while the profits will flow through to those same owners. What if, as in the case of Trump's casinos, the LLC loses money? The owners get to claim it as a loss on their personal income taxes, but aren't actually presented with a bill for that loss. In addition, Trump usually paid himself a developer fee, consulting or management fee that was not tied to the profit or loss of the property. So if the venture tanked, he still received his hefty fee, and got to reduce his taxable income by his share of the loss. If the upfront money was provided by investors, he wasn't personally out any cash. If the project was funded by a bank loan, he habitually defaulted.
So why is he perceived as a successful businessman? "The Apprentice".
The real world Trump was a serial failure who defaulted on loans, mismanaged businesses, didn't pay contractors and was a bumbling idiot when it came to the myriad details of running a successful business. But the fictional Trump presented on "The Apprentice" painted him as a business genius, and this is the image that people who didn't know any better had of Losin' Donnie. Based on tax returns obtained by The New York Times, Trump's primary income in the nineties was from his work on "The Apprentice", and not from any of his real estate ventures. His actual businesses were losing money, enabling him to pay little or no federal taxes for a decade. Of course his television appearances, paired with frequent coverage in the New York tabloids gave him celebrity name recognition that would serve him well when he rode down that escalator in 2015.
Trump's fictional business acumen was one of the selling points of his candidacy in 2016. Of course, even being a successful businessman doesn't necessarily translate into being an effective president, governor or legislator. In business, the bottom line is paramount - not so in the world of governance. (But that's another article) Nonetheless, the myth persists being CEO of a large corporation constitutes relevant experience for the office of President of the United States. A lot of Americans bought into that myth, as well as the lie that Losin' Donnie was actually successful.
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