As long as you’ve inherited a ton of money, being a terrible businessman isn’t necessarily a problem. For example, it can prevent you from having to pay federal taxes for a decade or two:
Donald J. Trump declared a $916 million loss on his 1995 income tax returns, a tax deduction so substantial it could have allowed him to legally avoid paying any federal income taxes for up to 18 years, records obtained by The New York Times show.
The 1995 tax records, never before disclosed, reveal the extraordinary tax benefits that Mr. Trump, the Republican presidential nominee, derived from the financial wreckage he left behind in the early 1990s through mismanagement of three Atlantic City casinos, his ill-fated foray into the airline business and his ill-timed purchase of the Plaza Hotel in Manhattan.
Tax experts hired by The Times to analyze Mr. Trump’s 1995 records said tax rules that are especially advantageous to wealthy filers would have allowed Mr. Trump to use his $916 million loss to cancel out an equivalent amount of taxable income over an 18-year period.
It is overwhelmingly likely that two of the major theories for why Trump doesn’t want to release his tax returns — that they would show that he pays little or no federal taxes, that they would reveal him as a shitty businessperson who can’t make businesses profitable even though he refuses to pay a lot of people — are both correct. The story is also good by showing the massive tax advantages available to the .1%.
In related news, I strongly recommend Small Potatoes, the 30 for 30 documentary that concludes with Trump singlehandedly destroying the USFL.