I just finished a book titled, Lucky Loser by Russell Buttner and Susanne Craig
. They were New York Times reporters who have written extensively about Trump's finances. The book amounts to an autopsy of Donald Trump's career.
The book begins with the career of Trump's father Fred. Whatever his personality defects (His granddaughter, Mary, a clinical psychologist, believes that he was a sociopath). Fred Trump was an extremely talented and successful business person. Originally, he was a home builder. His success was based upon careful calculation and control of the costs of the houses he was building.
During the Great Depression, he took advantage of New Deal housing programs and his close ties to the Tammany Hall Democrats of Brooklyn and Queens to begin developing apartments. He exploited loopholes in the programs to vastly overstate building costs. Fred could then get mortgages which provided cash beyond construction costs.
Once the apartments were built, his penny pinching ways reasserted themselves in maintenance of the buildings. His vile reputation as a landlord spurred Woody Guthrie to write a song about his racist policies. Fred also created dummy companies to provide annual income to his children while avoiding gift and inheritance taxes.
All of this occurred well before Donald came of age. Fred first tried to groom his eldest son, Fred, jr to manage his empire. That did not work out, so Donald was drafted into the role of successor.
By now the American public is well acquainted with the grandiosity of Donald Trump's plans. Everything must be the biggest and the best and completely unprecedented. This was present from his earliest days as a public figure. His father continued to support Donald's pipedreams with the resources of his immense wealth. However, Donald did not adopt the methods which enabled Fred Trump to acquire that wealth. He never exercised the disciplined control of costs which made Fred so successful. Instead his father's great wealth became a cushion which disguised his repeated failures.
From the reporting in this book, it appears that, with the possible exception of Trump Tower and a Wall Street office building, Donald Trump has never made a profit in any of his businesses. In the early 2000s, The Apprentice and the sponsorship opportunities the show generated were enough to keep him afloat financially. He was also the beneficiary of tax breaks generously extended in light of his business losses. In short, the myth of Donald Trump, master businessman, which he assiduously promoted is merely the fantasy of a delusional narcissist.