Lucky Loser: How Donald Trump Squandered His Father's Fortune and Created the Illusion of Success

Lucky Loser provides the most extensive reporting yet on the business acumen of Donald Trump. The book is heavily footnoted and uses sources like the IRS tax returns of the Trump Organization, reports filed with the New Jersey Casino Control Commission, other court filings, and extensive interviews with people who had worked with Trump over the years.

The book begins with a detailed history of how Donald Trump's father, Fred Trump, built the family fortune and the reputation of the Trump family that gave Donald so much support. In his early years, Fred Trump introduced a number of creative approaches for building and financing apartments during the period after WW II.

The book then continues with Donald Trump and his brothers as they show more were growing up. As Donald Trump entered into business Fred Trump was happy to let him spread the impression that Fred Trump's success and fortune was also to Donald's credit. This allowed Donald to project the illusion of success very early. During this period, the media was happy to report on Donald's wealth without verifying any of the claims which allowed him to get away with making exaggerated claims of all types. The book also shows, based upon the refusal to give him tax abatements, that Donald Trump began early to blame opposition to anything he tried as just an effort to attack him personally. The book also reviews the many court cases brought by Donald Trump and Roy Cohn attacking news people who questioned his wealth. Most of these cases were dismissed in the courts but they served to intimidate anyone who criticized him.

Donald Trump's involvements with the Atlantic City casinos is reported in great depth aided by the official reports of the Casino Commission. The public assertions of Trump were often contradicted by the official filings with the commission. This phase of Trump's career also showed him to be a businessman who could not manage the costs of his projects and could not balance expenditures to expected and actual revenues. As a result, all of his projects ended up with negative cash flows which could only be bailed out by money coming from his father. Numerous examples were also provided of Trump's lack of due diligence for the projects he invested in saying that Trump would decide to invest in projects despite experts warning him of problems. Remarkably, banks at this time were willing to loan him substantial amounts of money that he would not be able to repay.

Trump's finances were in dire straits when he was saved by the producers of The Apprentice. The producer of the show had learned that they could sell product placement as part of every episode allowing Trump to get 50% of all of those revenues. The chapters on the show also reveal how tawdry Trump's offices were when the producers first visited Trump tower to find smelly carpets and chipped furniture instead of the polished environment one would expect from a billionaire's offices. They also discovered that Trump's desk was virtually empty of actual business work and was instead littered only with clippings that had mentioned Trump.

Revenue from The Apprentice and the product placement deals was Trump's main source of income for many years. Trump tried to maximize this revenue by widely signing endorsement deals including with unsavory characters and foolish projects. For example, a number of the people involved in Trump University and other ventures were actual con men. The book also tells the story of people who, trusting Trump's name, would invest their money in apartments or projects that were never built. The book concludes with Trump's presidency and the run-up to the 2024 election. Unfortunately, the reporting of Trump's business dealings from this period is sadly very thin.

The book will be interesting to people who want a better understanding of Trump's businesses and his business skills. show less

Fascinating and shocking look at Trump's real estate career, his fortune, and his brand. The authors spent years researching all of this, and their meticulous handling of massive amounts of data is compelling and most instructive.

The book is doing really well on explaining the dealings of Trump, going into tax avoidance and similar stuff. Very good read.

The writing is excellent, highly recommend.

Great book. Likely it will be be read by many for years to come; and should be.

One of the best books on Trump.
Well researched.