Lucky Loser tells the story of Donald Trump’s less-than-stellar business career and how he was able to misrepresent it as a success.

It is written by New York Times investigative journalists, Russ Buettner and Susanne Craig. Both have won Pulitzer Prizes for earlier analyses of Trump. Another badge of honour is Trump sued them – and lost.

They are by no means the first writers to expose the Potemkin village that is Trump’s business empire. A telling insider account came from Trump’s niece, psychologist Mary Trump, who revealed the creator of Donald’s fortune was his father Fred.

Setting things straight

However, at more than 500 pages, including more than 40 pages of notes on sources, this new book is the most comprehensive rendering. It is detailed, clearly written and has been well-reviewed in the financial press and by economic historian Brad de Long.

The authors aim to draw on financial statements and interviews to “set straight Donald Trump’s chaotic onslaught of untruths and misdirection”.

A large part of the Trump mythology is the lie that he is a self-made billionaire. In the presidential debate with Hillary Clinton, Trump sought to downplay the contribution of his father, saying “my father gave me a very small loan”. The book reveals his father’s contribution, in today’s money, was around half a billion dollars.

Trump’s first piece of luck was being born the son of hard-working, cautious and competent residential property developer Fred Trump, the son of a German immigrant. His second was that Fred’s eldest son did not have the ruthless drive to become Fred’s successor, and Fred did not consider his daughters as potential successors. So despite some characteristics that were the antithesis of his father, Donald became his heir.

The book describes Fred’s career in some detail. The first hundred pages are mostly about him. Once Fred stepped back, Trump diversified his father’s company to form what the authors term “an eclectic conglomerate untethered from any core competency.”

Another piece of luck was been chosen to star in the reality television series The Apprentice, from which he made a lot of money, including from licensing deals, for the small amount of time he spent on it.

The producers of this series have a lot to answer for, as they wanted to present their star as the astute businessman  they knew him not to be. As they said, it was “not a documentary”. But it enormously and misleadingly raised Trump’s profile.

Wins followed by losses

The authors describe how some of Trump’s ventures, such as the development of Trump Tower, went well as the Manhattan property market boomed. He also profited from some “greenmailing” (buying shares in a company with the stated or implied intention of taking it over and then selling the shares at a higher price), facilitated by exaggerated accounts in the media of his wealth.

But Trump used up much of the proceeds of his few successes covering his losses on a range of his other business ventures.

Among his notable failures was Trump University, where he paid A$37 million to settle lawsuits for fraud. Many other property projects, Scottish golf courses, Trump Ice bottled water and Trump Mortgage, never turned a profit. And the punters were not the only ones losing money in Trump casinos.

While he has fought to keep them secret, what has emerged from Trump’s tax returns are a series of huge losses.

A conundrum not really addressed in the book is why so many bankers were willing to lend to him.

The book concentrates on Trump’s career before the 2016 election, when the flawed US electoral system turned his almost 3 million vote loss on the popular vote into a win in the electoral college. As president, he disregarded conflicts of interest. As the authors note, parties wanting to influence the president could funnel money to him by booking blocks of rooms at his hotel.

After 81 million Americans voted to fire him in 2020, Trump’s businesses again performed poorly.

Trump’s current wealth is estimated by Forbes at A$5.7 billion (less than it was a decade ago). But about half of this is from his majority stake in Truth Social, promoted as a right-wing alternative to Twitter. (Now, it could be said, an even more right-wing forum than X.) It has tiny and falling revenues and makes large losses. If Trump loses the election, its value will probably soon be close to zero. It is regarded as a “meme stock”.

Buettner and Craig conclude Trump “would have been better off betting on the sharemarket than on himself”. Analysis cited in The Economist in 2018 concluded that had Trump just put the money from his father into a sharemarket index fund he would have had A$2.9 billion in 2018. Given subsequent rises in the US stockmarket that would have grown to around A$5.9 billion by now, more than most estimates of his wealth.

Forbes reached a similar conclusion, as did De Long and US political commentator Professor Robert Reich. The self-described business genius destroyed rather than created value.

A poor tycoon and a poor president

This business record of mismanaging an inheritance is reflected in Trump’s economic performance as president. He inherited the world’s largest economy from Obama. By the end of his term it was more than 10% smaller than China’s economy. Historians rank him one of the worst performing presidents on economic management (and much else). The public gave him the lowest approval ratings during his presidential term.

Trump has indeed been a “lucky loser”. But if this deeply flawed man is returned to the presidency, the world will be an unlucky loser.