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Lucky Loser — behind the myths of Donald Trump’s fortunes

Russ Buettner and Susanne Craig lay bare the financial facade — and the credulous system that believed the boasts

Another day, another indictment. The latest charges against Donald Trump do not involve paying hush money to a porn star or conspiring to subvert the 2020 election. They appear in a new book which strikes at the heart of the Trump myth: the notion that he is a self-made billionaire who personifies the American dream.

Lucky Loser, an exhaustive study of Trump’s business record, suggests exactly the opposite. Trump owed everything to his father Fred, one of the country’s top housebuilders who made his fortune in the post-second world war construction boom. With a couple of exceptions, Trump’s own casino and real estate deals veered between indifferent and disastrous. 

In every instance, owning or having an option on trophy assets beat building profitable businesses. Trump was going nowhere fast until he debuted as the blowhard host of NBC’s The Apprentice — a gladiatorial management contest filmed inside his gilded tower on Fifth Avenue. The show skyrocketed in the ratings, providing Trump with a financial lifeline and a platform for his successful campaign for the White House in 2016.

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