Donald Trump do not involve paying hush money to a porn star or conspiring to subvert 2020 election, and his notion that he is a self-made billionaire who personifies the American dream. 

Born to a rich father who made him the beneficiary of his own highly lucrative investments, Trump received the equivalent of more than $500 million today via means that required no business expertise whatsoever.

Drawing on over twenty years’ worth of Trump’s confidential tax information, including the tax returns he tried to conceal, alongside business records and interviews with Trump insiders, New York Times investigative reporters Russ Buettner and Susanne Craig track Trump’s financial rise and fall, and rise and fall again. For decades, he squanders his fortunes on money losing businesses, only to be saved yet again by financial serendipity. He tacks his name above the door of every building, while taking out huge loans he’ll never repay. He obsesses over appearances, while ignoring threats to the bottom line and mounting costly lawsuits against city officials. He tarnishes the value of his name by allowing anyone with a big enough check to use it, and cheats the television producer who not only rescues him from bankruptcy but casts him as a business savant – the public image that will carry him to the White House.

Lucky Loser reveals in detail Trump’s business record, suggesting the opposite, and he owed everything to his father Fred, one of America’s top house builders who made his fortune in the post second world war construction boom. 

Trump’s casino and real estate deals veered towards disastrous, as in every instance owning or having an option on trophy assets beat building profitable businesses. 

Trump was not going anywhere until he debuted as the host of NBC’s The Apprentice a management contest fitted inside his gilded tower on Fifth Avenue. The show got top ratings providing Trump with financial lifeline, and a platform for his successful campaign for the White House in 2016.

Pulitzer Award-winning New York Times journalists Ross Buettner and Susanne Craig’s exposes on Trump Tax record revealing  that Trump paid $750 in Federal income  tax in 2017, the year he became president. In 2008, he paid no federal income tax during a year in which he collected $18.5m   from celebrity endorsements, licensing deals and $14.8 million from The Apprentice. Trump in fact paid no federal income tax in 11 of the 18 years they examined. Trump refused to hand over his tax returns until ordered to do so by the US Supreme Court in 2021. Lucky Loser’s release have been timed to puncture the Republican candidate ahead of the presidential election in November.

The story of Trump alleging pushing aside his alcoholic older brother Freddie Jr to take over the Trump Estate empire, written by Trump’s niece Mary Trump.

Buettner and Craig blame Trump’s grip on the popular imagination on American’s awe of celebrity, “Our tendency to conflate the trapping of wealth with expertise and ability. Our eagerness to believe people of apparent status will not lie to us. Our inability to distinguish the fruits of hard work from those of sheer luck”. According to them the US tax system is rigged in favour of privileged insiders like Trump.

Lucky Loser shows how media credulousness fuelled Trump’s rise.

The New York banks were equally gullible, lending freely Trump’s personal guarantees. Wall Street only became aware after Trump’s casino empire collapsed in the mid1990s, facing a wholesale disposal of assets, although Trump escaped personal bankruptcy. 

The Apprentice,  exported from UK Alan Sugar’s The Apprentice, brought in product placement. Burger King, General Motors, Unilever all the top consumer product companies appeared on the show. At one pointy Trump was earning $1 million an episode from licensing and sponsorship deals. In the show the winning apprentice would receive $250, 000 and a year’s placement  in the Trump organisation. 

Jeff Nuclear boss of NBC News and Entertainment admitted, “ You were casting an actor… He was playing a part. We knew that. It’s called reality television, but it’s never real per se.”

Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the illusion of success by Russ Buettner and Sussane Craig, Bodley Head £25/ Penguin Press $35, 528 pages.