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

By: Russ Buettner, Susanne Craig

Published by Penguin Group, 2025-09-23

An Instant New York Times Bestseller • A Washington Post Notable Book • A Financial Times Best Business Book of the Year

“A first-rate financial thriller . . . Lucky Loser is one of those rare Trump books that deserve, even demand, to be read.” –Alexander Nazaryan, The New York Times

From the Pulitzer Prize-winning reporters behind the 2018 bombshell New York Times exposé of President Trump’s finances, an explosive investigation into the history of Donald Trump’s wealth, revealing how one of the country’s biggest business failures lied his way into the White House

Soon after announcing his first campaign for the US presidency, Donald J. Trump told a national television audience that life “has not been easy for me. It has not been easy for me.” Building on a narrative he had been telling for decades, he spun a hardscrabble fable of how he parlayed a small loan from his father into a multi-billion-dollar business and real estate empire. This feat, he argued, made him singularly qualified to lead the country. Except: None of it was true. As his wealthy father’s chosen successor, Trump received the equivalent today of more than $500 million in family money. He collected a second windfall thanks to Mark Burnett, the revolutionary television producer who made Trump a star. In truth, Trump's empire was underwritten, and at times saved, by the equivalent of more than $1 billion that came his way without any of the business expertise he claimed.

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. A masterpiece of narrative reporting, Lucky Loser is a meticulous examination spanning nearly a century, filled with scoops from Trump Tower, Mar-a-Lago, Atlantic City, and the set of The Apprentice. Here for the first time is the definitive true accounting of Trump and his money–what he had, what he lost, and what he has left–and the myth of Trump, the self-made billionaire, exposed.