Lucky Loser (book)

Lucky Loser: How Donald Trump Squandered His Father's Fortune and Created The Illusion of Success is a nonfiction book written by New York Times investigative journalists Susanne Craig and Russ Buettner and published on September 17, 2024 by Penguin Random House LLC. It covers Donald Trump's inherited wealth, financial and business practices, with insights into his claims on being a self-made man.

The book delves into how Trump's father Fred Trump's wealth and fortune was used as a financial leverage for his son. It challenges the long-standing narrative that Trump built his empire from a modest loan, instead saying that he inherited the equivalent of over $400 million from his father. Craig and Buettner say that Trump, despite receiving substantial financial backing, repeatedly lost money on ventures, only to be bailed out by luck or the efforts of others. He was able to use the television show The Apprentice to rebrand himself during financially difficult times, ultimately leading to his political ascent.

In September 2025, Trump sued Penguin Random House and the New York Times for $15 billion in damages, alleging that the book is defamatory.