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Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created The Illusion of Success is a nonfiction book by New York Times investigative journalists Susanne Craig and Russ Buettner. It was published on September 17, 2024 by Penguin Random House LLC.

It covers Donald Trump’s inherited wealth, financial and business practices alongside providing insights into his many claims on being a self-made man. The book also delves into Trump’s father Fred Trump’s wealth and fortune and how that was used as a financial leverage for his son and challenges the long-standing narrative that Trump built his empire from a modest loan, instead revealing that he inherited the equivalent of over $400 million from his father.

Demonstrating how Trump, despite receiving substantial financial backing, repeatedly lost money on ventures only to be bailed out by luck or the efforts of others was able to use the television show The Apprentice to rebrand himself during financially difficult times, ultimately leading to his political ascent​.

Background

On October 1, 2016, The New York Times published an article co-authored by Craig, which stated that Donald Trump had reported a loss of $916 million in 1995, which could have allowed him to avoid paying income taxes for up to eighteen years. In subsequent television interviews, Craig identified herself as the reporter who had received a portion of Trump's 1995 tax records in her mailbox from an anonymous sender, who was later revealed to be Mary L. Trump.

On October 2 2018, Craig and Buetner were among the three investigative journalists for The New York Times that wrote a 14,000 word exposé that revealed Trump’s many fraudulent business practices and tax schemes and refuted the former President's claims of self-made wealth and entrepreneurial accomplishments. The story is among the longest ever published by the paper and involved over 100,000 pages of of documents both from from public sources and confidential disclosures. These included "mortgages and deeds, probate records, financial disclosure reports, regulatory records and civil court files," for publicly available documents and private records such as "bank statements, financial audits, accounting ledgers, cash disbursement reports, invoices and canceled checks."

They, alongside David Barstow, went on to win the Pulitzer Prize for Explanatory Reporting in 2019 “for an exhaustive 18-month investigation of President Donald Trump’s finances that debunked his claims of self-made wealth and revealed a business empire riddled with tax dodges." They also shared the 2019 George Polk Award for Political Reporting.

Synopsis

The book is split into four parts alongside an introduction and epilogue.

Part I

Part II

Part III

Part IV

Allegations

Inheritance vs. Self-Made Narrative

The book reveals that Trump inherited the equivalent of over $400 million from his father, Fred Trump, directly contradicting Trump’s public narrative that he built his real estate empire from a small loan.

Consistent Business Failures

Trump’s financial history is marked by a series of failed business ventures, including casinos, airlines, and real estate projects. Despite this, the authors allege that he was repeatedly bailed out either by family support or fortuitous financial deals.

Tax Avoidance

The book presents allegations that Trump engaged in aggressive tax avoidance strategies, including declaring significant losses in his businesses to offset his tax liabilities over many years. These practices, while possibly legal, call into question the accuracy of Trump's portrayal of his financial success.

The Apprentice’s Role

Lucky Loser alleges that Trump’s role on *The Apprentice* played a crucial part in reviving his public image as a successful businessman during a period when his real financial situation was far from robust. The show rebranded him, helping him monetize his persona despite mounting financial difficulties.

Licensing and Debt Maneuvering

The book details how Trump relied on licensing his name for various businesses and taking on large amounts of debt, often with minimal personal financial risk. Many of these deals led to lawsuits and financial entanglements that he was able to sidestep, often without fulfilling the loans.

These allegations are supported by years of investigative reporting and are documented through the authors' access to Trump’s tax filings, making them significant contributions to understanding the real financial story behind Trump's public persona.

The authors received a cease and desist letter from Trump’s lawyers regarding the chapter on The Apprentice

Reception

Promotion

Critical reception

References

1. "Donald Trump Tax Records Show He Could Have Avoided Taxes for Nearly Two Decades, The Times Found". The New York Times. October 2, 2016.
2. "Tax documents are 'important window' into Trump". NBC News. October 4, 2016. Retrieved 2021-03-04.
3. Drum, Kevin (2018-10-02). "Times Report: Trump Wealth Largely Based on Tax Scams and Bailouts From Dad". Mother Jones. Retrieved 2024-09-22.
4. "David Barstow, Susanne Craig and Russ Buettner of The New York Times". Pulitzer.org. 2019. Retrieved 20 May 2021.
5. Polk, Eileen (February 19, 2019). "New York Times Wins Two George Polk Awards". The New York Times. Retrieved 20 May 2021.