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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

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.