Billions of dollars in business losses, repeatedly bankrupt, stiffed thousands of subcontractors

Trump has flaunted the trappings of a billionaire such as gold plated or gold painted toilet fixtures at various properties. But his leaked tax returns dating back to 1985,¹ together with returns from years 2015-2022 that were released by the House Ways and Means Committee,² show that between 1985 and 1994, Trump lost more money than almost any other US private citizen during that era.³ Trump's losses amount to billions, as demonstrated, for example, by his remarks at a rally on August 29, 2024, in Pottersville, Michigan, referring to just his losses in San Francisco:

I lost billions of dollars, billions of dollars. You know, somebody said, 'What do you think you lost?.' I said, 'Probably two, three billion.'⁴

Trump exhibited the troubled and overstated condition of his finances, for example, by faking his way onto the Forbes 400 richest list in 1984 despite his assets actually being $5 million.⁵ He later took a middle-income New York State tax deduction in two quarterly filings in 2016.⁶ Notable instances of Trump's repeated business failures explain why he is mocked as "the hobo's idea of a billionaire."

In 1990, the year before the first of his four major bankruptcies,⁷ Trump touted his net worth at $3 billion.⁸ Actually, though, he couldn't pay bills⁹ and an audit found his balance to be $295 million in the red.¹⁰ In 2011, his wildly fluctuating claims of billionaire worth were finally laughed out of court, which examined five years of his tax records.

In 1993, he twice begged his siblings for loans.¹¹ Yet he deadpanned later that in 1993, his financial affairs "were going really great."¹² After unloading some billion dollars in personal debt on a public company in 1995 and 1996,¹³ its stock price plunged to four cents on the dollar¹⁴ before it too went bankrupt.¹⁵

Shareholders and bondholders in that public company lost $1.5 billion,¹⁶ just as Trump had stiffed hundreds of subcontractors, paying them fifty cents or less on the dollar.¹⁷ Yet afterward, Trump touted this public stock offering as "one of the great deals."¹⁸

Trump rarely actually made the charitable donations he touted in recent years,¹⁹ as other poses of billionaire status also proved bogus. His Mar-O-Lago estate in Florida was secretly mortgaged for its full $8 million value.²⁰

A Trump property in Scotland bills itself as "the world's greatest golf course."²¹ But that credit was from a shadowy rating service upon whose board Trump himself served.²² It is run by "Joey No Socks,"²³ a convicted, Mafia-linked felon.²⁴

1. The New York Times, "Donald Trump Tax Records Show He Could Have Avoided Taxes for Nearly Two Decades, The Times Found," October 2, 2016, https://www.nytimes.com/2016/10/02/us/politics/donald-trump-taxes.html; The New York Times, "11 Takeaways From The Times's Investigation Into Trump's Wealth - The New York Times," October 2, 2018, https://www.nytimes.com/2018/10/02/us/politics/donald-trump-wealth-fred-trump.html; The New York Times, "Decade in the Red: Trump Tax Figures Show Over $1 Billion in Business Losses," May 7, 2019, https://www.nytimes.com/interactive/2019/05/07/us/politics/donald-trump-taxes.html; The New York Times, "Trump's Taxes Show Chronic Losses and Years of Income Tax Avoidance," September 27, 2020, https://www.nytimes.com/interactive/2020/09/27/us/donald-trump-taxes.html.
2. CNN, "Donald Trump: Key takeaways from six years of former president's tax returns," December 30, 2022, https://www.cnn.com/2022/12/30/politics/donald-trump-tax-returns-released/index.html.
3. The New York Times, May 7, 2019, op. cit.
4. MSNBC, "Opinion | Trump's rambling is getting worse," September 3, 2024, https://www.msnbc.com/opinion/msnbc-opinion/trump-age-harris-ramble-rcna168979.
5. The Washington Post, "Trump lied to me about his wealth to get onto the Forbes 400. Here are the tapes.," April 20, 2018, https://www.washingtonpost.com/outlook/trump-lied-to-me-about-his-wealth-to-get-onto-the-forbes-400-here-are-the-tapes/2018/04/20/ac762b08-4287-11e8-8569-26fda6b404c7_story.html.
6. CNN, "Trump campaign insists income-based New York tax credit is in error," June 6, 2016, https://www.cnn.com/2016/06/06/politics/donald-trump-new-york-tax-credit-income-error/index.html.
7. David Cay Johnston, The Making of Donald Trump (New York: Melville House, 2016), p. 93.
8. Johnston, The Making of Donald Trump, pp. 77, 86.
9. Johnston, The Making of Donald Trump, p. 87.
10. Johnston, The Making of Donald Trump, p. 89.
11. Timothy O'Brien, TrumpNation: The Art of Being the Donald, Kindle Ed. (New York: Open Road Media, 2015), Loc 2527-2537.
12. The Washington Post, "Trump's tax mystery points toward the dealings around his first bankruptcies," October 3, 2016, https://www.washingtonpost.com/business/economy/trumps-tax-mystery-points-toward-the-dealings-around-his-rst-bankruptcies/2016/10/03/6e217ba4-8975-11e6-bff0-d53f592f176e_story.html.
13. The New York Times, "How Donald Trump Bankrupted His Atlantic City Casinos, but Still Earned Millions," June 11, 2016, https://www.nytimes.com/2016/06/12/nyregion/donald-trump-atlantic-city.html; The Washington Post, "As its stock collapsed, Trump's firm gave him huge bonuses and paid for his jet," June 12, 2016, https://www.washingtonpost.com/business/economy/as-its-stock-collapsed-trumps-firm-gave-him-huge-bonuses-and-paid-for-his-jet/2016/06/12/58458918-2766-11e6-b989-4e5479715b54_story.html.
14. The Washington Post, June 12, 2016, op. cit.
15. The Washington Post, June 12, 2016, op. cit.; The New York Times, June 11, 2016, op. cit.
16. The New York Times, June 11, 2016, op. cit.; Johnston, The Making of Donald Trump, p. 93.
17. USA Today, "USA Today exclusive: Hundreds allege Donald Trump doesn't pay his bills," June 9, 2016, https://www.usatoday.com/story/news/politics/elections/2016/06/09/donald-trump-unpaid-bills-republican-president-laswuits/85297274/; AP News, "'Little guy' contractors still angry at Trump Taj bankruptcy," June 28, 2016, https://apnews.com/article/10bbe40a86774bac9ad1fbd3a936c808.
18. The Washington Post, June 12, 2016, op. cit.
19. The Washington Post, "Trump promised personal gifts on 'Celebrity Apprentice.' Here's who really paid.," August 18, 2016, https://www.washingtonpost.com/politics/trump-promised-personal-gifts-on-celebrity-apprentice-heres-who-really-paid/2016/08/18/b8d087b4-5d9a-11e6-af8e-54aa2e849447_story.html; The Washington Post, "Editorial Board, Opinion, "Mr. Trump's fake charity," July 3, 2016, https://www.washingtonpost.com/opinions/mr-trumps-fake-charity/2016/07/03/fbcd52e2-3e44-11e6-84e8-1580c7db5275_story.html; The Washington Post, "Trump promised millions to charity. We found less than $10,000 over 7 years," June 28, 2016, https://www.washingtonpost.com/politics/trump-promised-millions-to-charity-we-found-less-than-10000-over-7-years/2016/06/28/cbab5d1a-37dd-11e6-8f7c-d4c723a2becb_story.html; The Washington Post, "Editorial Board, Opinion, Trump's slimy, shameless approach to philanthropy," September 21, 2016, https://www.washingtonpost.com/opinions/trumps-slimy-shameless-approach-to-philanthropy/2016/09/21/436b8ade-8034-11e6-a52d-9a865a0ed0d4_story.html.
20. Johnston, The Making of Donald Trump, pp. 81-82.
21. Johnston, The Making of Donald Trump, p. 155.
22. Johnston, The Making of Donald Trump, p. 155-160.
23. Ibid.
24. Ibid.