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  • Denis Pepin

Don the Con: The Long and Sordid History of Trump’s Bankruptcies and Failures

Updated: May 12

Close-up of Donald Trump
Donald Trump (CyberNesco)

Donald Trump, the former president and self-proclaimed billionaire, has a long history of bankruptcies and failures. He has filed for Chapter 11 bankruptcy protection six times, more than any other major U.S. corporation in the last 30 years. He has also been sued for fraud, defamation, and breach of contract by countless individuals and entities, including his former students, customers, and investors.

Now, amid heightened uncertainty, Donald Trump is currently grappling with securing a bond for a $464 million judgment, and his legal team faces challenges in meeting the deadline to post the appeal bond. If the penalty is upheld on appeal, he will indeed shoulder a significant financial burden. Additionally, recently he has deposited a bond of more than $91 million to appeal the $83 million judgment against him in the case brought by E. Jean Carroll.

Some of his most notorious failures include:


Trump Shuttle: An airline bought in 1989 and operated between New York, Boston, and Washington D.C. It was plagued by high costs, low revenues, and safety issues. Trump defaulted on his loans and sold the airline in 1992 at a loss of over $100 million.


Trump Casinos: A series of gambling venues that Trump owned or operated in Atlantic City and elsewhere. They were supposed to be the crown jewels of his empire, but they turned out to be colossal disasters. Trump's involvement in the casino business included multiple bankruptcies, such as Trump Taj Mahal in 1991, Trump Plaza Hotel and Casino in 2014, and Trump Entertainment Resorts in 2014. The failures underscored the volatility of the casino industry and Trump's inability to manage it. He also faced lawsuits from contractors, employees, and regulators who accused him of cheating, stiffing, and deceiving them.


Trump University: A for-profit education company that promised to teach students the secrets of Trump's success in real estate. It was shut down in 2010 after multiple lawsuits accused it of being a scam that charged exorbitant fees and provided worthless courses. Trump agreed to pay $25 million to settle the lawsuits in 2016.


Trump Vodka: A brand of vodka that Trump launched in 2005 and claimed to be one of the best in the world. In reality, it was produced in the Netherlands and Germany by Drinks Americas under license from the Trump Organization. The vodka was discontinued in the U.S. in 2011 due to poor sales and lawsuits over unpaid bills and royalties. Trump also falsely claimed that he drank Trump Vodka, when in fact he is a non-drinker and never tasted it.


Trump Steak: A line of premium steaks that Trump launched in 2007 and sold exclusively through The Sharper Image, a retailer of gadgets and novelty items. The steaks were discontinued after two months due to poor sales and negative reviews. Trump blamed the failure on the retailer, saying it was "not the right place" to sell steaks.


Trump Foundation: A charitable organization that Trump founded in 1988 and claimed to support various causes and groups. In reality, it was a vehicle for Trump to enrich himself and his family, evade taxes, and influence politics. The foundation was shut down in 2018 after multiple investigations and lawsuits accused it of being a sham that violated state and federal laws. Trump agreed to pay $2 million to settle the lawsuits and admitted to misusing the foundation’s funds.


Trump’s Election Fraud: A baseless and dangerous campaign that Trump launched after losing the 2020 presidential election to Joe Biden. He refused to concede and claimed, without evidence, that the election was rigged and stolen by widespread voter fraud. He and his allies filed dozens of lawsuits in various states but failed to overturn any results. He also pressured election officials, lawmakers, and even his own vice president to overturn the will of the people. He incited a violent mob of his supporters to storm the U.S. Capitol on January 6, 2021, in an attempt to stop the certification of Biden’s victory. He was impeached for a second time for his role in the insurrection, but acquitted by the Senate. He continues to spread lies and conspiracy theories about the election, undermining democracy and the rule of law.

Understanding the Essence of Donald Trump

Two factors propelled Donald Trump to the top of the con world: a windfall inheritance from his father and a remarkable talent for manipulation. The wealth provided a springboard, allowing him to cultivate an image of power and influence. His cunning personality fueled a relentless pursuit of personal gain, ultimately positioning him at the top of power as the U.S. President.


The Art of the Deal, a 1987 memoir and business advice book that Trump co-authored with ghostwriter Tony Schwartz. It was a bestseller and helped boost Trump's fame and fortune. However, Schwartz later regretted his involvement and said that he wrote most of the book and that Trump lied about his achievements and finances. He also called Trump a "sociopath" and a "con artist".

Trump’s many failures and disasters show that he is not the master dealmaker he pretends to be, but a master of lies and illusions. He is a failed businessman who has gone bankrupt multiple times. He is a loser who cannot lead. For many, he is known as Don the Con for his ability to trick both the influential and the common people into bailing him out. He has exploited his fame, his connections, and his loyal supporters to avoid the responsibility and the repercussions of his actions. He has manipulated the system for his own gain, leaving behind a trail of broken promises, unpaid debts, and ruined lives. And now he is ready to do the same to the whole US and the world.


Those who support Donald Trump should understand that he is not being targeted by Biden or the Democrats. He has always acted like a victim and whined about unfairness whenever his dishonesty was revealed. He is a fraudster, a swindler, a chronic liar who has never done a fair deal in his life, only ones where he cheats the other party by taking their money and making them renegotiate a contract and pay him more to get their money back. He deceives judges, accountants, financiers, contractors, lawmakers, followers, friends, media, and the public. This is Don the Con.


Don’t let the Trump-Abyss Drag You Down!

Trump-Abyss is a blog that reveals the harmful truth of Donald Trump. His actions have undermined democratic principles, provoked unrest, and disseminated false information. He has brought us perilously close to a nuclear conflict, estranged friendly nations, and strengthened adversaries. His conduct has demonstrated a profound disregard for the welfare of society and the principles of justice.

Share the Trump-Abyss blog with your friends, and family, and on social media platforms. The more people are aware of the dangers of a Trump’s presidency, the more they can take action to prevent or mitigate them. Together, we can defend our democracy and our planet from the Trump-Abyss. You have the power to stand up for what is right and fight for a better future. Whether you choose to vote, protest, donate, or educate, you are making a difference in the world.


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