$364 Million Civil Fraud Judgment and Judicial Finding of Fraud (critical) A New York judge (Judge Arthur Engoron) ruled on February 16, 2024, that Donald Trump must pay a $364 million penalty (plus interest, totaling over $450 million based on related content) over a yearslong scheme to 'dupe banks and others' by falsely inflating his wealth and assets by billions of dollars. This ruling was described as a legal and financial blow that could permanently damage his business empire. A New York appeals court later threw out the 'massive financial penalty' but narrowly upheld a finding against him (Aug 21, 2025), confirming the underlying findings of wrongdoing.. History of Six Corporate Bankruptcies (high) Donald Trump has filed for corporate bankruptcy a total of six times. Although he has never filed for personal bankruptcy, this history reflects a pattern of significant corporate financial failure and restructuring.. Violations of Court Gag Order (high) In the New York business fraud lawsuit against the Trump Organization, a gag order was placed on Trump forbidding him from publicly disparaging court staff. He was fined $5,000 and $10,000 in October for two separate violations of this order, indicating non-compliance with judicial mandates.. Associated Company (DWAC) $18 Million SEC Penalty (high) Digital World Acquisition Company (DWAC), which was involved in a deal with Trump Media & Technology Group, agreed to pay an $18 million SEC penalty contingent on the deal going forward. This resolves an investigation into the company.. Finding of Fraud in Business Practices (Reputation) (high) Multiple sources confirm a judge ruled that Donald Trump committed fraud for years while building his real estate empire, specifically by misrepresenting his wealth by hundreds of millions of dollars. This judicial finding fundamentally damages the reputation of his core business practices and integrity.. Significant Corporate Debt Load Upon Leaving Office (high) As of July 29, 2022, when Donald Trump left the White House, his business was facing $900 million of debt coming due within the following four years, highlighting significant short-to-medium term financial pressure.. Ongoing Legal Challenges and Allegations (high) Donald Trump faces a 'very long list of allegations' and was the subject of four pending legal challenges at the time of winning the election (Jan 20, 2025). He is consistently identified as facing 'legal troubles' regarding his business and political actions.. Association with SEC Violations by Appointee's Firm (medium) Cantor Fitzgerald, a Wall Street firm led by President-elect Donald Trump’s pick to serve as Commerce Secretary, paid a $6.75 million civil penalty to settle SEC charges related to violations of securities laws. While the firm settled and did not admit guilt, the association connects the administration's leadership choices to significant compliance failures.. Lawsuit Filed by Former Personal Driver (medium) Noel Cintron, Donald Trump's personal driver before his presidency, filed a lawsuit (Cintron v Trump Organization LLC) with the Supreme Court in July 2018.