Multiple Criminal Indictments (critical) Donald Trump has been indicted in four separate criminal cases, making him the first U.S. President in history to face criminal charges. The first indictment occurred on March 30, 2023, in New York over hush-money payments.. Massive Civil Fraud Judgment and Business Ban in New York (critical) A New York judge ruled that Donald Trump committed fraud by repeatedly misrepresenting his wealth. He was ordered to pay $354,868,768 (plus interest, potentially totaling $463.9 million) in penalties and was barred from doing business in New York for three years. His sons, Donald Jr. and Eric, were also fined $4 million each and barred for two years.. Judicial Finding of Intentional Business Fraud (critical) A New York judge determined that Donald Trump committed fraud by falsely inflating his wealth and assets by 'billions of dollars' to secure favorable loans and insurance rates. The judge noted the defendants' 'complete lack of contrition and remorse borders on pathological.'. Significant Defamation Judgment (high) A jury ordered Donald Trump to pay the writer E Jean Carroll $83.3 million for defaming her, adding to his substantial financial liabilities from civil cases.. SEC Regulatory Fine Related to Business Merger (DWAC) (high) Digital World Acquisition Company (DWAC), related to Trump Media & Technology Group, agreed to pay an $18 million SEC penalty contingent on the merger going ahead. This indicates regulatory violations in the business sphere.. Enduring Controversy over 2020 Election (high) The controversy over the 2020 U.S. presidential election remains one of the most significant and enduring scandals surrounding the subject, spanning legal actions and political developments from 2016 through 2025.