Throughout his career as a businessman and politician, Donald Trump has been involved in numerous legal disputes, resulting in substantial fines, settlements, and court battles. This article presents a comprehensive timeline of these events, spanning from the 1980s to the present day, as well as ongoing investigations.

1980s

• 1988: $750,000 – Anti-trust lawsuit settlement with Bally.

1990s

• 1990: $750,000 – Defamation lawsuit for predicting Trump Taj Mahal would fail.
• 1991: $200,000 – Settlement for removing black workers from casino floor.
• 1991: $30,000 – Fine for circumventing state regulations.
• 1992: $250,000 – Federal Election Commission (FEC) penalty for exceeding campaign contribution limits.
• 1998: $1.375 million – Settlement for underpaying pension funds in a class action lawsuit.
• 1998: $1.4 million – Settlement for hiring undocumented workers.
• 1998: $447,000 – Money laundering violations.

2000s

• 2000: $250,000 – New York City Housing Authority settlement for racial discrimination in housing practices.
• 2000: $250,000 – Settlement with New York State Lobby Commission.
• 2006: $100,000 – Fine for Palm Beach flag ordinance violation.
• 2006: $25,000 – Fine by New York State Department of Environmental Conservation for improper demolition project licensing.

2010s

• 2013: $18,000 – Fine by Federal Trade Commission for multi-level marketing violations.
• 2014: $32,000 – Trump Hotel Collection fine for improper hazardous materials storage.
• 2015: $799,000 – Defamation settlement related to Trump University student.
• 2015: $10 million – Money laundering violations.
• 2016: $25 million – Settlement in Trump University fraud lawsuit.
• 2016: $50,000 – Fine for data and credit card breaches.
• 2016: $1.3 million – Penalty for FEC disclosure errors.
• 2017: $25,000 – Civil penalty to the IRS for political contribution through the Trump Foundation.
• 2018: $1 million – Penalty for pollution control violations at a Trump golf course.
• 2018: $2 million – Fine paid by the Trump Organization to the state of New York for misusing charitable assets to intervene in the 2016 election.
• 2019: $2 million – Settlement for misusing Trump Foundation to settle lawsuits and support his campaign.
• 2019: $290,000 – Settlement with Scotland over wind farm dispute.

2020s

• 2020: $2.1 million – Settlement for defrauding prospective Trump Tower buyers.
• 2021: $122 million – Trump campaign forced to refund contributions to donors.
• 2022: $110,000 – Contempt of court fine.
• 2022: $750,000 – Fine for funneling inaugural funds to Trump businesses.
• 2022: $1.6 million – Conviction for 17 counts of criminal tax fraud.
• 2023: CFO sentenced to prison (related to Trump Organization tax fraud).
• 2023: $10,000 – Fine for attacking court personnel.
• 2023: $1 million – Court sanctions for a bogus lawsuit, with $171,000 to be paid to Hillary Clinton.
• 2023: $5 million – E. Jean Carroll sexual assault verdict.
• 2024: $83.3 million – E. Jean Carroll defamation verdict.
• 2024: $392,000 – Court sanctions for bogus lawsuit against New York Times.
• 2024: $453 million – Settlement for business fraud.
• 2024: Convicted felon – Found guilty of 34 felony counts of falsifying business records in a scheme to illegally influence the 2016 election.

Ongoing and Notable Investigations as of May 30th, 2024

• Various ongoing lawsuits and investigations into Trump Organization’s financial practices by the New York Attorney General and other entities.
• Legal issues related to the January 6 insurrection and subsequent investigations.
• Classified documents investigation and potential Espionage Act violations being looked at by the Justice Department.

This extensive list highlights the complex legal history of Donald Trump and the significant financial implications of his actions. As investigations continue, it is likely that this list will grow, providing further insight into the controversies surrounding the former president.