| 2000-01-01 | Trump, Epstein, Maxwell, and Melania at Mar-a-Lago Charity Event Donald Trump · Jeffrey Epstein · Ghislaine Maxwell · Melania Trump | | confirmed |
| 1999-01-01 | Trump Launches Model Management Agency with Systematic Visa Violations Donald Trump · Trump Model Management · Alexia Palmer · Rachel Blais | | confirmed |
| 1998-01-01 | Deutsche Bank Loans Trump $2.5 Billion Despite Russian Money Laundering and Red Flags Deutsche Bank · Donald Trump · Trump Organization · Russian Oligarchs · +1 |
| confirmed |
| 1996-06-20 | Trump Acquires Miss Universe Organization from ITT Corp Donald Trump · ITT Corporation · Madison Square Garden |
| confirmed |
| 1993-12-20 | Epstein Attends Trump's Wedding to Marla Maples Jeffrey Epstein · Donald Trump · Marla Maples | | confirmed |
| 1993-01-01 | Trump appears in Epstein aircraft logbooks multiple times (DOJ exhibits) Donald Trump · Jeffrey Epstein | | confirmed |
| 1992-11-01 | Trump and Epstein at Mar-a-Lago Party with NFL Cheerleaders Donald Trump · Jeffrey Epstein | | confirmed |
| 1992-11-01 | Trump Plaza Hotel in Manhattan Files for Bankruptcy Protection Donald Trump |
| reported |
| 1992-03-09 | Trump Castle and Trump Plaza File Simultaneous Bankruptcies Donald Trump |
| reported |
| 1991-07-01 | Trump Taj Mahal Files First Bankruptcy After Junk Bond Collapse Donald Trump |
| confirmed |
| 1991-07-01 | Trump's Six Bankruptcies: Pattern of Borrowing Heavily and Walking Away Donald Trump |
| confirmed |
| 1991-06-05 | Trump Plaza Fined $200,000 for Removing Black Employees from Gaming Floor Donald Trump · Robert LiButti · Kip Brown |
| confirmed |
| 1991-01-01 | Saudi Prince Alwaleed bin Talal purchases Trump yacht during financial crisis Prince Alwaleed bin Talal · Donald Trump · Trump Organization · Saudi Arabia |
| confirmed |
| 1990-01-01 | Epstein Purchases Property Near Mar-a-Lago Jeffrey Epstein · Donald Trump | | confirmed |
| 1990-01-01 | Trump Taj Mahal Casino Opens with $675 Million Junk Bond Debt Crisis Donald Trump · Carl Icahn · Marvin Roffman · Trump Taj Mahal |
| confirmed |
| 1989-05-01 | Trump Demands Death Penalty in $85,000 Ads Against Central Park Five Donald Trump · Yusef Salaam · Korey Wise · Antron McCray · +2 |
| confirmed |
| 1978-03-06 | DOJ Returns to Court: Trump Violated 1975 Discrimination Settlement Donald Trump · Fred Trump · Roy Cohn |
| confirmed |
| 1975-06-10 | Trump Settles Housing Discrimination Case Without Admitting Guilt Donald Trump · Fred Trump · Roy Cohn |
| confirmed |
| 1973-10-15 | DOJ Sues Trump and Father for Systemic Housing Discrimination Donald Trump · Fred Trump · Roy Cohn |
| confirmed |