Impeached December 19, 1998 on two counts: perjury before a grand jury and obstruction of justice; acquitted by Senate February 12, 1999 (45-55 on perjury; 50-50 on obstruction; both short of 67 needed)

Paula Jones sexual harassment lawsuit (1994-1998); settled for $850,000 without admission of guilt; Clinton was held in civil contempt and fined $90,686 for false testimony

Juanita Broaddrick alleged in 1999 that Clinton raped her in a Little Rock hotel room in 1978 when he was Arkansas Attorney General; Clinton denied the allegation through his attorney

Flight logs document at least 26 trips on Jeffrey Epstein's private jet "Lolita Express" between 2001-2003; including flights to Epstein's private island Little St. James; Clinton denied visiting the island

Pardoned fugitive financier Marc Rich on his last day in office January 20, 2001; Rich's ex-wife Denise Rich had donated $450,000 to the Clinton Library and $100,000 to Hillary Clinton's Senate campaign

Signed the Gramm-Leach-Bliley Act in 1999 repealing key provisions of Glass-Steagall; the regulatory firewall between commercial and investment banking; cited as contributing to the 2008 financial crisis

Signed the 1994 Violent Crime Control and Law Enforcement Act; which included mandatory minimum sentences, three-strikes provisions, and $9.7 billion in prison funding; contributing to mass incarceration that disproportionately affected Black Americans

Monica Lewinsky affair (1995-1997); Clinton lied under oath about the relationship; his statement "I did not have sexual relations with that woman" became synonymous with presidential deception

Operation Infinite Reach (1998); cruise missile strikes on Sudan pharmaceutical factory (Al-Shifa) and Afghanistan; Sudan strike widely criticized as destruction of civilian pharmaceutical infrastructure

Whitewater controversy; the Clintons' involvement in a failed Arkansas real estate venture; independent counsel investigation lasted from 1994-2002