Donald Trump's ongoing characterization of Hillary Clinton as “Crooked Hillary” isn't complicated in its intent. By calling his opponent “Crooked Hillary” more often than he calls her anything else, his goal is to hammer the listener over the head with his argument about Clinton's core challenge: The swirl of allegations and insinuations that surround her past political work.
As is often the case, though, Trump's argument against his opponent is one that might just as easily be leveled against him. Over the past four decades, Trump, his employees and his businesses have been the subject of a range of investigations at every level of government.
1973: The Justice Department files a housing discrimination lawsuit against the Trump Organization. After federal investigators established that prospective black tenants were being turned away from Trump properties, the feds filed a lawsuit against Trump's company, for which Trump was then acting as president. The case was settled, with the Trumps not admitting wrongdoing but signing a consent decree that mandated the Trumps advertise that minority applicants had an equal opportunity to rent at their properties.
1978: The Trump Organization was accused of violating the consent decree. The Village Voice reported in 1978 that the Trumps had continued to discriminate against minorities, and that “racially discriminatory conduct by Trump agents has occurred with such frequency that it has created a substantial impediment to the full enjoyment of equal opportunity.”
1979: Trump is allegedly investigated for bribery. A book written in 1992 by the Voice's Wayne Barrett, “Trump: The Deals and the Downfall,” alleged that Trump was the subject of a bribery investigation in 1979 and a racketeering investigation two years later, according to a contemporaneous Associated Press review. The allegations appear to stem from Trump's role in the then-mob-infested world of construction in New York.
1980: Trump is subpoenaed by the FBI to discuss his links to a mob-connected Teamsters official. Teamster John Cody had been given a number of free apartments by developers, as David Cay Johnston reported for Politico earlier this year. Trump denied giving Cody an apartment at Trump Tower, but a “female friend” of Cody's got three apartments in the building after Trump assisted her in obtaining a mortgage. “In the summer of 1982 Cody, then under indictment,” Johnston writes, “ordered a citywide strike — but the concrete work continued at Trump Tower.”
1987: The Federal Trade Commission recommends that the Justice Department prosecute Trump. As the New York Times reported at the time, the FTC said that Trump's use of a “parking agreement” violated the law. (A “parking agreement” is a term referring to the potential buyer of a business having a third party buy stock in the business before the acquisition to both hide his interest in the purchase.) Trump settled with the government for $750,000.
1988: Trump was investigated by the U.S. Attorney for money-laundering. As Barrett wrote in the New York Daily News earlier this year, a federal investigation into Trump's role in helping alleged mobster Robert Hopkins launder money by purchasing two apartments in Trump Tower was dropped after Trump announced that he'd raise money for the mayoral campaign of the sitting U.S. Attorney — Rudy Giuliani.
1990: The SEC investigated whether Trump violated the law in buying and selling stock. USA Today broke the story, reporting that the SEC was looking into whether Trump and the investment bank Bear, Stearns partnered to commit insider trading. The allegation, the newspaper reported, was that Bear, Stearns gave Trump a heads-up on big purchases placed by other clients. The investigation doesn't seem to have gone anywhere.
1991: Trump's father is caught buying casino chips in lieu of giving Trump a loan. At the height of Trump's financial troubles, his father Fred Trump purchased $3.5 million in gaming chips from one of Trump's casinos, Trump Castle, infusing the business with cash. New Jersey regulators deemed the purchase illegal financial assistance, and the casino eventually accepted a $65,000 fine and admitted to violating the law.
1991: Trump Plaza is fined for discrimination. As reported by USA Today earlier this year, Trump Plaza casino was fined $200,000 for discrimination after it was determined that the casino's pit bosses would rotate craps dealers who weren't white men off the tables when alleged mobster Robert Libutti came to play. Later that year, Trump's Atlantic City casinos were also fined for giving Libutti nine luxury cars.
1992: A congressional report links Trump's businesses to Asian organized crime. Mentions of Trump businesses are sprinkled throughout a 1992 report on Asian organized crime in the United States. Crime bosses who ran the Chinatown bus system put together trips to Trump businesses in Atlantic City, the report alleges, but other people with links to organized crime booked shows at Trump venues and in 1987, one was indicted on a charge of providing kickbacks to executives at Trump Castle. More specifically, Danny Leung was a vice president at Trump Taj Mahal who was known by law enforcement to be linked to organized crime syndicates.
2000: Trump fined for failing to disclose anti-gaming political ads. In 2000, Trump spent over $300,000 lobbying against proposed new casinos run by Native American groups, including $150,000 in newspaper ads. Those newspaper ads didn't identify the sponsor, a violation of lobbying rules. As a result, Trump agreed to a $250,000 fine and to run ads admitting his role in the effort.
2002: The Securities and Exchange Commission took action against Trump Hotels and Casino Resorts for “misleading” earnings reports. In the first-ever agency action of its kind, the SEC “found that Trump Hotels, through the conduct of its chief executive officer, its chief financial officer and its treasurer, violated the antifraud provisions of the Securities Exchange Act by knowingly or recklessly issuing a materially misleading press release.”
2010 and 2013: States investigate Trump University. In 2010, the state of Texas opened an investigation into the business practices of Trump University, the now-infamous real estate seminar program run by Trump. Three years later, the state of New York filed a fraud lawsuit against the business. (The recent legal fight over Trump University has been centered on class-action lawsuits against the “school” filed in California.)
2011: A criminal case looking at misrepresentations to Trump Soho tenants was closed after the tenants settled. A group of people who'd bought condominiums in the recent Trump Soho development said that Trump and his employees told them that units were selling more quickly than was the case, creating an artificial sense of demand. The Times reported that a criminal investigation was opened, but when Trump settled with the tenants, a stipulation of the settlement was that they tell prosecutors that they didn't want the investigation to proceed. The case was closed.
2016: The state of New York opens an investigation into the Trump Foundation. After Post reporting revealed a number of questionable practices by the Trump Foundation, the state's attorney general opened an investigation into the foundation's practices.
2016: The Trump Foundation pays a fine for an improper campaign contribution. That reporting also uncovered a gift made from the foundation (a 501(c)(3)) to a political committee run by Florida attorney general Pam Bondi. That's not allowed, and the foundation paid a fine of $2,500.