The breadth of Trump’s controversies is truly yuge, ranging from allegations of mafia ties to unscrupulous business dealings, and from racial discrimination to alleged marital rape. The stretch over more than four decades, from the mid-1970s to the present day. To catalogue the full sweep of allegations would require thousands of words and lump together the trivial with the truly scandalous. Including business deals that have simply failed, without any hint of impropriety, would require thousands more. This is a snapshot of some of the most interesting and largest of those scandals.
Racial Housing Discrimination
Where and when: New York City, 1973-1975
The upshot: The Trumps hired attorney Roy Cohn, who had worked for Joe McCarthy and whom Michael Kinsley once indelibly labeled “innocent of a variety of federal crimes.” They sued the Justice Department for $100 million. In the end, however, the Trumps settled with the government, promising not to discriminate and submitting to regular review by the New York Urban League—though crucially not admitting guilt.
Where and when: New York and Atlantic City, 1970s- ?
The dirt: Trump has been linked to the mafia many times over the years, with varying degrees of closeness. Many of the connections seem to be the sorts of interactions with mobsters that were inevitable for a guy in the construction and casino businesses at the time. For example, organized crime controlled the 1980s New York City concrete business, so that anyone building in the city likely brushed up against it. While Trump has portrayed himself as an unwitting participant, not everyone agrees. There have been a string of other allegations, too, many reported by investigative journalist Wayne Barrett. Cohn, Trump’s lawyer, also represented the Genovese crime family boss Tony Salerno. Barrett also reported a series of transactions involving organized crime, and alleged that Trump paid twice market rate to a mob figure for the land under Trump Plaza in Atlantic City. Michael Isikoff has also reported that Trump was close to Robert LiButti, an associate of John Gotti, inviting him on his yacht and helicopter. In one case, Trump’s company bought LiButti nine luxury cars.
Where and when: 2005-2010, online
The dirt: In 2005, the Trump announced an eponymous “university” to teach his real-estate development secrets. Students ponied up as much as $35,000—some after being suckered in by slick free “seminars”—to learn how to get rich. One ad promised they would “learn from Donald Trump’s handpicked instructors, and that participants would have access to Trump’s real estate ‘secrets.’” In fact, Trump had little to do with the curriculum or the instructors. Many of the “students” have since complained that Trump U. was a scam. At one time, it had some prestigious instructors, but over time the “faculty” became a motley bunch of misfits. (It was also never really a “university” by any definition, and it changed its name to the “Trump Entrepreneur Initiative,” because as it happened, the school was violating New York law by operating without an educational license.)
The upshot: The school shut down in 2010, but the litigation continues. New York is suing Trump, alleging the Trump U. bilked students out of $40 million. He’s also the subject of two class-action suits in California. Meanwhile, Trump appears to have been trying to intimidate plaintiffs, including countersuing one for $1 million (a favorite Trump litigation tactic) and refusing to let her withdraw from the suit. (The countersuit was thrown out.) His lawyers have cited positive reviews, but former students say they were pressured to give those.
Where and when: New York City, 1982-1986
The upshot: Trump gave in. He settled with tenants and agreed to monitoring. The building still stands today, and his son Eric owns a unit on the top floor.
The Four Bankruptcies
Where and when: 1991, 1992, 2004, 2009
The dirt: Four times in his career, Trump’s companies have entered bankruptcy.
- In the late 1980s, after insisting that his major qualification to build a new casino in Atlantic City was that he wouldn’t need to use junk bonds, Trump used junk bonds to build Trump Taj Mahal. He built the casino, but couldn’t keep up with interest payments, so his company declared bankruptcy in 1991. He had to sell his yacht, his airline, and half his ownership in the casino.
- A year later, another of Trump’s Atlantic City casinos, the Trump Plaza, went bust after losing more than $550 million. Trump gave up his stake but otherwise insulated himself personally from losses, and managed to keep his CEO title, even though he surrendered any salary or role in day-to-day operations. By the time all was said and done, he had some $900 million in personal debt.
- Trump bounced back over the following decade, but by 2004, Trump Hotels and Casino Resorts was $1.8 billion in debt. The company filed for bankruptcy and emerged as Trump Entertainment Resorts. Trump himself was the chairman of the new company, but he no longer had a controlling stake in it.
- Five years later, after the real-estate collapse, Trump Entertainment Resorts once again went bankrupt. Trump resigned from the board, but the company retained his name. In 2014, he successfully sued to take his name off the company and its casinos—one of which had already closed, and the other of which was near closing.
The upshot: Trump is very touchy about any implication that he personally declared bankruptcy, arguing—just as he explains away his campaign contributions to Democrats—that he’s just playing the game: “We’ll have the company. We’ll throw it into a chapter. We’ll negotiate with the banks. We’ll make a fantastic deal. We’ll use those. But they were never personal. This is nothing personal. You know, it’s like on The Apprentice. It’s not personal. It’s just business. Okay? If you look at our greatest people, Carl Icahn with TWA and so many others. Leon Black, Linens-n-Things and others. Henry Kravis. A lot of ‘em, everybody. But with me it’s ‘Oh, you did—’ this is a business thing. I’ve used the laws of this country to pare debt.”
The Undocumented Polish Workers
Where and when: New York City, 1980
The dirt: In order to construct his signature Trump Tower, the builder first had to demolish the Bonwit Teller store, an architecturally beloved Art Deco edifice. The work had to be done fast, and so managers hired 200 undocumented Polish workers to tear it down, paying them substandard wages for backbreaking work—$5 per hour, when they were paid at all. The workers didn’t wear hard hats and often slept at the site. When the workers complained about their back pay, they were allegedly threatened with deportation. Trump said he was unaware that illegal immigrants were working at the site.
The upshot: In 1991, a federal judge found Trump and other defendants guilty of conspiring to avoid paying union pension and welfare contributions for the workers. The decision was appealed, with partial victories for both sides, and ultimately settled privately in 1999. In a February GOP debate, Marco Rubio brought up the story to accuse Trump of hypocrisy in his stance on illegal immigration.
Alleged Marital Rape
Where and when: New York City, 1989
The dirt: While married to Ivana Trump, Donald Trump became angry at her—according to a book by Harry Hurt, over a painful scalp-reduction surgery—and allegedly forcibly had sex with her. Ivana Trump said during a deposition in their divorce case that she “felt violated” and that her husband had raped her. Later, Ivana Trump released a statement saying: “During a deposition given by me in connection with my matrimonial case, I stated that my husband had raped me. [O]n one occasion during 1989, Mr. Trump and I had marital relations in which he behaved very differently toward me than he had during our marriage. As a woman, I felt violated, as the love and tenderness, which he normally exhibited towards me, was absent. I referred to this as a ‘rape,’ but I do not want my words to be interpreted in a literal or criminal sense.”
Read more: The Daily Beast
Breaking Casino Rules
Where and when: New York and New Jersey, various
The dirt: Trump has been repeatedly fined for breaking rules related to his operation of casinos. In 1990, with Trump Taj Mahal in trouble, Trump’s father Fred strolled in and bought 700 chips worth a total of $3.5 million. The purchase helped the casino pay debt that was due, but because Fred Trump had no plans to gamble, the New Jersey gaming commission ruled that it was a loan that violated operating rules. Trump paid a $30,000 fine; in the end, the loan didn’t prevent a bankruptcy the following year. As noted above, New Jersey also fined Trump $200,000 for arranging to keep black employees away from mafioso Robert LiButti’s gambling table. In 1991, the Casino Control Commission fined Trump’s company another $450,000 for buying LiButti nine luxury cars. And in 2000, Trump was fined $250,000 for breaking New York state law in lobbying to prevent an Indian casino from opening in the Catskills, for fear it would compete against his Atlantic City casinos.
The upshot: Trump admitted no wrongdoing in the New York case. He’s now out of the casino business.
Where and when: New Jersey, 1986
The dirt: In 1986, Trump decided he wanted to expand his casino empire in Atlantic City. His plan was to mount a hostile takeover of two casino companies, Holiday and Bally. Trump started buying up stock in the companies with an eye toward gaining control. But Bally realized what was going on and sued him for antitrust violations. “Trump hopes to wrest control of Bally from its public shareholders without paying them the control premium they otherwise could command had they been adequately informed of Trump’s intentions,” the company argued.
Condo Hotel Shenanigans
Where and when: New York, Florida, Mexico, mid-2000s
The dirt: Trump was heavily involved in condo hotels, a pre-real-estate crash fixation in which people would buy units that they’d only use for a portion of the year. The rest of the time, the units would be rented out as hotel rooms, with the developer and the owner sharing the profit. For a variety of reasons, condo hotels turned out to be a terrible idea. The result has been a slew of lawsuits by condo buyers who claim they were bilked. Central to many of these is the question of what Trump’s role in the projects was. In recent years, Trump has often essentially sold his name rights to developers—he gets a payoff, and they get the aura of luxury his name imparts. But in some of the condo-hotel suits, buyers complain that they bought the properties as investments because of his imprimatur, only to realize he was barely involved. (Similar complaints have been made about his involvement in a multilevel marketing scheme.)
The upshot: In the case of Trump SoHo, in Manhattan, Trump’s partners turned out to have a lengthy criminal past. Trump said he didn’t know that, but—atypically—settled a lawsuit with buyers (while, typically, not admitting any wrongdoing). Another, Trump International Hotel & Tower Fort Lauderdale, went into foreclosure, and Trump has sued the complex’s developer. In 2013, he settled a suit with prospective buyers who lost millions when a development in Baja Mexico went under. Trump blamed the developers again, saying he had only licensed his name.
Where and when: Jupiter, Florida, 2016
The dirt: Trump picked Corey Lewandowski to manage his campaign, despite a relatively short resume. For a long time, that seemed to work well for both—Trump soared to the lead in GOP polls. But Lewandowski hit a rough patch in early March. As Breitbart reporter Michelle Fields tried to ask Trump a question after a press conference, Lewandowski reached out and wrenched her out of the way. Lewandowski and Trump insisted the incident had never happened and that Fields was “delusional,” even though witnesses attested to having seen it.
The upshot: Surveillance footage acquired by Jupiter Police from Trump National, site of the press conference, clearly showed what had happened. Lewandowski has been charged with battery. Trump has said he may have been the one in danger, since Fields’s pen could have been a bomb.
Suing Journalist Tim O’Brien for Libel
Where and when: New York City, 2006-2009
The dirt: In 2005, then-New York Times reporter Tim O’Brien published the book TrumpNation, in which he reported that Trump was actually only worth $150-250 million, not the billions he claimed. Trump, incensed, sued O’Brien for $5 billion. (That’s one way to become a billionaire.)
The upshot: Trump’s suit against O’Brien was tossed. More recently, O’Brien has mocked Trump’s current claims about his net worth. Trump, meanwhile, has said on the campaign trail—and, mindblowingly, in an interview with the Washington Post editorial board—that he wants to make it easier to sue for libel.