Donald Trump is now president and not just a private citizen, but that doesn’t mean he’s free of the controversies that dogged him in his former life.
Last week, a few days before Trump’s inauguration, the former Apprentice contestant Summer Zervos sued him in New York State, accusing the president of defamation. Zervos, who’s represented by the famous lawyer Gloria Allred, was one of the several women who accused Trump of sexual assault or misconduct prior to the election. She claims that he kissed her and pressed his genitals against her nonconsensually. Trump denied those claims, saying all of the women who had accused him had made their stories up. So Zervos sued him for defamation.
“I wanted to give Mr. Trump the opportunity to retract his false statements about me and the other women who came forward,” she said, as my colleague Nora Kelly reported. She added that she would withdraw the suit if Trump said she had been truthful. That seems unlikely, because a spokeswoman dismissed the suit immediately.
It’s unusual for a president to be in such a legal situation—though not entirely unprecedented. Bill Clinton settled a suit for sexual harassment filed by Paula Jones. Zervos’s suit serves to underscore an even more unusual fact, though, which is that Trump won election despite a raft of allegations of sexual harassment and misconduct lodged by women in multiple places, from different eras.
The 2016 presidential campaign saw a long string of stories showing scandals involving Trump, both large and small—from questionable business dealings to allegations of sexual assault. While they did not derail his presidential hopes, many of them remain live issues as Trump begins his transition to the White House.
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. They stretch over more than four decades, from the mid-1970s to the present day. To catalog 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.
Where and when: Various, 1970s–2005
The dirt: Even before the release of a 2005 video in which he boasted about sexually assaulting women—“Grab them by the pussy. You can do anything,” he said, as well as “I just start kissing them. It’s like a magnet. Just kiss. I don’t even wait. And when you’re a star they let you do it. You can do anything”—there’s a long line of allegations against Trump. Jill Harth says Trump assaulted her in the 1990s. Trump’s ex-wife Ivana Trump once suggested he had raped her, though she has since recanted her story. Former Miss Utah Temple Taggart said he kissed her on the lips inappropriately. But since the release, more women have come forward. Two told The New York Times that Trump had assaulted them, one saying he tried to put his hand up her skirt on a flight in the 1970s and another saying he forcibly kissed her. A Florida woman says Trump groped her. A former People reporter recounted an alleged assault at his Mar-a-Lago debate, and says he told her, “You know we’re going to have an affair, don’t you?” Several former teen pageant contestants said Trump walked in on them while they were naked or partially dressed.
The upshot: Trump denies all of the allegations. In the sexual-assault cases, Trump faces the difficulty that he in some cases bragged openly about just the behavior of which he has been accused—whether grabbing or forcibly kissing. Trump has demanded a retraction from the Times, and has threatened to sue several outlets. The paper, in a letter, refused. A woman who brought a rape case against Trump (twice) withdrew her suit in November, but in January, Summer Zervos sued Trump for defamation, after he labeled her claims of sexual assault false.
Where and when: Various, 1992–present
The dirt: The Boston Globe’s Matt Viser reports on the mess of the American Dream pageant in 1992. After years of attending beauty pageants—Trump seems to have always enjoyed the company of beautiful, scantily clad women—he decided he wanted to get in on the business himself, meeting with George Houraney and Jill Harth, a couple that ran the American Dream pageant. It was an ill-fated effort. Harth and Houraney alleged that Trump started making passes at her almost immediately. On one occasion, Trump allegedly asked them to bring some models to a party. Harth alleges Trump groped her at the party. In a limo afterward, another model said she heard him say that “all women are bimbos” and most “gold diggers.” Trump reportedly joined another model in bed, uninvited, late at night. On other occasions, he forced Harth into bedrooms and made passes at her, she said. But after the contest, Trump broke off dealings. Harth sued Trump, alleging sexual misbehavior, while the couple together sued him for breach of contract. In the suit, they also alleged that Trump had kept black women out of the pageant.
The upshot: The couple settled with Trump for an unannounced sum, and Harth dropped her suit. Trump has denied all the allegations. But it wasn’t Trump’s last turn in the pageant business. A few years later, he bought the Miss Universe pageant, which also includes Miss USA and Miss Teen USA. “Honestly, when I bought [Miss Universe], the bathing suits got smaller and the heels got higher and the ratings went up,” he boasted to Vanity Fair later. In 2012, he won a $5 million suit against a former contestant who claimed the contest was rigged. By 2015, he operated Miss Universe as a joint venture with NBC, but after he slurred Mexican immigrants at his campaign launch, Univision and NBC both announced they would not air the pageant. Trump bought out NBC’s share, then promptly sold the company. He sued Univision but settled in February. The terms were undisclosed.
Where and when: New York City, 1973–75
The dirt: The Department of Justice sued Trump and his father Fred in 1973 for housing discrimination at 39 sites around New York. “The government contended that Trump Management had refused to rent or negotiate rentals ‘because of race and color,’” The New York Times reported. “It also charged that the company had required different rental terms and conditions because of race and that it had misrepresented to blacks that apartments were not available.” Trump called the accusations “absolutely ridiculous.”
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. The Times has much more on the long history of allegations at Trump-owned properties.
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 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, 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.
The upshot: Though Trump has been questioned in court or under oath about the ties, he’s never been convicted of anything. A New Jersey Division of Gaming Enforcement report after Barrett’s 1992 book on Trump generally found no mafia-related wrong-doing on Trump’s part. Trump Plaza was fined $200,000 for keeping black employees away from LiButti’s table, at his behest, and for the gift of the cars, though Trump personally was not penalized.
Where and when: 2005–10, 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. In November 2016, Trump agreed to settle a series of lawsuits related to the school for $25 million. Trump did not admit any wrongdoing as part of the settlement. But he had insisted for months that he would not settle the suit because he expected to win. For a time, he appeared 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 cited positive reviews, but former students say they were pressured to give those. Trump also mounted a lengthy attack on the judge, claiming his ethnicity made him biased. Trump has been widely repudiated across the board, with fellow Republicans openly calling him racist.
Where and when: New York City, 1982–86
The scoop: In 1981, Trump scooped up a building on Central Park South, reasoning that the existing structure was a dump, but the land it was on would be a great place for luxury condos. Trump’s problem was that the existing tenants were—understandably and predictably—unwilling to let go of their rent-controlled apartments on Central Park. Trump used every trick in the book to get them out. He tried to reverse exceptions the previous landlord had given to knock down walls, threatening eviction. Tenants said he cut off heat and hot water. Building management refused to make repairs; two tenants swore in court that mushrooms grew on their carpet from a leak. Perhaps Trump’s most outlandish move was to place newspaper ads offering to house homeless New Yorkers in empty units—because, as Trump wrote in The Art of the Deal, he didn’t intend to fill units with permanent residents anyway. City officials turned him down, saying the idea did not seem appropriate. Typically, Trump also sued tenants for $150 million when they complained.
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.
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.”
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. Meanwhile, Massimo Calabresi shows that testimony under oath shows Trump was aware of illegal immigrants being employed there.
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.”
The upshot: When The Daily Beast reported on the incident, Trump’s right-hand man Michael Cohen threatened reporters and claimed—incorrectly—that a man cannot legally rape his wife. The case is one of several cases where Trump has been accused of misogyny, including his comments about Megyn Kelly early in the primary campaign or his fury at a lawyer who, during a deposition, asked for a break to pump breast milk. “You’re disgusting,” Trump said, and walked out. (Wayne Barrett collects some lowlights here.)
Read more: The Daily Beast
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.
The upshot: Trump gave up the attempt in 1987, but the Federal Trade Commission fined him $750,000 for failing to disclose his purchases of stock in the two companies, which exceeded minimum disclosure levels.
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 was arrested for battery, but the prosecutor opted not to press charges. Trump has said he may have been the one in danger, because Fields’s pen could have been a bomb.
Where and when: New York City, 2006–09
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. The Post combed through Trump’s deposition in the case and found 30 instances where Trump admitted to having lied.
Where and when: various, 1980s–present
The dirt: Contractors, waiters, dishwashers, and plumbers who have worked at Trump projects say that his company stiffed them for work, refusing to pay for services rendered. USA Today did a lengthy review, finding that some of those contracts were for hundreds of thousands of dollars, many owed to small businesses that failed or struggled to continue because of unpaid bills. (Trump was also found to have improperly withheld compensation in the undocumented Polish worker controversy.)
The upshot: Trump has offered various excuses, including shoddy workmanship, but the scale of the problem—hundreds of allegations—makes that hard to credit. In some cases, even the lawyers Trump has hired to defend him have sued him for failing to pony up their fees. In one lawsuit, a Trump employee admitted in court that a painter was stiffed because managers determined they had “already paid enough.” The cases are damaging because they show Trump not driving a hard bargain with other businesses, but harming ordinary, hard-working Americans. More recently, several contractors filed $5 million in liens against Trump’s new hotel in Washington, alleging he has not paid them for services rendered.
Where and when: Boca Raton and elsewhere, 2005–?
The dirt: Around the same time Donald Trump was operating Trump University, the allegedly fraudulent real-estate seminar for which he’s now being sued, he also franchised his name to Irene and Mike Milin, serial operators of get-rich-quick schemes. Unlike Trump U., Trump did not own the company. Instead, he licensed his name, appearing in an informercial and promising falsely that he would hand-pick instructors. (He made a similar promise with Trump U.) As Jonathan Martin reports, the course materials at Trump Institute consisted in part of textbooks that were plagiarized.
The upshot: The Milins were forced to declare bankruptcy in 2008, in part because of the law-enforcement investigations and lawsuits against their company. Trump Institute continued on for a few years afterward. A Trump aide says he was unaware of the plagiarism, but said he stood by the curriculum.
Where and when: various, 2016
The dirt: The Daily Beast noticed in FEC filings that the Trump campaign spent more than $55,000 buying his own book Crippled America: How to Make America Great Again. (The book has since been retitled Great Again: How to Fix Our Crippled America for the paperback edition.) That means Trump used donor money to his campaign to buy a book, sending the cash back to himself. Copies were given to delegates at the Republican National Convention.
The upshot: The maneuver could break FEC rules, campaign expert Paul S. Ryan told the Beast: “It’s fine for a candidate’s book to be purchased by his committee, but it’s impermissible to receive royalties from the publisher ... There’s a well established precedent from the FEC that funds from the campaign account can’t end up in your own pocket.” The Huffington Post also noticed that Trump jacked up rent for campaign offices when he stopped funding his own campaign.
Read more: The Daily Beast
Where and when: New York, 1999–?
The dirt: Former models who worked for Trump Model Management say that they and others worked for the agency in the United States despite not having proper permits. Some of them worked on tourist visas, either never getting the correct permits or else getting them only after working in the U.S. illegally for months.
The upshot: The story is embarrassing for Trump, who has argued that U.S. immigration laws should be much more strictly enforced. Some models also received H-1B visas, a special type of permit for workers in specialized industries—a program that Trump has criticized on the campaign trail this year.
Read more: Mother Jones
Where and when: Various, 1988–present
The dirt: Though Donald Trump often promises to give to charity, his foundation has proven rather skimpy on the gifts over the years—and when it has given, the money has often come from pockets other than Trump’s, including outside donors and even NBC. In the mid-2000s, Trump reconfigured the charity as a pass-through, soliciting donations from others and then giving the money away as though from himself. It appears that the foundation did not have the requisite legal permission from New York State to gather donations. In a few cases, the foundation also reported making donations it had not made. There’s special scrutiny on one $25,000 donation it did give, to a group supporting Florida Attorney General Pam Bondi, which arrived just days before she quashed an investigation into Trump University and the Trump Institute. Trump also appears to have used $258,000 in foundation money, most of it given by other donors and not himself, to settle legal disputes, including donations to charity in lieu of paying fines. Trump directed more than $2 million in income to the foundation, and if he didn’t pay taxes on them—his campaign for the most part refused to say—it would be illegal tax-dodging.
The upshot: The foundation appears to have broken IRS rules on “self-dealing” by paying to resolve the legal disputes as well as buying a portrait of Trump and a Tim Tebow helmet that went back to the Trump family. In November, in tax filings posted online, the Trump Foundation said it had violated self-dealing rules in 2015 and in previous, indeterminate, years. On the donation, Trump and Bondi both say there was no quid-pro-quo, but the donation was an illegal one for a charitable nonprofit, and the foundation had to pay a $2,500 fine. Liberal watchdog group Citizens for Responsibility and Ethics in Washington charges other laws may have been broken as well. New York Attorney General Eric Schneiderman has reportedly launched an investigation into the foundation. Schneiderman has also informed the foundation that it is in violation of rules on fundraising and ordered it to quit. Trump has announced plans to close his foundation, but reportedly cannot do so while it is under investigation.
Where and when: Cuba, 1998–present
The dirt: Although U.S. law prohibits American commercial involvement in Cuba, there’s evidence to suggest that the Trump Organization has been active on the island for almost two decades. In 1998, as the Clinton administration loosened some restrictions, Trump scouted business opportunities, and according to documents viewed by Newsweek, spent $68,000 there, likely in violation of the law. More recently, Trump executives have traveled to Cuba in apparent scouting trips for golf resorts, BusinessWeek reports.
The upshot: Trump and his company have not commented in any detail on either report. One Trump executive told BusinessWeek that his travel to Cuba was unrelated to the company, while another associate said he’d discussed forming a company with Trump to run golf courses in Cuba. Experts said these activities would all likely fall afoul of current rules.