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Last week, media coverage of Donald Trump may have hit an inflection point, when major news outlets, while covering Trump’s latest birther shenanigans, characterized the GOP presidential nominee’s remarks as a lie. Though Trump has scored more pants-on-fire false statements than any other candidate in this campaign, mainstream news outlets have struggled over whether and how to use the L-word when reporting on him. With this birther-driven breakthrough in coverage, there now remain plenty of brazenly untrue assertions—deliberate lies or not—uttered by Trump that warrant close examination. One topic ripe for such scrutiny is Trump’s associations with organized crime. For years during his business career, Trump worked or associated with proven or alleged mobsters. (Trump’s longtime lawyer, the thuggish and deceased Roy Cohn, repped numerous Mafia bosses, some of whom were connected to Trump projects.) Yet when asked about his links to the mob, Trump has repeatedly made false comments and has contradicted himself—to such a degree it seems he has flat-out lied about these relationships, even when he was under oath.

If elected president, Trump would be in charge of federal law enforcement. So his attitude toward the mob could well be deemed a highly significant campaign issue—as could his long record of not telling the truth about his ties to organized crime. Here are some of the strongest examples of when Trump has spoken falsely on this matter.

The time Trump falsely denied in a deposition that he associated with any mob associates: In 2005, journalist Timothy O’Brien published a book on Trump, TrumpNation: The Art of Being the Donald, in which he referenced an already established fact: that in the early 1980s Trump began his casino empire in Atlantic City, New Jersey, by leasing property owned by Kenneth Shapiro and Daniel Sullivan. Shapiro, O’Brien wrote, was a “street-level gangster with close ties to the Philadelphia mob,” and Sullivan was a “Mafia associate, FBI informant and labor negotiator.” (Trump also had obtained Sullivan’s assistance when he had trouble with undocumented Polish workers who were demolishing the Bonwit Teller building in Manhattan to make way for Trump Tower.)

After the book came out, Trump sued O’Brien for libel and requested $5 billion in damages—not for O’Brien’s reporting on Trump’s connection to these mob-linked guys, but for the reporter’s assertion that the self-proclaimed billionaire was actually only worth between $150 million and $250 million. In 2007—two years before a New Jersey judge tossed out the case—Trump was questioned during a deposition. Over the course of the two-day-long interrogation, Trump was forced repeatedly to acknowledge having made false statements. And at one point, a lawyer for O’Brien and his publisher asked Trump a straightforward question: “Have you ever before associated with individuals you knew were associated with organized crime?”

Trump, who was testifying under oath, answered, “Not that I know of.”

That was a clear and unequivocal response. But it was not true. Two years earlier, O’Brien had interviewed Trump and specifically asked him about Sullivan and Shapiro. O’Brien, now an editor and writer at Bloomberg, has provided Mother Jones with a transcript of the interview, and it conclusively shows that Trump believed that these two men were associated with organized crime:

Trump: They were tough guys. In fact, they say that Dan Sullivan was the guy that killed Jimmy Hoffa. I don’t know if you ever heard that. O’Brien: I have heard that. And that he was, you know… Trump: A lot of people say O’Brien: What I heard about both of them, and that anybody who wanted to get anything done down there [in Atlantic City], that if you wanted to deal with labor you had to deal with Sullivan, if you wanted to deal with politics you had to deal with Shapiro. Trump: That was only in their imagination. O’Brien: So that wasn’t true? Trump: Yeah, it was really bullshit. But, but they were tough guys. And not good guys. O’Brien: How do you handle people like that? Trump: I just was able to handle them. And I, really, I was able to handle them. I found Sullivan to be the tougher of the two. I started hearing reports about Sullivan, that he killed Jimmy Hoffa…. O’Brien: Weren’t you worried about (1) getting screwed over (2) would you be able to hold on to the whole thing yourself (3) any kind of reputational risk given that they were tough guys? Trump: I wasn’t worried because I felt I could handle it, but I felt I’d get a partner. But getting a partner wasn’t easy. And reputational, I didn’t want to have anything to do with those guys because I had heard bad, I had heard good and bad. Sullivan was like a con man and he would convince you that he’s virtually working for the FBI. You know, he’d always, and ultimately he was sent to jail on income tax evasion and it was the FBI that testified against him. O’Brien: What was Shapiro like? Trump: He was like a third-rate, local, real estate mob guy. Nothing spectacular. And I, you know, I got lucky. I heard a rumor that Sullivan, because Sullivan was a great con man, I heard a rumor that Sullivan killed Jimmy Hoffa. And because I heard that rumor I kept my guard up. You know, I said, “Hey, I don’t want to be friends with this guy.”

So here was Trump connecting Sullivan to the Hoffa murder and calling Shapiro a “mob guy.” And though Trump told O’Brien that he didn’t want to be friends with Sullivan, he did explore investing in a drywall company with Sullivan. (Trump backed out of the deal so that he wouldn’t complicate his application for a casino license in New Jersey.) After New Jersey regulators in 1982 granted Trump that casino license, they compelled the real estate mogul to buy the property that he had leased from Shapiro and Sullivan because of their backgrounds. Shapiro later told a federal grand jury that he had illegally funneled thousands of dollars to the Atlantic City mayor on Trump’s behalf—a charge Trump denied.

Trump was well aware that Sullivan and Shapiro were mobbed up, yet in the 2007 deposition he stated he had never associated with persons with such ties. He appears to have lied under oath in this instance.

The Trump campaign did not respond to a request for comment regarding Trump’s 2007 deposition statements and other remarks he has made over the years related to his interactions with mob associates.

The time Trump told Tim Russert he had nothing to do with organized crime figures: In the fall of 1999, Donald Trump renounced his Republican Party membership and declared he was considering running for president the following year on the Reform Party ticket. His exploratory bid would last only a few months. But during that stretch, he appeared on Meet the Press, and moderator Tim Russert asked Trump about his ties to organized crime. Trump cut him off to insist he had no such connections (despite his previous dealings with Sullivan, Shapiro, and others linked to the mob). Here’s the exchange:

Russert: Another book written suggested that because you are in the construction business, because you’re in the casino business, you’ve had relations with members of organized crime. Trump: False. I mean—you know, the funny thing about the casino business, in particular in Atlantic City, as an example, you have to go through a very brilliant casino control system. Every check you write, every deal you make, even outside of Atlantic City. I’m talking if I build a building in New York I send in papers as to who’s building it, who’s the concrete people, etc., etc. Everything I do is under scrutiny. And one of the things different, I think, about me is that my life has been, Tim, a very, very open book. More so than virtually any politician that you interview on Sundays.

Russert pressed on:

Russert: But you’ve never had to meet with, to do business with any organized figure in order to build buildings or do… Trump: I never have had to, and, to be honest with you, being a celebrity at a very high level is a good thing. Because they sort of—and they’re—I’m not saying the mob doesn’t exist. But they want to keep it low. They want to really keep it low. The last thing they want to do is meet with Donald Trump and have 500 paparazzi taking pictures. The answer is no. And I think, in that way—and I must tell you, I think, in that way, celebrity has been a positive for me.

Trump neglected to mention that he got his start in Atlantic City via a business deal with Shapiro and Sullivan. Nor did he refer to working with a cement company owned by Mafia chieftains and with a mob-linked union official when he was building Trump Tower. But eight months earlier, when he was not making moves to run for president, Trump did clearly state that he had in the past done business with organized crime figures. Talking to the Associated Press about his Miss USA pageant, Trump remarked, “Usually, I build buildings. I have to deal with the unions, the mob, some of the roughest men you’ve ever seen in your life. I come here and see these incredible beauties. It’s a lot of fun.”

So while discussing his hot-shot life, Trump practically boasted that as a builder he had to handle organized crime tough guys. As a possible presidential candidate, he claimed he had nothing to do with the mob. Only one of these statements can be true.

The time Trump said he couldn’t recall a mobbed-up criminal who worked for his company: Last December, Trump was asked by a reporter about a man named Felix Sater who had once been involved in a Mafia-linked stock swindle. “Felix Sater, boy, I have to even think about it,” Trump answered. “I’m not that familiar with him.” Not that familiar? Sater had worked with the Trump Organization, and Trump had been questioned about Sater in at least three depositions, including the 2007 deposition in Trump’s failed lawsuit against Timothy O’Brien.

Sater had not been mentioned in O’Brien’s book. But two days before the deposition, the New York Times revealed that Sater was doing business with Trump. The newspaper noted that Sater was something of a mysterious figure with a criminal past, and it reported:

A federal complaint brought against him in a 1998 money laundering and stock manipulation case was filed in secret and remains under seal. A subsequent indictment in March 2000 stemming from the same investigation described Mr. Sater as an “unindicted co-conspirator” and a key figure in a $40 million scheme involving 19 stockbrokers and organized crime figures from four Mafia families.

Sater, according to the Times, also “became embroiled in a plan to buy anti-aircraft missiles on the black market for the Central Intelligence Agency in either Russia or Afghanistan, depending on which of his former associates is telling the story.” The newspaper reported that he was now working for the Bayrock Group, “a partner in the Trump SoHo, a sleek, 46-story glass tower condominium hotel under construction on a newly fashionable section of Spring Street.”

It was certainly a story to receive much notice in New York: an arms-dealing, Mafia-connected man of international mystery in cahoots with the city’s most famous developer. Naturally, O’Brien’s lawyer asked Trump about him, and Trump said he had only had “limited” interactions with Sater. “Have you severed your ties with the Bayrock Group as a result of this?” Trump was asked. He replied, “Well, I’m looking into it, because I wasn’t happy with the story.” He added, “people that were trying to find things out about [Sater] have been unable to.”

Trump did not sever ties with Sater and the Bayrock Group. In fact, the following year Trump’s lawyers asked Sater to testify in Trump’s lawsuit against O’Brien. And two years after that, Sater officially joined the Trump Organization as a “senior advisor”: he was provided Trump Organization business cards and office space. Last year, a Trump lawyer said Sater had searched for high-end real estate deals for Trump’s company. Sater, who was born in the Soviet Union and later was a US government informant on organized crime and national security cases, has claimed that he met regularly with Trump and discussed deals in Los Angles, Ukraine, and China and that in 2006 he escorted Donald Trump Jr. and Ivanka Trump when the two Trump children visited Moscow.

Trump was asked about Sater in depositions related to other cases in 2011 and 2013. In the first, Trump acknowledged that he used to speak to Sater “for a period of time.” Yet in the second, he said, “if he were sitting in the room right now, I really wouldn’t know what he looked like.” Last year ABC News reported, “Trump and Sater can be seen together in photographs attending a Denver business conference in 2005, and the two men posed on stage together at the 2007 launch party for the Trump SoHo Hotel and Condominium project.”

Sater, who served prison time in the United States for a 1991 first-degree assault in which he stabbed a man in the face with a broken glass, was at first a PR headache for Trump but then became a senior adviser within Trump’s company. And Trump has had to answer questions about him in several serious legal proceedings. So how could he have said he was not familiar with him?

The time Trump denied knowing a mobster who threatened to castrate him: In 1991, the Philadelphia Inquirer asked Trump about Robert LiButti, a famous horse breeder and high-stakes gambler with ties to infamous Mafia boss John Gotti. At the time, New Jersey regulators were investigating allegations that the the Trump Plaza casino had repeatedly removed women and African Americans from craps tables after LiButti griped about their presence while playing. “I have heard he is a high roller, but if he was standing here in front of me, I wouldn’t know what he looked like,” Trump told the newspaper. And when Yahoo News in March asked Trump about this 1991 inquiry that resulted in a $200,000 fine, Trump responded, “During the years I very successfully ran the casino business, I knew many high rollers. I assume Mr. LiButti was one of them, but I don’t recognize the name.”

There’s reason to believe Trump was fibbing in both instances. As Yahoo News reported:

Edith Creamer, LiButti’s daughter, told Yahoo News in two recent telephone interviews that Trump’s account was false and that Trump and her father knew each other quite well. “He’s a liar,” said Creamer. “Of course he knew him. I flew in the [Trump] helicopter with [Trump’s then-wife] Ivana and the kids. My dad flew it up and down [to Atlantic City]. My 35th birthday party was at the Plaza and Donald was there. After the party, we went on his boat, his big yacht. I like Trump, but it pisses me off that he denies knowing my father. That hurts me.

The Yahoo News story by Michael Isikoff pointed out that a 1991 book written by John O’Donnell, the former president of the Trump Plaza casino, described a 1988 meeting between Trump and LiButti aboard Trump’s private helicopter. During this flight, according to O’Donnell, Trump discussed buying a racehorse for $500,000 from LiButti. Isikoff also obtained the full transcript of a wiretapped meeting in 1990 between LiButti and a top Trump executive in which LiButti made numerous references to his conversations with Trump and recounted an occasion when Trump personally handed him a check after he lost $350,000 at the craps table. (It was a supposedly a gift to keep LiButti happy so he would continue gambling at the Trump Plaza—and Trump has denied this occurred.) Speaking about Trump’s romantic life, then much in the news, LiButti said, “He’s lost that aggressiveness…Walks around like a f***ing banana. I can’t believe it’s Donald Trump. I don’t understand it.”

And there’s more. A new book by journalist David Cay Johnston reports that Trump took a fancy to LiButti’s daughter and that when the mob-connected gambler learned about this he confronted the casino mogul and said, “Donald, I’ll fucking pull your balls from your legs.”

Trump, according to Johnston, “lavished gifts on [Robert] LiButti, was generous with his time, and, less graciously, repeatedly tried to seduce the gambler’s grown daughter.” And for Edith LiButti’s 35th birthday, the book says, Trump offered her a rather generous present: a cream-colored Mercedes-Benz convertible. Trump’s casino, Johnston adds, was hit with a $450,000 fine for giving LiButti as gifts nine ultraluxury cars—three Ferraris, three Rolls-Royces, two Bentleys, and a Mercedes—that were quickly converted into cash.

Would a casino owner and playboy really not recognize a high-stakes player who lost over $11 million at his tables, who received exorbitant gifts as comps, and who once threatened him with castration? That’s not a safe bet. Consider this: In March, Trump insisted to Yahoo News that he didn’t know LiButti. A few weeks ago, he told the Wall Street Journal: “LiButti was a high-roller in Atlantic City. I found him to be a nice guy. But I had nothing to do with him.” In one instance, he claimed he didn’t know the man; in the other, he said he considered him a fine fellow. Once again, both remarks cannot be true.

* * *

“If people were like me, there would be no mob, because I don’t play that game.” That’s what Trump told the Wall Street Journal recently, when the newspaper was examining his mob links. But that story noted that Trump in the late 1970s and early 1980s forged an important relationship with John Cody, a local union leader who controlled cement truck drivers and who was close to Mafia bosses Carlo Gambino and Paul Castellano. Cody’s son Michael told the Journal that Trump received preferential treatment from his father and obtained cement for Trump Tower even when Cody called a strike. (In a 1992 book, reporter Wayne Barrett noted that a female friend of John Cody, who had no visible means of support, ended up owning three apartments in Trump Tower. Cody occasionally stayed at these apartments and invested $500,000 in the units.) And Johnston recently pointed out in Politico that when Trump was building Trump Tower, he used concrete (which he bought at inflated prices) from a firm owned through fronts by Castellano and another Mafia chieftain named Anthony “Fat Tony” Salerno. (Castellano and Salerno each were clients of Roy Cohn when he was working for Trump.)

Trump told the Journal that he is “the cleanest guy there is.” But that was just another lie. How clean is it to lie under oath about interacting with mob-linked thugs? No other presidential candidate has had such an extensive and publicly known record of business deals with mob associates—and of making false and contradictory statements to keep these dirty connections from becoming a major campaign controversy.