He dated A-list actress Anne Hathaway, hobnobbed with former President Bill Clinton and Sen. Hillary Clinton and negotiated a business deal with billionaire Ron Burkle.
But on Tuesday, Italian businessman Raffaello Follieri's high-flying lifestyle came crashing down when he was arrested on charges that he posed as a representative of the Vatican to fleece wealthy investors who sought to buy and redevelop Catholic Church properties in the United States.
"In short, your honor, he is a con man, and he was able to defraud a lot of people out of a lot of money over a long period of time," Assistant U.S. Attorney Reed Michael Brodsky told Magistrate Judge Henry B. Pitman in a Manhattan federal court on Tuesday. "The evidence in this case is overwhelming because he left a trail of evidence."
Follieri was charged with 12 counts of wire fraud and money laundering. Federal prosecutors say Follieri plundered up to $6 million from his real estate investment company to furnish a lavish lifestyle that included a $37,000-a-month apartment overlooking Rockefeller Center in New York, a $100,000 chartered jet trip to the Dominican Republic and a $30,000 "house call" from his private physician who was flown to London to provide a "minor medical treatment."
If the prosecution's charges are true, the question arises: How was Follieri able to fool the rich and powerful for so long?
"Why do they call it a con game? Con is short for confidence. A person cons by engendering confidence," said forensic psychiatrist and ABC News consultant Dr. Michael Welner. "People who were attracted to celebrity, he gave them celebrity. He was dating a fancy actress. For people who want a certain respectability and power, he gave them Bill Clinton and the Catholic Church. To people who would convey respectability on someone's visibility and notoriety, he gave them appearances courtesy of paparazzi.
"This individual clearly traded on his relationships," Welner continued. "When you get a reference from Bill Clinton, you don't need anything else. He used the entrée of his acquaintances in a who-you-know world for access. That's how a world that's otherwise closed deals with references."
According to the Wall Street Journal, Clinton adviser Douglas Band helped Follieri get into business with the former president and Clinton's good friend, billionaire Burkle. In 2005, Burkle's Los Angeles investment firm Yucaipa Cos., where Clinton was a partner and adviser, agreed to invest up to $100 million in Follieri's church-property venture. For his role, Band was a paid $400,000 fee, only some of which he kept, according to the Journal.
Two years later, Burkle sued Follieri in Delaware state court for misusing $55 million. The lawsuit read like a preview of the current federal case against Follieri.
"The improper personal exchanges included, among other things, excessive use and inappropriate private jet travel for Follieri, his actress girlfriend and his father," the lawsuit said.
Follieri settled the suit out of court. But before their business dealings turned sour, Follieri met with Clinton several times and even partied with the former president and his wife at designer Oscar de la Renta's home in the Dominican Republic.
Research psychologist and trial consultant Cynthia Cohen said a high-flying con artist would have little compunction about lying to people.
"Somebody sporting in lies is less likely to be caught," she told ABCNews.com. "They have less emotional connection to lying. This guy had no conscience. He has no morality. He's at that very base level where lies don't make a difference to him."
Allegedly, that includes lying about his involvement with the Catholic Church.
According to the government's case, Follieri claimed that "the Vatican formally appointed him to manage its financial affairs and that he met with the Pope in person when he visited Rome." It adds that Follieri also paid two monsignors to wear robes of a higher clerical rank in order to create "the false impression" that he had close ties to the Vatican.
"There is an absence of humanity to look someone in the eye and form a personal relationship with that person in order to deceive them, steal from them and thus betray them," said Welner, who is pioneering research to help juries distinguish the worst of crimes on what is being called the Depravity Scale.
He added that such a person is both "parasitic" and lacking in empathy.
"They suck off other people for their own benefit," he said. "And they act without empathy."
Welner believes Follieri was motivated by the desire for attention and greed — why else would he need a $37,000-a-month apartment? — and he operated in an arena rife with both.
"It takes a person who understands greed to exploit others' greed," Welner said. "He took advantage of their greed to feed his greed because he understands greed."
"The easiest thing about the con is people think they're getting the better end of deal," Todd Robbins, the author of "The Modern Con Man: How to Get Something for Nothing." "The person perpetrating the crime makes people think he has some inside information that other people don't have, that they can use for their benefit. He fans the flames of the victims' greed."
While Burkle broke off dealings with Follieri after he suspected wrongdoing, former girlfriend Hathaway stuck by him through the lawsuit, after he was arrested for writing a bad check for $215,000 and after his charity — which she once served on the board of — came under investigation earlier this month by the New York State Attorney General's Office.
At the time the lawsuit was filed, Hathaway's spokesman said she had "faith the court system will sort this out." And even in next month's issue of "In Style" magazine, where Hathaway appears on the cover, she talked about looking forward to buying a home with Follieri. She broke up with him last week.
"Many women have been caught by lies from men," Cohen said. "Once you're connected to someone, you want to believe them, unless your radar is up. The girlfriend gets caught up in emotion."
"You're talking about someone making choices in the setting of a long-term relationship," Welner said. "No one uses reason in love and intimate attachment. She is not the first well-meaning individual who is very attached to someone who had good qualities but ultimately turned out to be a dirt bag."