Is Anne Hathaway's Ex a Con Man?

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.

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