A would-be Italian playboy who dated the Hollywood star Anne Hathaway was sentenced last night to four and a half years in jail for cheating investors out of millions of dollars to keep up with his celebrity friends.

Raffaello Follieri, who dated the star of The Devil Wears Prada for four years until his arrest, boasted that his ties to the Vatican allowed him to buy church property at discount prices.

Follieri, 30, who once hosted the presidential candidate John McCain on a rented yacht in the Adriatic, told the judge in New York, said: “I made some terrible mistakes. I always thought I could repair all the wrongdoing but I was wrong.”

He pleaded guilty to swindling investors, including Yucaipa Cos, the investment company run by Ron Burkle, a supermarket magnate. “I just hope that some day those who have been hurt by my actions will forgive me,” he added.

Passing sentence yesterday, Judge John Koeltl said that the crime was aggravated by the fact that Follieri had masqueraded as a representative of a religious organisation and spent his criminal proceeds on “lavish personal expenses”.

He imposed forfeiture of $2.44 million of Follieri’s property and said that he would consider ordering restitution to the victims. “The defendant will suffer not only a substantial term of imprisonment but also financial ruin,” the judge said.

The prosecution suggested that Follieri, from Foggia in Italy, used his relationship with Hathaway to lure investors. Follieri’s deceit began in 2004 when he formed a company with his father, who was convicted in Italy of embezzling funds in 2005.

Follieri claimed that top Vatican officials had authorised him to represent the Catholic Church in the US in the sale of church properties. He showed investors a fake letter from the late Pope John Paul II and said that he regularly met the Pope.

The prosecution said that he shamelessly misled investors and church officials, even hiring two bishops to travel with him.

FBI agents recovered a letter from the safe of Follieri from Cardinal Angelo Sodano, at the time Secretary of State of the Vatican. The Cardinal said that he was perturbed by the way Follieri was exploiting his ties to the Cardinal’s nephew.

Follieri did bid at auctions but was outbid by estate agent companies. Instead he spent money from investors on expensive clothes, holidays, a $37,000-a-month apartment in Manhattan and private jets.

The prosecution had argued that Follieri deserved a long sentence. They noted that, in seeking leniency he had sent the judge photographs of himself with the Pope.

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