"I live off money that women give me," the "Swiss gigolo" told his country's police in 2001.
But when he allegedly tried to hoodwink BMW heiress Susanne Klatten, Helg Sgarbi got too greedy.
On Monday Sgarbi goes on trial in Munich charged with blackmailing a string of wealthy women out of millions of euros.
If convicted, the smooth-talking Sgarbi, who told his wealthy conquests he was a "special Swiss representative in crisis zones," according to the charge sheet, faces up to 10 years in prison.
According to prosecutors he first met Klatten, who has a personal fortune of over $13 billion according to the Forbes Rich List, at the Lanserhof exclusive Austrian health resort in July 2007.
At first the married mother-of-three spurned his advances, but when Sgarbi turned up unexpectedly in the south of France where she was on holiday the following month, they began an affair.
Later in August they met in a Holiday Inn hotel in Munich – suitably downmarket for Klatten not to run into any acquaintances – for an "intimate" encounter that Sgarbi secretly filmed, according to the charge sheet.
In September they met at the same hotel and this time Sgarbi allegedly said that he needed €10 million euros because he had injured a little girl in a car crash in Florida – asking Klatten to lend him €7 million euros.
Klatten believed him, handing over the sum in the underground garage of the
Holiday Inn a cardboard box containing seven plastic folders each containing stacks of €500 banknotes.
But then Sgarbi went for the big one, telling the 46-year-old to leave her husband and put €290 million into a trust fund to fund their new life together.
Klatten balked, and ended the relationship. But then Sgarbi turned nasty, according to prosecutors, threatening to send compromising video footage of the two together to the press and to her husband, among others.
This time he allegedly demanded €49 million, which he subsequently reduced to €14 million, and set a deadline of January 15 last year. But she had long since informed the police, and Sgarbi was arrested.
Klatten was not Sgarbi's only victim.
According to German magazine Stern, he first came to the attention of Geneva police in 2001 because his "fiancé" Countess Verena du Pasquier-Geubels - 50 years his senior - had gone to the police.
The countess, who owns a chateau on Lake Geneva, first met Sgarbi – then called Russak – in May 2001 when she was 83 after he sent three red roses to her table in a luxury hotel in Monte Carlo.
Feeling sorry for Sgarbi, she dropped the charges after he returned 20 million Swiss francs to her. She even paid the lawyers' fees of 750,000 Swiss francs. She died in 2002, and Russak changed his name to Sgarbi.
According to the charge sheet, he used a similar strategy each time, saying he needed millions of euros because he had injured a child in a road accident. In one case he persuaded a woman, who had already allegedly given him a million euros, to hand over another €1.5 million to pay off the Mafia, according to the charge sheet.
The woman, who has not been named, took out a loan at Swiss bank UBS -which she is still paying off - and handed him the cash at a train station in February 2007.
"He didn't even say thank you," the woman told Stern magazine.