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Accused conman Simon Gann poses covered in U.S. $100 bills in this undated handout photo.
Accused conman Simon Gann poses covered in U.S. $100 bills in this undated handout photo.

From Globe T.O.

Gambling, sex, Asperger's and my twin con-man brother Add to ...

Stephen Reid was sitting at the bar in Castro's Lounge, a Beaches watering hole where he's a regular, when he noticed the new guy a few seats down.

The stranger was wearing jeans, a Chelsea soccer jersey, and a thick woollen coat - a bit much for the April weather. The two solo bar-sitters started talking. The stranger said he'd earned his doctorate at the prestigious Massachusetts Institute of Technology, and Mr. Reid, a well-spoken 41-year-old with a doctorate in sciences himself, was intrigued.

Introducing himself as Giancarlo Dinatale, the acquaintance apparently worked for Goldman Sachs, where he had developed a differential calculus model for stock markets. He also told Mr. Reid he planned on buying a $750,000 home in the Beaches (with cash) and flying in a designer from New York. But there was a glitch.

"He told me this story about how he'd been in Starbucks a few days earlier and his wallet and passport had been stolen, along with his laptop," Mr. Reid remembered him saying as they went outside for a smoke that night, around four months ago. "He asked if I could help him out a bit. I thought he sounded pretty legitimate."

Mr. Reid lent the man $300.

The next day, they met again and Mr. Dinatale said he'd spent the cash on applying for new documents. He asked for another $160, which Mr. Reid provided, as well as a sofa to crash on. Mr. Reid also bought him dinner. They played chess and poker, and Mr. Dinatale was skilled at both. Yet over the week or so they knew each other, the man wore the same clothes and "obviously wasn't showering."

When they met to settle the loans, Mr. Dinatale didn't show up, but later called and apologized. He'd miss another scheduled meet. Mr. Reid never saw him, or his $460, again.

Mr. Reid wasn't his only alleged mark. In fact, there is a website devoted to people who claim to have been duped by this man, whom police have identified as someone named Simon Gann. A homeless, about-to-be-deported gambler who says he has Asperger's Syndrome, Mr. Gann now sits in a Toronto jail, facing 20 charges, including 14 for fraud and two each of harassment, theft and threatening damage.

He is alleged to have worked across Toronto, bilking his marks of sums that seldom exceeded a few hundred dollars. He did not go to M.I.T. And he is not to be confused with his identical twin brother, Jordan, who once posed as a doctor and also wound up in custody.

An awkward man of many talents

About a year ago, Michelle Inder was travelling in Tegucigalpa, Honduras, when a man approached her in her hotel. Initially she brushed him off, but when the stranger, Samir Benzema, pinned down her accent - she was a New Zealander and travel buff living in England - they started talking. Mr. Benzema spoke several languages, some to her, others into his BlackBerry.

"I was like, 'Wow, this guy is really interesting. He speaks 10 different languages, and is telling me he works for Goldman Sachs in New York,'" says Ms. Inder, 33. He told her he was a card whiz, though she then watched him throw away $5,000 at a blackjack table.

He had also carried a bag of American money, which he said had as much as $50,000 in it. A day later, he claimed it was stolen, and began asking her for cash, promising he'd repay her.

"You look back and you think, 'How could I be so stupid?' It was very dubious. So many red flags."

In the end, Michelle lent or spent about $4,500 (U.S.) on the man. Much of it he withdrew directly from her credit card. After she left him to rejoin her tour in nearby Costa Rica, she asked for it back.

"He's like, 'All you cared about was money, you never cared about me,' " she says, sighing. "It was insane."

The inconsistencies occurred to her only later. At one hotel, a letter was addressed to a different name: Gann, which Mr. Benzema dismissed as a mistake. Days later, the name Simon Gann popped up in an e-mail. When she asked, he said it was one of his six names. Unconvinced, she Googled him.

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