Renting to the Italian Mob!
After listing a 1BR apartment in the Chicago suburbs, I ended up showing the property to a woman and her daughter who said they were originally from Chicago but have been living in Italy for the last 25yrs. They seemed very nice, asked lots of questions, and even added me as a friend on FB (which was a little odd). After a few days more questions started to arise; the woman was going to have her dad move in at some point, they were going to be gone for some months, and they wanted to send payments from an account in Italy.
They were also adamant about not providing social security numbers on the application. I talked to the woman's dad who was going to move in, and he sounded like he was straight out of the Sopranos. "We're going to pay you rent, and you don't ask any questions" was one comment.
I started doing internet searches on the family name, and sure enough made the connection. They were part of an Italian Mob family out of Kenosha. I found lots of news articles that linked the older man with mafiosos that have been arrested or murdered! Sure there were plenty of red flags to begin with, but I definitely didn't expect this.