Police in Chicago know Shermain Miles by face, but not for a good reason. Ms. Miles, who is frequently taken into custody by cops for being drunk or undressed on the street, has been arrested 396 times since 1978. Miles has used 83 different aliases during her many arrests.

Over the years, Miles has been arrested 92 times for theft, 65 for disorderly conduct, 59 for prostitution-related crimes and five for robbery or attempted robbery and the list goes on.

Chicago’s system hasn’t been able to help Miles because the prisons are overcrowded and there’s not much money in the city for mental health care. So what ends up happening is that Miles becomes part of the criminal system’s revolving door. Although Miles is described as being “acutely psychotic” she has never been given the long term help she needs.

To her credit, Miles, 51, knows how to work the system. She’s an expert at getting her cases postponed and faking medical illness so that she can be taken to the hospital, all of which costs the city money.

Miles’ troubles began when she was a just a child as she dodged beatings from her mother.

“We were all abused by my mom, but Shermain was abused more than any of us,” said one of Miles’ two sisters, who lives in the Southwest suburbs. “It’s the root cause of all her problems.”

Miles’ sister said she survived because, after their mother’s death, she was put in a foster home where people loved her. That wasn’t the case for her Shermain.

Miles usually sleeps on the street because she often gets in fights in homeless shelters and so the question remains, what can the city do for people like Miles?

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