Since 1978, Chicago Police alone have arrested [Shermain] Miles 396 times, mostly on the North Side — under at least 83 different aliases. Those arrests include 92 for theft, 65 for disorderly conduct, 59 for prostitution-related crimes and five for robbery or attempted robbery.
The frustrating truth: The system — strapped by overcrowded prisons and cuts to mental health funding — hasn’t been able to save Miles from herself or to help the communities she menaces. Nothing has worked. Not jail. Not prison. Not countless psychological exams for the woman described as being “acutely psychotic.”
Miles is a master at working the system, says [Officer Tom] Rolon. She fakes seizures that mean costly hospital visits. She gets judges to delay her cases. And then she returns to the streets to be arrested again and again.
To the relief of many, Miles, 51, is currently in prison in downstate Lincoln. Police arrested her last August, when — after a day of allegedly slapping, punching and generally harassing folks on a stretch of Broadway in Uptown — she is accused of chasing after Ald. James Cappleman (46th). That arrest landed her back in prison for a possible parole violation of a 2010 conviction for robbing a 75-year-old Bosnian immigrant at knifepoint.
Miles’ run-ins with police started decades ago. Her first arrest in the city came in 1978, for allegedly breaking into a car. Since then, police have detained her for assault, burglary, drug possession and public indecency — among many other crimes. Miles’ busiest year was 1988, when police made 25 arrests. In the majority of those cases, Miles is arrested, released and never convicted; Rolon says that’s partly because Miles knows how to work the system — getting judges to delay cases so that her victims get frustrated, stop coming to court and then the case is dismissed.
The Cook County state’s attorney’s office counts 73 convictions in all.
“We also need her to come to court,” said Fabio Valentini, chief of Cook County’s Criminal Prosecutions Bureau. “You can see that in a great many cases, she fails to appear in court.”