Since 1978, Chicago Police alone have arrested Shermain Miles - a black woman - 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. Miles is a master at working the system. 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 — so many times that she ranks in the top 1% for all current CPD arrestees. To the relief of many, Miles, 51, is currently in prison in downstate Lincoln. Police arrested her in August 2013, when — after a day of 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 Mujo Cesic - a 75-year-old Bosnian immigrant - at knife-point. Miles spent her childhood dodging feet, fists and anything else her mother found to inflict pain. “We were all abused by my mom, but Shermain was abused more than any of us,” said one of Miles’ two sisters. “It’s the root cause of all her problems.” The sister said that the state ultimately plucked her and her sister from their home in the Cabrini-Green housing project. Their mother died in 1994, and the sister said that she never knew their father. Miles never adjusted to foster care. By the time she was 14, Miles’ life on the streets had begun. She got pregnant as a teenager, and has an adult daughter living in Minnesota. Miles’ run-ins with police started decades ago. Her first arrest in the city came in 1978, for 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; 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.” Valentini defends his office’s handling of Miles’ more recent cases, saying that whenever she’s been charged with a felony — 10 times, according to prosecutors — she is convicted. He also says that within the last year, Miles’ cases have been assigned to a single, community-based prosecutor available to talk over concerns with the public and police about Miles’ activities. On the rare occasion when Miles has served prison time, she benefits from a state law that automatically cuts an inmate’s term in half for a range of crimes; that’s why she served only three years of a six-year term for robbing Cesic in 2008. But in 1993, Miles served about seven months of a two-year prison term — her first Illinois prison stay — stemming from an attempted robbery charge. In that case, Miles received about five months’ credit for good behavior, said Illinois Department of Corrections spokeswoman Stacey Solano. After Miles’ most recent release from prison in April 2011, CPD arrested her six times before she was finally sent back to prison.