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Chicago Woman Arrested 396 Times Since 1978

Shermain Miles

Shermain Miles

A Chicago woman who’s racked up nearly 400 arrests over 35 years — while using at least 83 different aliases — is currently behind bars in downstate Illinois.

But considering how she’s bobbed and weaved in and out of the justice system for nearly four decades, one question remains: How long, after she is released, until she winds up imprisoned again?

According to a Chicago Sun-Times report, 51-year-old Shermain Miles was arrested last August after she allegedly chased after Chicago Ald. James Cappleman (45th) and slapped, punched and harassed a number of other individuals along Broadway Street in the city’s Uptown neighborhood.

Miles was imprisoned in Lincoln, Ill., due to a possible parole violation on a 2010 conviction for robbing a 75-year-old at knifepoint, the paper reports. The Illinois Prisoner Review Board is expected to decide whether she violated her parole — and if she found to have done so, she will likely remain held until next April. If not, she may be released.

According to the Sun-Times, Miles came from an abusive upbringing and was first arrested in 1978 for allegedly breaking into a car. Through the years, she has also been arrested for burglary, assault, drug possession and public indecency and convicted on 73 separate occasions. In one year alone, in 1988, she was arrested 25 times. She has also spent significant amounts of times in mental health hospitals and was imprisoned at least 10 times, largely living on the streets when she wasn’t behind bars.

At the time of her arrest last summer, Cappleman described Miles as someone who has long “terrorized the community” with her behavior. He said he hopes “to get this woman help, so she is off the streets,” the Chicago Tribune previously reported.

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