Chicago Woman Has Been Arrested 396 Times Since 1978

Well, I suppose we all have to reach for the top:

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. On Tuesday, 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.

All joking aside, it seems clear that this is a woman who has been deeply troubled for a very long period of time. The probability that we’re dealing with mental illness, alcoholism, or drug abuse, or all three in some combination, is really quite high. The fact that she didn’t get the help she needed may well be as much an indictment against the way we deal with mentally ill people as it is an indictment against her.

FILED UNDER: Crime, , ,
Doug Mataconis
About Doug Mataconis
Doug Mataconis held a B.A. in Political Science from Rutgers University and J.D. from George Mason University School of Law. He joined the staff of OTB in May 2010 and contributed a staggering 16,483 posts before his retirement in January 2020. He passed far too young in July 2021.


  1. Gustopher says:

    I kind of hope the police have a party for her when she hits her 400th arrest. And that we actually start taking care of our mentally ill.

    The first is probably more likely.

  2. Dave Schuler says:

    The amazing thing is that she’s not actually a member of the City Council.

  3. And Dave Schuler wins the comment thread.

  4. By the way, 396 arrests over 35 years averages out at 11 arrests a year.

  5. Tyrell says:

    This woman is obviously violent and a threat to society. Why she is out roaming the streets is a perfect example of the revolving door courtroom justice with soft judges who are more concerned about the criminals than their victims. Judges need to be held accountable. This woman should have been locked up and the key thrown away long ago.

  6. matt bernius says:

    You really don’t understand the first thing about how our legal system actually works do you?

    Seriously, turn off the right wing radio, close WND, and actually do some research on.

  7. Neil Hudelson says:


    Is this a parody of an idiot? If you are being sarcastic you are much too good at it.

  8. Jim M says:

    Give her a retroactive abortion.

  9. Tony W says:

    For better or worse, the prison system is our mental health system today.

    I personally feel a rich nation owes its most vulnerable citizens a better lot in life, but reasonable minds can disagree. It is, nevertheless, difficult for me to understand how “fiscal conservatives” feel they are somehow saving taxpayer dollars by continually reducing funding for mental health services.

  10. Justinian says:

    According to the alderman whom she allegedly attacked, this woman

    “has a history of pulling a knife and holding it to people’s necks.”

    Source is here

    It has been said that the world would be a much different place if the people who decided whether countries go to war were the same people who had to fight them.

    And, the world would be a different place if those here writing to exculpate Shermain Miles and blame society instead were the ones same ones who have had a knife placed at their throats.

    We do have, however, the opinion of exactly such a person. The full story is shown below:

    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.

    On Tuesday, the Illinois Prisoner Review Board is set to decide whether Miles violated the terms of her parole; if she did, it’s likely she’ll be held until April 2014, when her parole expires.

    Mujo Cesic, Miles’ victim in the knife robbery, wants another option.

    “She should never be released,” said Cesic, a firefighter in his native Bosnia who spoke through a translator.

    Source is here.

    Notice that the Bosnian immigrant’s opinion is essentially the same as that of Tyrell, above, which was ridiculed as “the parady of an idiot.”

    And liberals wonder how they got their reputation for caring only for the perpetrators, and nothing for the victims, of crime.

  11. Tony W says:


    And liberals wonder how they got their reputation for caring only for the perpetrators, and nothing for the victims, of crime.

    And here’s an example of a typical “conservative” coming to the party late and complaining that somebody drank all the beer.

    If we get help for these people before they are perpetrators, we prevent the crime in the first place. Spin it however you like, but that’s what liberals advocate. “Conservatives” such as our friend Justinian are simply reactionary – ‘penny wise and pound foolish’.

  12. Justinian says:

    In reply to Tony W, above:

    It is unfortunate, to be sure, that the woman had so abusive a mother that the state had to separate her from her mother, and then it was this woman’s misfortune that her state-appointed foster parents were not all that good either, apparently. But even in this the state already did a lot to help her, since her foster parents were surely much better than her natural mother. She has also been in and out of mental health facilities, where, again, she received help, and surely at state expense. All these are preventive measures, provided by the state, and they did not work. She is also said to be good at gaming the system, which again shows that if there were more preventive measures, she would just game them into ineffictiveness like all the others. (All this information is from the articles cited in my original post.)

    Not even God can change the past. Once a crime has been committed, it cannot be prevented. No society, ever, has prevented all its crimes. Crime happens, and, when it does, it is beyond prevention. Everyone in political discourse, left, right, and center, must confront this simple fact.

    For the case at hand, the surest, and in fact the only, way to prevent this woman from committing further crimes is to separate her from society, whether through prison or asylum. It is the only viable crime-prevention method left. It is not reactionary: it is realistic.