There are “three time losers” in some recidivist cases and then there is Shermain Miles. For Miles, the magic number is 396. That’s right, she has racked up roughly 400 arrests since 1978 but insists that 396 is the magic number and that she is now considering a change in her lifestyle.

Some might have found number 3 or 30 or 300 to be that moment that concentrates your mind. However, Miles, 51, insists “I’m really not that bad a person.” When approached by a reporter after being put on a train back to Chicago, Miles threatened “I got a lawyer to sue y’all.” Actually, she has had what appears hundreds of lawyers.

She has had 73 convictions in total over the years and is a poster child for habitual offender sentencing. Her last victim was Chicago Alderman James Cappleman in a physical assault. Before that, she robbed Mujo Cesic, a 75-year-old Bosnian immigrant, at knife point.

The neighborhood has told reporters that Miles has terrorized locals and is a continual menace. She has a history of alcohol abuse in addition to her criminal propensities. The question is when a society should impose a much longer sentence for such a habitual criminal pattern rather than continuing the cycle of arrests and releases.

What do you think?