While Boston, Massachusetts maintains its colonial past, it's ranked as one of the world's leading metropolitan areas for education and innovation. In the heart of downtown, however, is a reminder that not everyone is on the right track. According to Sheriff Andrea Cabral, "The percentages of mental illness are off the charts. They are shocking. It's much harder once people begin to get older, to tackle those deficits that have been growing and growing and growing over a period of time." In this hour: an old school bank robber maintains his swagger; an inmate with an imaginary friend proves to be a challenge for the jail, and a shocking act lands his sister behind bars, as well.