During the next few years, Humphreys appears to have been involved in several jewel thefts and burglaries and by age 16, he was serving a 60-day sentence for petty larceny in Chicago's Bridewell Jail. The original charge had been one of felony burglary (which would have carried a much stiffer sentence) but Humphreys had convinced the prosecutor to change the charge. According to a later acquaintance of Humphreys, the young criminal's private ultimatum to the prosecutor went something like this: "You try to get me indicted for burglary and I will weep in front of the grand jury. They probably won't indict me because I am only 16 years old. But even if you get me to court, the do-gooders will say that because of my extreme youth I ought not to be sent to prison. However, if you reduce the charge to one of petty larceny, I will plead guilty. I will get a light sentence. You will get a conviction that looks good on your record. Everybody will be happy. What's more, you will receive a suitable gift before the case goes to court".