“JACK ROLLING”
“Jack rolling” may be anything from picking a man’s pocket in a crowd to robbing him while he is drunk or asleep. On every “stem” there are a goodly number of men who occasionally or continually “roll” their fellow-tramps. Nearly every migrant who makes periodical trips to the city after having saved his earnings for three or four months can tell of at least one encounter with the “jack roller.” Scarcely a day goes by on Madison Street but some man is relieved of a “stake” by some “jack” who will, perhaps, come around later and join in denouncing men who will rob a workingman.
The average hobo is often indiscreet with his money, and especially so when he is drunk. He often displays it, even scatters it at times. This is a great temptation to men who have been living “close to their bellies” for months. As unpopular as the “jack roller” is among the tramps there are few who would overlook an opportunity to take a few dollars from a “drunk,” seeing that he was in possession of money that someone else was bound to take sooner or later.
7. An investigator became acquainted with two men who were jack rollers who operated on Madison Street west of Halsted. They were well dressed for the “street” though not so well groomed as to be conspicuous. The investigator pretended to them that he had just spent ninety days in the jail in Salt Lake City for “rolling” a drunk. They had no sympathy for a man who would get drunk and wallow in the gutter. “He’s not entitled to have any money.” Neither of these men drank but they “chased women” and one of them played the races. Neither had any scruples against taking money from a drunken or sleeping man. They were able to justify themselves as easily as the peddlers and beggars do. Said one of them, “Everybody is eating on everybody he can get at, and they don’t care where they bite. Believe me, as long as I can play safe I’m going to get mine.”