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The word pickpocket first emerged in the late 1500s to describe a person who steals wallets, money, and other valuables from the pockets of other people. Pickpockets have a lengthy history throughout the world and have likely existed as long as people have carried valuables with them. Edwin Sutherland placed pickpockets in a class of skilled criminals that includes shoplifters, confidence men, and check writers. He described these types of criminals as professional thieves who have great acting skills and principally depend on their wits and talking ability. While pickpocketing could conceivably be committed by just about anyone of any age, race, or gender, it was not uncommon for children to engage in the “trade” in early American cities. This topic is an important one to explore because many societal factors coalesced to allow pickpocketing, and juvenile pickpockets in particular, to flourish in large American cities in the 1800s.

Ample references to pickpockets in the United States can be found in newspapers dating back to at least the 1800s. A New York Times article from 1865 describes a “swell mob” of pickpockets who would rush toward city cars in the evening and go about emptying the pockets of the crowd. Pocket picking persists to this day, and the method has remained largely unchanged. John Young, a former criminal investigator with the Amtrak Police Department, states that contemporary pickpockets tend to operate in places where large crowds of people congregate (e.g., cities or train stations) and will typically bump into their intended victim in an effort to distract him/her long enough to steal his/her wallet or other valuables.

Pickpockets like Fagin in Charles Dickens's Oliver Twist (depicted above) have often been romanticized in literature. Historical research of pickpocketing reveals that an entire subculture existing during the 1800s shared their techniques by word of mouth, leaving little documentation. Many well-known American pickpockets started their careers at a young age.

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Pickpockets have oft been romanticized in classic literature through colorful characters like Charles Dickens's controversial character Fagin, who teaches children the finer points of pocket picking in his veritable school for crime. Fictional accounts aside, historical examinations of pick-pocketing reveal an entire subculture that existed in the 1800s; many well-known American pickpockets began their criminal careers as children. Understanding the history of pickpocketing is no easy task because of the deeply secretive nature of the pickpocketing subculture that existed primarily in larger American cities during the 1800s. Timothy Gilfoyle, who has written extensively on juvenile pickpockets, notes that records are scarce, as the subculture of juvenile pickpockets was largely organized around an oral culture that left little written evidence. Gilfoyle goes on to state that the lack of written records coupled with the fact that pickpocketing was, for the most part, an invisible crime makes historical analysis of the subject very difficult. However, historians have been very clear on the factors that precipitated and allowed juvenile pickpockets to flourish. With industrialization in the United States came an infusion of people into large cities, and large-scale factories (or sweatshops) largely replaced craftsmen and skilled laborers. As a consequence, many children who might previously have been engaged in an apprenticeship were largely left to their own devices. All of these factors converged, along with the fact that school attendance was not compulsory in the 1800s, to result in an abundance of juvenile pickpockets. The newsboy profession often overlapped with pick-pocketing. George Appo, who is perhaps the most famous American pickpocket, revealed that he and a fellow newsboy were able to pickpocket for a full two years before police apprehended them. Another pickpocket and newsboy, Larry Caulfield, is quoted as saying, “I made a great deal of money at picking pockets, without getting into difficulties with the police.” The “newspaper dodge” was a favored tactic among newsboy pocket pickers. This strategy involved waving a newspaper in the face of a potential victim and while he/she was distracted, the newsboy would reach into the victim's pocket and remove any valuables. Larry Caulfield would often board crowded streetcars and shove a newspaper in the face of male passengers and yell “News, boss?” in an effort to divert the attention of his intended victim. Caulfield bragged, “If you will stand for a newspaper under your chin, I can get even your socks.” So many of these children posed as newsboys that it was vitually impossible to tell a real newsboy from a thief.

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