Examples are many, but it's 1973's Harry in Your Pocket that perfectly embodies both the sex appeal of classic pickpocketing and the whiff of nostalgia that clings to it. Harry, a suave master wire played by James Coburn, himself trained by a Fagin from the unspecified "old country," recruits two young people to his canon. Inside his swank penthouse in Seattle, he explains the deal: "No whoring, no strong-arm. I have rules! Lots of rules!" His stalls act fastidiously, dress impeccably, travel in style, and stay in only the finest hotels. But there are hard times ahead. Society is changing. Harry's aging partner Casey is losing his edge, misty with nostalgia for the old days. "There's no sense of craft anymore," he tells a promising young stall. "Nowadays youngsters haven't got it, no patience, no discipline, they don't want to spend the time to learn. So they … hit some poor old lady over the head and grab her purse. … It shouldn't be allowed!" But there's something even more troubling afoot. "Credit cards are not going to go away," Harry tells Casey. "Like anything, money will disappear."
"Do away with money?" cries Casey. "That's ridiculous!"
"Communism! It's criminal!"
The movie was right on both counts, even if its timing was off. Pickpocketing continued to flourish for two decades after Harry's day, but extinctions take a long time. Even earlier, in 1960, Popular Science had older hooks already grousing that the next generation will be the one that finally casts the vaunted skill into disuse for good: "The old ones die off," the writer explained, "and the newer generations lack the gumption and application it takes to learn the business."
There are still a handful of pickpockets working cities, and some old-fashioned troupes on the road, according to Bob Arno, hitting big sporting events and smaller towns with "lax judicial environments" and police less adept at spotting dippers. They'll do it a while longer, if they don't make the jump into fraud or catch a felony rap. But by the looks of it, the day may not be far off when the fabled American hook of yore, stooped and trembling of hand, walks that subway platform one last time, pausing for just a brief instant to drop your empty wallet in the trash before calling it a day.