If a particular subway train was not crowded enough, he and other pickpockets would manipulate the playing field. Mr. Rose said he and Mr. Simmons would delay southbound trains in Harlem, holding open the doors at the 116th and 110th Street stations. “It would be a two- or three-minute delay, or maybe a bit more,” he said. But that was all it took for the downstream platforms to fill with passengers waiting for the next train to arrive. By the time Mr. Rose rode into the station, they would be packing his car, providing ideal working conditions.

Mr. Rose said he would try to strike before the train reached Times Square or Union Square, where there was a high concentration of transit police officers, particularly those in plain clothes who spend their days looking for pickpockets. Mr. Rose admitted to a fascination with the officers who pursued him, discussing them by name and speaking admiringly of their knowledge of pickpockets.

While many pickpockets work with a partner to serve as a lookout, Mr. Rose generally did not.

“Wilfred Rose can work by himself because the crowd becomes his partner,” Mr. Dones said, adding that Mr. Rose was skilled at identifying plainclothes officers. “He always assumes someone is tailing him,” Mr. Dones went on, adding that Mr. Rose often did what he called the “French Connection”: stepping into a subway car and then exiting quickly, to see if he was being followed.

On his back, Mr. Rose often carried a string knapsack, with a change of T-shirt and ball cap so that he could alter his appearance if the police were looking for him, detectives said.

Asked about his success at avoiding arrest, Mr. Rose dismissed any suggestion that he was the best pickpocket in New York. “I don’t think so,” Mr. Rose said, mentioning others who might deserve that honor. He singled out a man named Rudy Brown, a pickpocket with a record of robbery and larceny convictions, who Mr. Rose said tried to teach him how to pick a pocket behind his back (a maneuver Mr. Rose never mastered) and how to remove cash from a wallet while it is in someone’s pocket (which Mr. Rose said he could sometimes do).

In New York, pickpockets tend to stick to their turf. There are crews that work only department stores. A number of the “topside” pickpockets, as the police refer to those who work the streets, are South American, detectives said. Subway pickpockets tend to be lifelong New Yorkers.

Traditionally, pickpockets met at diners to find a partner to work with for the day, current and former detectives said. One “shape-up” location, as detectives call the gathering places, was a deli near 122nd Street and Adam Clayton Powell Boulevard, but that was several years ago. There was little socializing, Mr. Rose said, adding that “shotplayers aren’t boozy” and rarely meet in bars.