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The Pickpocket’s Tale

Wilfred Rose, 58, is one of the “Nifty 50” — pickpockets whose mug shots are on flash cards studied by plainclothes transit police officers.Credit...Illustration by Kyle T. Webster

Wilfred Rose, 58, spent a career studying the pants pockets of New Yorkers, always on the lookout for “a nice stiff wallet” full of cash, or better yet, the fainter outline of a dozen folded bills.

When he describes sizing up a promising mark, his eyes stop blinking and he leans forward. “When they are wearing a suit, or nice pants, you can visualize it,” said Mr. Rose, whom detectives describe as one of the city’s craftiest pickpockets. “You know when it’s there.”

For years, Mr. Rose had his run of New York, largely evading detection and arrest. His tales of larceny cover four decades.

There was the time, nearly 20 years ago when the heavyweight bout at Madison Square Garden devolved into a riot, brawls erupting in the ring and the stands. Amid the chaos, Mr. Rose recalled, he smelled opportunity. He seized on a target, a Japanese tourist whose pocket bore the outline of a wad of bills, and struck quickly, disappearing into the crowd with Japanese currency worth several thousand dollars.

Then there are times when he stole with kindness. Mr. Rose recounted an episode at an airport when he spotted a man at the baggage carousel, the outline of a fat envelope visible. Mr. Rose offered a hand with the man’s luggage, the victim never noticing the envelope being lifted from his pocket. Inside, Mr. Rose said, were $5,000 and a diamond ring.

Then there was the time, he claims, that he decided to show off after spotting an off-duty sergeant, a renowned chaser of pickpockets, on his way to Yankee Stadium. Mr. Rose sidled up to him in the crowded train, plucked a roll of $300 from the man’s pocket and slipped $30 or $35 of his own money, in smaller denominations, into the sergeant’s pants. When the sergeant recognized Mr. Rose one stop later, he patted his pocket, reassured to feel money there. (In an interview, the sergeant, now retired, denied ever being bested by Mr. Rose.)

But that was a long time ago. These are lean years for pickpockets. People carry more credit cards and less cash; men wear suits less, and tightfitting pants more. The young thieves of today have turned to high-tech methods, like skimming A.T.M.s.

And pickpockets like Mr. Rose have been left behind. His last larceny, in March, on an uptown No. 2 train, ended with his arrest and his sentencing this month to one and one-half to three years in state prison, where Mr. Rose — who has done short stints in jail — has never done time.

“We’re disappearing,” he said wistfully in a recent interview at the Manhattan Detention Complex, where he told his life story. “In a few years, there won’t be any of us left.”

Mr. Rose is one of about 50 pickpockets whose mug shots are on flash cards studied by plainclothes subway officers. They call the thieves the “Nifty 50.”

“I would say he’s one of the best,” said Nelson Dones, a retired detective who put together the training cards.

Some of the thieves have a shtick. There is Francisco Hita, who when caught touching someone’s wallet, pretends to be deaf, the police say, responding with gesticulations of incomprehension. There is an older man who pretends to be stricken by palsy while on a bus, and then uses a behind-the-back maneuver to infiltrate the pocket of the passenger next to him.

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Mr. Rose would use his middle finger and back of his forefinger to pick the pockets of strangers.Credit...Illustration by Kyle T. Webster

There are flashy dressers, like the 5-foot-3 Duval Simmons, whose reputation is so well known among the police that he says he sometimes sits on his hands while riding the subway, so he cannot be accused of stealing. Mr. Simmons, an occasional partner of Mr. Rose’s, said he honed his skills on a jacket that hung in his closet, tying bells to it to measure how heavy his hand was.

Mr. Rose’s notoriety stems from how infrequently he has been arrested, and how, at least in the last 15 years, he has never been caught in the act by plainclothes officers.

While some details of Mr. Rose’s story are impossible to verify independently, he was well known to the police and had a reputation for being careful. “He’s been plaguing New York for decades,” said Mr. Dones, who spent 14 years chasing pickpockets. “We’ve seen him so many times over the years, yet we’ve never been able to catch him” — at least, in the act of stealing. Veteran detectives expressed surprise at Mr. Rose’s recent arrest, both for its rarity and because he was caught working with a partner — he normally worked alone.

“I’m too old for this,” Mr. Rose said during one of several jailhouse interviews. “I used to think of it as a game. But jail makes you think of it as stealing.”

And the game has changed. Pickpockets now are not interested only in the cash, of which there is less; increasingly, they sell or share credit-card information with identity-theft rings.

Mr. Rose is dismissive of the younger generation of street criminals and refused to train apprentice pickpockets. “Young people, they aren’t interested in this,” Mr. Rose said. “It takes too much patience.”

He is a slight man but has long, insistent fingers, and eyes set wide apart. Pickpockets call each other “shotplayers.” Asked to reflect on his career, Mr. Rose said, “Shotplayer — I don’t even want to hear that word anymore.”

After his release, he vowed, he will reform. “I’m done with this life,” he said. “I’m going to buy a bike and become a messenger. That’s what I’m going to do. I want a job.”

Born in the Virgin Islands, Mr. Rose moved to Harlem as a child to live with an aunt. He said he became fascinated with pickpockets after watching Sherlock Holmes movies, fixating on scenes in which prostitutes stole customers’ wallets. “Their hands would come out of the shadows,” he recalled, smiling at the memory. He did not finish elementary school. He learned his craft from an older thief named Sidney who befriended him.

When Sidney’s wife would come home, Sidney would — either for sport or for beer money — pick her purse as he greeted her at the door. That was the first time Mr. Rose had a chance to study a pickpocket in action.

His first arrest came in the early 1970s, as he worked the crowds outside the Apollo Theater. Much of his life revolved around the theater, which was just a few blocks from his home; there he met his wife, Grace, striking up a conversation with her as she waited in line.

Over the next decades, he developed a set of self-imposed guidelines: Look for a target who appears relaxed, preferably a “stranger,” his term for a tourist or a foreigner. (New Yorkers, he said, have a tendency to react more violently.) When possible, avoid stealing from women.

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Mr. Rose was arrested in March at an Upper West Side subway station and was sentenced this month to one and one-half to three years in state prison.Credit...Illustration by Kyle T. Webster

“It’s a matter of principle, but they also seem to carry only a little cash,” Mr. Rose said. “In a woman’s wallet, it’s 10 credit cards.”

In the jail’s visiting room, Mr. Rose demonstrated his main technique. Placing a thumb on the outside of the pants for leverage, he used a forefinger in an upward scratching motion, showing how he would tug at the pocket lining.

“We call it ‘winding it up.’ It raises the cash,” he said. When the money is accessible, Mr. Rose forms pincers with his middle finger and the back of his forefinger to extract the cash.

Beyond technique, he said, what’s needed is a crowd. Some of his favorite spots include parades along Fifth Avenue and busy subway trains.

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.

They frequently traveled across the country, working the crowd outside sporting events, said Mr. Rose. Mr. Dones said he once traveled to Las Vegas with several detectives to watch Manny Pacquiao fight Miguel Cotto, only to recognize a New York pickpocket in the crowd.

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Nelson Dones, a retired detective, said Mr. Rose, a veteran pickpocket, was “one of the best.”Credit...Illustration by Kyle T. Webster

But Mr. Rose said he had not worked outside a prizefight or a Super Bowl in decades.

In his heyday, he recalled, he blew through most of the money he stole, taking his wife on trips. The couple have been together since 1976 and married in 1989. She had a daughter of her own and together they had three children, all boys. He had a clothing store at Bergen Street and Nostrand Avenue in Brooklyn for a time. That folded. He worked other odd jobs, too, but he always stole.

In the 1980s, he said, he “might take three wallets in a night.” But personal circumstances led him to slow down: He and his wife had a son, Malick, in 1989. He was autistic, and Mr. Rose said he needed to be home more and could not risk being incarcerated.

“I didn’t take risks once he was born,” Mr. Rose said. “I’ve been very careful. I’d been taking care of him his whole life.” Mr. Rose said he spent most afternoons with his son visiting Crotona and Central Parks.

He decided to turn over a new leaf, of sorts: He began to sell marijuana in dime-bag quantities.

Mr. Rose said his wife preferred that he “just sell a little weed,” because if arrested, he would generally face misdemeanor charges rather than a felony charge for larceny. “It is safer,” he said. “My wife worries about me.”

Selling marijuana became harder in the late 1990s, Mr. Rose said, with increased competition from dealers and more scrutiny from the police.

Then in 2007, a fire broke out in a neighbor’s apartment in Mr. Rose’s building in the Bronx. At the time, Mr. Rose was behind bars in a city jail after an arrest as a pickpocket. Both Malick and Ms. Rose’s daughter, who suffered from seizures, were inside, unsupervised, and ended up with severe smoke inhalation, Mr. Rose said.

In the years after the fire, the health of both children deteriorated rapidly; Ms. Rose’s daughter died in 2009, and Malick in 2011. Mr. Rose said that after his son died, he began stealing at a faster clip. “I was lost. I had nobody to take care of. After that I began doing this more,” he said.

When Mr. Rose was arrested this last time, he was in the company of an older accomplice, Otis Williams, 59. The two were working the No. 2 train when, the police say, Mr. Williams moved in on a woman’s purse. The woman said she recalled being bumped and later realized that her wallet was missing. The men got off the train at West 72nd Street, where police officers watched as Mr. Williams rifled through a wallet, taking out the cash and then discarding the wallet in the trash. When the men were stopped. Mr. Williams had $60 of the woman’s money, and Mr. Rose held $40.

On the day of Mr. Rose’s sentencing, his wife of 25 years sat in the courtroom, recounting his kindness and wondering what she would tell their sons.

“He has two sons who don’t even know what he does,” Ms. Rose said, describing her husband as a devoted and patient father. “We have our secrets.”

Asked how it was possible their sons didn’t know, Ms. Rose said, “Trust me, it’s possible.”

She said she dreaded the prospect of being separated from him for the next year. “I had a dream he was knocking on the door,” she said. Awakened and believing it was real, she jumped up and walked right into a glass table in the living room, shattering it. “Next thing I knew I was on the floor,” she said.

In the end, she added, the worst that could be said of her husband was that he was a thief.

“So what?” Ms. Rose said. “He never hurt anybody, never got in fights — never bothered no women, never hurt anybody.

“All they can say is he’s a thief,” she added. “That’s all.”

Susan Beachy and Alain Delaquérière contributed research.

A version of this article appears in print on  , Section MB, Page 1 of the New York edition with the headline: The Pickpocket’s Tale. Order Reprints | Today’s Paper | Subscribe

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