True Story

Spirit, Southwest Airlines Magazine


Something about Sherman “O.T.” Powell made you want to trust him. As he walked across the stage of the posh Players Club in Manhattan in 2003, the 56-year-old flashed a smile. You wouldn’t know that a few months before, he was sleeping in a park, drinking from a paper bag, and smoking crack. Dressed in a dapper gold vest and matching tie, and with stiff-as-a-board posture and a humorous squint, he didn’t look like a professional thief, because he isn’t. Not anymore.

But he was understandably nervous. This private club, where members pay $1,500 in annual dues, was founded by Edwin Booth, brother of John Wilkes Booth and the greatest Shakespearean actor of his day. Such stellar names as Mark Twain, Ernest Hemingway, Lynn Redgrave, and Morgan Freeman are written among the roster of Players. To this day, members include the rich and famous. Tough crowd.

Good evening, ladies and gentlemen.

O.T. pushed the first words out nervously, his voice wound tight.

My name is O.T., and I’m a retired pickpocket.


I did say “retired.” If I wasn’t, it’d be too late anyway.

Laughter. He’s got them right where he wants them.

O.T. is one of thousands of storytellers who, since the 1990s, have gotten up on stage and shared a story with no notes, no music, and no pyrotechnics, thanks to a nonprofit outfit called The Moth. This year, 15 million people across the world will hear someone like O.T.—or more high-profile cultural figures such as Adam Gopnik, Padma Lakshmi, Ethan Hawke, Malcolm Gladwell, and Jonathan Franzen—participate in a Moth-branded podcast, public radio broadcast, or one of the 168 live performances taking place in four American cities.

Though the stories usually last less than 15 minutes, the spoils can be significant—past Moth storytellers have gone on to sign publishing deals, book off-Broadway shows, hold regular radio spots, and garner Hollywood interest. Take Steve Osborne, a brawny, tough-talking ex-policeman who spent 20 years with the NYPD. A Moth regular who tells cop stories in a thick New York accent, he has leveraged his storytelling chops into two screenplays, acted as a script consultant on TV shows and movies, and just closed a deal with a major network that will turn his tales into a weekly drama. But the best times are the times when he can tell his stories in live performance. “There’s no better feeling than when one of the stories comes together,” Osborne says. “You walk off the stage, you hit a home run. There’s nothing better than that.”

The Moth didn’t set out to transform lives when it got its start in Saint Simon’s Island, Georgia, in the 1990s. Back then, novelist and poet George Dawes Green would gather with friends on a porch for nights of Jack Daniel’s and recounting true tales. The only strangers were the dozen or so moths that snuck in through a hole in the screen. The group began referring to itself as the Moths.

In 1997, Green moved to New York City, and he was flummoxed. No one seemed to listen. Everyone was too busy waiting to jump in and speak. He decided to host an event in his living room, where one person got to be center stage while others sat quietly. He called it The Moth. Stories of the storytelling spread, and before long so many people attended the gathering that Green moved it to a neighborhood club.

Today, The Moth is funded by donations, grants, corporate sponsorship, and box-office sales. Now available on 240 public stations, The Moth Radio Hour received the 2010 Peabody Award for excellence in electronic media, and its companion podcast gets downloaded nearly 1.5 million times every month.

Then there are the live shows. At the most prominent ones, Moth directors work with performers to shape their story before they go on to tell it. The tales are less polished at the monthly open-mic slams in Los Angeles, Chicago, Detroit, and New York City. Lines for tickets (which start at $8) begin forming nearly two hours before show time, as scales of nervous storyteller hopefuls and audience members arrive early, angling for a seat. Each slam has a theme—food, confusion, fireworks, money—and 10 names get drawn from a hat. Those selected tell a five-minute-long tale. Judges rate it, and the winner competes against other winners in subsequent Moth gatherings.

Storytelling seems, officially, to have become a trend. Similar series have cropped up across the country—Story Lab in Chicago and The Story Space in Boston; Los Angeles hosts a storytelling festival; next year the National Storytelling Network, an organization  formed in 1998, will host its biennial conference in Cincinnati. Each event offers a smorgasbord of true tales from people like O.T., the kind of characters  you don’t often get to meet, or, in some instances, want to meet. When you hear his story, you might think to yourself, I would have crossed the street to avoid this guy. This guy was a thief. A likeable one, but a thief nonetheless.

Let me tell you how I got acquainted with this way of life. I’m from St. Louis, Missouri. I was about 15 years old. It was in the summer, around May or June. I was working at Ray’s Pool Room. And these guys came in, there were about six of them, multicolored outfits, looked like human peacocks coming through the door. The cars matched their suits, and they had bankrolls big enough to choke a horse.

I had been confused about what I wanted to be in life, but when I see these guys I said, “Whatever they is, that’s what I want to be.”

So as fate would have it, they stayed right around the corner from my mother. And so I made myself acquainted with them, and I became their errand boy. I would run to the store, I would get the food, I would take their car and get it washed, I would walk the dog and all this stuff. And in the process, I would get a few dollars, and I would learn how to cheat in cards, and I would learn how to cheat in dice.

Then one day, he said, a group of women rolled into Ray’s. They were bragging about lifting hundreds of dollars from people’s pockets. Real money, not the penny ante cash O.T. was earning from cards and dice.

So I go to my tutor and said, “I want to be a pickpocket.”

Get yourself to New York, the man advised, sending O.T. off with a letter of introduction and a dose of age-old wisdom: “If you can make it there ….” He packed his bags that night.

At this point in the telling of his story, O.T.’s fists were balled and his arms bent like those of a T-Rex. His audience was gripped, too. “The Moth and storytelling is human connection at its most primal form,” says Catherine Burns, an impassioned brunette who serves as The Moth’s artistic director. She’s speaking from her tidy office in a bustling area of Soho in Manhattan. “In the midst of this technological revolution, it’s not surprising to me that people are looking to return to their roots.”

Of course, she’s right. We need stories to lure us out of our own heads and back into the lives or our family and friends. We want more than a status update about a breakfast cereal or someone’s child’s potty-training escapades. We crave more than a “like” on Facebook or a retweeted Tweet. Storytelling is to entertainment as the slow food movement is to dining—it’s fresh and it’s local. “At The Moth, you feel like you’re sitting at a campfire and connecting with one person,” says Burns.

A recent Princeton University study shows the connection to be more than metaphorical. If all goes well with a story, the study found, the storyteller and the listeners’ brains are actually in sync. In 2010, researchers Greg J. Stephens, Lauren J. Silbert, and Uri Hasson peered at the brains of a storyteller and a 12-person audience with the help of functional magnetic resonance imaging. The storyteller shared an unrehearsed dramatic memory about going to prom as a freshman. The scans showed that the same areas of the brain, in both the storyteller and the listeners, were stimulated at the same points in a story. Storytelling, it turns out, unites us on a biological level. Understanding one another connects us, literally, as human beings. Even better, it can connect us to ourselves.

In 2003, O.T. wasn’t sure what to do with himself. He had bottomed out. Too shaky from drugs and alcohol to earn or even steal a living, he had nowhere to go; he’d been estranged from his family in St. Louis since his teens. So he checked into a homeless shelter and rehab center on Manhattan’s Lower East Side and began attending recovery meetings. Those meetings gave him a chance to tell his story again and again to other residents. He says it served as a kind of therapy.

One day, a staffer at the shelter told him that a Moth storytelling coach would be coming in to work with residents. The goal of the MothShop Community Program is to bring out storytellers who wouldn’t ordinarily find an outlet to share the personal tales—or to find The Moth. “O.T. would have probably never walked into the Players Club or The Cooper Union to see a show,” says Burns, the artistic director. “It was a selfish motive, in that we were trying to find the real stories of New York.”

They hit the jackpot with O.T.; that first workshop led straight to his gig, a few months later, at the Player’s Club. “It seemed at the time like a risk, but it was one of the greatest shows in Moth history,” says Burns. “And O.T. kind of stole the show.”

At the same time, MothShop organizers say that the 10-week workshop often has a profound effect on its participants. Each week, the classes encourage ex-felons, homeless men and women, and struggling teens to examine their lives and learn from the past. “The process of putting your life in order with a beginning, middle, and end forces you to see cause and effect,” says Burns. “And it can actually be empowering to see that you do have more control over your life than you think.”

O.T. wasn’t thinking so much about putting his past in order. He was thinking about how to escape it. Storytelling might distract him from the compulsion to drink. So he signed up, along with other shelter residents. “It helped me to get rid of the demons,” he says.

Besides, he was already overflowing with stories. O.T. was more than a pickpocket. He was also a confidence man, and he had the credentials to go with the title. As a self-described master of the con, which, he says, “is just telling a story,” he insinuates himself into a scene, gaining the audience’s trust, getting people to give him something for nothing.

Even before he started picking pockets, O.T. fast-talked people out of their cash using an array of tactics straight out of the classic 1973 film Paper Moon. He’d hit all the major sports events—the Super Bowl, the Kentucky Derby, boxing matches—anywhere that his marks would have pockets full of cash. Sometimes he’d flat-out play people for suckers by cooking up some story about making fast cash. Flashing his own roll of dough (strips of newspaper bookended by a couple of real bills), O.T. would convince total strangers to hand over hundreds of dollars on the promise that he would return in a couple of hours with their money multiplied. Usually, only the greedy fell for his cons. If O.T.  could see “larceny” in their eyes, he knew the game was on.

The scamming didn’t stop there. A talented pickpocket insinuates himself into a crowd, makes himself trustworthy, or just loses himself in the setting. He uses finesse and sleight of hand. A good storyteller does the same thing. He can lead you so deeply into a story you forget you’re being led.

I get to New York, and I check into the Howard Johnson’s at Eighth Avenue and 52nd Street. The gypsy place is about three blocks down the street; this little storefront with two ladies in the front reading palms and all this … I go in and say I’m looking for Ralphie. Ralphie comes out and I give him the letter. I give him the $500 [tuition].

He takes me in the back and all you can see is mannequins, everywhere. Mannequins with coats on, mannequins with no coats on. Mannequins with pocketbooks and mannequins with just pockets. He introduces me to this guy called the Fat Man, and the Fat Man was to be my teacher, right? So the Fat Man comes out and says, “You’re a pickpocket?”

I said yeah.

He said, “Let me see what you can do.”

So all these pocketbooks and all these wallets, you know those bells you can put on baby booties? Well, everything has a bell on it: the wallets, the pocketbooks. If you pick something and the bell rings it means you’re caught. So I’m going through this crowd picking the wallets and picking the pocketbooks and bells ringing … ding ding ding ding.

“You’re not a pickpocket,” the Fat Man said. “We better start from the beginning.”

He was graceful. He would go through a crowd of mannequins, smooth as a panther. He would go on the balls of his feet like a ballet dancer. And he would go through and wouldn’t a bell ring and he’d come out on the other end of the crowd with six or seven wallets. I said, “That’s what I want to be like. I’m going to be just like that.”

He spent three months practicing from 9 a.m. to 12 p.m., every day but Sunday, getting his wrist slapped every now and then by the Fat Man. “Gently, boy, gently, like a pianist,” the Fat Man told him.

Right after he “graduated” from pickpocket school, O.T. headed to Grand Central Station. He stayed for several weeks until he “got hot”—until the police started watching him. So he moved uptown to 57th and Third, working the bus stops and the buses themselves.

One day I’m on the bus and it’s crowded. And as I’m going through the crowd I hit this old lady—she got on pearls and beautiful diamond earrings, so I hit Mom and get her wallet, close the bag, and when you close the bag you gotta cough—AHEM—and make sure she don’t hear the sound. So I close that bag and hit this guy’s inside pocket. I spin around and hit this other guy’s back pocket. So I’m coming through and out of the corner of my eye I see these police lights. Then the bus driver starts pulling over to the curb where there ain’t no bus sign at. I look out of the corner of my eye again. Here comes a guy with a crew cut—I know he’s five-0. He’s trying to get through the crowd to get toward me.

The audience was deadly quiet, hanging onto the story—which suddenly shifted in tone.

So as he’s pushing toward me, I’m putting back wallets—POP-POP-POP—putting all the wallets back.

By the time I get to the front door and the sergeant gets on, he says, “Grab him!”

“Got him, Sarge. We’ve got him!”

And the sergeant grabs me, I say, “I didn’t do anything!”

“Search him!”

“He don’t have no wallets on him. I thought you said he had wallets!”

He said, “I’m telling you I’ve been watching him.”

Next the police officer asked the woman to check her purse, and there she found her wallet. He went to the two other victims, who both produced their wallets. Exasperated and furious, the cops told O.T. to get off the bus.

And I go around the corner and by the time I get around the corner I kind of speed up my walk, and I look up and I start laughing. “Well, Big Man, you might have taught me how to get it out of pockets, but you sure as hell didn’t teach me how to put it back.”

He recalled the Fat Man’s advice:

If there is just three wallets in the world, and the president has one and the pope has one, make sure you have the third one.

And, though he technically didn’t end up with any wallets, the audience was convinced: all in all, O.T. did end up with that third one.

After the show, one audience member after another slapped him on the back, congratulated him, and asked him if he does standup.  The Moth gave him $50—one of the few above-board payouts he’d ever received. He got invited back again and again to share his story. He told it at a nursing home and shared it during a conference of attorneys. (“My father always wanted me to be a lawyer,” he told the crowd. “Many years later, I asked him why. He said, ‘Son, if you can be a lawyer, you can get paid whether you win or you lose.’”) He went on a two-week Moth tour that took him through Denver, San Francisco, and Seattle. He told a story about being on a chain gang in a prison in Arkansas, another about making bootleg alcohol in New York’s Attica Correctional Facility. But the audience favorite is his original story about pickpocket school and returning wallets.

“Why do people love it?” he asks. “Because it’s different from other Moth stories; because you have someone that’s a pickpocket. I’m a real criminal—that’s the bottom line.”

I’m a criminal. The present tense keeps his past alive, swagger and all, and, in O.T.’s mind, turns his life into something more than arrests and drugs and loneliness.

Now 64, O.T. lives in an efficiency apartment in East Harlem, a home the shelter helped him find in 2004. In his tiny, spotless space, medications surround the television set. Photos and clippings fill a cork board on the wall between his bathroom and his bedroom, press about his Moth appearances: photos of him in the “society” pages of a magazine while on the road with The Moth; photos of his many onstage appearances; photos of friends at the shelter. “I donate to Feed the Children,” he says, pointing to another snapshot. “These are African kids who they send pictures of.”

O.T. sits in an overstuffed chair and watches a VHS tape of a televised performance he did of one of his pickpocket story. He laughs when the crowd laughs, and he mouths his own words like a stage dad might. His whole life revolves around storytelling now. He attends Alcoholics Anonymous meetings and shares his story. He attends Narcotics Anonymous meetings and shares his story. He’s working on an autobiography that he hopes to sell one day, but the manuscript is taking longer than he expected. Writing, he says, is more difficult for him than talking.

O.T. recently became a deacon at his church, where he shares his experiences with drugs, alcohol, and crime and tries to lead people down a healthier path than the one he took. His pastor, the Reverend Leamon Morgan, of the Holy Ghost Deliverance Church on Manhattan’s Lower East Side, says that O.T.’s history has made him even more valuable to church members. “There’s a lot of people now where he was,” says Morgan. “He can tell them how he’s changed his life and helped change a lot of people’s lives.”

For O.T., storytelling began as a way to save himself from himself. Now, it’s his way of giving back. On a table below the bulletin board are more press clippings—stories on the subject of pickpocketing. In 2010, he did an interview with The Daily News in which he gave pointers on how to avoid being a pickpocket victim. Around the same time, a local news station interviewed him about schooling women on how to protect their belongings.

O.T. says it’s his way of trying to make up for the crimes he perpetrated. “When I think back on it, it was because of us that there were people who couldn’t pay their mortgage or their rent or their car note or whatever the case may be,” he says quietly. “And if I claim to have turned my life around—truly turned it around—then I should be willing to make some sort of repentance.”

Not surprisingly, O.T. has been banished from the community of hustlers that once constituted for him a family of sorts. While many of his old friends have died or gone to prison, the rest won’t talk to him. “I’ve been kind of eight-balled,” he says. “They don’t particularly care about me for exposing the game.”

While there’s no doubt he has changed from his con-game days, you can still see the hustle. Like when he asks this reporter if he’ll get paid for sharing his story. (He will not.) Or when he frequently, laughingly recalls something a fellow pickpocket once said to him: “We came up together, stealing people’s money, now you’re telling them how we did it—and you’re still getting paid?”