7 Weird Things I Learned as a Pickpocket in the Modern World

In four and a half years of semi-professional pocket burgling, I made at least $10,000, maybe a little more. That won't even get you through Bumfuck County Community College without loan debt. But my marks were losing out on a weekend shopping trip to Hot Topic -- a tragedy that ranks slightly above "Dick Cheney stubs his toe" -- whereas I needed food money.

Every now and then, I hit the lottery. One time, I pulled a wallet from a guy that had five $100 bills and a 50, all crisp and brand new, without so much as a crease. I wasn't even in high school yet, and with about two seconds of physical effort, I had made enough to pay my family's rent. But then a little voice popped into my head and told me it was a trap. I had flashes of memories: the guy walking in front of me, stopping where I could see him, as though he wanted me to notice him. I shoved the money back in the wallet, left it on the ground, and left the mall as quickly as I could.

It was the biggest find of my career and I tossed it, because paranoia is more effective than any cop.

I was the kind of kid who always sympathized with the villains in crime movies. I was poor as hell, and coming into a bunch of money was the greatest thing I could imagine (Finally! I can buy a new Ferrari! And shoes! To press on the pedals!). But the criminal that stood out to me the most was the pickpocket. He was like a spy, but with more immediate financial gain and less torture by Russian secret police. And Lady Internet was there to pop my crime-cherry with YouTube tutorials, books, forum posts ... it was as easy as looking up a pie recipe.

The two things that formed my learner's bible were a forum post that couldn't have been written by anyone older than 24 and a scanned PDF file of a book written by a magician who explained how pickpocketing works. I had no idea if "GrandMastaThief" was legit, but testing on myself allowed me to get the mechanics down in less than an hour.

But this isn't like welding, where a lot of low-stakes practice helps with the real work. You're stealing from live people. To get better at that, you've got to get out in the field.

I got so overloaded that I threw up in my mouth a few times and had to walk to the other side of the store, sit on a patio furniture display, and wait until I had calmed down. I forced myself to go for it. I walked up behind a guy and pulled his wallet. He had loose pockets. It was easy enough. He turned around and looked at me right as I took my hands out from my own pockets, which now contained his wallet. I almost blurted out "I'm sorry! It's my first day!"

But I didn't say anything. Neither did he.

He had $76 and change in his wallet. I put his coins into one of those plastic breast cancer donation boxes. I threw the wallet and his credit cards away. That was a safety measure on my part. Identity theft was a big deal on the news, and I was less worried about being accused of taking someone's cash than being accused of taking their credit card.

We live in a very private society, where everyone has their own personal bubble. We hardly make eye contact anymore, and physical contact with strangers is, best case scenario, probably some minor form of sexual harassment. Not to mention all the other anxieties that come with committing a crime of any kind. So yeah, that first pull was as hard as an Ent at an arboretum.

I got better and better and, of course, more confident. It got to the point where I was rarely unsure of myself. But after a couple years, that old paranoia crept up again. I began to think things were a little too easy. I noticed people smiling at me politely, as if they had been watching me, and a little voice thought up more and more conspiracy theories. That's sorta the whole issue with crime as an income. Living under the shadow of a felony every day puts your head in full-time Alex Jones mode.

You've seen it in movies: I make some sort of abrupt physical contact with someone as I'm doing the pull. The human mind focuses on the greater impact and ignores the far more worrying gentle tug on the butt.

Then comes the escape. If you don't want to get punched in the teeth for slamming into somebody wholly unprovoked, you've got to control the conversation and lead them. When I first started, I'd stutter and mumble and probably seemed like I was high on something. The key was to appear honestly submissive, like someone who'd fucked up and knew it. You want to make the mark feel like the asshole in this scenario.

Sometimes all that took was to furrow my brow for a second after an insult, as though I was going to cry. Other times I could look to someone nearby and they would try to calm him down. You can't simply act surprised -- if you're sad or scared, suddenly you've made him the villain and you have become the victim.

People have a lot on their minds. Bills, work, comment-fights on Facebook ... the last thing the man on the street worries about is his wallet. I can't count how many times I would botch a pull, or my timing would be awful, and the mark still wouldn't notice. Scientists call it inattention blindness, and it basically means your brain works like an old Scooby-Doo cartoon, looping footage you've seen before whenever you're somewhere familiar. I'm sure some people went hours before they noticed their pocket was empty.

Over the years, four people have confronted me about the bump. Only one of them actually reached into my pocket and found their wallet. I claimed it was my first time, and he let me off with nothing but a sound cussing-out (holy shit, the "first day" excuse really works). Two of the others called a security guard -- that scared me. I was young and didn't yet fully understand that security guards are to cops what the Salvation Army is to a regular army. The first guard laughed it off: "No way -- he's just some kid."

The second time, the mark accused me right after I'd taken his cash and tossed the wallet on the floor. Someone found that wallet while we argued, and the guard said, "Obviously someone just found your wallet first and took the cash." I only had $15 in my wallet, so obviously I was innocent.

Like I said: Salvation Army.

One of my marks had a cash clip separate from his wallet. I watched him pay and stick the clip back in his shoe. It took me thirty seconds to figure out what to do. I just walked ahead of the guy and then knelt down to tie my own shoes. As he passed, I reached over, lifted his pant leg up, and grabbed the clip after bumping him with my shoulder. If you're reading this right now, buddy, you should know I spent some of that money on the worst service and food I'd ever received at an A&W. I got violently ill. I hope that brings you closure.

Wallet chains, as douchey as their rep may be, are one of the best ways to keep your wallet safe, but they're not flawless. I went to the state fair once and got three different wallets from guys who had chains. All it took was a little set of cutters.

You can't do the whole maneuver in one move. But I'd follow behind them, cut the chain, and make the pull a little later. One of them did notice his chain had been cut, but he just looked at it, looked around, and then kept walking. What else was he going to do, frisk all the carnies? Do you want Hep C? Because that's how you get Hep C.

Ultimately, my advice to you if you want to be totally safe against pickpockets is to get a debit card and then swallow it. Or you could start dressing like a dickhead. Notice I said wallet chains were one of the best methods of protection, not the best. That would be ...

One day, out of nowhere, the end came. Guys started wearing skinny jeans. Some dudes wore them down below their ass, yet still yoga-pants tight, thus combining the worst of both worlds together, like a Reese's Cup made out of dirt and feces. That made wallets harder to pull, but not impossible. Worse were the guys who wore them all the way up. The pockets were just too tight, and I didn't want to risk using a razor blade in my limited territory; my presence would have become too obvious. Fashion sense actually got so stupid it came back around to practical again.

It was mostly rich young kids in designer jeans that I targeted, so I shifted my demographic and stopped pulling from young guys in favor of grown men. But then I started to feel bad, stealing from people who earned it. I still felt like a secret agent, but it wasn't suave Pierce-Brosnan-Bond; it was book-Bond, the depressed alcoholic murderer.

My mom had a better job, my family had more money -- I was stealing for kicks, rather than food. So I quit.

Pickpocketing was wrong, I know that. But up until sixteen months ago, it was the best thing that ever happened to me. It let me live like a "normal" kid when my family didn't have the money to feed itself. Now I have a job, a conscience, and a sixteen-month-old daughter. I can never go back. But instincts die hard; to this day, every pocket looks like the glowing, lootable corpse of a video game enemy.

For more insider perspectives, check out 5 Things You Learn About Rich People Working at a Nice Hotel and 5 Horrifying Things Only Garbagemen Know About Your Town.

Got a story to share with Cracked? Send us an email.

Spread some pickpocketing awareness to your friends going abroad. Click the Facebook 'share' button below.