My First Great Heist


Okay look. I shouldn’t be telling you about this. I should take it to my grave; that would be the smart thing. But some stories deserve to be told. 

Like most people, I’ve long dreamt of a life of crime. Being a master thief or con artist; living on the lam; stealing art and jewels and, inevitably, saving the lives of innocent bystanders; exchanging witty barbs with the detectives on my trail and occasionally teaming up with them to thwart actual bad guys. Pure romance and excitement. 

But somehow it just never happened. Sure there was my brief stint as a teenage hitchhiker that led to a car chase and several hours in jail, and this one time I kind of broke into an old lady’s house but that doesn’t count, but mostly I’ve stayed on the boring side of the law.

Never even shoplifted. I know this seems unlikely; I was certainly that type of teen. But while my friends were inside the Rite Aid filling their pockets with all sorts of wonderful things, I was the girl standing outside trying not to panic and expecting to hear police sirens at any moment. 

It was never really a “morals” thing for me. I didn’t refrain from theft because it was wrong. I was just too scared of getting caught. I was more than happy to be a receiver of stolen goods, chewing the gum my braver friends grabbed so cavalierly. I was embarrassed by my timidity, but not embarrassed enough to overcome it.

This fear stopped me from shoplifting, stopped me from robbing banks, stopped me from traveling around the world with a gang of like-minded art lovers. It was a part of me. I accepted it and, like so many people, settled down into a quiet life of paying for things.

But for the past few years, it has been troubling me again. I’m getting older, and I know that we’re not in this world forever. Am I really going to live my entire life without ever once experiencing the danger, the thrill, the risks and rewards, of planning and executing a heist?

I shared these thoughts with a friend and former employer* who, in addition to being a beloved television star, steals stuff all the time. I have a very nice collection of salt and pepper shakers he has stolen from restaurants for me. He agreed that it was wrong to live my life in fear, and gave me a lot of important tips like “don’t be obvious about it” and “just put it in your pocket.” 

And so, armed with this encouragement and expertise, I made the decision. 

Time for a heist.


The first step in preparing for my crime was re-watching every episode of the TV show Leverage. I do this every other year anyway, so it wasn’t a big deal. I also watched Oceans 11-13, Oceans 8, and The Sting (which I know is about cons but it’s so good) and To Catch a Thief, because I should know how the people wanting to catch thieves think, and, best of all,  How to Steal a Million (even though that was probably more than I’d steal, especially when you adjust for inflation). 


One of the things I learned is that it’s important to figure out what it is you’re going to steal. After a lot of thought, I decided on a tube of chapstick. Small enough to fit in my hand, cheap enough that if I got caught it would not be a felony, and I have tons of half-used tubes floating around the bottom of my purse, which would add to the plausible deniability if they happened to search me.


Choosing the right store from which to steal was important; obviously it had to be a large chain store because stealing from a big faceless corporation is sticking it to the man, while stealing from an individually owned corner store is just being a jerk. I didn’t want to be a jerk. 

It would need to be somewhere fairly nearby because I’d want to go there a few times beforehand to scope it out, but it shouldn’t be somewhere I went all the time because if I got caught I’d have to stop shopping there (even if they let me go it would be so damn awkward) and that would be a huge inconvenience.

I decided a drugstore would be better than a grocery store, because so many grocery stores keep their chapstick right by the registers and I definitely would not be able to do it if the cashier person was right there. Drugstores usually have chapstick in the aisles as well as near the front.

In scoping out possible locations, I realized that often, the chapstick sold in the aisles is in multi-packs, with the individual tubes up front by the register (possibly because of thieves like me). This would not do; a multipack would be way too big to conceal in my hand, and much more noticeable if it was there and then wasn’t there. I added “individual tubes sold in the chapstick section not just by the register” to my list of store requirements.

I found the perfect place. A large chain about a mile from my house, that I don’t go to all that often because the parking lot is more complicated than that of a similar store a block away. I wandered around and found that they have a bin of individual tubes of chapsticks in a spot that can’t be easily seen from the register or the pharmacy counter. Perfection.


I told my therapist all about it (after making certain that she didn’t have to report plans to break the law unless I was actively planning to kill someone, which I was [and am] not). She didn’t see any major problems with my plan and has assured me she is okay with me writing about the conversation. 


I visited a few times so that I’d know the general lay of the land; I tried to see where the cameras were but quickly realized I was bad at spotting cameras and was just going to have to assume they were everywhere. Medium-sized drugstores in L.A. probably don’t have the same “eye-in-the-sky” system as Las Vegas casinos, but better to err on the side of caution.

I made sure I knew exactly where the chapstick was. Of course I also made sure I had a general sense of how everything was laid out, so that on the day I would know the location of not just the chapstick but also the items I intended to actually purchase. Wandering around lost is a good way to get attention from sales clerks, suspicious and helpful alike. But the main thing was knowing where they kept the chapstick. I made a map, and studied it.


During these visits I bought a fair amount of shampoo and toothpaste and pens that I didn’t technically need right then, but it’s not like that stuff goes bad. It’ll get used eventually. 


I considered a variety of disguises – my husband is a theater guy so we own an awful lot of wigs – but reluctantly realized it wasn’t the way to go. The problem with a disguise is that it gets in the way of a vital part of my plan: plausible deniability. It’s probably harder to claim you didn’t mean to drop something into your purse when you also have to explain why you’re dressed like a dowager duchess and speaking in an accent best described as “baffling.”


The good news is that these days it’s fine to walk into a store wearing a mask. I made sure that every time I went in I had a boring light-blue mask, instead of the more noticeable bright red and purple masks I tend to favor.


Sleight-of-hand has never been my thing; my hands are small and my coordination is atrocious. I realized when I was pretty young I would never be a pickpocket, and made my peace with it mostly. 

So I put in some time practicing picking up a chapstick, hiding it in my hand, and dropping it into my purse. At first I practiced in front of the TV, but I also made sure I could do it while walking.

I also practiced saying “what?” and “oh!” in a voice that made it clear I was completely confused and unaware that there was anything in my purse that shouldn’t be there.

Every time I went into a store, I paid close attention to how I acted when I was not shoplifting, so I could recreate the behavior. It’s hard to “act natural” if you don’t know how you act when you are natural.



After several weeks of preparation and painstaking planning, it was time to carry out the crime. I had everything ready; I knew what I needed to do and how to do it.

Mostly the chickening-out happened before I got to the store; I’d be in the car on my way and realize that I had lots of other things I should do instead. I tried to get around this by deciding that it didn’t have to be that one store; if I happened to be out and about and was driving past a drugstore I would stop and go in, intending to steal a chapstick, only to realize once inside that I was absolutely not going to do that.

I only chickened out while inside the actual store I’d originally chosen a couple times. Three times, tops.



It was an ordinary Monday evening. I got off at six. I needed conditioner. I drove to the chosen drugstore and sat in my parked car for several minutes, probably not more than ten, going over the plan and working up courage.  I considered listening to “Eye of the Tiger” but decided against it. I wanted to go unnoticed; if I got “Eye of the Tiger”-levels of pumped up I would probably run into the store and loudly announce that I was there to steal the chapstick. I spent some time considering other songs that might be good but eventually realized I was stalling. I texted my friend, the one I mentioned who steals stuff, and told him what I was about to do. This was partly to stall some more, but also because I am much more likely to actually do a thing if not doing it would be embarrassing. It’s how I got myself to bungee jump, years ago – I bragged about my plans to jump so much, backing out would have been humiliating.

Finally, when I couldn’t think of any more reasons to sit in the car, I went into the store. I wasn’t the only person shopping, but it also wasn’t crowded. This was ideal; if I was the only person the staff might be bored enough to watch me, and if it was crowded I might have been seen by another shopper who probably would have considered it their civic duty to report me. Or maybe they’d keep quiet and blackmail me later. A problem either way.

I carried my purse over my left shoulder and picked up the basket with my right hand.

I strolled towards the back of the store where chapstick is kept. The cough drops are right next to the chapstick, so I tried to walk like I was on my way to get cough drops.

I stopped by the bin of chapsticks as if I was just noticing them, and put an “oh that’s right, I need chapstick” expression on my face. 

Only something was wrong – instead of the ordinary “original” chapstick, the only kind I like, there was now a mix of flavored chapsticks. I was momentarily thrown, but quickly recovered. I know how important it is to roll with the punches when being a thief.

I reached into the bin with my left hand, taking two coconut chapsticks. 

I resumed walking, still holding both chapsticks in my hand. 

They didn’t have my cough drops (drugstores are often low on cough drops these days; I assume there was some sort of problem in a cough drops factory but I haven’t looked into it). I turned and walked away from the cough drops and chapsticks.

Then I stopped, put down my basket, and started rummaging in my purse for my phone. I reached into my purse with my (empty) right hand, holding it open with my left. As I did, I let one of the chapsticks slide from my left hand into the  purse. 

I was immediately certain everyone had seen me but I kept cool. Instead of looking around guiltily like I wanted, I calmly checked the shopping list on my phone (the list I’d made especially for this occasion) and then turned the phone off and used the reflection in the dark screen to see if anyone behind me was staring or pointing. No one was. 

I picked up the basket with my right hand again, and walked down the snacks aisle and grabbed a box of crackers. As I did, I acted as if I’d just remembered that the one remaining chapstick was in my left hand and tossed it into the basket. Then I moved around the store with purpose, getting the other items off the list but not rushing. 

I’d considered getting something embarrassing, like a giant tub of hemorrhoid cream or similar, with the idea that it would make people look away from me. It also would explain why I looked flustered. But in the moment I realized I’d forgotten to find out where the hemorrhoid cream was kept, and I didn’t want to spend time looking for it and possibly draw attention. I’d just written “cream” on the shopping list, so I grabbed some hand cream from the travel section as I walked by. That way the items in my basket matched the shopping list.

I’d spent a fair amount of time, in the early stages of planning, thinking about whether to do self-checkout. I decided no, because I imagine they’re more careful about watching for shoplifting at the self-checkout. Then it turned out it didn’t matter because this store didn’t even have self-checkout. 

As I waited in the short line for the one open register, I took a diet sprite from the nearby cooler. If I got away with my crime, I’d want a drink to celebrate. Also it gave me something to do, to distract from the fact that my purse seemed to have grown three sizes and was probably going to somehow develop an alarm with flashing lights at any moment. 

Finally I made it to the counter. I unloaded everything out of the basket and when I got to the chapstick I held it up, looked confused, said “I thought I grabbed two of these,” looked into the basket and around on the floor, shrugged, and grabbed another chapstick off the rack next to me (again, only flavored chapsticks available. This time I got vanilla). 

This was more of the “plausible deniability” part of my plan. If anyone pointed out I’d put the stolen chapstick in my purse I could say, “Oh! That’s where it went! Remember, I said I’d thought I’d had two!” Plausible deniability.

The checkout guy seemed to take forever checking me out. As he was scanning my items and putting them in the bag I’d provided, he got some kind of call on his headset. He kept saying, “uh huh,” and “okay” and occasionally glancing at me. My heart was pounding– certain he was talking to his manager, who was telling him to stall me until the police arrived. 

He got off the call and asked me to put in my rewards number. Instead of just saying I didn’t have one, like I’d planned, I got flustered and started to enter my number but then remembered I didn’t want to give them a way to ID me and switched the last two digits. This did not turn out to be the number of someone who had a card, so I “tried again” with a different number, this one the number of the office I worked at twelve years ago that I don’t know why I remember. When it didn’t work either, I said it was okay and no I didn’t have time to sign up for a new rewards card.

I paid in cash, so they wouldn’t have my name off my credit card, and finally took my bag and left. 

I walked out of the store with no problem. There were no police waiting. It was possible the call he’d gotten on his headset hadn’t even been about me.

I breathed in the cool night air and the relief I felt was almost overwhelming. Only then, when I got to the car, I couldn’t find my keys in my purse. My panic rose as I searched. I put my purse on the hood of the car and went through it with both hands. The seconds were ticking by and I desperately wanted to get out of there. I started to wonder if I could have somehow dropped the keys in the store. What if I’d somehow accidentally left them in the bin of chapsticks? I knew it made no sense, but I slowly became certain that that was what I’d done. Then I found them, tucked into a side pocket I’d never noticed before. My hands shook as I opened the car, turned it on, and drove away. 

I went three blocks before pulling over and parking. I sat panting, full of joy and pride and shame and adrenaline. I couldn’t believe I had gotten away with it. I took a picture of the chapstick to text to my friend, and drove home. I told my husband what I’d done so he could appreciate that he was married to a master thief. Then I found an envelope, wrote “theft” on it in big letters, and put the chapstick inside. I didn’t want it to get mixed in with all the other chapsticks I own.

It wasn’t over yet. I had more to do. But before I finished the plan, I needed to let things cool down. I know they expect criminals to return to the scene of the crime, and I wasn’t going to make that mistake. I waited a week before taking the envelope from the bookcase shelf and tucking it back into my purse. After work that day, I again drove to the drugstore. I wore a light jacket this time, which fit the weather – it was about 50° out. The sleeves hung loose part way over my hands, which meant it was impossible to see the chapstick hidden in my palm. It was okay, now, that I lacked sleight-of-hand skills — there are after all no laws about entering a drugstore carrying a chapstick.

I walked again to the chapstick bin and reached in, but instead of taking one, I let the already-stolen chapstick drop from my palm into my fingers.

I put it in the basket and quickly walked away. I grabbed some other things off the shelves almost at random – I hadn’t thought to make a shopping list this time – and got in line.

It was a long line. The woman in front of me looked like she probably made her living as an extra on tv shows that needed extras who looked like meth addicts. She was commenting on the purchases of the  people around her and I was terrified she was going to mention my chapstick, but she was much more interested in the Chex Mix I’d picked out. She seemed shocked that I didn’t prefer the “bold” flavor.

I finally checked out, with a different guy this time. I held my breath as he scanned the chapstick, but apparently they hadn’t inventoried the stock and discovered it had been stolen yet, because it came up on the register like normal. I suddenly had a hard time keeping my face straight. The store was selling me a chapstick that had been in my home for a week. The fools!

I left the store, feeling exhilarated and, once again, deeply relieved. I’d enjoyed my time of being a criminal, but was also glad it was over.

The next morning I tucked the once-stolen, now-paid-for chapstick into an envelope labeled “crime,” then put that in a larger padded envelope and mailed it to my friend. It isn’t quite as good as the salt and pepper shakers he steals for me, but it is something. 

I also had the two chapsticks I’d actually bought during the initial theft. I couldn’t use them; they were flavored and the smell would be sure to give me a headache. But I also didn’t want to just throw them out; they were a big part of an important moment in my life. After some dithering I put them on the “free stuff” table in the break room at work. I like thinking of them out there, being used by someone who has no idea they were involved in a heist.


Everything is different now, of course. I see the world in a whole new light, in a whole new way. Now that I am a master thief who is capable of such incredible feats of stealth, trickery, and acting like everything’s totally normal no big deal, paying for things is an act of saintly benevolence. It’s all I can do to not say “you’re welcome” when I pull out my wallet. Plus I’m constantly wrestling with temptation. The knowledge is always there. In the past three weeks I have not trusted myself to go to any museums or fancy stores or rich peoples’ houses or zoos. 


I have no current plans for future heists, but I can not in good conscience make any promises. 


To be continued?


*Beloved television star French Stewart

Author: Sarah McKinley Oakes

Sarah McKinley Oakes is an L.A.-area writer, nanny, and library clerk. Her other website is, where she writes up old restaurants but barely mentions the food. To contact Sarah, email her at, or DM the Hatpin Slayer Facebook page

4 thoughts on “My First Great Heist

  1. I loved this, being a master criminal myself. My maybe favorite line among very many was:
    ” I realized when I was pretty young I would never be a pickpocket, and made my peace
    with it mostly.”


  2. This was thoroughly entertaining and hilarious. My favorite line: ‘I tried to walk like I was on my way to get cough drops.’ hahahaha
    Love, love, love this!

  3. i am also an as-yet-unrealized master criminal. my heart was racing as i read this tale. you are very brave, and i will have to thieve vicariously through you. eeek!

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