Have you ever suspected that someone was not who they said they were? Did they seem a little off to you? Perhaps that they were really an agent of the law, hiding in plain sight for the purpose of investigation?
Well, these stories come from people who did not expect a thing when they stupidly got involved in an undercover operation and survived to share the tale on Reddit. Some are a source of embarrassment. Some are a source for PTSD. All are true.
He Said The Wrong Thing At The Wrong Place At The Wrong Time
“Back in college, I was classmates with a lady who needed lots of help to get her footing after not being in school for a while. Because of all my help, I quickly became part of her family and was always being invited to her family get togethers.
Her husband was cool. We talked sports, played pool, stuff like that. But anytime I or any of my friends would ask what he did for a living, he’d get cagey about it. So we’d drop it.
The way I found out he was an undercover cop was because I almost blew his cover in public.
At the time, I worked in a mall. On my way to work one day, I saw him, with a group of dudes who looked sketchy. I rolled up on him.
‘Hey, man, what’s up?’ I asked him. ‘What you up to, bro?’
The dude looked at me like he had just seen a ghost. He quickly proceeded to berate me and act like he did not know who the heck I was. All the while though, he was making these eyes that said, Get the heck out of here. I was completely oblivious.
Eventually, the dudes he was with came up out of a store and quickly assumed I was a problem. They started threatening me. He played it off like I was some punk who was being put in his place and that he handled it. Everything was cool until one of the cats he was with suggested they do something to me. For a split second, no one knew if he was being serious.
‘Just messing with you kid,’ he said, spontaneously. ‘Get the heck outta here.’
I ran like crazy to the first exit I could find.
Weeks later, I ran into my friend’s husband in a more calm environment and asked what the heck had happened. He explained to me that I had bumped into him while on duty and that the guys he was with were from a gang of traffickers he was casing. I almost blew his cover by asking about his family, a family he wasn’t supposed to have according to the gang he was casing.
He told me I was lucky. The guy who threatened to kill me was high as heck. That was probably the only reason he did not follow through. Long story short, a few days later, they raided the whole group and brought it all down. He quickly asked for a division transfer because of what happened with us at the mall.”
A Case Of Mistaken Identity Makes Way For Hilarity
“My cousin told me this crazy story of what happened to him while he was in the city. He is a stand-up prop comedian and was there for a gig. He was walking down the street when this man walked in front of him.
‘Hey, what’s up?’ the guy said, casually.
Before he could get more than a sentence out, the guy literally ripped his shirt open, revealing a badge,
‘POLICE! FREEZE!!’ he screamed.
Needless to say, my cousin was terrified. It was pretty clear that this man had waited his entire life for this single moment in which he would scare the heck out some random guy while screaming that famous line.
Apparently, they thought he was a dealer, due to some kind of tip or something. They searched his bag and person.
‘Look at his eyes,’ said one of the cops who joined after the enthusiast spectacle of making my cousin poop himself. ‘He even looks high.’
My cousin has a bit of a funny bug-eyed look when he’s scared.
Imagine this: a bunch of cops standing around a scrawny, curly-haired guy as they pull out prop after prop from his bag as if it’s some kind of sketch on a hidden-camera TV show. Heck, I’d watch that. In the end, they found nothing illegal and concluded that my cousin is the harmless, non-athletic, skinny, tall dude that he is.
My family has not forgotten this story.”
Wedding Bells Could Not Drown Out The Volume Of Suspicion
“My parents have a great story from their wedding night. My father’s cousin was high up in the state police doing undercover work, trying to bust a crime ring. He was invited to the wedding and they decided it was OK to break cover for it.
My mom’s side of the family are a little more rough and tumble. Her father brought a few of his hunting buddies to the wedding. My parents had never met them before, but he was the father of the bride. He got to bring whoever he wanted.
At the wedding ceremony, my father’s cousin looked uncomfortable the whole time. At the reception, the cousin gave my father his gift, a short congratulations, and then left. Next up to pay respects was my grandpa and his hunting buddies. One hunting buddy handed my dad $1,000 in cash.
‘Hey,’ the buddy said to my dad, ‘I don’t know you but sorry I’m an imbecile.’
Then, he left. My parents thought nothing of it and the wedding ended.
The following week, they were preparing for their honeymoon when the state police came knocking. It turned out that the hunting buddy was suspect Number 1 in the undercover case that my dad’s cousin was working. The police were there to protect the wedding photos and guest list, expecting that the crime ring would come looking for names and retribution.
The wedding compromised my father’s cousin’s cover and he was forced to move on the gang all become of my parent’s wedding.”
He Thought He Found An Intruder In His Backyard
“I once had a 10/10 adrenaline rush when I found an undercover officer in my backyard crawling through my bushes.
As the story goes, my best friend’s girlfriend and some other friends were over at my house. When the girlfriend arrived, she was all freaked out because some guy said he was going to follow her home after work and assault her.
Suddenly, I heard my dog bark frantically like there was a raccoon or something he really didn’t like out back. I went to investigate. I had a C02 pellet shooter from the states that looked totally real and pierced skin easily. It was not anything that would kill anyone unless I got a real lucky shot. I had the thing waiting on the coffee table because I was ready to mess this guy up if he actually came to follow this poor girl home. I picked it up and went outside.
I saw this figure as it finished hopping over my fence into an empty lot.
‘GET THE HECK OUT OF HERE,’ I called out. ‘I’LL MESS YOU UP.’
The guy continued to crawl through the bushes toward the highway. I shot twice at the fence, nowhere near the guy, as a warning shot. Although it was just air, it still sounds menacing and the pellets stuck into the wood rather than bounced, giving off that nice whpt sound.
I put the shooter on my hip, completely prepared to chin strike the guy, press the barrel to his neck, and go into the empty lot. I did not see him anywhere, so I went onto the highway, checking corners and keeping my distance from any possible hiding spots. I got to a big tree along a fence. I looked both ways.
Hmm. He must have run, I thought.
I was about to give up when I heard a twig snap from behind the big tree. I turned, startled, and pointed my very real-looking ‘weapon’ at the tree where I could see the glimmer of this guy’s eyes looking back at me. I put the shooter back by my hip to avoid it being wrestled away from me and turned the corner.
‘Identify yourself. Now,’ I ordered.
The guy flipped out his badge with one hand. He had his other hand on his holster.
‘I am working an undercover operation,’ he explained and told me his name and badge number. ‘Do not draw your weapon or I will draw mine. I am sorry I spooked your dog. Please call non-emergency should you have any concerns regarding this matter.’
If I lived anywhere other than Canada, I would be dead.
The messed up part was that the guy was posing as a construction laborer at a house being built next door from me. I could only tell because he wore the same hat on site as the one I saw him wearing that night. I also worked construction at the time, so I would often see him loading and unloading when I was leaving or coming home.
One day, I parked on the street across from his site. He glared at me as I walked by. It took everything in me to not say, ‘Thanks for not shooting me.'”
This Woman Was An Undercover Cop Magnet
“I have had two encounters with undercover cops.
The first was in Daytona Beach on spring break. The lobby was jam packed with wasted college students (myself included) waiting on the elevator. I was standing next to this dude in his late 30s, wearing khaki cargo shorts, a white T-shirt, and an unbuttoned Hawaiian-style shirt. Around his neck was a chain with a police officer’s badge on one of those leather holders. He was talking to another guy, also dressed casually wearing a badge. He noticed very-wasted me staring at him.
‘Hey,’ said to me, after a moment. ‘Do you have any pot?’
I said, no. Then, I thought for a couple seconds about why a not-so-undercover cop would blatantly ask me a question like that. I asked him if that actually works. He said it did, and surprisingly often.
The second time was when I was working as an exotic dancer at a club that was not on the good side of one of the county officials. Said official owned land and houses near that club and was incensed that the club had opened, affecting the value of his property. As a result, the club had a lot of visits from adult beverage control board enforcement officers, health inspectors, etc., in an effort to get the club shut down.
It was a regular night and some guy asked for a lap dance. We headed upstairs. I sat on his lap facing away from him. Then, I slid down between his knees to the floor. Then, I slid my hands over his knees, down his shins to his ankles. My hand hit something on his ankle. I froze, because it was most certainly a loaded weapon.
I looked back at him, trying hard not to freak out because this guy was very likely an undercover officer. The guy looked at me, smiled a very small smile, and told me it was OK. I didn’t do anything wrong. I got up. He thanked me, walked downstairs, and left. I was too shaken up to do anything else the rest of the night. I just sat in the dressing room, convinced the club was going to get raided or something.”
She Struggled To Sell Her Story
“A friend and I were approached outside a bar one night by a woman who was clearly 35 trying to act 22. She asked us if we had any coke connections, but used terminology that was both outdated and not widely used in those corners of our community. We gave her the runaround. By the end of it, she knew that we knew what her deal was.
Inside, she was flanked by two frat-boy looking dudes who clearly were slugging water. She looked dejected and kept making gestures in our direction like she knew she had blown her cover. We didn’t say it directly to her, but we made sure the patrons knew not to engage her.”
All He Was Guilty Of Was A Noise Complaint, But That Was Not Enough For The Authorities
“I had a firsthand experience with an undercover cop who was trying to bust me for anything. It was wonderfully surreal.
I had an apartment over a store in the center of a small town, downtown, all-commercial area. Being a musician and into noise and industrial music, we would sometimes generate noise that would bounce through the downtown buildings and be heard two blocks away. Cops came to the door one night.
‘We’ve got complaints and we are asking you to keep the volume down,’ the cops told me.
Noting that they said ‘ask,’ I immediately countered with, ‘Asking. So, legally, I don’t have to, right?’
They looked disappointed and said that was the case. I thanked them, closed the door, and resumed being obnoxiously loud.
A bit later, I was blasting some Skinny Puppy with the windows open. Around 3 am, some guy started yelling up to my window. I looked out my window to see some strong-looking guy with a ten-speed trying to get my attention. He said he liked the music. It seemed ridiculous to me, so I went down to talk with him.
Immediately, I noticed he was wearing an adult beverage as a cologne. It was as if he rubbed his T-shirt with something. He started off by going on about how he worked at the nuke plant and gets tested for illicit substances, but yet he wanted to get some pot. I told him that I didn’t do that and didn’t even really drink much. But, he persisted with his weird story of wanting to buy, even though he said his work does random tests.
I was enjoying this whole thing as minutes ticked away. Then, he said one of the oddest things.
‘You got a sister?’ he asked.
I told him I do.
‘I want to do your sister.’
I laughed. I had no idea what he was trying to do with that. Maybe it was to antagonize me.
‘Good luck with that,’ I replied.
He was getting nowhere, so he went back to the pot. By chance, someone I knew was walking in the distance a block away. I pointed at her and said,
‘Go talk to her,’ I said, pointing in her direction. ‘I know she smokes pot.’
He, of course, ignored that.
Finally, a cop car sped up and stopped behind him. The undercover cop tried to wave him on without me noticing, but it was so hard to miss, as the guy flapped his fingers while tucked to his leg. The cop drove off. I figured I had seen enough.
‘So, you’re working, huh?’ I asked.
‘Yeah,’ he said, sheepishly.
There was not much for him to say at that point. There had been about 15 to 30 minutes of this nonsense. He got on his ten-speed and pedaled off into the night. I continued to make epic noise pollution of the downtown and never was bothered again by any cops.”
Her “New Mom Friend” Had A Hidden Agenda
“I was at a water park rave. I was 21 and had way too much liquid confidence. I just started going around asking people for Molly. Eventually, I asked a women who was about 30. She said she wanted to join me in trying to find some.
OK. What the heck? Come on, new mom. Let’s find some Molly.
I kept asking people. She was tagging along, so I started getting to know her. We ended up becoming good friends. Then, she told me she was an undercover cop.
‘You’re adorable but, wow, you’re an idiot,’ she said verbatim.
Honestly, they should have employed me because I found free Molly about 20 minutes later.
So, an undercover cop had to hang out with 21-year-old, white-girl-wasted me for about an entire hour – an hour which included some light puking, fighting with my boyfriend, a brief emotional breakdown because I couldn’t relax enough to pee in the pool when surrounded by people, collecting as many smokes as I could from people and smoking like 20 at one time for no reason, trying to set my new mom friend up with a bunch of dudes, and repeatedly mooning people, then cracking up and high-fiving myself.”
You Never Know Who You’ll Meet In A Dilapidated Neighborhood
“I once considered buying and fixing up a home with beautiful architecture in a once-vibrant neighborhood that, over a century or so, had descended into an infestation of substance abuse anarchy. But, it was presumably up-and-coming – buy on the cheap and get a huge return.
After walking through the wreckage, seeing the remnants of fires from squatters who had broken in, and so on, I realized I wasn’t up to the task and passed. Some time later, the realtor told me a police officer who wasn’t intimidated by the area had bought it.
A year or two afterward, the neighborhood was on enough of an upswing that they were looking for volunteers for a tour of homes. I volunteered. To my surprise, the property I had considered was part of my assignment. Excited, I walked through and marveled at the vast improvement. In the kitchen, I encountered the owner and told him I had seen it in its darkest days and praised his job well done.
Continuing the small talk, I commented on how his being a police officer must help him with being comfortable in the still rough neighborhood. He immediately, and abruptly, corrected me, insisting he was a firefighter a couple stations over. With puzzlement at both my misunderstanding and his reaction, I kind of apologized and brought the conversation to an end.
While walking in another part of the house, I was surprised by a tug at my arm. The owner pulled me into the small laundry room where he informed me he was working the area. He didn’t want any of his neighbors to know he was a cop. I almost blew the dude’s perfect cover.”
Living On The Wrong End Of The Law Came Back To Get Him
“In college, I developed a liking for opioids and it quickly spiraled out of control. I could not afford my habit, so I started selling to afford using. I sold very small amounts and only to my ‘friends.’ It was a horrible thing to do, but addiction makes you do crazy things and not think clearly.
A kid I regularly sold to, who I’ll call Larry, came over my house one night with his ‘best friend from high school.’ The kid looked to be in his early 20s and I considered Larry to be a very good friend of mine. I had know him all four years of college and hung out with him fairly regularly. He asked if his friend could have my number as he was moving to our area for work and needed a connect. I said sure, and that was that.
I never sold on campus, but, for some reason, this kid only wanted to meet me in the parking lot on campus. I kept telling him no until, finally, one time, I hit a dry patch and needed all the help I could get. I agreed to meet him in the school parking lot.
I gave him two pills for $60 and turned to get out of his truck. I felt a hand on my forearm and turned to see another guy with one hand on me and a loaded weapon in the other pointed directly at me. I figured I was getting robbed. It turned out to be the police. My ‘friend’ had set me, and others, up in an effort to get his sentence reduced.
I didn’t end up helping the cops. Instead, I went into rehab, then jail. I was released on parole and concurrent probation. I was facing a mandatory minimum of four years. The judge said I should have thanked him for his lenience as I could have gone to jail for up to 30 years. Fortunately, I’m still alive. I know a lot of people who lost the fight with addiction.”
She Tended The Bar, While He Kept Watch
“I was a bartender in Florida for a summer. I was in my mid 20s and was often left to man the bar and lobby by myself on weekends. It was a bit nerve wracking as a woman, but it was a lot of fun helping tourists and such, until one day.
This guy showed up at my bar and instantly moved to sit at the far corner with his back to the wall so he could watch the door. I had instant red flags about him being a cop, but in plain clothes. It was not a problem. I asked him what he wanted to drink. He nursed a couple glasses of water while he people-watched. Eventually, called it a night.
He kept showing up every few days. When things were slower, I would strike up a few conversations with him or get him involved with a few of the others at my bar so everyone would have a good time. He kept the same story that he was a local undertaker. I kept up the story that he was drinking some clear beverage on the rocks.
A month went by when another lone weekend shift came. My boss left me with a wooden bat with a weight on the end named ‘Justin Case’ and left me alone. I jokingly told my ‘not cop’ regular about it when he showed up. Naturally, this was the weekend a local dealer showed up with a girl on his arm.
He was already off his rocker when he sat down at my bar. After a couple of shots, started picking fights with my customers. After my attempts to interject myself to calm the guy down, the cop got up and walked over to ask the man to leave. The dealer pushed the cop and started making fun of his outfit and height. I asked the dealer to leave. The cop reinforced what I said.
The dealer challenged the cop to a fight outside my establishment. The door had not closed before the cop had this dude on the ground and in cuffs. As for the girl? She vanished out the back door while everything went down.
I thought that would be the end of everything since my usual stopped showing up, but he caught wind of my last weekend working in town before leaving so he came to see me. When it was a bit quiet and I wasn’t busy, he flagged me over and handed me a little slip of paper with his badge number.
He told me that he was undercover to bust that guy and would not have been able to talk to so many people for information without my help. I told him to get a better story and to stop acting like a cop so much because I had him pegged from day one. We both laughed and I finally got him to have a drink with me later that week when neither of us were working.”
The Stranger On The Train
“When I was 18, I was on a school sponsored ski trip with my senior class. One of the parents chaperoning was an undercover cop. At one of our train stops, a guy came up to me and asked if I wanted to buy any weed or pills.
‘Sorry, man,’ I replied. ‘None of us here do any of that.’
He said OK, and left. I casually mentioned it to the parents afterwards, thinking nothing would come of it.
As we all boarded back on the train, some friends and I went to the entertainment car (if you want to call it that) where you could get drinks and snacks and play games. A couple of friends and I sat down to play cards when the dude who offered to sell to me came to the cart. He sat down with us to play cards and pretty much told me his life story. He told me where he was going, what he was doing, his first name, last name, where he was born, etc.
Word got to the undercover cop parent what happened. He approached me and asked for a favor. He wanted me to go find the guy and ask him to come back to the train cart where the parents were to make a buy. I went through the cars until I found the guy sleeping. I woke him up.
‘Hey,’ I told him, ‘I don’t want to buy anything, but my dad is interested in buying.’
The dude said OK, and followed me back to the car. I introduced him to my fake dad and a couple of the other parents pretending like they wanted to buy. We all sat there watching this go down as my fake dad, the undercover cop, bought a few pills off the dude. The dude then walked away and went back to sleep. The cop then told me we were going to wait until we crossed into Nebraska border lines, where he had jurisdiction to bust him.
Once we crossed into Nebraska, we stopped at the town of McCook, where a bunch of cops were waiting. The train stopped and the cops boarded the train. In order to get off the train, the cops and the dealer had to walk right past my entire class, including me. As the cops kicked this dude out of the train, he stared me down the entire time. My heart was racing and I was scared. Luckily, my classmates knew that I was scared out of my mind and surrounded me to protect me.
It turned out that the dude was fleeing Boulder and was heading to Florida to buy a trailer house with his girlfriend. He had a warrant out for his arrest in Boulder. There were a couple news articles written about it, but my name was never mentioned. I had many parents write me personal letters thanking me for for being so brave and helping. I felt like a dweeb for snitching on the guy, but I guess you shouldn’t try and sell illicit substances to kids.”