45 Private Investigators Share The Strangest Things They’ve Encountered On The Job

Doing a standard pre-employment background check on a guy, found that he was found guilty in a sexual harassment case. Didn't have the case details at that point and the guy denied it was him. Pulled more details from the case and confirmed that it was definitely him... And that he was convicted of indecent exposure. The guy finally admitted it was him, but claimed it wasn't as bad as it seemed. Pulled the court transcripts. Turns out he flashed a 12-year-old on the beach and said "ever seen one of these before?" He did not get the job.

Former PI, about 30 years ago.

For me, the amount of people faking disability claims was huge. It made up at least 70% of our cases but it was also easy to prove..way more than other types of cases.

Normally, we'd just hang outside their house and wait for them to take groceries out of their trunk, walk down their porch steps, etc.

But one hilarious case that I will never forget was the one where a man claimed he hurt his shoulder and lost movement of his right arm as a result. We waited outside his house, and on day 1 he came out and got into his car. So we followed him....to the batting cages where we recorded him swinging a bat all day.

Worked as a PI for about a year once when I was much younger. This wasn't a case I took, which will be obvious by the end why I didn't.

We had an office on the ground floor of a building near the county courthouse, with a door that opened to the street. This meant we actually got a fair amount of foot traffic. If I had nothing going, I closed the office round 5pm. Around 4:45pm a lady comes in asking all the usual questions. "Are you REALLY a PI?" "What cases do you take?" "How much do you charge?" Yada Yada Yada, I spend 10 minutes going through all that. This lady seem pretty wound up, which is not unusual, people don't come in looking for a PI when everything is great. Often it's because they are having one of the worst experiences of their lives and are desperate for help and haven't gotten it elsewhere.

I ask her to tell me what brought her in today and be as detailed as possible. She tells me that someone stole her ideas and now she's being followed. I'm thinking, great, potential intellectual property case. I ask her to start from the beginning, what were these ideas? She starts telling me about here last gynecological exam. I immediately stop her and ask her what this has to do with her ideas being stolen. She flips out.

She begins screaming about how the doctor implanted a listening device inside her and that's how they are stealing her ideas. I do my best not to react. She screams, "You don't believe me either! But I have proof!" She runs out of the office and comes back a minute later with a large envelope. She pulls out x-rays of her pelvic region and shoves them in my face. "See! Right there, that white spot on my ovary, that's the listening device!" I agree that there is a small white dot, but tell her I'm not a doctor or an expert in listening devices and can't confirm that it is one. In reality, it didn't look like anything to me, I know it wasn't an electronic device of any kind, let allow one that can capture you ideas and transmit them to vans that were following you around now.

She goes on to tell me how the doctor was in on it and they were stealing her ideas and making them into TV shows for Telemundo. This is the part where I tell you this middle aged, blonde haired, blue eyed lady didn't speak a word of spanish.

I ask her about the vans that were following her. They were different colors and often different drivers. But they were definitely following her around and that's how they were collecting her ideas. I'm looking for a polite way to tell this lady I won't be taking her case, but she won't let up and insists I do something about it. I finally catch a break. I tell her the retainer amount I would need to get started. She responds, "Well I don't have that kind of money. When we win in court you can have half the settlement."

In the state I live in, only lawyers can work on contingency. Meaning their payment is contingent on them winning the case. PIs and all people that might work for these lawyers still have to be paid no matter what. I tell the lady this. I thought she was about to explode. I tell her I can't break the law, but if she were to find a lawyer willing to take up her case, I could work for that lawyer as their PI.

She calms down and says thanks for hearing her out. I say no problem. I ask her if there was a family member she could call or a doctor she did trust that she could see. She tells me she's not crazy and storms out. I felt horrible for her, she was obviously living in terror and needed professional help. This was the first time I encountered the seriously mentally ill. In retrospect, I should have called the police and tried to have them intervene, I regret that. I can look back now and cut myself some slack for being young, and caught alone and off guard, but I still wish I would have done more. At the time I just wanted to get her to leave peacefully.

Worked as a PI for 9 months, the company I was with investigated employee workers comp fraud. I'd follow people who supposedly had injuries so debilitating they couldn't work, and then film them doing things like carrying 3 jugs of detergent through a grocery store, or lifting a massive concrete tortoise out of a garden bed and moving it to the other side of the yard.

Most interesting thing was a job I did in another state, and I filmed a guy about a mile away in farm field slowly take apart a small plane he had sitting in a field over a period of 8 hours when he supposedly had a back injury so bad he couldn't lift 10 pounds. Maxed out my camera memory, ended up taking pictures the last 4 hours every time he moved a piece of plane.

Small piece of advice: if you're committing workers comp fraud and the company's insurance tells you to go to a specific doctor...they have paid PI people to wait for you there and follow you home/around for the day. They wanted to get you in a specific place to be followed after you pretended to be hurt so they can show after you went and did things you shouldn't be able to.

I was living in Tokyo. Someone posted an ad looking for someone to do some investigative work. I was broke and interviewed for a job despite not knowing anything about private investigation.

A Japanese woman who spoke good English had a crush on a white guy. She wanted someone to investigate where he hung out, then befriend him, then introduce him to her.

I declined the job. But later on she hired me to do some marketing work for her. Unsurprisingly, one of the worst marketing clients I ever had, purely because she didn't respect boundaries. Shoulda seen that coming. :p.

A couple was divorcing and the wife was sure her husband was sticking random items of hers up his a**.

He was.

I got hired to follow another investigator who, turns out, was hired to follow me.

A mother hired me to look into the new boyfriend of her daughter who was way older than she was. She said there was just something off about him, and she was right. They broke up in the middle of the case so it got cut short and I never got to the bottom of everything, but he had like 5 different current addresses (some apartments and some private homes) all in different cities, and he had multiple cars registered in different states of which none of the plates were coming back as registered to him or a family member (in fact, one of his trucks was registered to a dead couple he had no affiliation with).

Also ran a vehicle sighting report and one of his cars was all over the place in like 3 different states over the course of a year, spotted parked in the driveways or random homes he had no seeming affiliation with. Very weird. I still wonder what I would’ve found if I kept digging.

EDIT: the databases are subscription based, but they’re not unlimited use. You have a certain number of searches per month based on whatever tier you select, and I had the lowest tier since I was just starting out my agency at the time. You also have limits to the features you can use. The more features, the more money. It’s easy to blow through all your credits very fast, especially in cases like this.

Vehicle sighting reports weren’t included and were $25 a search. I believe tow trucks and police vehicles with license plate technology capture the plates as they drive by. One particular vehicle of his just happened to have a lot of hits. I ran my own plate as a test and it’s never been spotted anywhere before, so it’s a hit or miss.

No I didn’t report anything to the police. They honestly wouldn’t give the slightest s**t if I did. Hate to say it, but that’s the truth.

I located and assisted in serving my husbands sleezy former boss which led to his arrest on federal charges. Good times.

I was a fraud investigator for a finance company. I went to interview a small business who we had lent to, got there first thing in the morning. Walked in and had just introduced myself when a dude walked out of the back with a black clean sack. He got a shock I was there dropped the clean sack and bundles of cash just fell out and on to the floor. Said quickly I wasn’t there for that and they needed to pay for the equipment they had secured and not paid a cent for. It was paid before I got back in the office.

Way back in like 1998, we surveiled a house for an older guy who thought his younger wife was cheating on him. I wasnt on this shift, but heard the same story from everyone there. They wired the house and waited in the van behind the back fence. Guy leaves on a business trip. Lady gets dropped home by the Chauffeur. He carries her bags into the bedroom.
Suddenly, he slaps her HARD across the face knocking her back onto the bed. One of my coworkers jumped out of the van thinking she’s about to get hurt. Before he gets to the sliding glass door, he hears over the radio (from the other guy watching the video feed), “come on back, she likes it.” She then proceeded to also bang the pool boy.
When my boss informed the client, he just asked, “How much?”
Back then camera equipment was expensive, and we rented it. He just wrote a check for $10k on the spot.
My boss checked in with him later and said the old guy had a private collection of vhs tapes.
So. There’s that.

I have a story about this. My Brother was a PI in the early 90's. He worked for a law firm. I was in my early 20's and so he got me a gig as a process server.

He was working a particularly nasty divorce case. Husband was a Jordanian national married to an american woman (one of several wives) who was over being the broodmare in the family and wanted out. Also, she worked for Nasa.

He was tasked with going into their house, which was in her name (she wasn't living there, she was in an apartment until this was settled) and getting a briefcase with financial information in it. Since I was the process server, I had to go along in case someone was home for whatever reason.

We went and waited down the road until everyone left and went in and got the briefcase. no big deal. We take it back to the attorney's office and he calls the lady and says he has it. She gives him the combination he opens it and it was full of technical plans from Boeing for the Apache helicopter.

Attorney says "Fuck", instantly shuts the briefcase, tells me and my brother to leave now, so we did. We never heard any more about that case at all, other than he contacted the FBI over it.

True story. Hired to watch someone who had been the victim of repeated, serious vandalism. Because of reasons, it was thought to be related to d***s or organized crime, possibly a scheme to sell protection. What we found by watching the victim was tons of d***s, organized crime connections, and revealed the mayor of a small city to be having an affair with someone well connected to the d**g trade. As to the vandalism, an ex-boyfriend was eventually caught in the act; it had nothing to do with the d***s and crime.

Edit:.bc this blew up. It was a very small city, if you're not from the area you've probably never heard of it. My memory is that the mayor was eventually outed for the affair a few years later and that neither the city nor local media really cared; small city, basically a town. I think maybe it also wasn't much of a secret. All of the affair and d***s were out in the open in public. We would only see things with some deniability, though. Things such as duffle bags being exchanged, we didn't know what was in the bags but the manner in which they were exchanged, by dead drop, indicated the content were illicit.

Caught a guy on disability carpooling Amish kids to school.

Was insurance fraud case. in southern MD. For a week I watched a supposed completely disabled person shuttle kids in a blue station wagon to a public school. Pick up and drop off. Long time ago, 20+ years, video'd it all on a handheld VHS cam. Even got video of what looked like a cash payout by one of the parents at the end of the week.
He then drove to the local 7-11 and bought a 'bagfull' of scratch offs. Weird times.

Working for an insurance company in the IT department and created a secured file server for our disability insurance investigator to upload video. Worked closely with him so I got all the stories. Primarily just catching people who were 100% disabled building fences, unloading bags of groceries and walking them up two flights of stairs, just doing things things they physically said they cannot do.

It was one of my last cases that I worked on. It was for a child custody/paternity case.This case was the one that made me rethink what I was doing and I got very disturbed by what I was asked to do. This is the case that made me stop being a PI

Our client was denying that the child in question was actually his and was fighting the child support case. He believed that the mother of the child was a serial adulterer. So much so that he spent THOUSANDS on the case for us to make sure there was evidence to support his claim.

The icing on the "sh*t cake" was when my case manager told me that client wanted video evidence that the child did not look like him. The client told us that we had to record the child at play.

So here I am, beside a playground, in a completely limo tinted car, videotaping a 9 year old. I couldn't have felt worse about my life choices. To this day I have never felt like such a creep before. I hated that case and the case manager.

Two weeks later I handed in my resignation.

We did mostly disability fraud. Most PI work is insurance because it’s consistent and easy to bill.

It’s basically professional doorknob watching. Show up to site around 4am, sit there all day and see nothing. Take timestampped photo or video every hour. Sit in car all day peeing in Gatorade bottles and watching movies. Go home, submit report that nothing happened and you saw nothing.

Sometimes catch people claiming disability working out at a gym or cleaning gutters, basic normal stuff that people claiming disability shouldn’t be able to do.

Weirdest thing I ever saw was a municipal client that wanted surveillance on a dude suspected of violating a zoning ordinance by manufacturing fertilizer in his house. Never confirmed any of that but that would be stinky if true.

Sometimes you have to follow the subject in a vehicle and that requires a crazy amount of traffic violations, mostly running red lights and speeding.

Most contracts want you to break surveillance if you get noticed. You just switch cars and try again the next day.

All things considered, awful job. Little career growth. Crazy hours. Inconsistent work. Licenses can be difficult to acquire so mostly you work for a company that holds a license and never progress. You’ll miss holidays and family events. S**t retirement.

If you think you like that work, be a cop and then make detective. At least you get a pension.

I was asked to help my boss fire another investigator do to his short temper. I was told to arrive at 7:30 because he likes to arrive at 8:00.

So like any other day I woke up and started to drive to work through a fucking blizzard and didn't end up getting there till 7:40. Go to my boss and says he already fired the guy.

What the fuck man what if he lashed out and what not and I wasn't there.

His reply was he didn't, but he wanted me to stick around just in case.

So I sat there for 4 hours drinking coffee on double time which was great until I had to file the 2 page report on me drinking coffee

Tldr. Drank coffee for 35 bucks an hour.

Not a PI, but I met one. I was at my friend's house and he got a knock on the door. The dude was black (EDIT: Congolese to be specific).

"Hello, sir, are you X?"

"Yeah, why?"

"[explains that he's a PI and that he'd like to talk in private]"

"Nah, I'm fine just talking here at the door."

"[shows him a picture] Do you know this man? His name is Y."

"Yeah, that's my great-uncle, he's vacationing in the Congo right now, why?"

"I'm sorry sir, but your great-uncle died of hepatitis. [elaborates how his great-uncle, a priest, banged some hooker and got infected and died]"

I was in the living room eating pizza the whole time, pretending to be watching TV.

I've worked a few bizarre cases, including one involving a stolen horse and almost getting shot by rednecks. But due to legal reasons, not sure if I can mention that one.

There was a workers compensation case I worked last year. I was told to get film of this older lady who had supposedly be on total disability due to a severe ankle injury. Seems cut in dry. But she lived in a motel in the middle of nowhere Pennsylvania. The motel was called "Johnnies" I looked up the place online, and found reviews of it on google. There were really sh**ty reviews including one that said the place was mostly run by the owner's son, who was a druggie and would ask people who stayed there if he could buy any prescription d***s they had. That isn't sketchy at all.

So I show up to this 'motel' which looked like it hasn't been renovated in 40 years. It was a small motel, had about 14 rooms. I have no idea what room the person I'm supposed to find is in. I figure I should talk to someone at the front desk. There is no front desk. The office part of the motel looked boarded up. But next to it was one of the motel rooms, and in the window of the room was an "Open" sign. On the door it was a sign that said "office" and instructions for long term customers of the hotel on where to drop their payment. There was a door bell. I rang it and waited. The guy who opened the door looked exactly like Kenny Powers from Eastbound and Down. He was wearing a Ninja Turtles t-shirt and Hawaiian shorts. He tells me to come in. I walk in and what I walk into is just a room with 1 desk. Nothing else. There was shag carpeting and really dark colored walls and a lava lamp on the desk. I realize that this was the owner's son, Johnny Jr. I give him some fake story how I'm an insurance adjust looking for this lady, he then replies "Oh Mary? She lives in the room next to me, want me to go get her?" This is a problem because I have absolutely no backstory on what to tell this lady. She was repped by an attorney and likely knew a PI might be looking for her. I tell him, no, I just needed to confirm she lived her and bolted.

Now, park in the parking lot with view of the room Johnny Jr pointed at. A couple hours go by and then some old guy is standing near my car getting stuff out of his car. Johnny Jr walks out and starts talking to him. I realize the older guy is Johnny Sr. They are literally standing right next to my car and I can hear everything they say. What proceeds to happen is they start talking about me, well at least the "insurance adjuster" who visited earlier. Johnny Sr having seen some sh*t in his day immediately says "that wasn't an insurance adjust you idiot, that was a PI, insurance adjusters don't work on Sunday" He tells Johnny Jr to tell Mary to watch out that a PI might be in the parking lot.

My car is tinted. I think I'll be fine. Except, the parking lot I'm in is shared with a Diner. The owner of the diner comes out and starts talking to Johnny Sr. Apparently I parked in front of a shed that the cleaning staff for the motel use. Johnny Sr now starts talking to the owner of the diner asking her if my car belonged to any of her employees or any of the people in the diner currently. She says she'll ask and she leaves. Johnny Sr then goes into on of the motel rooms, where apparently he lives. He constantly stands in the door way looking at my car. I leave as soon as he looks the other way.

I would come back later in the day and would get film of the lady I was supposed to watch. Was totally faking her injury. Johnny Jr and his girlfriend actually came out a couple times and tried figuring out what cars might be a PI's car. But because they saw my car earlier that day, they didn't seem to suspect it as suspicious.