39 Cases Private Investigators Can’t Forget

Most interesting case? A wife hired us to follow her husband, thinking he was cheating. He wasn’t. Turns out, every weekend, he’d drive two hours away, check into a cheap motel, and spend the entire night dressed as a clown, performing birthday shows for terminally ill children at a local hospice.

He never told anyone. Didn’t want attention or praise — just said it made him “feel like a human again” after losing his own kid years ago. Client was shocked. Divorce canceled. Marriage got stronger.

Some people hide affairs. Others hide their healing.

FINALLY! A question I can answer! Been a P.I. For a going on a year now and the strangest case I had was of a woman asking us to find out if her husband was cheating on her. She said there was something off in the house as if feeling something and she wanted to know what it was. So she suspected her husband of cheating.


So I show up and install Nanny Cam's in her house for the weekend upon her approval and where to place them. She works all weekend and this was the best route. Well 3 days go by and I collect the footage and come to find out the husband was "touching" his 8 year old step daughter. After seeing that I rushed to the court house with a copy of the footage and got a court order for the police to go and get him.

I was asked by a lady to investigate her husband because he might be cheating on her. He used to come back late at night with smell of womans perfume. Turns out he was taking dancing classes and he didn't tell his wife.

Was hired to follow a woman who claimed she was completely blind (collecting insurance money of course). Spent the day following her around as she DROVE from store to store in a church van.

randomuser8765:

Wow, she must have really good hearing and smell.

Neilsen17:

Smells like a left turn in 400ft.

Not a PI here, but someone who was confronted by one and told it was the weirdest thing he's had to do.

A roommate I had in college was a strange guy. This guy came from the other side of the country (I'm US). He went out at all hours of the night, never showed up for class, slept during the day, and drank more energy drinks than is healthy. His parents were worried about him, apparently, and hired a PI to trail him.

Now, living in a college dorm in a part of campus where only freshman live makes an adult who isn't janitorial staff stick out like a sore thumb. So, I picked up fairly quickly that this guy was hanging around the dorms. Thought he was just cruising for some freshman, and didn't bother him.

A few weeks later, I was walking back from the dining hall, and he approached me (it was a public place) asking if we could talk somewhere private. I was weirded out and told him we could talk right here.

He told me he was a PI hired by my roommates parents to trail him because his parents were concerned, and he wanted to ask me about my roommate's dorm habits. We then left to the coffee shop to talk about my roommate.

My roommate apparently liked to go walk on the beach at night for stupid amounts of time, hang out at Steak and Shake playing game on his phone and Nintendo DS for hours on end, and cruise thrift shops for some reason. I told the guy that the dude just slept and didn't even have any personal affects in the room besides his clothes.

The PI and I both realized that this kid pretty much had no direction or motivation in life, and his parents usually pushed him to do everything. He said that this kid's behavior was the most bizarre pattern of activity he's pretty much seen.

To explain the kid's actions, college was the first alone time he's ever had, and he was savoring it doing whatever he wanted. I ended up feeling for the guy and reached out to him. He changed majors from engineering to a psychology degree because he wanted to learn how the mind worked, and he suddenly became super-interested in college. Ended up being a cool guy once he realized he was not in his parent's grasp anymore.

Someone wanted to know what their cat was up to when they were working. Paid me to tail it. I don't like wasting my time but the works not always busy as a PI. Turns out the cat just walks around the streets, licks itself and climbs trees....

Anon:

Day 17: This is the 4th mouse he's caught. He doesn't even f**king eat them. He just loves the thrill of the k*ll.

fwng:

This would be me as a PI. I wouldn't even need someone to give me a case. I'd just do it.

I had a case referred to me by an attorney I worked for involving a woman who was convinced that her condo maintenance man was going into her home while she was gone and moving things around. She had bought the condo from him originally. (In other words, it was his former condo).

I met her to discuss the case and she seemed rational, she was an attractive older woman, the guy would obviously be familiar with the condo layout and would have access, and hell, I've seen weirder things. So we proceeded. She agreed to let me install a hidden camera setup with a motion detector. She was to call me if anything happened to make her think he'd been there.
A couple of days go by and she calls. I go by and get the tape (this was before digital recording) and check it out. There's nothing on it but her. I meet her to tell her this and she says, " He must have some machine that makes him invisible. He's a space alien, after all." She had not previously mentioned this vital tidbit of information.

I told her that that level of technology was beyond my ability to deal with and that we should talk it over with her attorney to determine the best course of action going forward.
I called the attorney to let him know that our client had some issues, and we were able to get her some psychological help.

But most importantly, her check was good. :).

Did surveillance on a nurse. She was supposedly so disabled that she couldn't work. They suspected she was working. Easiest surveillance I ever did. I arrived. She got in her car 10 minutes later. Followed her, with no complication, to a strip club where she went in and began doing her thing.

Club had a posted prohibition on video. So I had to go in and watch her dance so that I could testify that I saw her dancing when it went to court. Over the next few days I followed her to three other strip clubs and did the same.

That month I turned in the sketchiest expense report of my life.

Eventually it went before the WC Board. When the judge asked why she was stripping she just shrugged and said she made twice as much money than when she was nursing.

Benefits got yanked. Insurance company was happy. But the company lawyer gave me the nickname "Detective T**s" which, most regrettably, stuck and spread to all of the other lawyers I dealt with.

Worse night of my life, man.

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

He was.

Anon:

So many questions.

you_are_d00med (OP):

Man I wish I could post video. What you dont realize is I didnt set up cameras in the bathrooms so you gotta picture this dude walking around the house with this toothbrush sticking out of his a*s. Because of course he is naked, I would assume the clothing pushing on it would make it more uncomfortable than it already was. And dude had a semi. I am still scarred from these images. I could never tell if it was bristles out or in tho.

Stiflerradi:

Why does every thing smell like sh*t?!
Ohhh...

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.

That was the most bizarre thing that ever happened to me during my time as a PI, but there were a couple of close runners-up.

My work partner and I were watching a guy who was cheating on his wife. We were at a restaurant where they were eating dinner together. Had snuck over to his car to put a GPS tracker underneath the fender. At the same time there was another PI team working to put a PI tracker on the girlfriend’s car lol. We never made contact with the other team, but we sort of gave each other just a wink and a nod. Turns out they worked at the same hospital and were each cheating on their spouses with each other but we’re also cheating on each other with multiple other people. It was a hot mess and a lot to keep track of.

Client wanted to know why her dog was getting fat.

Turns out the dog was getting fed by almost every stranger it encountered while wandering around outside during the day.

I'm a PI (among other things.)

I haven't had any bizarre tasks, though I have had some interesting situations, and I've performed surveillance on cheating spouses as well as factual worker's compensation and public liability matters.

One matter which really made an impression on me was where a person had a fatal vehicle incident and a claim was made that it was a workplace injury. I don't know what on earth happened with this claim but it was five years before the insurer gave it to me.

There were some questions about it - the person making the claim alleged to be the worker's wife, though work colleagues did not know her, and also the incident was almost 200km from the workplace.

When I spoke to former colleagues a lot of them struggled to remember him. This really was so sad. It left a deep impression on me that what are we once we are dead if we are not even memories.

I did, however, learn he stayed at a caravan park during the working week. I called that place but the owner said it had changed hands and he didn't know the guy, he didn't have any old records, and he didn't know where the former owner was. He did remember the former owner's name however.

I called everyone in the phone book for the state with that name. I finally got my man, and he remembered the deceased vividly ... along with his wife and son. It was tremendous! I learned the guy would stay near the workplace during the week and travel back home, to a remote town, for weekends.

I drove all the way to that town but couldn't find the wife. She wasn't at any address I had, nor did she answer her phone. I got petrol and asked at the counter if they knew the family, and they said it might be so-and-so and directed me to a house. I went there, turned out to be the wife's parents, they called the daughter, she arrived and both mother and daughter had a big cry while showing me all their photographs of the guy. It was very moving, and I was so relieved to have real evidence the guy ever actually existed after how his co-workers were finding it hard to remember him.

The story was very sad; he died on the way to work on a Monday morning. Normally he would travel to the caravan on a Friday night but this particular weekend was mother's day. He stayed Sunday night and travelled Monday, early in the morning, ran off the road and passed away :(

I was able to determine the lady was genuinely his wife, that he was on his way to the workplace, that it was his regular route to work, and so on. I supplied this to the insurer. I never - well, rarely ever - hear what happens to a matter so I only hope it was finally settled.

I found a lady who'd been missing for twenty years out of pure, dumb luck. I was getting lunch another town over and she walked out of a resale shop across the street. It was so unexpected that the only footage I could get on her was with my s****y phone camera.

Otherwise, I don't get a ton of "bizarre" cases. Most of the time, I'm just doing insurance fraud cases since that's where the money is. The most interesting part is looking at their background info and piecing together what kind of person they are based on their spending habits. Then you take that information, make a quick and dirty psychological profile, and try to predict their movements based on it. I've gotten pretty good at it.

avesthasnosleeves:

So many questions... How did you know it was her? I mean...20 years - she'd look totally different, right? And why was she missing? We want answers! (Ok, maybe just me, but...)

44Renegade (OP):

She actually looked about the same, plus some wrinkles and a little rattier hair. I'd also literally just gotten finished looking over the case file, so the image was still fresh in my mind. I also have the special gift of never forgetting faces. If I meet you once, I'll recognize you five years from now, even if I don't recall from where.
She basically just went off the grid for personal reasons. Finding her was kind of a pain in the a*s, and truth be told, if it wasn't for that happy accident, I probably wouldn't have found her. All I had to go on was a vague last known location. I was hired by her sister who had received instructions to find her from their father shortly before he passed away. The video was a little spotty, but it was enough to confirm that she was the person I was looking for. I never got to witness the reunion and I'm not sure what happened to them after my job was done.

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 "s**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.

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.

All right, here goes. After I got out of the Navy, I worked for one of the top PI firms in Houston. Because of my electronics background, I'd usually go along on the jobs where were were checking for bugs and hidden surveillance devices.

We got a call from a client who was sure that his office was bugged because his client knew everything that he was doing before he did it. His office was a mobile trailer that was on his client's site. He was a subcontractor for a big oilfield construction company.

We did a full electronic sweep and found nothing (this was back in the early nineties, didn't have to worry about burst transmissions, etc.) No devices implanted in his phones. He insisted on a full physical sweep of the trailer, inside and out. So we crawled under the trailer and got a ladder and inspected the roof. Still nothing.

We're getting ready to leave and he says: "Look, I'm not crazy. Pick up the phone, press 9 to get an outside line, and you'll start hearing all sorts or clicky sounds." Turns our his office phones were routed through the corporate PBX of his client. They didn't have to bug his office, they could just "pick up an extension" inside the main building and listen in to whatever they wanted. We weren't even sure if it was illegal. We advised him to install a private phone line that he paid for if he wanted private conversations. We ended up billing him like two grand for that visit.

I was asked to help my boss fire another investigator due 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 f*****g blizzard and didn't end up getting there till 7:40. Go to my boss and says he already fired the guy.

What the f**k 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.

Was asked by a prospective client to kidnap a child who's parents were in the middle of an ugly custody battle, the one parent was keeping the child in violation of a court order and this family member thought this would be the easiest solution, nope, passed on that one. One of the funniest things about the PI business that we saw over and over was clients coming in mad as hell wanting something done saying "cost is no object", right up until we told them we charged $100 per hour, then cost suddenly became an object.