Private investigators and detectives have been mythologized for decades. A lot of us are fascinated by the idea of a professional mystery-solver, available for hire. (Wouldn't it be great if we could all afford our own Sherlock Holmes to get answers when someone in our life is acting shady?) But part of being a private investigator is getting yourself into situations that are less than ideal, and digging for information you might otherwise have never wanted to know.
Here, private investigators share their most interesting case.
(Comments have been edited for clarity)
A Wild Web Of Lies
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“I investigate the backgrounds of witnesses for our cases. I found someone who was pretending to be someone else who had died as a kid. My boss alerted the feds and they investigated and found out he had faked his death 20 years before to avoid an embezzlement trial. He got convicted for having a false identity because he filed taxes using the fake name. Not sure whatever happened with the original embezzlement charge.”
It Still Bothers Me To This Day
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“I was hired once by a man who I didn’t know at all. He just called me one day, saying he’d seen my ads and needed me to investigate a few matters. I was sent $2,000 in the mail, which was way more than my normal asking price. I should’ve known something was up when he told me his rules:
1) No talking about the case to anyone.
2) No contacting the police or any other form of law enforcement during the case.
3) All contact between him and myself must be via phone only.
4) No arguing or negotiating – I either accept the conditions and the money or I decline.
I thought all of this was weird at the time, but I wasn’t gonna send back $2,000. So I accepted the case. Day by day, it just kept getting weirder and weirder. The mystery client kept asking me questions about the guy I was trailing. The client wanted to know the guy’s daily schedule, where he was hanging out, if he had family or friends living with him, etc. Abruptly, after a week, I was told to stop following him and that my services weren’t needed anymore, but I was still going to be paid all the same. Another week went by, and I was sitting on my couch, watching the news. The main story was that the guy I had been investigating had been killed, and the police said most likely it was a hit job. After that, I stopped working as a private investigator. Knowing I was part of a murder tore me apart. I still don’t know why that man was killed or who it was that hired me.”
The Things Investigators Have To Do For “Work”
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“I did surveillance on a nurse. She was supposedly so disabled that she couldn’t work anymore. They suspected she was working on the side. It was the easiest surveillance I ever did. I arrived. The woman got in her car 10 minutes later. I followed her, with no complication, to an adult club where she went in and began doing her thing.
The club had a posted prohibition on taking videos. So I had to go in and watch her dance so that I could testify I saw her dancing when the case went to court. Over the next few days, I followed her to three other clubs and did the same.
That month I turned in the sketchiest expense report of my life.
Eventually, it went before the Workers’ Compensation Board. When the judge asked why she was stripping, she just shrugged and said she made twice as much money as she did when she was a nurse.
Her benefits got yanked, and the insurance company was happy.”
A Really Hard Couple To Track Down
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“I’m an attorney and occasionally need to hire a private investigator to track someone down. We had a case where a husband and wife died within a few months of each other of natural causes. They had a mortgage with a small balance, but the bank didn’t want to foreclose because it was such a small amount, yet they couldn’t write off the sum either. My office was retained to see if the remaining family would pay it off and get title of the house.
I did my normal search and couldn’t find any next of kin. I can always find someone. I spoke to the neighbors, who were friends with the couple for 20 years but they knew nothing. They said they felt foolish because in reality, they didn’t really know the departed couple on any deep level. The deceased never mentioned family, where they were from, or anything about their past.
I reached out to our private investigator who asked for a week to get a report to me. He calls me a week later and says he needs more time, so I grant it. Finally, he calls to say there’s no report and he’ll give me a discount on the bill. He can’t find them. There is no record of the couple, they simply appear from out of nowhere in the 80s. In fact, the couples’ first record of existence is the mortgage application. In the 1980s, this couple would have been in their 40s.
When I asked for further explanation, the private investigator just said, ‘This must be witness protection.'”
Sometimes A Situation Is Not What It Looks Like
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“A woman in her midlife, presumably between 45 to 50, was found dead behind a dumpster around a local bar in the middle of December.
She was wearing a skirt that was pulled up to her waist, and leggings that were pulled down, and torn in multiple spots. She also had abrasions around her buttocks, the heels, thigh, and wrists.
At first, the cops are thinking that they have an abuse or a possible assault case on their hands.
However, certain things were not adding up. Even though it was mid-December, that particular bar was fairly populated, and thus, someone should have reported at least hearing a woman in distress, as the dumpster was near the parking lot of the bar.
Also, the abrasions on her buttocks were rather strange, as if someone had dragged her across the cement floor. Some experts state that it is possibly due to livor mortis (‘marks’ caused by settling of the blood).
After some investigation, they find no traces or physical proof that suggested abuse nor forced intercourse. No bodily fluids, saliva, or hair, were found.
Eventually, it was revealed that due to the loneliness of losing her husband and daughters (husband through divorce and daughters who simply grew up and started their own lives), this woman went to the bar hoping to potentially meet a new partner but instead got carried away drinking.
Once outside in the freezing cold, she wanted to take a leak and hid behind the dumpster. While doing so, she started slowly suffering from hypothermia due to the cold winter wind and lowered body temperature caused by her drinking. She begins feeling hot (due to paradoxical undressing, caused by hypothermia), and presumably strips off her jacket, and other pieces of clothing. At this point, the hypothermia is really getting to her and she begins slowly losing consciousness.
While laying on the freezing ground, skirt pulled up and leggings down, she begins convulsing, which leaves abrasions on her body. Leaving behind a curious scene that appeared as if she had been taken advantage of.”
When You Can Admire Their Commitment To Their Lies
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“I mainly trail people to investigate false workers’ compensation claims.
Some guy claimed to have a foot or ankle injury and said he couldn’t work. He had to attend some sort of meeting though, so he pulled up in the parking lot, got out of his car absolutely fine, and pulled a walking boot out of the trunk. He took his shoe off, put it on, and hobbled inside. Then came back out sometime later, took the boot off, and tossed it back in the trunk. Then got in the car and drove off.
Pretty sure he got in quite a bit of trouble for that one.”
“We Almost Called The Police On Her”
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“The strangest case the firm I worked for handled was towards the end of last year.
The job was given to us by another agency. It was for that evening (an important detail as it meant we did not have time to screen the job and get all the details we would normally ask for), and the brief was that the client suspected her husband was having an affair with a co-worker. The husband worked at a hotel.
We sent two agents to monitor him at work, requiring several hours of effort, all the while putting more and more on the expenses tab as the team had to keep buying drinks to avoid raising suspicion. The client would phone for updates every 20 minutes, despite being told not to make contact and that a full report would be issued in short order.
The agents managed to tail the individual until the end of his shift (noticing nothing unusual) and discreetly followed him home, deciding to give the client a call and confirm the address he had come to was his house and not the co-worker he was allegedly cheating with. The client evaded the question and demanded the team go back to the hotel.
Confused and irritated, the agents went back and were greeted by the sight of the client scrambling out of a bush, binoculars in hand, directly opposite the hotel. Judging from the state of her clothes, it seemed as though she had been there most of the evening.
Furious, the agents questioned her. It turned out that the man they had been watching wasn’t her husband, but rather someone she was involved with casually who was no longer returning her calls.
Stern words were had (and management even talked about involving the police) and we blacklisted her. She did, however, pay promptly and in full.”
She Wanted Me To Go Above And Beyond… Way Beyond
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“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, so it was his former residence.
I met her to discuss the case and she seemed rational. She was an attractive older woman, and the guy would obviously have been familiar with the condo layout and would have access, and anyway, I’d 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 went by and she called. I went over and got the tape (this was before digital recording) and checked it out. There was nothing on it but her. I met her to tell her this and she said, ‘He must have some machine that makes him invisible. He’s a space alien, after all.’ She was being 100% serious. 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.”
When A Parent Trusts Their Instincts
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“My uncle was a private investigator for a little over six years while going to law school. He once received a case from a man who believed that his mother may be trying to kill his children when she babysat them. He believed this because when the client was a child, his parents regularly beat him and his siblings. When he finally moved out and in with his girlfriend, his father threatened that he ‘would learn the hard way.’ Anyway, my uncle’s client started having children, his mother very openly spoke of her dislike for his wife and her kin, which scared the client. My uncle spent nine weeks collecting evidence that confirmed his client’s worst fear. The client’s mother would discipline the children in very brutal ways. Some of the evidence he collected was footage of her: beating them with anything she had in her hand (spoons, pans, cutting board, remote etc.), heating metal utensils and pressing them onto their bodies, punching them in the back of the head (these children were between the ages of 3 and 6 at the time), cutting the oldest on two separate occasions, practically waterboarding them, and other things that my uncle didn’t want to describe. My uncle reported his findings to both the police and child protective services before getting permission from his client to pick up the children and take them to his apartment where the police, the client, and my uncle would meet. The client’s mother was arrested and stripped of any rights to see the children and her own son filed a restraining order against her.”
The Bank Statements Told All
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“I’m a freelance private investigator. I was hired by this woman going through a divorce. With something like this, I normally ask for my client’s bank statements, receipts, and general travel plans they’ve had for the year.
Her (soon to be ex-) husband had changed passwords and locked her out of joint bank accounts, just to be a jerk. So I called up the bank and explained the situation on the speakerphone with her. My client was not technologically talented so I took care of going through the banking website and resetting her password. Turns out, for whatever reason, after the password reset her account had overall access instead of giving us access to her limited personal purchases. I could now see her, the husband, and the maid’s bank statements. I found out at that point that the maid was issued a card to expense whenever she picked up the couple’s son from school or made other purchases related to her job.
With this information, I later noticed inconsistencies in the bank statements. The husband was supposed to be away on a business trip in Boston at a certain time but I found purchases of dinners and flowers in New York. I got the name of the flower store and inquired if they had a record of purchases and an address of delivery. I found out the flowers purchased were the maid’s favorite flowers and that it was a carryout order. I then found a purchase for food at a gas station on the maid’s card which coincided with a gas purchase on the husband’s card. I checked the maid’s schedule, and she had been off work and ‘unavailable’ to work that day.”
He Spent Thousands When He Could’ve Just Done A DNA Test
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“It was one of the 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 for a living. I was very disturbed by what I was asked to do.
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 crazy cake was when my case manager told me the 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 tinted limo 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. I hated that case and the case manager.
Two weeks later, I handed in my resignation.”
We Finally Told Her We Couldn’t Take Her Money
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“I worked for a private investigator firm.
The saddest case we had was a stunning woman in her 20s whose 60ish-year-old accountant husband was suspected of sleeping with his secretary (who looked like she had fallen out of the ugly tree and hit every branch on the way down).
The client hired us to follow him on a night he was ‘working late.’ Sure enough, he and the floozy secretary left the office on time and went to a bar together. After a few drinks they retired to her car and we got some pretty clear footage of them shagging in the back seat. Classy!
We gave the footage and report to the client who promptly burst into tears and paid the $1,800 or so invoice.
The saddest part of the story is she came back four times. Each time, he was caught literally with his pants down. At the secretary’s house, shagging in the car, shagging in the office with the blinds open in the middle of the day – you name it.
After about $15,000 worth of invoices, we actually sat down with her and explained we were going to stop taking her work. It was just cruel to keep taking her money to show her footage of her husband banging his ugly bimbo over and over and over.
We never saw her again. I hope she took him for all he was worth.”
I Trailed Her To A Middle-Of-Nowhere Motel
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“I’ve worked a few bizarre cases, including one involving a stolen horse and almost getting shot by rednecks. But for legal reasons, I’m not sure if I can discuss those.
I worked a workers’ compensation case last year. I was told to get film of this older lady who had supposedly been on total disability due to a severe ankle injury. Seemed cut-and-dry. But she lived in a motel in the middle of nowhere in Pennsylvania. The motel was called ‘Johnny’s.’ I looked up the place online and found reviews of it on Google. There were really terrible reviews, including one that said the place was mostly run by the owner’s son, who was an addict and would ask people who stayed there if he could buy any prescription medications they had. That isn’t sketchy at all.
So I showed up to this ‘motel,’ which looks like it hasn’t been renovated in 40 years. It was a small motel and had about 14 rooms. I had no idea what room the person I was supposed to be looking for is in. I figures I should talk to someone at the front desk. There was 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, there was a sign that said ‘office’ and instructions for long-term customers of the hotel telling them where to drop off their payment. There was a doorbell. 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 told me to come in. I walked into a room with one desk. Nothing else. There were shag carpeting, really dark colored walls, and a lava lamp on the desk. I realized that this had to be the owner’s son, Johnny Jr.
I gave him some fake story about how I was an insurance agent looking for this lady, and he then replied, ‘Oh Mary? She lives in the room next to me. Want me to go get her?’ This was a problem because I had absolutely no backstory for what to tell this lady. She was repped by an attorney and likely knew a private investigator might be looking for her. I told him, no, I just needed to confirm she lived there and I bolted.
Now I was parked in the parking lot with a view of the room Johnny Jr. had pointed at. A couple hours went by and then some old guy was standing near my car, getting stuff out of his vehicle. Johnny Jr. walked out and started talking to him. I realized the older guy was Johnny Sr. They were literally standing right next to my car and I could hear everything they say. They started talking about me – well, at least the ‘insurance agent’ who visited earlier. Johnny Sr., having seen some wild stuff in his day, immediately said, ‘That wasn’t an insurance agent, you idiot. That was a private investigator. Insurance agents don’t work on Sunday.’ He told Johnny Jr. to tell Mary to watch out because a private investigator might be in the parking lot.
My car was tinted. I thought I’d be fine. Except, the parking lot I was in was shared with a diner. The owner of the diner came out and started talking to Johnny Sr. Apparently, I’d parked in front of a shed that the cleaning staff for the motel use. Now Johnny Sr. started 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 said she’d ask and left. Johnny Sr. then went into one of the motel rooms, where apparently he lived. He constantly stood in the doorway, looking at my car. I left as soon as he looked the other way.
I ended up coming back later in the day and getting videos of the lady I was supposed to watch. She was totally faking her injury. Johnny Jr. and his girlfriend actually came out a couple of times and tried figuring out which car might be the private investigator’s car. But because they saw mine parked earlier that day, they didn’t seem to think it was suspicious.”
When The Results Are Even Worse Than Suspected
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“I’ve been a private investigator for almost a year now, and the strangest case I had was a woman asking us to find out if her husband was cheating on her. She said there was something off in the house. She said she just felt in her bones there was something suspicious going on, and she had to know what it was. She suspected her husband was cheating.
I show up and install nanny cams in her house for the weekend, with her approval and her instructions for where to place them. She worked all weekend, so we decided this was the best route. Well, three days went by and I collected the footage. Come to find out, the husband was actually ‘touching’ his 8-year-old stepdaughter. After seeing that, I rushed to the courthouse with a copy of the footage and got a court order for the police to go and get him.”
An Easy Case To Crack
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“I got hired to follow a woman who claimed she was completely blind (collecting insurance money of course). I spent the day following her around as she DROVE from store to store in a church van.”