Our American Cousins: 22 Private Investigators Confess To The Weirdest, Most Messed Up Cases They Ever Had

Whilst somewhat unorthodox, we have collated some stories as told by American PI’s for your amusement…

1. Wife Wants To Know If Husband Is Sticking Her Things Up His Butt

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

Man I wish I could post video. What you don’t realize is I didn’t set up cameras in the bathrooms so you gotta picture this dude walking around the house with this toothbrush sticking out of his butt. 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.

2. Cursed By A Cult

I’m a private fire investigator. I’ve seen some people do some weird stuff but one of the strangest was the guy who was convinced that the church next door set his house on fire.

He told us about how they came over and prayed on his car that it would break down, then it did. Then they came over and prayed that his house would burn down, and it did.

Turns out the “church” next door is kind of a cult. And by kind of, I mean really a cult.
But they didn’t burn the house. The tenant’s crazy ex-boyfriend did. Thought I was going to get to interview cult members for a while though.

3. Earning The Nickname “Detective T1ts”

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 T1ts” which, most regrettably, stuck and spread to all of the other lawyers I dealt with.
Worst night of my life, man.

4. Jesus, Take The Wheel!

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.

5. Ace Ventura, Pet Detective

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…

6. College Student Is The Weirdest Case This PI Ever Had

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.

7. Paranoid Rich Men Will Pay For Anything

Former PI here. Most cases I worked on were for large litigation firms and finance institutions (fraud, embezzlement, insider trading, etc). But we would get the occasional eccentric millionaire with strange requests. One guy hated his brother and hired us a number of times to look into him regarding different matters. I personally had to investigate whether his brother was improperly using his title of ambassador or former ambassador. Apparently, there are many laws about this. Another hedge fund manager hired us to look into him (he was investigating himself) to see what kind of information is out there that could be used to hold him or his family ransom. This same guy had previously hired my firm to go through porn sites after his girlfriend’s ex-boyfriend claimed she was a porn star.

8. Chasing Down A Dead Man

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 traveled 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.

9. Casing Mary

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 poor 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 drugs 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 here 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 stuff 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 one of the motel rooms, where apparently he lives. He constantly stands in the doorway 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.

10. Two Grand In Fees Because The Guy Was Dumb

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 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 out 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.

11. Withholding Essential Info

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.

12. This Is Some International Spy Stuff

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 “F**k”, 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.

13. Employment Background Check Turns Up Dirt

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.

14. Snitches Get Stitches

My friend is a PI. Apparently, municipal waste management drivers were dealing drugs from the trucks. He was hired to ride around with the supposed ring leader as ‘the new guy’. Upper management got word of it and wanted to hire a PI before calling the cops and the local media getting word of it. First day on this job he was riding around on the back of the truck and woke up in the hospital with a cracked skull/serious concussion. Supposedly fell off the back and hit his head. He doesn’t remember a thing. He’s a strong/athletic guy who I don’t see falling off very easily. We think something very sketchy happened but were never able to prove anything.

15. What, A Guy Can’t Be Smoke Crack To Kill The Pain?

I worked for a PI company that mostly handled workers compensation cases for insurance companies or other employers.

Assigned to a case in Seattle where a guy was claiming an upper back and shoulder injury. After a few hours on site at his house, he pulls up in a truck, proceeds to empty the truck bed of landscaping equipment ALONE. After he has put everything away, he walks over to the side of his neighbors house, pulls out a piece of the siding of the building, withdraws a crack pipe and smokes it in front of me, all on camera.
Another case in Texas, I was following a guy (Back injury) to the mall where he met up with a woman that was NOT his wife (I had already identified her the previous day) and followed them as they shopped around and then back to his vehicle where they proceeded to have sex in the car IN THE MIDDLE OF THE MALL PARKING LOT! I filmed it of course, but I had to call my boss to make sure that I could send this to the client.

16. $140 Worth Of Coffee

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 blizzard and didn’t end up getting there till 7:40. Go to my boss and says he already fired the guy.

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 two-page report on me drinking coffee for $35 an hour.

17. The Last Case

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 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.

18. Doggo Doin His Hustle

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.

19. Ruining The Romance

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 smelling of women’s perfume. Turns out he was taking dancing classes and he didn’t tell his wife.

20. A String Of Hilarious Rookie Mistakes

A few years back I accidently became the owner of a detective agency. I intended to just be an investment partner, but the owner and actual PI died shortly after I made my investment and – I now owned a detective agency.

After quickly getting the various legal licenses, etc., I just started taking cases. The entirety of what I knew about how to be a PI was from various TV shows, movies, and books. For cases, I would just rely on random people whose life has become so bad that they decide calling a PI is the next logical step. Much later I learned that normal PIs never take these so-called “domestic” cases because they are always a huge mess. Real PIs get almost all of the work from lawyers and hire off-duty cops to do all of the leg work. As a result, I had a TON of crazy cases. Several TV seasons worth. Here are a few classics:

• Guy calls me to help catch his neighbor who is knocking over his trashcans at night. We set up a small night vision camera to catch the guy. Watch the video the next day – it is the wind. The client freaks out, says that his neighbor could have had an invisibility field or could have been moving too fast (like the Flash) to show up on camera. Wants to pay us thousands of dollars to rent a heat-seeking camera or one that can shoot thousands of frames per second… Turns out lots of crazy people call PIs to investigate the TV controlling them, alien abduction, etc.
• Seventh Day Adventist lady in an abusive relationship who wants to divorce her husband but apparently needs the husband’s permission, which he won’t give her. So she wants us to hire a prostitute to seduce him, get it on video, and then mail that to the church leaders to show the marriage is broken.
• Criminal who is serving 20 years in jail for hiring a hit man (who happened to be an undercover cop) to kill his friend. In prison, he came into some money and hired us to prove he was innocent. His plan to do this was to have us tell his friend that he better recant his testimony or else our client would use his new money to hire a hitman to kill him “for real this time.” This criminal genius told us this plan on a recorded phone call from jail.
• Get hired by a wife to see if her husband is sleeping with his secretary. We follow them, recording them going into his single-bed hotel room at 10:20pm after a nice dinner and leaving together the next morning at 8am. She says it proves nothing, that they could have just been working late…
• Guy calls to ask for Paddy, my late partner. We tell him he is dead. Conversation that follows goes like this:

Bob: Dead? Tell him its Bob.
Davevr: Bob – Paddy is dead.
B: sure, ok, whatever. Who’s this?
D: This is Dave. How can I help you?
B: Dave huh? Dave… yeah, Dave, I think Paddy mentioned you.
D: I doubt it, but go ahead. How can we help?
B: I was just calling to make sure the thing is still on for Friday?
D: What thing?
B: The thing, you know…
D: I don’t know, Bob. What?
B: Well yeah, I know you don’t “know”, but is it on?
D: Bob, I have no idea what you are talking about.
B: Ok, I get it. Of course you don’t know. But – all I’m saying is, we’re good, right?
D: We are not good Bob. I don’t know what you are talking about.
B: Of course. Got it. No idea. Great. Friday?
D: Bob, Paddy is dead so whatever you think is happening on Friday is not happening. Understand?
B: Perfectly. Tell him I will see him then.

Different call, also asking for Paddy. Conversation goes like this: Guy: I was told to ask for Paddy.

Davevr: Paddy’s dead. This is Dave, how can I help?
G: Hmm, I was told to ask for Paddy.
D: You did that, I told you he was dead, so can I help or not?
G: Well, OK. I need to disappear.
D: What do you mean, disappear? Like, from your girlfriend or from the Feds? (I literally had no idea what he meant)
G: Really disappear. Like, dead.
D: I don’t know what movies you have watched, but there is no way to disappear unless you have a ton of money and a body. (I made this line up on the spot btw just to shut the guy up).
G: I have 3 million in cash. Body is no problem. Can you help or not?
D: …. I can’t talk about this on a cell phone. click
Never called back. Later found (from tracing the # that called me) it belong to a real estate investor who was being sued for millions in back taxes from the government who died in a private plane crash about a week after that call…

The list goes on and on…

In case you are wondering, I am no longer in this business and the business itself no longer exists.

21. A “Monster” Case

I’ve been a P.I. for about 3 years – mostly for disability fraud, no cheating wives or anything. Coolest/strangest thing I observed was a low-level criminal (who was supposed to be disabled), who would spend all day going from Walmart to Walmart.

In each Walmart, he would fill the shopping cart full to the brim with energy drinks (Monster I think), walk briskly out the door without paying, throw them in his trunk, and take off like a bat out of hell.
At the end of the day, he sold a trunk-load of energy drinks to a corner store and I videotaped him walking out with a wad of cash.

Definitely not as exciting as the movies, but it was a fun day for me.

22. A Laundry List Of Weirdness

I am a private investigator and I have come across many cases. I will label a few of them.

● A police department in a small town in the Appalachian Mountains wanted me to keep an eye on an old lady.
● A manager at a Walmart in Indiana wanted me to watch a couple of employees because he thought they were talking about him behind his back.
● A retirement home hired me to watch one of their tenants, the tenant was a 90 year old lady with Epilepsy, but the pay was great though.
● A casino in Reno hired me to watch everyone who uses a certain slot machine.
● A trucking company made me follow one of their drivers, who was pulling a shipping container from Salt Lake City to Ottawa.
● A factory manager hired me to watch his employees while he jacked off furiously in his office.
● A tenant of an apartment building hired me to watch his landlord, who also hired me to watch the tenant.
The weirdest one of all? A Donald Trump supporter hired me to watch his neighbor because he was convinced his neighbor was “A Soviet”.