39 Cases Private Investigators Can’t Forget

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.

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.

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.

Not my personal experience but one of my Grandfather's countless "war stories":

After retiring as a cop, he took on a PI gig and was once involved in an open/shut injury related case which was about to award a massive insurance payout and go forward with a huge lawsuit.

The person he was investigating was apparently made to be quadriplegic after a work related accident, he even had a doctor confirm that he indeed had irreversibly damaged his limbs. My Grandfather decides to go out on a final "ah f**k it" check in after about a week of investigation. It was all for formalities sake, as again, the guy basically already had won.

When he gets to the quadriplegic man's neighborhood however, he was quite surprised to see this man fixing shingles on his roof.

At his final court hearing, this f****r gets wheeled in on a bed all dramatically, literally hooked up to IVs and s**t. The Judge tells him to walk over to the stand, everyone's like wtf but eventually he's hassled so hard with evidence he just gets up.
Apparently the Doctor, the "victim" (and I believe his lawyers but don't quote me on that though) were all going to split the insurance payoff and the money from the lawsuit.

Always fun times in Grandpa-land.

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.

OK, not a PI, but my boss hired one.

He never told me but I was snooping around the network one day and came across a document that was cut-and-paste e-mails between the boss and a PI.

I worked for a playground design/construction company. Very small, and the boss was an absolute p***k. He may have been bipolar because he would be happy one minute and then the tiniest problem (like a slide being a different colour to what he thought it should be) would send him off the rails for the rest of the day.

Anyway, according to this document, he was suspicious that his competitor was able to offer playgrounds cheaper than him and still make money. He had a strong suspicion that the competitor was using illegal immigrants to build the playgrounds and paying them in cash, for less than the minimum wage. This is in Australia, not the US, so this is probably very uncommon here.

The PI went to a construction site and talked to the workers. He returned a report that stated that the workers were co-operative, they did not appear to be foreign, they spoke English very well, they even showed him their drivers licences. He left totally satisfied that the workers were legitimate Australian citizens.

Boss refused to pay.

The rest of the document was the PI arguing that he did work and should be paid for it (a few thousand dollars I think) while a*****e boss' argument was that the workers were definitely illegal immigrants, he just knew it, and if the PI couldn't prove it then he wasn't a very good PI and therefore shouldn't be paid.

My uncle is a PI. He got tasked with investigating a collision at an intersection. He found a nearby business that happened to have a camera facing the road which would have collected the footage and got said footage of the collision.

The client was definitely in the wrong and caused the accident, then the client was seen a***ing the other driver while damaging his own car further.

It was meant to be an insurance scam where the client could say they hired a PI but found nothing which legitimizes his word, however he rolled snake eyes and ended up incriminating himself.

My uncle still got paid.

Keep watch on the front of the house to see which neighbour was letting their dog s**t on the yard without picking it up. 3 weeks later a homeless guy opens the blast doors. Case closed.

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.

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 h****r and got infected and died]"

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

Way late to the party. Also not the PI, I'm the person who paid the PI bill for this one.

We hired a PI to provide proof of life.

The guy suing me completely disappeared, to the point where for 6 months even his own lawyer could not reach him. His lawyer is 400 miles away. No one had the guy's real address (only address anyone had was a FedEx store that he did not work at). But the employees did say that the guy comes in every few days to collect mail.

Since we had so little information we actually had a PI sit out front the FedEx store until we got a picture of the guy alive.

That whole case (still ongoing) is a huge pile of WTF. My lawyer friends enjoy laughing at me over the lawsuit because it is so bizarre.

There once was this dude who had his emails leaked. I had to sift through many of them and there was countless of weird instances where words for various food was used in conexts that didn't make sense. I realized it had to be code for something and after further research I realized the words where most likely code for young children and I was dealing with p********s. I ended up getting help from the public and the case started trending on twitter. Turns out we were uncovering a major network of businesses that are used or have been used as human trafficking fronts.


He hasn't been arrested yet though.

A weird dad paid us thousand and thousands to watch his daughter during her first two years of college. Went to her tennis matches, friended her from various sock puppet accounts, ate at the restaurant she worked at, etc. Certainly not the strangest case or circumstances, but one where I’ve been tempted in the years since to reach out and let her know of the insane invasion of privacy.

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.

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. Shit retirement.

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

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 am 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 s*x 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. She was kinda hot too so...

I did surveillance for insurance fraud/workers comp cases for a short time. We would usually just be assigned to someone for a couple of days, unless we found something that warranted more time. On my first day watching this guy he leaves his house about 7 hours into the 8 hour (for me) day. I follow him out of the neighborhood, out of the town... onto the highway... still on the highway... into the metro area... into downtown (oh s**t where is this guy going to?) ... and into a valet parking ramp. I panicked a bit because I had my video camera, laptop, and all the background paperwork sitting on the passenger seat next to me. I was able to shove all that stuff away or grab it into a pocket before I turned the car over to the valet. Ended up riding the elevator out of the garage with the guy and his family. They were going to see the seasonal holiday light parade thing, so that was nice to watch at least.

Worked with a PI every once in a while as a second car for surveillance. Surprised me how many people live off lies. Con artist types and scammers, renter scams were very common.

Employee theft also very common, found that employees from a popular drink company were selling pallets of product on the side. The scam was pretty elaborate to account for the missing product.

Couple cases of husbands who traveled alot for work had multiple families, as in another set of wife and kids.

Found that a young rich woman's fiancé not only didn't go to the college he claimed but actually had no degree at all, no job at all, no income at all. Dude would leave the house in a suit and tie and spend most of the day in a diner reading newpapers. Crazy how long he lived off her without her knowledge.

Caught a guy on disability carpooling Amish kids to school.