Private Investigators Disclose Their Most Outrageous Cases

Breaking And Entering

I’m a private investigator. One time, I was hired by this really famous author to test the security system at his Hawaii vacation home using my professional expertise. 

So basically, I had to try and break into his house and see if I could succeed—but there was an unexpected twist. Unfortunately, his British caretaker didn’t realize that this was going on and set his two dogs on me thinking I was a real crook.

I had to escape by hot wiring his Ferrari.

The guy in the next story heard everything about his friend’s legendary great-uncle

Eavesdropping

Not a private investigator myself, but I once overheard an unbelievable conversation with one. I was at my friend’s house and he got a knock on the door. 

The dude said: “Hello, sir, are you X?” My friend replied: “Yeah, why?” The guy then proceeded to explain that he was a private investigator and that he’d like to talk somewhere in private.

My friend said: “Nah, I’m fine just talking here at the door.” The man then showed my friend a picture and said: “Do you know this man? His name is Y.” My friend replied: “Yeah, that’s my great-uncle. 

He’s vacationing in the Congo right now, why?” The detective replied: “I’m sorry sir, but your great-uncle just passed on from hepatitis.”

The man then elaborated on how his great-uncle, a priest, had slept with some lady of the night while on vacation, and got infected and passed on. 

Apparently, someone had hired this investigator to track down the poor guy’s relatives and inform them of what had happened. I was in the living room eating pizza the whole time, pretending to be watching TV.

The woman in the next story would not leave this married man alone

Stalker Alert

My significant other had a stalker who would send him flowers. We would come out to our front garden to find notes or gifts—it was a secured area—and once got a glassine envelope left at the front door with strange white powder in it. 

Nothing happened to us, so it probably wasn’t harmful, but still really weird and frightening.

Then, crazy letters started getting sent to neighbors about how awful I was, that I was a thief or even worse. This went on for a couple of months, so we hired a guy who came highly recommended by our attorney. 

BOOM. Caught ’em. It turned out to be a married woman who had a bad crush on my husband. We didn’t press charges, but we had the attorney scare the living heck out of her.

That was the end of it. I’m sure this wasn’t the most difficult case he ever had, but he was so quick with the result—it was mind-blowing that our life was put back right so quickly.

The guy in the next story had a story so unbelievable that the P.I. was laughing all the way to the bank

Monitoring The Neighbor

I accidentally became the owner of a detective agency. I intended to just be an investment partner, but the owner and actual P.I. passed on shortly after I made my investment and I now owned a detective agency. After quickly getting the various licenses, etc., I just started taking cases.

The entirety of what I knew about how to be a P.I. was from various TV shows. I would just rely on random people whose life has become so bad that they decide calling a P.I. is the next logical step. I learned that normal P.I.s never take these so-called “domestic” cases because they are always a huge mess.

The guy calls me to help catch his neighbor who is knocking over his trash cans at night. We set up a small night vision camera to catch the guy. Watch the video the next day—it’s the wind.

The client freaks out and 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.

It turns out lots of people call P.I.s to investigate the TV controlling them, alien abduction, etc.

Lesson learned!

The cheating man in the next story went a bit too far to get back at his ex-wife.

The Watcher

My ex-husband went off the deep end when I left him three years ago, despite the fact that he was cheating on ME every step of the way. Anyway, I moved 1,000 miles away and began to restart my life. 

One day, about a month after leaving him, I checked my mail and saw that I had a huge, heavy envelope in the box. When I opened it, I was horrified.

It was photos of me doing all the activities of my daily life, but the photos were clearly taken from afar, and without my knowledge. 

Immediately, I contacted my attorney. It turns out, my ex was hoping to catch me with someone else because he wanted to try to sue me for abandonment. It was awful, and it took me a long time to feel safe and secure in my new home.

The P.I. in the next story got a little frustrated doing a case

All In A Day’s Work

We had to follow this cheating husband to the beach in Florida. I got paid to go hang out in a nice beach town. Didn’t get a lot of sleep, though, thanks to having to be up gathering video evidence after they went to bed, but it by far beats the normal jobs. What’s crazy is, the daughter was able to catfish her father and get more evidence.

He also had a stupidly easy password on Match.com, so we could see everything he was saying and planning. 

Of course, what’s sad is people cheating, and they have to know their partner knows they’re cheating, but they keep doing it even though their partner asks for a divorce and they refuse. Usually, the cheater is better off financially if they’d go ahead and leave.

No one is happy but they just keep going. What was infuriating was just straight-up busting someone with perfect evidence of infidelity, and then the client goes and takes them back and ruins all of our work. 

The law is infidelity evidence only counts if the offended party does not take them back or sleeps with them, so it’s annoyingly fragile in these dramatic relationships.

The woman in the next story wasn’t paid enough for what she saw on the job.

The Things You See

My wife was a P.I. Not a lot of research, mostly documenting insurance scams. In the last case she ever worked, she was staking out a house, trying to get a man who was claiming not to be able to work because of his car accident, doing stuff he says he can’t do. 

He opens his front door, and she starts videotaping, hoping he’ll start doing yard work or something.

Instead, he pulls out his you-know-what and starts going to town on himself on his front step for a few minutes before walking back inside. The tape became legendary comedy material in the office she was working at.

The guy in the next story almost got featured on a TV special about a case.