7 Private Investigators Reveal Their Most Shocking and Crazy Cases

From keeping an eye on their clients' partners to rummaging through piles of documents, hoping to find the proper evidence crucial for winning the case, private investigators witness many strange things as part of their jobs.

Some private investigators opened up about their work experience, sharing some of the most shocking moments with other Redditors. They never thought their job would make them work on such crazy cases.

Comments have been edited for clarity and grammar.

1. Someone Went into Her Condo

u/DoktorInferno: 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, and the guy would obviously be familiar with the condo layout and would have access. I've seen weirder things, so we proceeded.

She agreed to let me install a hidden camera setup with a motion detector. She would call me if anything happened to make her think he had 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 never 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 discuss it 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.

2. The Case That Made Me Quit My Job

u/Kryimsson: 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, 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 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, besides a playground, in an entirely 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.

3. Threatening His Friend

u/davevr: A criminal was serving 20 years in jail for hiring a hit man (who happened to be an undercover cop) to get rid of 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 end his life "for real this time." This criminal genius told us this plan on a recorded phone call from jail.

4. Finding the Biological Mother

u/MjolnirPants: I briefly worked for a PI when I was younger (like 19). Getting the job was a funny story itself. I was walking past the office, which is in a tiny strip mall smack in the middle of a residential neighborhood.

On a whim, I decided to go in and see what an actual PI's office looked like. It was pretty unremarkable, except for the huge biker sitting at the only desk in a polo shirt and slacks.

We got to chatting, and I asked if he was hiring. He laughed and asked me what kind of work I was expecting. I told him, "Probably a lot of boring work sifting through papers in the library and courthouse."

He laughed again (he did that a lot. We called him Santa because of that and his white beard) and gave me the job.

I worked there for three months, during which we did a lot of insurance work. That mainly consisted of sitting in a car, reading a book, occasionally taking pictures of some guy in a neck brace or leg cast walking to or from his car, and two or three times taking photos of a guy playing baseball or basketball in his back yard.

But Santa also had a much-reduced rate for tracking down biological parents/siblings/children. We had one case where this woman in her thirties wanted to find her bio mom.

We went on our usual course, visiting courthouses, city halls, and libraries to track the biological mother down. We spent a whole month on it (we also worked on other cases during that time), which was a bit longer than usual, as the woman didn't know her mother's name, only her adopted parents, who had passed years ago.

The woman didn't have any adoption paperwork and didn't know where it would be filled (this was in the 90s when not everything was digital).

I finally found the adoption paperwork in a courthouse in the next county and got a name. I was running late (Santa didn't let me work overtime), so I made to drop off the copies of the paperwork at his office and go, but the guy stopped me before I could leave.

He was all excited by the mother's name—it was his wife. His wife had given up a baby for adoption 30-something years ago.

He called his wife, who dug up her copies of the adoption paperwork from back when, and sure enough, it was a match.

We called the client, who didn't answer, then went and picked up his wife and drove to the client's home. She's on the phone with her adopted sister, talking about our effort.

The PI and his wife immediately hugged the woman, who was very confused. Both were too emotional to get the words out, so I explained that the woman was her bio mom and the PI her husband.

It was a beautiful scene. That memory is one of the things that has kept me from turning bitter over the years. It was enough to put off my then-imminent loss of faith in God for another decade, knowing that this woman had hired her bio mom's husband to find her bio mom.

5. No One Remembered Him

u/mgdmw: 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 case that really made an impression on me was when a person had a fatal vehicle incident, and a claim was made that it was a workplace injury. I don't know what 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, many struggled to remember him. This 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 to that town but couldn't find the wife. She wasn't at any of the addresses 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, and it turned out to be the wife's parents. They called their daughter, and she arrived. Then, the mother and daughter cried while showing me all their photographs of the guy.

It was very moving, and I was so relieved to have actual 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. Usually, he would travel to the caravan on a Friday night, but this particular weekend was Mother's Day. He stayed Sunday night and traveled on 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 hear what happens to a matter, so I only hope it is finally settled.

6. He Wanted to Find His Father

u/RoryDeanWinning: When I was a spunky teen working in my dad's PI office, a kid with a crush on me paid me good money to find his dad (who had a crazy common name).

It turned out his dad was now a woman living just a few miles away from our corrupt small town. He still had an awesome car, though.

7. The Fishing Trip I'll Never Forget

u/[deleted]: As a private detective, I thought I'd seen it all. That was until this woman asked me to follow her husband. A routine job, I thought. But nothing prepared me for what I was about to uncover.

So, this lady's husband goes fishing with her dad and brother and returns home with his back all scratched up, making up stories about branches or bugs. She's curious, but the men just shrug it off. My job? Follow them and see what's up.

I track them down to this remote shack by a lake. Expecting maybe some secret rendezvous, I peek inside, only to see something I'd never even imagined. All three men, stark naked, engaging in what can only be described as a bizarre ritual.

They're standing in a circle, backs to each other, chanting and scratching each other's backs with handmade wooden talismans. It was like some ancient brotherhood or secret society thing, far from any fishing I've ever heard of!

I couldn't believe my eyes. It was one of those moments that remind you the world's full of surprises, no matter how much you think you've seen. What a day that was!

Have you ever interacted with a private investigator? Or has one of your friends ever hired one? We would love to know about your experience!