Private investigations are, well, private, but some cases are too memorable not to share. Recently, Redditor u/Forgetadapassword asked the private investigators of the Reddit community to share the strangest or most interesting cases they've worked, and my jaw is on the floor:
1."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. The daughter and the boyfriend 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, five 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 a 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, I ran a vehicle sighting report, and one of his cars was all over the place in, like, three different states over the course of a year, parked in the driveways of random homes he seemingly had no affiliation with, either. Very weird. I still wonder what I would've found had I kept digging."
2."I was a former PI about 30 years ago. For me, the number of people faking disability claims was huge. It made up at least 70% of our cases, but it was also easy to prove — way more than other types of cases. Normally, we'd just hang out outside their house and wait for them to take groceries out of their trunk, walk down the porch steps, etc. But one hilarious case that I will never forget was the one where a man claimed he hurt his shoulder and lost movement of his right arm as a result. We waited outside his house, and on day one, he came out and got into his car. We followed him to the batting cages, where we recorded him swinging a bat all day."
3."I was 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."
4."True story: I was hired to watch someone who had been the victim of repeated, serious vandalism, for reasons thought to be related to drugs or organized crime. What we found by watching the victim was tons of drugs and organized crime connections, and we also revealed that the mayor of a small city was having an affair with someone well-connected to the drug trade. As to the vandalism, an ex-boyfriend was eventually caught in the act; it had nothing to do with drugs and crime."
5."Way back in 1998, we surveilled a house for an older guy who thought his younger wife was cheating on him. I wasn't on this shift, but I heard the same story from everyone who was there. They'd wired the house and were waiting in a van behind the back fence. The older guy had gone on a business trip. The younger wife got dropped off at the house by the chauffeur. He carried her bags into the bedroom. Suddenly, he slapped her HARD across the face and knocked her back onto the bed."
"One of my coworkers jumped out of the van, thinking she was about to get seriously hurt. But before he got to the sliding glass door, another guy watching the video feed said on the radio, 'Come back, she likes it.' The younger wife then proceeded to bang the pool boy. When my boss informed our client about his wife's doings, he just asked, 'How much?' Back then, camera equipment was expensive, and we had rented it. Our client just wrote a check for $10K on the spot. My boss checked in with him later and said that he had a private collection of VHS tapes. So...there's that."
6."I caught a guy on disability carpooling Amish kids to school."
7."I was a fraud investigator for a finance company. I went to interview a small business that we had lent to, and I got there first thing in the morning. I walked in and had just introduced myself when a dude walked out of the back with a black sack. He looked shocked and dropped the sack, and bundles of cash just fell out and onto the floor. I quickly said that I wasn't there for that, and that 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."
8."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 work's not always as busy as a private investigator. Turns out, the cat just walks around the streets, licks itself, and climbs trees."
9."A couple was divorcing, and the wife was sure her husband was sticking random items of hers up his ass. He was."
10."My work partner and I were watching a guy who was cheating on his wife. We were at a restaurant where they were eating dinner together. I'd snuck over to his car to put a GPS tracker underneath the fender. At the same time, there was another PI team working to put a tracker on the girlfriend's car. We never made contact with the other team, but we sort of gave each other just a wink and a nod. Turns out, the guy and the girlfriend worked at the same hospital and were cheating on their spouses, not just with each other, but with multiple other people. It was a hot mess, and a lot to keep track of."
11."We did mostly disability fraud. Most PI work is insurance because it's consistent and easy to bill. It's basically professional doorknob watching: you show up to the site at around 4 a.m., sit there all day, take timestamped photos or videos every hour, then sit in the car all day peeing in Gatorade bottles and watching movies. Then, you go home and submit the report. The weirdest thing I've worked on, though, was when a municipal client wanted surveillance on a dude suspected of violating a zoning ordinance by manufacturing fertilizer in his house. I never confirmed any of it, but it would be stinky if true."
12."A weird dad paid us thousands and thousands of dollars to watch his daughter during her first two years of college. We went to her tennis matches, friended her from various sock pupper accounts, ate at the restaurant she worked at, etc. It's certainly not the strangest case or circumstance, but one where I've been tempted in the years since to reach out and let her know of the wild invasion of privacy."
13."I worked with a private investigator once in a while as a second car for surveillance. It surprised me how many people live off lies. Con artists, scammers, and renter scams were very common. Employee theft was also very common. In one case, we found that a young rich woman's fiancé not only didn't go to college like he claimed, but had no degree, no job, and no income at all. The dude would leave the house in a suit and tie and spend most of the day in a diner reading newspapers. It was wild how long he lived off his wife without her knowledge."
14."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 this guy, so she wanted someone to investigate where he hung out, befriend him, and then introduce him to her. I declined the job. Later on, she hired me to do some marketing work for her. Unsurprisingly, she was one of the worst marketing clients I ever had, purely because she didn't respect boundaries. I should've seen that coming."
15."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. Mind you, she bought the condo from him originally, so the condo was formerly the maintenance man's. I met her and discussed the case, and she seemed rational. She was an attractive older woman, and the guy would obviously be familiar with the condo layout and have access. So, we proceeded. She agreed to let me install a hidden camera setup with a motion detector, and she was to call me if anything happened to make her think the man had been inside. 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 was nothing on it but her. I met her to tell her that, 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. But, most importantly, her check was good."
16."I worked as a PI for nine months. The company I was with investigated employee workers' comp fraud. I'd follow people who supposedly had injuries so debilitating that they couldn't work, then film them doing things like carrying three jugs of detergent through a grocery store, or lifting a massive concrete tortoise out of a garden bed and moving it to the other side of the yard. The most interesting thing I've seen, though, was a job I did in another state. I filmed a guy about a mile away in a farm field, slowly taking apart a small plane he had sitting there for over eight hours, despite claiming he had a back injury so bad that he couldn't lift 10 pounds. I maxed out my camera memory and ended up taking pictures for the last four hours."
"Small piece of advice: if you're committing workers' comp fraud and the company's insurance tells you to go to a specific doctor...they have paid PI people to wait for you there and follow you home/around for the day. They wanted to get you in a specific place to be followed after you pretended to be hurt."
17."After I got out of the Navy, I worked for one of the top private investigator firms in Houston. Because of my electronics background, I'd usually go along on the jobs where we checked for bugs and hidden surveillance devices. We got a call from a client, a subcontractor for a big oilfield construction company, 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. We did a full electronic sweep and found nothing (this was back in the early '90s, so we didn't have to worry about burst transmissions, etc.). He insisted on a full physical sweep of the trailer, inside and out, so we crawled under the trailer, got a ladder, and inspected the roof. Nothing."
"We were getting ready to leave when he said, 'Look, I'm not crazy. Pick up the phone, press 9 to get an outside line, and you'll start hearing all sorts of 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. We ended up billing him, like, two grand for that visit."
18.Lastly: "Most interesting case? A wife hired us to follow her husband, thinking he was cheating. He wasn't. Turns out, every weekend, he'd drive two hours away, check into a cheap motel, and spend the entire night dressed as a clown, performing birthday shows for terminally ill children at a local hospice. He never told anyone because he didn't want the attention or praise. He just said it made him 'feel like a human again' after losing his kid years ago. The wife was shocked. The divorce got canceled, and their marriage got stronger. Some people hide affairs, while others hide their healing."
Well, that was wild. If you're a private investigator, what's the strangest or most interesting case you've worked? Let us know in the comments, or you can anonymously submit your story using the form below!
Note: Some stories have been edited for length and/or clarity.
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