A little while ago, Reddit user u/4scend posed the question, “Detectives and private investigators of Reddit, what is the strangest case you have come across?”
And there were so many wild stories! Here are some of the top responses:
We also included responses from private investigators in this thread.
1.“I got hired by a wife to see if her husband was sleeping with his secretary. We followed them and recorded them going into his single-bed hotel room at 10:20 p.m. after a nice dinner and leaving together the next morning at 8 a.m. She said it proves nothing, that they could have just been working late…”
2.“A criminal was serving 20 years in jail for hiring a hitman (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 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.”
3.“I’ve been a PI for about three years — mostly for disability fraud, no cheating wives or anything. The strangest thing I observed was a low-level criminal 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.”
4.“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. 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 went by, and she called. I went by and got the tape (this was before digital recording) and checked it out. There was nothing on it but her. I met her to tell her this, and she said, ‘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.”
5.“A Donald Trump supporter hired me to watch his neighbor because he was convinced his neighbor was ‘a Soviet.'”
6.“This case was my quickest (two hours). I picked up surveillance after the subject had dinner with his wife at Applebee’s. I followed him to a hospital parking garage, and he went in to visit his mother. I stayed to monitor the vehicle, and another showed up. The subject exited the hospital, jumped in the other vehicle, and got a blowjob. Case opened and closed in two hours. I was paid a $1,000 retainer and was able to keep all $1,000 since retainers are nonrefundable.”
7.“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.”
8.“PI for five years, and I had a few exciting cases. One incident was of a coach who was sleeping with one of the female players. One of the players who was benched hired me to document the coach sleeping with one of the starters on the team. They were careful with how they arranged their meetings, and it took me a bit to document it, but I ultimately got the information. A week later, the papers reported the coach had resigned to work in the family business. Another week later, the story broke with all the evidence I had collected.”
9.“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.”
10.“A couple was divorcing, and the wife was sure her husband was sticking random items of hers up his ass. He was.”
11.“A guy called me to help catch his neighbor, who was knocking over his trash cans at night. We set up a small night-vision camera to catch the guy and watched the video the next day — it was the wind. The client freaked out and said that his neighbor could have had an invisibility field or could have been moving too fast (like the Flash) to show up on camera. He wanted to pay us thousands of dollars to rent a heat-seeking camera or one that can shoot thousands of frames per second.”
12.“I was following a guy (back injury) to the mall where he met up with a woman who was NOT his wife (I had already identified her the previous day). I 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!”
13.“Cases where older people get a phone call from the ‘IRS,’ put tens of thousands of dollars on prepaid credit cards, and read the numbers off the back to the guy on the phone to pay their tax debt. This happens a lot, actually. It’s just weird that otherwise intelligent people can be talked into doing stuff this dumb. Please talk to your grandparents. Make sure they know this is a common scam, and there are many, many variants of this scam.”
“No reputable business or organization takes payments by iTunes gift cards. Their grandchild did not get locked up in Mexico, they aren’t overdue on their electric bill, their power is not about to be shut off, and the police don’t have an old warrant that they’ll dismiss for a small fee. A lot of these victims are so sold on the lie that store clerks will stop them in the middle of purchasing $3k in MoneyPak cards, TELL them that they are being scammed, and these victims will argue with them that they need to pay the guy on the phone.”
14.“Some guy assigned me to investigate another private investigator while simultaneously telling that private investigator to investigate me. Absolutely bizarre.”
15.“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 with the smell of a woman’s perfume. Turns out, he was taking dancing classes, and he didn’t tell his wife.”
16.“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 ’90s), 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, got a ladder, and inspected the roof. Still nothing.”
“We were getting ready to leave, and 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, $2,000 for that visit.”
17.And finally, “I did surveillance on a nurse. She was supposedly disabled and couldn’t work, but they suspected she was working. Easiest surveillance I ever did. I arrived, and she got in her car 10 minutes later. I followed her to a strip club, where she went in and began doing her thing. The club had a posted prohibition on video, so I had to 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 Workers’ Compensation 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, and the insurance company was happy. But the company lawyer gave me the nickname ‘Detective Tits,’ which, most regrettably, stuck and spread to all of the other lawyers I dealt with. Worse night of my life, man.”
What’s the wildest thing that ever happened at your job? LMK in the comments below!
Note: Some responses have been edited for length and/or clarity.
