I’ve never had any interest in being inlaw enforcement, but after watching about a hundred true crime documentaries, I have gained an immense appreciation for those who devote their lives to solving cases.And if you’re as curious about the mysterious lives ofdetectivesand private investigators as I am, you’ve come to the right place, pandas. One Reddit user invited PIs and detectives to recall some of theirstrangest cases, so we’ve gathered their most fascinating stories below. Enjoy scrolling through these tales that sound like they could be plots oftelevision shows, and keep reading to find a conversation with full-time private investigator Tony Smith!This post may includeaffiliate links.
I’ve never had any interest in being inlaw enforcement, but after watching about a hundred true crime documentaries, I have gained an immense appreciation for those who devote their lives to solving cases.
And if you’re as curious about the mysterious lives ofdetectivesand private investigators as I am, you’ve come to the right place, pandas. One Reddit user invited PIs and detectives to recall some of theirstrangest cases, so we’ve gathered their most fascinating stories below. Enjoy scrolling through these tales that sound like they could be plots oftelevision shows, and keep reading to find a conversation with full-time private investigator Tony Smith!
This post may includeaffiliate links.
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 the works not always busy as a PI. Turns out the cat just walks around the streets, licks itself and climbs trees….
To learn more about what it’s like to be adetective, we reached out to Tony Smith, a full-time private investigator, Operations Director atInsight Investigations, and Chairman of theWorld Association of Professional Investigators. Tony was kind enough to have a chat withBored Pandaand share some of his own experiences working in the field.“I am a full-time private investigator and have been so since 1978. During that time, I have come across many varying matters requiring Investigation, both in the UK and overseas,” he noted. “Being a ‘full service’ 24-hour agency, Insight Investigations undertakes enquiries ranging from the tracing of missing people to major Criminal Defense investigations and most anything in between.”
To learn more about what it’s like to be adetective, we reached out to Tony Smith, a full-time private investigator, Operations Director atInsight Investigations, and Chairman of theWorld Association of Professional Investigators. Tony was kind enough to have a chat withBored Pandaand share some of his own experiences working in the field.
“I am a full-time private investigator and have been so since 1978. During that time, I have come across many varying matters requiring Investigation, both in the UK and overseas,” he noted. “Being a ‘full service’ 24-hour agency, Insight Investigations undertakes enquiries ranging from the tracing of missing people to major Criminal Defense investigations and most anything in between.”
I got hired to follow another investigator who, turns out, was hired to follow me
Was hired to follow a woman who claimed she was completely blind (collecting insurance money of course). Spent the day following her around as she DROVE from store to store in a church van.
“It could be an ongoing romance scam that requires further work to locate the individual behind the scam, or it could be the continuing search for a missing person, a Criminal Defense case that may require interviewing witnesses or one of the many other cases that require attention in varying ways,” he explained.
“Whilst a fair amount of a PI’s work is office-based, the requirement for ‘field work’ remains, and this, in addition to the management of other Agents out on the road undertaking various tasks, makes for a full day which is rarely 9 to 5,” the expert says.
I’ve been a P.I. for about 3 years - mostly for disability fraud, no cheating wives or anything. Coolest/strangest thing I observed was a low level criminal (who was supposed to be disabled), 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 video taped him walking out with a wad of cash.Definitely not as exciting as the movies, but it was a fun day for me.
Tony also opened up about one of his most memorable cases. It included the identification and subsequent arrest of an individual who wasstalkinghis ex-partner with the intent of doing her and her family serious harm.“He was met on a high-end dating site and quickly moved in with his partner, and all seemed well. Unfortunately, the mother thought something wasn’t quite right and asked me to investigate this individual’s background,” Tony shared. “I eventually established that he had lied to gain entry to the UK and obtain very prestigious employment. He also had considerable criminal history in his native country.”
Tony also opened up about one of his most memorable cases. It included the identification and subsequent arrest of an individual who wasstalkinghis ex-partner with the intent of doing her and her family serious harm.
“He was met on a high-end dating site and quickly moved in with his partner, and all seemed well. Unfortunately, the mother thought something wasn’t quite right and asked me to investigate this individual’s background,” Tony shared. “I eventually established that he had lied to gain entry to the UK and obtain very prestigious employment. He also had considerable criminal history in his native country.”
A couple was divorcing and the wife was sure her husband was sticking random items of hers up his a**. He was.
We also asked the expert what he believes makes a great PI. “That’s a difficult one. Attention to detail is a must,” Tony says. “There are those that specialize in surveillance, interviewing, research, IT forensics and the like and as such can combine with others to create a ‘team’ that accomplishes most things, and one need never be stuck with a task, as someone somewhere will have the required skill to solve it. Rarely has there been a profession where the saying ‘Standing On The Shoulders of Giants’ can sometimes be more apt.”
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*****iles. 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.
All right, here goes. After I got out of the Navy, I worked for one of the top PI firms in Houston. Because of my electronics background, I’d usually go along on the jobs where were were checking for bugs and hidden surveillance devices.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 nineties, didn’t have to worry about burst transmissions, etc.) 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 and got a ladder and inspected the roof. Still nothing.We’re getting ready to leave and he says: “Look, I’m not crazy. Pick up the phone, press 9 to get an outside line, and you’ll start hearing all sorts or clicky sounds.” Turns our 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.
Doing a standard pre-employment background check on a guy, found that he was found guilty in a sexual harassment case. Didn’t have the case details at that point and the guy denied it was him. Pulled more details from the case and confirmed that it was definitely him… And that he was convicted of indecent exposure. The guy finally admitted it was him, but claimed it wasn’t as bad as it seemed. Pulled the court transcripts. Turns out he flashed a 12-year-old on the beach and said “ever seen one of these before?” He did not get the job.
Funniest to me, my brother in law is a private eye following around a worker comp victim with a bad back.He films the victim lifting a lawnmower into a truck bed. A riding lawnmower.
I am a private investigator and I have came across many cases. I will label a few of them.● A police department in a small town in the Appalachian Mountains wanted me to keep an eye on an old lady.● 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.● A retirement home hired me to watch one of their tenants, the tenant was a 90 year old lady with Epilepsy, but the pay was great though :)● A casino in Reno hired me to watch everyone who uses a certain slot machine.● A trucking company made me follow one of their drivers, who was pulling a shipping container from Salt Lake City to Ottawa.● A factory manager hired me to watch his employees whIle he jacked off furiously in his office.● A tenant of an apartment building hired me to watch his landlord, who also hired me to watch the tenant.The weirdest one of all? A Donald Trump supporter hired me to watch his neighbor because he was convinced his neighbor was “A Soviet”.
P.I. for 5 year, I had a few exciting, not necessarily strange cases. One incident was of a coach who was sleeping with one of the female players. One of the players that was benched hired me to document the coach for sleeping with one of the starters on the team…They were careful with how they arranged their meetings, and took me a bit to document it, but ultimately got the information. Fast forward a week later and the papers reporting the coach has resigned to work in the family business…fast forward another week later, the story broke with all the evidence I had collected (I was not named in the story as I had requested not to be.)Another case was my quickest (2 hours). Picked up surveillance after the subject had dinner with his wife at Applebee’s, followed to a hospital parking garage and he went in to visit his mother. I stayed to monitor the vehicle, and another shows up. The subject exited the hospital and jumped in the other vehicle…I then recorded him getting a bj. Case opened and closed in 2 hours (paid $1,000 retainer, was able to keep all $1,000 since retainers are non refundable I charged $60/hr and would’ve only made $120)….I have many many more stories….some funny, some really sad (I specialized in father’s rights cases).
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 used to be an investigator that specialised in work cover/injury claims. The type that you follow people with injuries around, see how they move, are they faking it and working a second job and scamming their workplace, that kind of thing. I was working a case where the guy in question would leave his house every morning, walk to the local park and take a st on the grass, pull out toilet paper, wipe himself off and continue with his walk. He lived in a very affluent suburb. Every day, same st.
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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.
Not a P.I but thought this may qualify.My grandfather (P.I) was asked to tail a well known beer delivery truck around its route leaving Central Scotland, traveling south then back again.Turns out my other grandfather was driving the truck! They never did speak from what I can remember
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.
I have a friend who is a PI. She is a former cop, retired. Says it is really boring; lots of sitting around on surveillance or digging for paperwork, working long crappy hours. Never carries a gun. Says being a woman is an advantage as people are more suspicious of a male.
My RA my sophomore year of college was a part time PI and bragged about it to the coed underclassman. Few weeks before spring break he’s seen with bruising and black eyes. Some guy he had been following to catch in an affair got a hold of him and beat him senseless.
My mom hired a private investigator on my dad way back when she was pregnant for me she felt like something was wrong cause he said “he just needed time away” In the end he was cheating and my mom left him.
I found a lady who’d been missing for twenty years out of pure, dumb luck. I was getting lunch another town over and she walked out of a resale shop across the street. It was so unexpected that the only footage I could get on her was with my s**tty phone camera. Otherwise, I don’t get a ton of “bizarre” cases. Most of the time, I’m just doing insurance fraud cases since that’s where the money is. The most interesting part is looking at their background info and piecing together what kind of person they are based on their spending habits. Then you take that information, make a quick and dirty psychological profile, and try to predict their movements based on it. I’ve gotten pretty good at it.
Not me personally, but I worked with a guy whose subject died on the first day of surveillance. D**g overdose. I’m sure the final report must have been legendary. “The claimant died.”.
A college of mine was a PI.He said the majority of his casework isn’t tailing people but serving court notices. He told me of a variety of really slimy ways he’d serve people, including disguises, high pressure tactics and weird social engineering.He’s out of it now because he’d had too many close calls. Serving divorce papers or notices of being sued where you have no idea of the state of mind of the person you’re serving to could get interesting to say the least.
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 prick. 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 asshole 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.
This girl’s family once tasked me with tracking her down and convincing her to go back to the family farm. Turns out she had moved to LA, become a porn star, and married an apparent millionaire, but it gets weirder: some of her friends tried to ransom her when she went missing. The husband, who didn’t actually have money of his own, pretended to pay the ransom with money from his daughter’s charity, while giving the bag man a fake ransom to make the hand off, and pocketing the money from the charity. Unbeknownst to the husband, his daughter actually hired the bag man to figure out what happened to the girl and the money to get it back, and he figured out the husband took it just as the girl got back from visiting her friends, unharmed. It was nuts. I heard the girlfriend of one of the guys who ransomed the girl even cut off her own toe to send to the husband to get him to pay. It was like something out of a f**king movie.
Cattle mutilations in the late 70’s.
Some guy assigned me to investigate another private investigator while simultaneously telling that private investigator to investigate me.Absolutely bizarre.
A private investigator came into the bar I was bartending at years ago and showed me two pictures. One of a girl in her early 20’s that her family was trying to find; the other of a guy in his late 20’s that they suspected she had run away with.The guy in the picture had a charge on his debit card from my bar a week earlier so the investigator came in hoping that I would remember if the girl was with him that night.I did not recognize the girl at all but I remembered the guy. He had come in with two other guys around his age, they got pretty drunk but all they really did was shoot pool. They didn’t cause any problems and they actually tipped me really well. I never heard anything else about the girl so I don’t know if the family eventually found her or if she disappeared for good. I just now remembered that her first name was Katie. I can’t remember the guys name though.
One unlucky respondent revealed they were asked to follow another member of staff who left work, as the boss suspected that rather than being ill, he was off to the pub.
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 sex 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…
My personal favorite case was this one wherein a guy with a video-game esque last name (akin to Gannon) had a criminal record against him. The record indicated that he had been charged with c***ine usage and that he had reportedly snorted the cocaine out of a Hooker’s as.
Someone hired me to follow his wife. He thought she might be cheating. They were a pretty rich couple and were married for a couple of years. Fast forward a few days of investigation and it turns out she was just meeting a friend in secrecy so she could just throw a few kisses and for a little bit of p**is touching. In the end the guy who hired me faked his own death and his wife clapped and gave me a 100$ bill.
One of the most bizzares task one was following a women and her friend to learn that she and her friend were cheating there husbands and all of the details being recored on reddit which i later found out!
My brother is a PI.A while back a dwarf came into his office (happens to also be our flat) and asked him to protect this box of Maltesers, and payed him £200 for it.We were both confused as to why we had to protect a box of chocolates but hey, money’s money.Wanting to find out more, we work out that this dwarf is a regular at this club. We pay it a visit and end up talking to a singer, who’s asking for news of him.We show her the Maltesers, and then we hear shouting. Two massive guys come charging towards her and take her away, kicking and screaming, towards a van. They drive away and we never see her again.We assume the dwarf is dead, so we keep the Maltesers and get on with our lives. A few weeks later, we get a letter from the singer with a single Malteser in it. Turns out she knew their purpose and switched the box of Maltesers when she got “kidnapped”.The Maltesers were diamonds covered in chocolate.We plan to go on a skiing holiday with the money but my brother broke his leg so the money was spent on medical bills. :/
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