12 Private Investigators And Detectives Detail The Strangest Cases They’ve Ever Come Across

I’ve never had any interest in being in law 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 of detectives and private investigators as I am, you’ve come to the right place, pandas. One Reddit user invited PIs and detectives to recall some of their strangest cases, so we’ve gathered their most fascinating stories below. Enjoy scrolling through these tales that sound like they could be plots of television shows, and keep reading to find a conversation with full-time private investigator Tony Smith!

12 PHOTOS

#1

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....

#2

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.

#3

I got hired to follow another investigator who, turns out, was hired to follow me

To learn more about what it's like to be a detective, we reached out to Tony Smith, a full-time private investigator, Operations Director at Insight Investigations, and Chairman of the World Association of Professional Investigators. Tony was kind enough to have a chat with Pictolic and 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."

#4

FINALLY! A question I can answer! Been a P.I. For a going on a year now and the strangest case I had was of a woman asking us to find out if her husband was cheating on her. She said there was something off in the house as if feeling something and she wanted to know what it was. So she suspected her husband of cheating.

So I show up and install Nanny Cam's in her house for the weekend upon her approval and where to place them. She works all weekend and this was the best route. Well 3 days go by and I collect the footage and come to find out the husband was "touching" his 8 year old step daughter. After seeing that I rushed to the court house with a copy of the footage and got a court order for the police to go and get him.

#5

Cases where older people get a phone call from the "IRS" and get tens of thousands of dollars on prepaid credit cards and read the numbers off the back to the guy on the phone with the Indian accent 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 their are many, many variants of this scam. No reputable business or organization takes payments by I-tunes gift cards. Their grandchild did not get locked up in Mexico, they aren't overdue on their electric bill and their power is about to be shut off, 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.

#6

Currently studying Criminal behavior analysis.

A woman in her midlife, presumably between 45 to 50, was found dead behind a dumpster around a local bar in the middle of December.

She was wearing a skirt that was pulled up to her waist, and leggings that were pulled down, and torn in multiple spots.
She also had abrasion around her buttocks, the heels, thigh, and wrists.

At first, the cops are thinking that they have a sexual abuse or a possible rape case on their hands.

However, certain things were not adding up. Even though it was mid December, that particular bar was fairly populated, and thus, someonr should have reported at least hearing a woman in distress as the dumpster was near the parkinglot of the bar.

Also, the abrasions on her buttocks were rather strange, as if someone had dragged her across the cement floor. Some state that it is possibly due to livor mortis ("marks" caused by setteling of the blood).

After some investigation, they found no traces of physical proofs that suggested neither sexual abuse nor rape. No semen, saliva, or hair, was found.

Later it was revealed that due to loneliness of losing her husband and daughters (husband through divorce and daughters simply grew up and started their own lives), this woman went to the bar to meet potentially a new partner but have gotten carried away drinking.

Once outside in the freezing cold, she wants to take a leak and hides herself behind the dumpster. While doing so, she is slowly suffering from hypothermia due to the cold winter wind and lowered body temperature caused by the alcohol. She begins feeling hot (due to paradoxical undressing, caused by hypothermia), she presumably stripes off her jacket, and other pieces of clothing. At this point, the hypothermia is really getting to her and she begins slowly losing conciousness.

While laying on the freezing ground, skirt pulled up and leggings down, she begins convulsing which leaves abrasions on her body. Leaving behind a curious scene that appeared as if she had been taken advantage of.

First, we wanted to know what a typical day on the job looks like for a private investigator. "An average day usually starts with the checking of emails and responding to what is required," Tony shared. "This is followed by the examination of the current files to ascertain what is required to be tasked that day."

"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.

#7

Did surveillance on a nurse. She was supposedly so disabled that she couldn't work. They suspected she was working. Easiest surveillance I ever did. I arrived. She got in her car 10 minutes later. Followed her, with no complication, to a strip club where she went in and began doing her thing.

Club had a posted prohibition on video. So I had to go in and 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 WC 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. 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.

#8

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.

Tony also opened up about one of his most memorable cases. It included the identification and subsequent arrest of an individual who was stalking his 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."

#10

A couple was divorcing and the wife was sure her husband was sticking random items of hers up his a**. He was.

#11

Ah, finally something I can share!

A few years back I accidently became the owner of a detective agency. I intended to just be an investment partner, but the owner and actual PI died shortly after I made my investment and lo - I now owned an detective agency.

After quickly getting the various legal licenses, etc., I just started taking cases. The entirety of what I knew about how to be a PI was from various TV shows, movies, and books. For cases, I would just rely on random people whose life has become so bad that they decide calling a PI is the next logical step. Much later I learned that normal PIs never take these so-called "domestic" cases because they are always a huge mess. Real PIs get almost all of the work from lawyers and hire off-duty cops to do all of the leg work. As a result, I had a TON of crazy cases. Several TV seasons worth. Here are a few classics:

- Guy calls me to help catch his neighbor who is knocking over his trashcans at night. We set up a small night vision camera to catch the guy. Watch the video the next day - it is the wind. The client freaks out, 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. Wants to pay us thousands of dollars to rent a heat-seeking camera or one that can shoot thousands of frames per second... Turns out lots of crazy people call PIs to investigate the TV controlling them, alien abduction, etc.

- Seventh Day Adventist lady in an abusive relationship who wants to divorce her husband but apparently needs the husband's permission, which he won't give her. So she wants us to hire a prostitute to seduce him, get it on video, and then mail that to the church leaders to show the marriage is broken.

- Criminal who is serving 20 years in jail for hiring a hit man (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 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 kill him "for real this time." This criminal genius told us this plan on a recorded phone call from jail.

- Get hired by a wife to see if her husband is sleeping with his secretary. We follow them, recording them going into his single-bed hotel room at 10:20pm after a nice dinner and leaving together the next morning at 8am. She says it proves nothing, that they could have just been working late...

- Guy calls to ask for Paddy, my late partner. We tell him he is dead. Conversation that follows goes like this:
Bob: Dead? Tell him its Bob.
Davevr: Bob - Paddy is dead.
B: sure, ok, whatever. Who's this?
D: This is Dave. How can I help you?
B: Dave huh? Dave... yeah, Dave, I think Paddy mentioned you.
D: I doubt it, but go ahead. How can we help?
B: I was just calling to make sure the thing is still on for Friday?
D: What thing?
B: The thing, you know...
D: I don't know, Bob. What?
B: Well yeah, I know you don't "know", but is it on?
D: Bob, I have no idea what you are talking about.
B: Ok, I get it. Of course you don't know. But - all I'm saying is, we're good, right?
D: We are not good Bob. I don't know what you are talking about.
B: Of course. Got it. No idea. Great. Friday?
D: Bob, Paddy is dead so whatever you think is happening on Friday is not happening. Understand?
B: Perfectly. Tell him I will see him then.

- Different call, also asking for Paddy. Conversation goes like this:
Guy: I was told to ask for Paddy.
Davevr: Paddy's dead. This is Dave, how can I help?
G: Hmm, I was told to ask for Paddy.
D: You did that, I told you he was dead, so can I help or not?
G: Well, OK. I need to disappear.
D: What do you mean, disappear? Like, from your girlfriend or from the Feds? (I literally had no idea what he meant)
G: Really disappear. Like, dead.
D: I don't know what movies you have watched, but there is no way to disappear unless you have a ton of money and a body. (I made this line up on the spot btw just to shut the guy up).
G: I have 3 million in cash. Body is no problem. Can you help or not?
D: .... I can't talk about this on a cell phone. *click*
Never called back. Later found (from tracing the # that called me) it belong to a real estate investor who was being sued for millions in back taxes from the government who died in a private plane crash about a week after that call...

The list goes on and on...

In case you are wondering, I am no longer in this business and the business itself no longer exists.

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."

#12

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".