Is there anything cooler than a private detective? Long trench coats, dipped hats, midnight chases in the rain…or else just lots and lots of dirt on some of the juiciest small-town scandals around. From long lost sisters to cheating partners, these private detective cases were full of twists and turns.
1. Put Me in, Coach
I was a P.I. for five years, 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 for sleeping with one of the starters on the team. The coach and the player were careful with how they arranged their meetings.
It took me a bit to document it, but ultimately I got the information. Fast forward a week later, and the papers reported that the coach had 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.
2. Let It Go, Dude
My ex-husband went off the deep end when I left him three years ago, despite the fact that he was cheating on ME every step of the way. Anyway, I moved 1,000 miles away and began to restart my life. One day, about a month after leaving him, I checked my mail and saw that I had a huge, heavy envelope in the box. When I opened it, I was horrified.
It was photos of me doing allllll the activities of my daily life, but the photos were clearly taken from afar, and without my knowledge. Immediately, I contacted my attorney. It turns out, my ex was hoping to catch me with someone else, because he wanted to try to sue me for abandonment. It was awful, and it took me a long time to feel safe and secure in my new home.
3. Save the Drama for Your Mama
My family has hired P.I.s on three separate occasions. All three of them found massive amounts of infidelity, with two of the three uncovering secret families. great-grandpa died, turns out to have had three wives simultaneously. My grandpa hired the P.I. to figure out the details and clear up the messy inheritance it caused.
Oddly enough, grandpa was on great terms with his newfound half-siblings for the rest of his life. Then, my uncle traveled a bunch to Mexico for work, so my suspicious aunt hired a P.I. to trail him. Turns out, he had an illegitimate family in Mexico. It caused a huge inheritance pain in the butt AGAIN when my uncle eventually died of natural causes.
But that wasn’t even the end of it for my crazy family. My cousin was married to a professional baseball player on the East coast. My folks suspected he was a cheater and hired a P.I. to trail him, turns out to be a rampant cheater for sure, divorce followed shortly. To this day, he's considered an un-person in my family, and no one will tell me what his name was or what team he played for.
4. Tie-Me-up Elmo
I once found a hogtied Elmo covered in white paint in the basement of a vacant building in a terrible part of town.
5. When the Hunter Becomes the Hunted
Oh man. I’m a P.I., and one time this guy made me as I was following him and started chasing me. It was actually good evidence because I just started videoing the speed and maneuvers we were doing as he chased me—he had his young boy with him in the car and it was a custody case. Lost him with the ol’ run a red light at a busy intersection.
Dude was not a good dad, from what I observed.
6. Hitting the Big Time
I guess I can contribute. I'm keeping this intentionally vague just because of the nature of things. My family member is a P.I. He was working a case a few years back. Hired to catch a spouse cheating, so normal case to have. Well, this initially typical case ended up kind of turning into a case dealing with a hitman being hired against the client by the client's cheating spouse.
I deactivated my Facebook for a while until things blew over at the suggestion of the P.I. and law enforcement, since the P.I. and I share a family name. I was happy to oblige. I was a bit scared because of the hitman and all. Kind of funny, but I didn't realize it was made into a kind of a TV special thing until we were watching the show over a year later and I noticed that the story seemed a bit familiar.
Then it showed some clips of the cheating spouse's home and I recognized it. I sometimes traveled with my relative to help with the case. Plus, there was a good taco place down the road, so I wasn't going to turn down a trip to get tacos. The TV special was a bit vague on how they were able to connect the hitman to the cheating spouse in court, but really it was due to evidence that the P.I.—my family member—collected and turned over.
They wanted to include that, but the P.I. relative did not want to be on TV.
7. On the Job
My significant other had a stalker who would send him flowers. We would come out to our front garden to find notes or gifts—it was a secured area—and once got a glassine envelope left at the front door with strange white powder in it. Nothing happened to us, so it probably wasn’t harmful, but still really weird and frightening.
Then, crazy letters started getting sent to neighbors about how awful I was, that I was a thief or even worse. This went on for a couple of months, so we hired a guy who came highly recommended by our attorney. BOOM. Caught 'em. It turned out to be a married woman who had a bad crush on my husband. We didn't press charges, but we had the attorney scare the living heck out of her.
That was the end of it. I’m sure this wasn't the most difficult case he ever had, but he was so quick with the result—it was mind-blowing that our life was put back right so quickly.
8. Family Matters
I'm not a private investigator, but I know someone who was a junior detective. This one case he had was an absolute mind-bender. So this guy had been cheating on his wife (the client), with her brother. Except—she claimed she didn't have a brother at all and grew up as an only child. So naturally, they were really curious to find out who this "brother" of hers was.
When they questioned the husband, he said that the guy who claimed to be his wife's "brother" said that "We've known each other for so long" and "I grew up with her" and all that jazz. At first, my friend assumed it was probably a long lost brother or something, but then when the husband was asked to describe the guy—get this. He described the wife's father.
According to the wife, her father wasn't there during her wedding and was replaced with her uncle instead. The husband hadn’t met him before. He was cheating on his wife with her father! Absolutely wild.
9. Magic Touch
I had one hired against me, and they found out everything. Tattoos that aren't visible normally, the address I lived at in a different country, medical records from an accident that happened six years prior, so many random things that aren't publicly available. It really, really creeped me out. Those people are like magicians.
See, I'm a bartender. When I was buying my house, the loan I was applying for switched mid-way through and I needed money to pad my bank account. One of my well-off regulars loaned it to me, complete with a contract and a pay-back date. However, he drafted two, and crumpled one up and tossed it. This came back to haunt me.
His wife found it and hired a P.I. against me. She confronted him about it. He told me the next day that she was listing off all the facts the detective told her about me. None of which the regular previously knew. He didn’t even know my age at the time, so there’s no way he knew all that other stuff.
10. It’s Like I Don’t Even Know You
I found out that the man I'd been involved with for six months had not one, not two, but three aliases.
11. More Than He Bargained for
One woman I was hired to investigate was married to a guy who made a decent living. He wasn't mega-rich, but he likely made around $250K a year. He started to suspect his wife was cheating on him, so we tailed her for the weekend. It was only one weekend, but we quickly discovered that she was selling herself on Craigslist and Backpage.
We caught over 13 men coming in and out of her motel room that weekend and found her ads online.
12. Clean Them out, Girls
That our cleaning ladies got involved with a smuggling ring and set us up for a robbery that totally emptied our house out.
13. A Familiar Face
Being a P.I. is super interesting in a lot of ways, but it can also ruin lives—your own included. A couple of years back, I was investigating something on Adult Friend Finder and discovered pictures of a close friend from high school who I had a massive crush on. Her husband had uploaded pictures of her, including her face, to try to meet women.
A lot of guys will do this, use pictures of their wives to try and set up a threesome, and then tell the other girl the wife wants him to meet with her first. My friend had no idea they were on there. It ruined her marriage and her friendship with me. I didn't care about what she and her husband did in the privacy of their own home, but she couldn't look me in the eye after it.
We hadn't been close after high school but it messed with sort of future friendship, which makes me sad. When I did tell her about finding that stuff, she admitted that her husband had cheated on her in the past, before they were married. I have no idea why she stayed with him.
14. When the Cat’s Away…
Last year, when I was 17, I pretended to be a private investigator just for fun. My neighbor gave me ten dollars to go look for his missing cat. I guess he just wanted me to have some fun and I was just fooling around. I was pretty sure I wouldn't find anything. But darn did I ever find something. A very big something.
At the bottom of my street, there was an old abandoned retirement home that had closed a couple of years after I moved in. I went there first and found a blood trail leading into the place. There wasn't a lot of blood, but just enough that it could have been the cat's blood. Case in point: It turns out the building was being used for an illicit substances operation.
After seeing that, I almost pooped myself because I was only going into the whole P.I. thing as a joke. I anonymously tipped off the authorities, who raided the place. Apparently, one of the guys accidentally attacked the cat, who started to wail loudly, and he was scared people would come to investigate. He couldn't bring himself to end the cat’s life, so he dragged it inside and forgot to clean the blood away.
It was one of the most thrilling yet terrifying things that I had ever gotten myself into. But hey, at least the cat lived and my neighbor got her back!
15. Prove Me Wrong
Some idiot in Nowhere, Kentucky reported a daycare center that they thought was a secret organization. We all thought they were stupid or crazy for doing it. Turns out, there really was a secret organization in the basement.
16. Money Can’t Buy Sanity
I actually have something for this. I don't have my license, but I work in a P.I. office. I'm the only administrative staff member. It's basically me and my Vietnam vet boss in a Ron Swanson-April Ludgate kind of situation. A story he told me recently comes to mind. He and his partner were once hired to sweep a house and look for any valuables.
They agreed to the case before knowing the full extent of the damage to the home because the lawyers were willing to pay well and our caseload was small at the time. The home was owned by a man who inherited a large fortune because his father had invested in a little movie that went on to become one of the biggest horror franchises of all time.
The son never worked a day in his life. He had a big mansion out in the boonies. No one ever saw him or his wife because they spent all of their time inside. The home was now empty because he went nuts and killed his wife and their dog. He was serving life in prison and the family's estate needed the home cleared. When my boss and his partner got in there, they realized how bad it was.
For years, this guy and his wife had been using substances in the house. Every square inch of the mansion was covered in trash. After binging, the two would puke and then just cover the vomit with trash and leave it there. The same went for the dog’s waste. This went on for years. In addition to the puke and animal waste, there were needles littered through the trash.
My boss had to buy hazmat suits to sweep the home and look for valuables. Apparently, there was a ton of diamond and gold jewelry just thrown right in with the filth. At one point, they found a table behind a door that was missed by the forensic crew completely covered in the wife's blood from where he had done the deed.
They also found an entire room full of kiln and ceramics supplies worth thousands of dollars, all untouched. I guess the guy decided he wanted to become a master potter before quickly abandoning that pursuit to become a creep. They could only access the home through one exterior door that wasn't blocked. When they eventually walked around the exterior of the home, they found that the guy had purchased himself a shark cage.
As in, he decided he wanted to become a shark photographer, and ignoring the fact that he didn't live right on the ocean, BOUGHT a shark cage and stuck it in the yard. Eventually, people started to invade the grounds and steal stuff from the home, and one day the shark cage just disappeared. This is the first one that came to mind because it just escalated so much as he relayed the story to me.
It's hard for me to tell a lot of these stories because of our confidentiality policy. My boss has other crazy stories from working private security for Paris Hilton, Snoop Dogg, and the Girls Gone Wild guy, and we have a few instances of having to serve papers to crazy people. This job is never boring.
17. The Invisible Man
I'm a lawyer who investigates the backgrounds of witnesses for our cases. I found someone who was pretending to be someone else who died as a kid. My boss alerted the feds and they investigated and found out he had faked his demise 20 years before to avoid an embezzlement trial. He got convicted for the false identity because he filed taxes in the fake name.
Not sure about the original embezzlement charge.
18. Mr. Veronica Mars
Okay, I have never hired a private investigator, but a friend of mine's dad was a P.I., and I helped him from time-to-time, kind of like Veronica Mars. The most common clients are trying to catch their spouses cheating, or trying to catch someone committing fraud for worker's comp. Those who are trying to catch their spouses cheating usually fall into two categories.
There are those who already know their spouse is cheating and who either want definitive proof for themselves or for a divorce, or people who are overly paranoid and have the disposable income to drop a few grand, oftentimes multiple times a year, on their baseless fears. The first ones are not very hard to catch. Unless the affair started at work or with someone they already knew, they likely met their partner on some sort of website.
You would be amazed at what a reverse image search can pull up. A little social engineering/trickery and you can friend them on Facebook and see all the pictures they post. Run it through a program and you can find just about any screen name they currently use. Run that through OK Cupid, Fetlife, AFF, etc. and even Reddit can give you a good head start.
Before things like Google RIS, I would manually search the websites to try and find them. If you know the city they live in, their birthday/age, if they have pets, and have pictures to compare, you can find a lot of profiles of spouses trying to cheat. My friend's dad didn't let me do much surveillance, so I mostly searched for things online, but I did spend some time sitting in parking lots, or in restaurants waiting for the person to leave.
I would text him when they did and he would do the actual following. This worked because nobody thought two 18-year-old guys sitting in front of Target listening to 90s alt-rock would be tailing them. People who commit affairs usually don't worry once they leave the neighborhood they live in. It’s a piece of cake. The people who were paranoid were often repeat customers, as I stated.
They would want to know about every person their spouse talked to. If a wife had a business lunch, the husband would be sure she was cheating on him. If a husband had to work late, the wife was sure he was meeting his mistress. They almost never amount to anything and often we would find evidence that the client was the one engaging in an affair.
Still, they were the client, and it was an easy way to make fairly regular cash, so we never let either party know the client had a side piece. The workers’ comp/insurance ones could sometimes be heartbreaking. Say a dude hurts his back and can't lift more than five pounds. They would want pictures of him picking up a gallon of milk at the grocery store, as it's over five pounds.
Or a grandmother putting a grandchild in a car seat. You follow them around enough and you will catch everyone doing something a doctor doesn't want them to do. Half the time, you would see the pain in their face as they lifted a gallon of milk or a bag of potatoes, but that doesn't appear in a picture. I hated helping out with these cases.
19. She’s Seen It All
My wife was a P.I. Not a lot of research, mostly documenting insurance scams. The last case she ever worked, she was staking out a house, trying to get a man who was claiming not to be able to work because of his car accident, doing stuff he says he can't do. He opens his front door, and she starts videotaping, hoping he'll start doing yard work or something.
Instead, he pulls out his you-know-what and starts going to town on himself on his front step for a few minutes before walking back inside. The tape became legendary comedy material in the office she was working at.
20. Don’t Look Under the Bed
My half brother said that he was a private investigator until he found a whole bunch of intimate toys under a murder victim’s bed.
21. Can You Paint With All the Colors of the Wind?
Ah, finally something I can share! A few years back, I accidentally became the owner of a detective agency. I intended to just be an investment partner, but the owner and actual P.I. passed on shortly after I made my investment and lo—I now owned a detective agency. After quickly getting the various licenses, etc., I just started taking cases.
The entirety of what I knew about how to be a P.I. 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 P.I. is the next logical step. Much later, I learned that normal P.I.s never take these so-called "domestic" cases because they are always a huge mess.
Real P.I.s get almost all of the work from lawyers and hire off-duty authorities to do all of the leg work. As a result, I had a TON of crazy cases. This is the best one. 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. It turns out lots of crazy people call P.I.s to investigate the TV controlling them, alien abduction, etc.
Lesson learned!
22. Beach Bummer
We had to follow this cheating husband to the beach in Florida. I got paid to go hang out in a nice beach town all day and night. Didn't get a lot of sleep, though, thanks to having to be up gathering video evidence after they went to bed, but it by far beat the normal jobs. What's crazy is, the daughter was able to catfish her father and get more evidence.
He also had a stupidly easy password on Match.com, so we could see everything he was saying and planning. Of course, what's sad is people cheating, and they have to know their partner knows they're cheating, but they keep doing it even though their partner asks for a divorce and they refuse. Usually, the cheater is better off financially if they'd go ahead and leave.
No one is happy but they just keep going. What was infuriating was just straight-up busting someone with perfect evidence of infidelity, and then the client goes and takes them back and ruins all of our work. The law is infidelity evidence only counts if the offended party does not take them back or sleeps with them, so it’s annoyingly fragile in these dramatic relationships.
23. Cheater, She Wrote
An old professor of mine had a wife who was a P.I. She was about five feet tall, cute and plump, with gray hair, big cheeks, and a sweet smile. She looked like a sweet old lady who could be the best grandma ever. This is exactly why she was an amazing P.I. No one ever saw her coming, if you know what I mean. She could get in and out of buildings with the information she needed by chatting people up and getting them to spill the tea—or even hand her copies documents needed.
They should really make a movie about her.
24. Holier Than Thou
There was Seventh Day Adventist lady in an abusive relationship who wanted to divorce her husband, but apparently she needed the husband's permission, which he won't give her. So she wanted us to hire a “lady of the night,” if you get my drift, to seduce him, get it on video, and then mail THAT to the church leaders to show the marriage is broken.
25. A Real Mastermind
I had a man who was serving 20 years for hiring a hitman (who happened to be an undercover cop) to kill his friend. In prison, he came into some money and hired me to prove he was innocent. His brilliant 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 genius told me this plan on a recorded phone call from the correctional facility.
26. The Curious Case of the Woman in the Night-time
Currently studying behavior analysis. A middle-aged woman, 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 investigators are thinking that they had a sinister 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, someone should have reported at least hearing a woman in distress, as the dumpster was near the parking lot of the bar.
Also, the abrasions on her buttocks were rather strange, as if someone had dragged her across the cement floor. After some investigation, they found no traces of physical evidence that suggested there was an attacker. No saliva or hair. Later, it was revealed that due to loneliness of losing her husband and her daughters having left home as adults, this woman went to the bar to meet a potential new partner.
But, she had gotten carried away drinking. Once outside in the freezing cold, she wants to take a leak and hides 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).
As a result, she presumably strips off her jacket and other pieces of clothing. At this point, the hypothermia is really getting to her badly and she begins slowly losing consciousness. While laying on the freezing ground, with her skirt pulled up and leggings down, she begins convulsing, which leaves abrasions on her body.
All this left behind a curious scene that appeared as if she had been taken advantage of.
27. Just a Little Innocent Fun
I got hired by a wife to see if her husband was sleeping with his secretary. We followed them, recording them going into his single-bed hotel room at 10:20 pm after a nice dinner and leaving together the next morning at 8 am. I think that it’s a slam dunk, but the wife’s reaction was heartbreaking. She suddenly went into total denial. She told me it proved nothing and that they could have just been working late.
Okay lady, you’re the one paying me.
28. Done and Dusted
Not me personally, but I worked with a guy whose subject kicked the bucket on the first day of surveillance. I'm sure the final report must have been legendary. "The claimant died."
29. The Worst Human on the Planet
One girl offered to watch her roommate's dog for the weekend, then got annoyed by its barking so set it on fire. She is the only truly evil person I've ever seen.
30. All the Better to See You With, My Dear
A woman I know had to get a private investigator as part of her divorce. The husband had been cheating, but in order to get infidelity as part of the divorce hearing, there needed to be a witness who saw him go to the other woman's house after 10 pm and stay there for at least an hour. It was a slam dunk, probably because the P.I. was so unassuming.
She was like a 50-year-old woman, who you never would’ve guessed was a P.I.
31. Power Napper
I used to do background checks for employment. The funniest one was a guy who was working for a large provincial hydro company and was trying to get a raise, so they wanted me to look into him. He relied solely on GPS. He had to drive to a remote site a few hundred kilometers away. The next day, the crew were waiting on him.
Finally, the foreman calls to see when he would arrive. The applicant answered sleepily and said his GPS signal stopped about 250 km in and he just turned around and went home. Didn't call anyone, use a map, just went home. He also used to take a little boat pretending to survey sites. Several times he was caught sleeping, just floating around in the boat.
The most surprising thing? He got the promotion he was seeking.
32. Sister, Sister
Someone I worked with was retiring and was going to spend her days being a P.I. which was pretty cool, I thought, and I asked her if she could help me with something that had been bothering me since I was 12 years old. My father, who was living across the country at the time, flew to see me and my brother just for a day.
I would find out years and years later that the reason he did that was that he had cancer, and wasn't sure if he was going to die or not. My dad doesn't talk about anything. He's the weirdest guy. Like, ever. Which brings me to the conversation we had that day. He told us that before he met our mom, he had knocked up this girl he worked with, and she kept the baby.
He had no relationship with her at all or her mother. He claims he wanted to, but she didn't want anything to do with him. But knowing my dad, I'm pretty sure that's all a load of hogwash. I bet he just bailed. He said he just wanted us to know that we had a half-sister, and then he just left. Like I mentioned before, weird guy.
So it was always in the back of my mind that I had a half-sister out there somewhere, and I was always curious about her, but my dad never brought it up again the few times a year he bothered talking to me at all. So I didn't know how I could find her. I tried searching the internet a few times, Facebook and things like that but I never got far.
So fast forward to when my co-worker tells me she's going to be a P.I. It hit me! I told her the story. I asked her what she would need to figure out who she was, and she said just my dad's name and date of birth, and she might be able to come up with something. Not even two weeks later, my amateur P.I. buddy is messaging me on Facebook and sends me to the woman she believes is my half-sister.
I remember it exactly because at the time I was out at a bar with my step-sister, and when we saw the photo we both looked at each other and were like "That's gotta be her!" I just had a strong feeling. So, in the time from when my dad told me about her, to the time the P.I. had found her (14 years?) I'd moved back to where I was born.
From what I could see on Facebook, my half-sister lived within 30 minutes, had just given birth, had a husband, and she just overall seemed really happy and cool! I was so happy for her. I reached out to her. Sent her a message on Facebook explaining who I was. I had no idea if she knew about me or not. So I told her I didn't want anything.
I just wanted her to know that I knew that we probably had the same dad. Then I waited, wondering if I should be upset about something that I never had in the first place. It took her almost a year to respond. The message went to some folder and she never saw it, but then she did! She confirmed that she was my half-sister!
We exchanged a few messages back and forth before finally meeting for lunch one day. It was a little awkward at first, but we're both a little awkward. And that's actually what was so crazy to me. The weird similarities we had with each other. The whole thing has been kind of surreal. Since then, we've met up for lunch a few different times, and went to a concert together.
I've never told my dad that I have a relationship with her. I told my half-sister that if she wants me to tell him anything, then I will, or put them in contact. But other than that, I don't see why I would. And he missed out big time, as far as I'm concerned. Because she's awesome! I wish I saw more of her. In fact, I’m going to text her right now and see if she's free for lunch.
33. Fire and Brimstone
I'm a private fire investigator. I once had a guy tell me that the church across the street would gather in the street and group-pray that his house burned down. Turns out, that wasn’t actually what happened, go figure. In actuality, the tenant who was staying there had a boyfriend who actually did the burning. It was NOT Jesus, as one church member claimed.
34. On the Wrong Side of History
Girl ran away from home. She had been getting bullied at school. It turns out her grandfather was a guard at Treblinka.
35. Gotta Keep Your Energy Up
I've been a P.I. for about 3 years—mostly for disability scams, no cheating wives or anything. The coolest-slash-strangest thing I observed was this low-level criminal. He was supposed to be disabled, but he 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.
Then he’d walk briskly out the door without paying, throw them in his trunk, and take off like a bat in the night. 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. That’s actually how I got him. Not quite the way I think he was intending to go out.
36. The Year of the Scammer
I deal with a lot of 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 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 and their power is about to be shut off.
The authorities 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 $3,000 in 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.
37. Mistaken Identity
I have had some ridiculous clients, but this one tops them all. A guy calls to ask for Paddy, who happens to be my late partner. We tell him he is dead. The conversation that follows goes like this: He says, “Dead? Tell him it’s Bob.” I say, “Bob, Paddy is dead.” He replies “Sure, ok, whatever. Who's this?” I say “This is Dave. How can I help you?”
He goes on: “Dave huh? Dave...yeah, Dave, I think Paddy mentioned you. I was just calling to make sure the thing is still on for Friday?” I say, “What thing?” He’s all like, the thing, you know. Super mysterious. I keep telling him I don’t know. He then says, “Well yeah, I know you don't ‘know,’ but is it on?”
I flat-out say, “Bob, I have no idea what you are talking about.” He replies, “Ok, I get it. Of course, you don't know. But—all I'm saying is, we're good, right?” I say, “We are not good Bob. I don't know what you are talking about.” He goes “Of course. Got it. No idea. Great. Friday?” By now I’m losing it. I tell him, “Bob, Paddy is dead, so whatever you think is happening on Friday is not happening. Do you understand?”
I couldn’t believe it when he replied, “Perfectly. Tell him I will see him then.” The weirdest thing was, this kind of thing happened again. Different call, also asking for Paddy. After the guy says he was told to ask for Paddy, the conversation went the same way. Then he told me he needed to disappear. I say, “What do you mean, disappear? Like, from your girlfriend or from the Feds?”
I literally had no idea what he meant. He says, “Really disappear. Like, dead.” I tell him there is no way to disappear unless you have a ton of money and a body. I made this line up on the spot, by the way, just to shut the guy up. Then he says, “I have 3 million in cash. The body is no problem. Can you help or not?” That’s when I knew that Paddy had been into some really bad stuff.
I told him I can’t talk about this on a cell phone. Hung up. Never called back. Later found, from tracing the number that called me on, that it belonged to a real estate investor who was being sued for millions in back taxes from the government. But that wasn’t even the most insane part. He perished in a private plane crash about a week after that call...
38. A Case Buffet
I am a private investigator and I have come across many cases. Once, a police department in a small town in the Appalachian Mountains wanted me to keep an eye on an old lady. Another time, 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 tenant of an apartment building hired me to watch his landlord, who also hired me to watch the tenant. 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. The weirdest one of all? A “Make America Great Again” supporter hired me to watch his neighbor.
Why? Because he was convinced his neighbor was "a Soviet."
39. Fair-Weather Friends
The most fun I ever had on a case was busting a workers’ comp cheat. The guy made my car since I was there a lot over a long time, so I used another car. Then it turned out the neighbor of the subject I was working on just let me use his carport. He'd hang out with me, we'd sit and shoot the breeze. P.I. work is mind-numbingly boring sometimes, but he’d provide drinks as we hid behind the woodpile or a car.
I hated it when that job ended.
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40. Doing Him a Solid
I once had a guy admit to setting his house on fire just because I was nice to him. I mean, it was super obvious and he knew I'd figured it out, but I just talked to him about football and all that, and right before I left he just flat out admitted to it. If all my jobs were as easy as that guy, I think I’d probably be a very rich man.
41. All in Two Days’ Work
I hired a P.I. to hunt down a customer who stiffed me for over $10k in airplane repairs. P.I. found him in two days. The guy had bought a house under his deceased brother's name and started up a courier business using his airplane. I already had a mechanic’s lien on his other aircraft, and in order to keep his business and license with the FAA, he was forced to pay me back.
The P.I. ended up comping the job because he found the guy so quickly that he felt bad about charging me.
42. Fool Me Once
We had a babysitter who we were pretty sure had been ripping us off. So, after we parted ways, we had our neighbor who was a P.I. do a background check. Turns out, every time things went missing, the babysitter had either a court appearance or another fine for their multiple offenses. Note to self, run the background check FIRST.
43. Whatever Floats Your Boat
There are some strange tastes out there. There was a couple that would hire me once a year to catch the wife getting intimate at a sleazy motel with the curtains open. The guy tried to play it off like he was actually trying to catch her. "I found a motel key that said room 109. I leave for work at 8 AM and my neighbor says she usually leaves at 9 AM every Tuesday, etc.”
If a dude wants to pay us a grand to take photos of his wife, I'll play the cameraman. It's easy money, and the risk that an altercation happens is almost nothing.
44. Bowling for Dollars
My firm had a bad faith insurance case several years ago. A guy had gotten hurt at work. He claimed he was disabled because he hurt his back, and could not lift anything or really engage in any type of physical activity. His disability insurance carrier failed to handle the claim and pay him what he was owed. There was a potential for relatively large damages.
In fact, the carrier filed in the court case what is known as an Offer to Confess Judgment. It's a way of agreeing to let judgment be taken for that amount. The plaintiff can accept the offer or reject it. However, if he rejects the offer, he is responsible for the defendant's attorneys' fees if the verdict ends up being less than the amount of the Offer to Confess Judgment.
The offer, in this case, was $ 750,000.00 He rejected the offer. A few weeks later, our P.I. found out that the plaintiff bowled every week. The P.I. got a video of the plaintiff bowling and copies of his score sheets going several years back through the date of the accident. It was clear he really was not disabled. He also found that the plaintiff had been in a car wreck and was making identical injury claims to the other driver's insurance carrier.
We filed a motion with the court to dismiss the lawsuit based upon perjury. The court set the motion for a hearing, but before that happened, the plaintiff dismissed his lawsuit. Smart choice.
45. All in the Family
My mom's biological father was basically cut out of her life when she was 3-4 years old. She never really knew him and my grandmother tried to keep his existence limited after she married another man—the one that I consider my grandfather. My mother knew basic information about her biological dad but no history about his life, medical history, how he looked, etc.
After my grandfather passed on, she began looking into it more and hired a P.I. Ultimately, after sending many emails to random people with little luck, she was able to get in contact with his first cousins. She discovered that both her biological father and his brother, whose children she had found, had died but her aunt and one of her sons lived one county away.
I ended up going with my mother to meet her cousins. It was really weird. She has certain features that didn't come from my grandmother that were clearly present with her cousins. It was a funny experience to meet them and talk about their uncle—my mom's father. Apparently, her father was very much of a jerk and ended up dying somewhat alone.
The cousins weren't close to their father either. I think my mom still gets emails from them every so often to be kept in the loop with some family happenings.
46. Somebody’s Watching You
My ex hired a P.I. against me to find anything and everything he could to try and twist it around and make it look like I was an unfit mother. He was trying to win a custody battle. The P.I. sat outside of my house, taking pictures and videos. He followed me in public and took videos and pictures. He gleaned anything he could from social media.
My friend tagged me in a post that said something like, "Drinking Friends, ASSEMBLE!" and that was presented as evidence that I was an alcoholic. Heck, I am the DD more often than anyone! We ended up settling before the trial came, so thankfully this folder of photos of me attending a street dance, *gasp* dancing, and printouts of any references to alcohol made on Facebook did not get presented in open court for me to defend every single action.
Unfortunately, he does present this "book of shame" to parent mediators, counselors, and anyone else he thinks should believe that I'm an alcoholic horrible mother. This left me with lingering paranoia and distrust, no surprise. I have had to leave public venues for fear that I'm being watched. Nothing has damaged me more than this.
47. The Case of the Imaginary Man
I hired a private investigator to see if a man was real. My dad, we will call him Henry, passed on when I was 15 years old. This was absolutely devastating, especially because my mom and I never really got along. I moved out as soon as I was 18. I asked for all of my important documents, including my birth certificate, but she never agreed to give those to me.
Instead, I took it upon myself to request a birth certificate from the state. I get it, and under the father’s information, there’s a name: “Michael.” When I confronted my mom about it, she said that she made up some man’s information. So I hired a private investigator to see if Michael was real.
Sadly, in the end, she was telling the truth—she just made up a name. I don’t know what’s wrong with my mom.
48. Common Mistake
Whenever anyone mentions a P.I. following someone for workers’ compensation, I always remember this great story. This P.I. came to court with a pile of evidence that this woman who was wheelchair-bound was running around doing errands. He shows all his stuff in court…and then the defense calls the person’s TWIN SISTER who moved in to help her after her accident.
That was, in fact, the person the P.I. had been stalking.
49. Leave No Trace
Not a P.I., but I’m an attorney and occasionally need to hire one to track someone down. We had a case where husband and wife passed on within a few months of each other of natural causes. They had a mortgage with a small balance, but the bank didn’t want to foreclose because it was such a small amount, yet they couldn’t write off that sum, either.
My office was retained to see if the family would pay it off and get title to the house. I did my normal search and couldn’t find any next of kin. Which was weird, because I always can find someone. I spoke to the neighbors, who were friends with the couple for 20 years, but the neighbors knew nothing. They said they felt foolish that in reality, they knew nothing of the departed couple.
The deceased never mentioned family, where they were from, or anything about their past. I reached out to our P.I., who asked for a week to get a report to me. P.I. calls me a week later and says he needs more time, I give it. Finally, the P.I. calls to say there’s no report and he’ll give a discount on the bill. He can’t find them. There is no record of the couple, they simply appeared in the 80s.
In fact, the couples’ first record of existence is the mortgage application. In the 1980s, this couple would have been in their 40s. When I asked for a further explanation, the P.I.’s answer was shocking. He told me, “This is for sure witness protection.”
50. Blood on Your Hands
I was hired once by a man who I didn't know. He just called me one day saying I saw your ads and I need you to investigate such and such. I was sent $2,000 in the mail, which was way more than my normal asking price. I should've known something was up when he told me his rules to follow. No talking about the case to anyone. No contacting the authorities or any other form of law enforcement during this case.
Only contacting the client by phone. No arguing; I could either accept it or not. I thought it was weird at the time, but I wasn't going to reject $2,000. Day by day it just kept getting weirder and weirder. He kept telling me, “Oh, what’s his daily schedule, where does he like to hang out, does he have any family members or friends that live with him?”
After a week, I was told to stop and that my services weren't needed anymore, but I was still paid. A week went by and I was sitting on my couch watching the news. What I saw next chilled me to my bones. The guy I’d been watching had been killed, most likely by a hitman, and authorities were investigating the case. To this day, I will never be a private investigator again, knowing I was a part of that.
I still don't know to this day why he was a target or who called me to investigate.
Sources: Reddit, , , ,
