Private Investigators Disclose Their Most Outrageous Cases

Things Are Not What They Seem

My father’s not an investigator, but he’s a lawyer and he used to have to look into people who were suing the insurance companies he worked for.

One woman claimed she was in a really bad car wreck and was suffering intense leg pain, back pain, neck pain, etc. This was back when MySpace was going strong. So my father Googled her and found her on MySpace.

It was filled with recent photos of her clubbing, dancing, and even horseback riding. Needless to say, she didn’t win her case. 

Now my dad, being a very sheltered individual, did not understand some of the terms he came across on her page—which led to a hilarious moment in court. He had to approach her and he asked: “I just have one question. What exactly does it mean to ‘get crunk?’”

The next story is about a nurse who was making some extra cash on the side

Suspicious Nightlife

I once did surveillance on a nurse. She was supposedly so disabled that she couldn’t work. They suspected she was secretly working, though. It was the easiest surveillance I ever did. 

I arrived. She got in her car ten minutes later. I followed her, with no complication, to a strip club where she went in and began doing her thing.

The club had a posted prohibition on taking videos. 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 entire life and career.

Eventually, it went before a judge. When the judge asked why she was stripping, she just shrugged and said that she made twice as much money as when she was nursing. Her benefits instantly got yanked. 

The insurance company was happy. But the company lawyer gave me the nickname “Detective Breasts” which, most regrettably, stuck and spread to all of the other lawyers I dealt with.

Worst night of my life, man.

The guy in the next story was convinced his phone was wiretapped

Stop Bugging Me

I worked for one of the top private investigator firms in Houston. Because of my electronics background, I’d usually go along on the jobs where we were checking for bugs and hidden surveillance devices. 

We once 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. No devices were implanted in his phones. 

We’re getting ready to leave and he says: “Look, I’m not crazy. Pick up the phone, press 9 and you’ll start hearing all sorts of clicking sounds.” Turns out his office phones were routed through the corporate PBX of his client.

So 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 advised him to install a private phone line. We ended up billing him like two grand for that visit.

The young P.I. in the next story would learn that it was not an easy job to do.

Not For The Faint Of Heart

A college friend of mine was a private investigator. He said that 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 served people, including wearing disguises, using high-pressure tactics, and experimenting with weird social engineering tricks.

He’s out of the field now because he’d had too many close calls. Serving divorce papers or notices of being sued where you have no idea what the state of mind of the person you’re serving is like could easily get interesting, to say the least. 

Let’s just say it’s a field that only people with a high tolerance for danger and excitement should go into.

The company in the next story would make a big mistake by replacing their best worker

Not Suitable For The Job

When I was an investigator, I was asked to train my replacement. She was in the process of firing all the old blood to pack the office with her friends. It was incredibly obvious that I was next on the hit list, and she wanted me to train a 19-year-old idiot and she was expected to do a very important job.

But I tried. I could not force her to pay attention to me, so I just explained everything while she played on her phone sitting next to me in my cube. 

Didn’t work out well for them. The boss actually chewed me out for not training her when everyone in the small office knew I went over the quirks of the McDonald’s contract with her for nearly half a day.

The salespeople had promised them the world to land the contract, and they had an extremely complicated system for adding new franchisees that were all on a spreadsheet that only I knew how to maintain. 

Not long after I was let go, we were no longer the official background check company for McDonald’s. That amounted to the firm almost immediately losing about half of its corporate clients.

The P.I. in the next story would find out that his client was not as innocent as he had claimed

Candid Camera

My uncle is a private investigator. He got tasked with investigating a collision at an intersection. He found a nearby business that happened to have a camera facing the road at the time and figured that it would have picked up some of the incidents. 

He collected the footage and got said footage of the collision. And he discovered that his client was definitely in the wrong and caused the accident.

But the video got so much worse. You then see the client attacking the other driver while damaging his own car further. It was meant to be an insurance scam where the client could say they hired a PI but found nothing. 

The intention was for that to legitimize his story. However, he didn’t count on a camera picking the whole thing up, and so he ended up incriminating himself.

My uncle still got paid for the job.

The next story is about a P.I. who got an interesting case to do and got unexpectedly caught.