The Sad, Strange and Sneaky World of Private Investigation
By: Marc Oakley
Tags: True Crime, Life Lessons, Society, Lifestyle, Gadgets

The Sad, Strange and Sneaky World of Private Investigation

Why it sucks to be a private dick

Photo courtesy of Libreshot

From Magnum P.I.’s impeccably tropical 'stache to Sherlock Holmes’ cerebral sleuthing, the allure of private investigation has been a mainstay of popular culture since the 1840s.

And in the real world, private eyes are everywhere. According to the U.S. Bureau of Labor Statistics, there were 36,200 private detectives and investigators employed in the United States in 2019. But private investigators aren’t limited to the U.S.; The World Association of Detectives (W.A.D), founded in 1921, represents members across the globe, from Guadeloupe to Vietnam.

So when I was given the opportunity to actually enter this murky and mysterious world myself, I jumped at it. The pay was terrible. In fact, it was shit. But I was between jobs and this wasn’t just another gig.

Behind the tinted windows of a nondescript expanse of suburban offices, my new crime-fighting headquarters awaited.

My friend, who we’ll call “Jill”, had recently been hired by the firm and was kind enough to put in a good word for me.

With a tinge of disappointment I learned that the position didn’t require me to physically stake out or follow targets; that would be up to our investigators. Instead, I’d be reviewing surveillance footage and conducting digital snooping in-office. My findings would be compiled into reports for a wide range of clients with a singular motive: detecting deceit.

After submitting an online application to my state’s Private Investigators’ Licensing Board, which asked me to list any body marks (tattoos, scars, birthmarks, etc.), I was given a “provisional registration” which allowed me to legally conduct private dickery. I was in. Behind the tinted windows of a nondescript expanse of suburban offices, my new crime-fighting headquarters awaited.

THE TOOLS

After meeting the team and sitting in on a few insurance claim interviews, I was introduced to one of the most powerful tools accessible to private investigators: TLO.

Boasting trillions of historical and current records, TLO is an online database that creates detailed reports containing a target’s personal and business information as well as criminal records, court documents and assets.

P.I. work is best-suited to the young, untethered or for those functioning on the fringes of society. And here I was, a part of this motley crew.

TLO’s website claims that “Every subject has a digital story.” They aren’t shitting around. Beyond addresses and employers, TLO can dig up liens, judgments, global watch lists, weapon permits, possible relatives, likely associates and even neighbors’ phone numbers. If recorded in any official way, TLO can pretty much track it down.

Having access to so much information on practically anybody on Earth made my head spin. And to be honest, for a moment my thirteen-year-old self had to fight the urge to dig up dirt on certain individuals who had both crossed my path — and me- throughout my life.

“Just don’t look up any celebrities,” Jill said in a matter-of-fact tone. “Some P.I. got into trouble not too long ago for looking up Britney Spears.”

THE CREW

No creepy mustaches. Well, maybe one. The first thing that really surprised me about the team of private investigators was that they were mostly females between the ages of 18 and 40. The type of people that you’d never suspect of tracking your every move. Of course, that’s the point.

Most were personable, some were hilarious. A few were battling with substance abuse issues which, at times, affected their ability to work. Many had struggled with relationships. Despite their personal challenges, all knew how to professionally disappear.

While my position was 9 to 5, the hours for our investigators were sporadic and inconsistent. It wasn’t uncommon for long-distance assignments to drop out of nowhere with little-to-no advance warning. One night they could be parked outside of a residence all night. The next, trailing a vehicle for hundreds of miles across state lines.

P.I. work is best-suited to the young, untethered or for those functioning on the fringes of society. And here I was, a part of this motley crew.

THE GADGETS

Thanks to tiny cameras and GPS technology, today’s private investigators have access to an arsenal of gadgets that help them track and surveil while staying virtually undetected. And we were no different.

Ideal for recording videos in bars, stores, gyms or strip clubs, the “key fob” is a tiny digital camera encased in plastic that looks identical to most modern wireless car keys. When attached to a key ring placed inconspicuously on top of a surface or held in one’s hand, it is nearly impossible to detect. The result was thousands of hours of footage of targets unwittingly being recorded.

Another favorite bow in our quiver was the GPS tracker. Looking like a hard drive with heavy-duty magnets on each end, the GPS tracker was a go-to tracking option for cases of suspected adultery.

By way of TLO or an account that we had with our state’s DMV, we would get the subject’s address and car information. Then, it was just up to one of our investigators to sneakily attach the tracker under the vehicle. Any movements could then be captured digitally.

THE CLIENTS

The lion’s share of our clients were insurance companies looking for footage to refute claims of work-inhibiting or debilitating injuries. Most people who are faking injuries are careful to stay on the down-low, but most aren’t careful enough.

Behind tinted windows (PI’s in my state are legally able to have darker tints) and armed with digital cameras, our investigators were deployed to stake out residences and follow targets everywhere they went for a specific time period. Hundreds of hours of footage — albeit generally uneventful — was captured.

To even the most optimistic souls, it’s easy to see how private investigation can slowly erode at one’s moral compass.

But sometimes we got lucky, and the good stuff was great. Like the guy who was supposedly hobbled and unable to work, caught swinging around free weights at the gym like The Rock on crack. Or the stripper who, also claiming debilitating injury, was caught driving hours across state lines to strip, drive back home and collect on insurance.

One way or another, strippers often made appearances in my reports, like the time two dozen or so engaged in a parking lot battle royale. Or the claim — gleaned from social media — that one unlucky patron had contracted pink eye from a stripper’s fart.

WHERE THERE’S SMOKE…

Suspected adultery or cheating made up, perhaps surprisingly, only a fraction of our business. Sadly, most people who asked us to track partners and spouses suspected of cheating had their suspicions confirmed. Herein lies the dark catch-22 of PI work; catching a philanderer (or philanderess) in the act makes an unhappy client unhappier (even if that sentiment eventually fades)by confirming their worst fears. Failing to provide proof of cheating means that you’re not doing your job. You’re damned if you do and you’re damned if you don’t.

To even the most optimistic souls, it’s easy to see how private investigation can slowly erode one’s moral compass. Soon after I took a job at a marketing agency, Jill had left private investigation as well.

“I knew it was time for a career change when I started to be bummed out that we didn’t find dirt on a person,” she confessed.

Jill had become another casualty in a field that requires one to always find the bad in others, instead of embracing the good.

If you’re fortunate enough to live a conflict-and-litigation-free life, there’s a good chance that you’ll never cross paths with a private investigator.

But if suspicions of infidelity have hijacked your relationship or if you’re claiming an injury that prevents you from working, pay special attention to that car that you keep seeing out of the corner of your eye or that person at the store who seems to be watching you more closely than normal. You might just be the target of a private investigator — numbed by endless exposure to countless cheats and scoundrels — watching patiently, waiting for you to fuck up.