Login or Register

Sign in with Facebook

Private detective -- have two words ever contained so much badass potential? Take a grizzled police detective, remove all those pesky "rules," and replace them with a fifth of Jack Daniels and a wicked-ass trench coat. You've got a private dick ready to be so goddamn cool, I can't even make a penis joke about the first half of this sentence. But Dick Tracy (still nothing) is pretty far from the reality of work as a private detective. I've been walking the mean streets of my East Coast city long enough to know that everything the movies say about this job is total crap. So before you put a down payment on that Colt .45 and head to the spy store for a sack full of hidden cameras, you'd better read on ...

5
Everything You Know About Surveillance Is Wrong

Hemera Technologies/AbleStock.com

Acting like a movie detective helped me screw my first case right into the ground. I was in a suburban neighborhood, parked straight across the street from the subject's house with my 200X zoom camera. I was living the dream, sitting in my car as I raked in the hourly pay. About 45 minutes later, the subject's car pulled out of the garage, I started to follow, and at the first stop sign, he got out of his car screaming at me. I hopped a curb and got the fuck out of there.

Jupiterimages/Photos.com/Getty Images
Only in my mind.

Just like that, all my carefully collected Badass Points fluttered away like gold rings from a wounded hedgehog. And I'd been lucky; usually that situation would have ended with someone calling the police. Blatant surveillance -- a PI parked Hollywood-style out in front of someone's house -- can actually land your ass in jail. The law considers that stalking, not detective work.

The pressure was on to not fuck up my next case, which (of course) guaranteed that I did. I wound up tailing a car through rush hour traffic when she started taking unnecessary detours. I thought I was going to get lucky and she was going to some other guy's house, but her detours brought her straight into the parking lot of a police station, where she immediately screamed to a group of officers. They pulled my Hollywood ass over and explained how fucking stupid I was. One of the cops told me a story about how his daughter plays hide and seek by covering her eyes. She thinks that if she can't see you, then you can't see her. At that point, that little 3-year-old girl was better at hiding than me.

Jupiterimages/Creatas/Getty Images
I had a slight edge in muay thai.

The trick with long-term surveillance is to push your luck as much as possible without getting caught. Remember when you were a little kid and you'd see the "Do not walk on the grass" sign, so you'd put one shoe on the grass just to see if you could get away with it? It's a lot like that. Except instead of using my shoe, it's an HD video camera. And instead of putting it on the grass, I'm filming you banging your barely legal girlfriend while your wife is at work.

4
Technology Has Its Limits

Image Source/Photodisc/Getty Images

I have a camera that lets me film from 200 yards away as if the person is right in front of me. Another camera lets me see in the dark. Most of the time when I'm tailing a suspect, I've already put a GPS tracker under their car or gotten permission from one of their family members to activate their phone GPS. But all that technology is useless if I'm not authorized to use it. Night vision cameras are like a gift straight from the hands of God to a PI, but they are close-range cameras. If I can't get on the property, that camera is as much help as stock tips from a homeless man.

Thinkstock/Stockbyte/Getty Images
"Put it all in Microsoft. They're destined for a hit."

If you aren't on a family plan or your spouse doesn't consent, I'm not tracking your phone. I can't even record any conversations you might have, because 38 states require at least one person's consent for a recording. Twelve states require everyone in the conversation to consent. Listening in on people is hard if you aren't the government. I can't wiretap your phone either, because I'm not someone at the NSA. Nor can I install any fancy spy software on your computer. Almost the whole galaxy of gadgets I could use to catch you wouldn't give me evidence I can legally use in court. If I break a law to crack a case, it isn't really cracked.

One time I was following a woman's husband who'd started "carpooling" every day with a co-worker. There was obviously more going on than saving gas, but the position of her house didn't allow us to see anything without blatantly trespassing in places we would easily be caught. They were very careful in public, and we couldn't gain access to their work because it was on government property. Our last resort was to drop a voice recorder in his car and hope that their conversations on the way to work would prove adulterous. Finally: some real-ass spy stuff. I was bugging cars, snooping in on sexy adultery talk, basically living in PI Valhalla. But the rampaging frost giants of wiretapping laws meant my skillful buggery wasn't admissible in court.


This picture should distract you guys from my use of the word "buggery."

In the end, our work didn't even matter. He and his wife had a fight and he admitted the whole thing in a fit of spiteful rage, just like in that one Raymond Chandler book where right before Marlowe cracks the whole case wide open his two chief suspects yell at each other in an Applebee's and decide to get a divorce.

Jessicafm
It was one of his lesser-known works.

Continue Reading Below

3
The Cops Are Not Your Friend

George Doyle/Stockbyte/Getty Images

The police will stop you eventually, and they will flip out at the crazy shit in your car. Any state trooper who pulls me over sees a young white dude with a bullet proof vest, a gun, and piles of electronics. Seldom do stops end with a friendly warning and me right back on the highway. More often, they call out the dogs and I spend an hour sitting by the side of the road while a bunch of men with guns stare at me like I just farted on their mom in an elevator.

Ryan McVay/Photodisc/Getty Images
"Next stop ... hell."

I was pulled over once in a bad part of D.C. My vest and ammo checked off every box on the cop's Gangbanger Bingo card, so I ended up in jail. It took five hours in holding with crackheads and criminals for them to confirm my identity. Since I was still on the clock, I probably made more money in jail than the guys being paid to keep me there.

Another time, a fellow investigator and I were on surveillance around 2 a.m. We were chilling in the car, heater on, hot mug of coffee between us, watching our target and eating pretzels as we tried not to be the first guy to use the pee bottle or, God forbid, the little coffee tin in the back we saved for poo. Before one of us could give in, all our sitting around spooked one of the residents. When we tried to leave the area, there was a roadblock and cops circling the whole neighborhood. We were handcuffed and detained for about two hours right in front of the house we were investigating. Sherlock Holmes never got nightsticked by a bobby while skulking outside Moriarty's place. Maybe Victorian-era neighbors were better at minding their damn business.

In most states, you're supposed to give a courtesy notification to The Man before you start an investigation. Of course, sometimes this makes you a target and ends with your cover blown anyway. It's a myth that most PIs are retired cops -- the skills required in the two jobs are totally different. Any veteran cop has spent his entire career doing openly all the stuff PIs have to keep hidden. Detective Justice Coppington knows that flashing his badge almost always gets people to talk. And if it doesn't, he can apply for warrants or a wiretap or whatever else he might need to get to the bottom of his case.

Jupiterimages/liquidlibrary/Getty Images
Above: Easy Mode.

2
The Job Isn't What You Think

Jeffrey Hamilton/Photodisc/Getty Images

I have had a depressing number of people hire me to catch their spouse cheating while holding the hand of their own boyfriend or girlfriend. What most people don't realize is that even if a couple is separated, until the divorce is final, having a boyfriend or girlfriend is still adultery. So you wind up in this weird situation where both people have moved on, but no one can be honest about it because then they'll lose the divorce game. It's like an unusually dark episode of Frasier.

David De Lossy/Photodisc/Getty Images
"Yahtzee! You get Christmas and Hanukkah!"

To hire my firm, it costs the customer $75 an hour plus expenses. We have many cases that include hours of surveillance a day for months. You know who can drop hundreds if not thousands of dollars a day to catch their husband or wife cheating? Very fucking rich people. There are a lot of couples who are getting divorced, already separated, and happily dating someone new who realize "I don't wanna lose half my shit." And then they come to me. I'm a ticket in the marriage lottery.

This ate at me for a while, until I realized that it's what's keeping me employed. You know what's delicious? Fresh lobster delivered to your hotel room at 2 a.m. because the client's wife is in the room across the hall with her new boyfriend. That $60 lobster is even more buttery and delicious knowing that it's going to be filed as a business expense and billed to the multimillionaire who hired me. THAT was a great job: I lived like a king for two weeks, and it turned out the woman was there with her sister, not some cabana boy.

David De Lossy/Photodisc/Getty Images
It was a lost opportunity for everyone.

Continue Reading Below

1
Everything Cool from the Movies Is Illegal

Darrin Klimek/Digital Vision/Getty

"The best part of being a private investigator is breaking into houses or finding unlocked windows in the middle of the night and snooping through people's stuff."

... said no PI ever in history. You want to snoop through houses or offices? Your desired career field is "burglar." It's illegal to bug houses, and it's extra double illegal to break into somebody's home and plant that bug.

Stockbyte/Stockbyte/Getty Images
"Illegal" here is a synonym for "fun."

I had a case go bad once: An abusive husband shook his tail, got back home, and confronted his wife about the surveillance. He put holes in his walls and screamed threats while I sat in my car -- armed -- trying to decide what to do. If I broke into that house and he wasn't pummeling her senseless, I'd go to prison.

My fear of prison lost out against my desire to sleep that night, and I entered the house, Glock drawn. Something funny happens when you make your way through a strange house with a gun in your hands -- you realize just how many weapons lie around the average house. Whiskey bottle? One of those upside the head could kill me. Huge black dildo? Traumatic brain injury waiting to happen.

Stockbyte/Stockbyte/Getty Images
We call these "chicken knives," and they've killed many of my friends.

I found her in the bedroom, beaten up but alive. Her husband got away -- not that I could have done much besides shout "citizen's arrest!" if I'd caught him. The whole "not a cop" thing is frustrating -- just having that badge makes criminal trespass way less risky. I got lucky that night. Her husband wasn't about to press charges. If he had, it might have landed me with a burglary conviction and anywhere from two to 30 years behind bars. For trying to be a good guy.

Aaaand that's pretty much this gig: break the law and solve the case fast, or spend 200 hours pooping in jars in the back of your Cadillac DeVille and solve the case legally.

Always on the go but can't get enough of those sweet, sweet dick jokes? We have an Android app and iOS reader for you to pick from so you never miss another article.

To turn on reply notifications, click here

569 Comments

Load Comments