A Detective Answers Every Question You've Ever Had About Being A PI

His appearance was clean, cool and deliberately ambiguous. Under the sanctuary of his aviators, his eyes silently scanned the room. He looked like a cross between Mike from Breaking Bad and Donald Sutherland. As soon as he walked into Supercompressor HQ, we knew we had found our man. 

Michael McKeever is a Manhattan-based, third-generation private detective who's been in the business for more than three decades—specializing in surveillance and being an overall mystery-tinged badass. We asked him everything we've ever wanted to know about the profession and about his wildest stories working on the streets of New York. The answers, should you choose to believe them, will paint a thoroughly accurate portrait of a professional PI.

So, what exactly do you do?

I do a lot of surveillance. Basically, someone who wonders, “what is this other person up to?” If it’s an insurance company (surveying someone on workers' comp), they'll ask “Is he back working?” “Does he use a cane?” “Is he as bad off as he says he is?” With domestic cases, “Is my partner fooling around?” “Why does he come home late?” Things like that.

Another very common request is locating people, and it could be for a lot of reasons. I had a case recently, a man hadn’t been in touch with his mother for 20 years and I helped him find her. It could be an old friend, an old flame, "the one that got away," someone they need information from, or someone they are just trying to reconnect with.

What kind of skills make for a good PI?

Patience. Number one. You can’t pick that up, or learn that really. You have to pay attention. You have to be the kind of person, if you sit in front of a door watching it for six hours, and you haven’t seen your guy. You KNOW he has not left. You have to know. You can’t sit there for an hour and then say, "Oh I have to get a cup of coffee," or "I have to go to the bathroom," and leave. You can’t have any gaps. Every time you leave, you are starting over. You have to plan accordingly, and be willing to make sacrifices in order to stay out there. It’s not a job for people who want to slack off. And you have to handle all the administrative duties yourself, too: billing, scheduling, etc. 

Can you handle cases outside of New York? 

You are allowed to work in other states, as long as it involves a New York client. I can’t solicit new clients in other states. Carrying business over to new states is allowed, if I’m working on something.

"A lot of police feel like they have the skills to be a PI, but that’s not actually true."


Did you ever do international work?

I went to Paris for a case. Another PI that I know, that knows I’m a good surveillance guy, wanted me to do some work for him. The client was a woman whose husband was a dotcom millionaire, and he was abruptly leaving the family for another woman in Paris. She didn’t know anything about this woman, you know? And she was going to be the stepmother of her children. So she wanted a little bit more info on the woman. Well—turns out she was in fact, a hooker. So her suspicions were valid. Right?

If you needed to locate someone, what's the ideal information you need to start?

Usually, this what I tell people: if you want to find someone, I need the name with the exact spelling, the DOB if you know it, the social security number (which generally people don’t know unless it’s family), and a last known, official address where they’ve lived within the past 15 years. Because that means they’ll be in our database. And that info alone can often lead me to the guy right in one of the databases, and it’s done right there. "Ok, now he lives in Hoboken, New Jersey—here’s his address."

These informational databases sound insane, how do you get access to them?

Well you have to be a licensed PI, and they have to review your information. You have to swear you know all the relevant privacy acts, and you won't violate them. Most of them, every time you log in and look for information, you need to click on boxes confirming you know the privacy laws. You know, every time you log on you are confirming you are using them the right way. The client has to have legitimate reasons for looking people up. They have to document their reasons and send them to me. They could be lying, of course, but you get as much official info as you can (legal docs, court papers) and trust them as much as you can. 

Has the internet cut into your business?

It has in a way, because people think they can get certain information themselves now (using internet searches and databases), but this is generally not true. Because the databases we subscribe to—and are allowed access to—are not available to the general public. You have to be a licensed private eye, and you have to be aware of certain regulations, like the Privacy Protection Act. The vast amount of things out there on the internet are things like info from old phone book data, things of that like.

Do you use Internet services in your cases?

That’s an interesting question. Recently I had a case, where a woman was looking for her father—never knew him, her mother had an affair with this guy who was in the Army in the mid-sixties, the guy went to Vietnam, and never came back to her. The woman knew his name (which is good), and was fairly sure he was from New Jersey. There were two people in the database with his exact name, one had a social that I recognized as being from New Jersey—so I found his address on Google Maps. And you know they have photos on there, sure enough, in the driveway was an American-made SUV (a lot of vets prefer American-made cars), and on the bumper: a Vietnam veteran bumper sticker. When I saw that I thought, "Okay, here we go."

Do you need to have a background in law enforcement to be a private detective?

You don’t have to be in law enforcement previously, but yeah, it does happen frequently when they retire or when their pay is cut. You know, a lot of police feel like they have the skillset to be a PI, but that’s not actually true. Being a police officer does not give you adequate training to be a PI. 

"So there’s five dead bodies. And now the FBI is really, really involved."


Do you have a relationship with local police? Do most private investigators?

I would say that’s kind of a myth. In my case, I come from a cop family; grandfather, father, uncles—I would never want to get a cop in trouble for helping me out, and that 's what it comes down to a lot of the time. Most cops wouldn't even do it in the first place, because they know how serious of a violation it is. A lot of times, cops become private eyes, then get in trouble for selling/buying information from their friends who are still on the force. If cops provide information that is confidential for money, everyone involved can be arrested.

I’ve even heard of guys hanging around the police station and waiting for people to leave their computers to go to the bathroom or whatever. I mean, that’s pretty low. And a lot of times, the shortcuts are just that. I don’t work that way. I don’t work for favors, and I don’t do favors. That’s how you have to be.

How much do you charge?

Besides quick locates, I have a $500 minimum. That's going to be for about four hours of surveillance, for just me alone. If you need two guys it's more. Sometimes we hire stringers (other private eyes ‘freelancing’) for bigger cases, then it’s more.

What's the longest you've worked on a case?

I’ve been on cases for 12-14 months, multiple years sometimes. Sometimes people want someone followed for years, and have no problem spending thousands and thousands of dollars. My biggest case was $50K at one point, now it's gone even beyond that...people are getting good intel, they want to keep tabs on someone...they’ll just keep going.

What was your most dangerous case?

I've done a lot of dangerous jobs. I’ve trailed pimps and criminals and all that, but there's one fraud case that comes to mind. The guy I was following was in the gold business, and he borrowed a lot of money he wasn’t really entitled to from a factoring company by faking his inventory numbers. Of course, he couldn’t pay it back (it was around $8 million), so the firm that lent him the money was going after him and wanted me to follow him to keep tabs on some of his assets. As it turns out, someone in his little firm (he had about eight employees) was working with the FBI. He found out and had the person he thought was helping the feds killed by a hitman.

Then he decided to have his bookkeeper killed—and the real irony is neither one of those women turned out to be the informant. When the hitman he hired came to kill the second woman, he was going to grab her, throw her in his van, and drive away with the body. She screamed so loudly that a few guys came to help her out, and the hitman ended up killing them too. So there’s five dead bodies. And now the FBI is really, really involved. I actually had to testify to connect the link between the guy and the hitman. I had seen the hitman going to and from the building where the guy worked on the days the hits were commissioned.

Once that happened, the job was over. The FBI was all over it at that point. We used to trail the guy with two cars, then the FBI started trailing the hitman and the guy with helicopters and all that stuff. They do things a little differently. It was called the CBS case, because it was a few technicians from CBS that came to the second woman’s aid and were killed inadvertently. Good samaritans, right?

"Just because someone has a gun doesn't mean they aren’t going to get shot. It’s not a shield."

Do most private eyes carry guns?

I don't think so. I used to, but I don't anymore. Retired cops often will, but cops tend to get a little paranoid about the dangers of the job. But just because someone has a gun doesn't mean they aren't going to get shot. It’s not a shield.

Have you ever had a gun pulled on you?

I’ve had guns pulled on me about four or five times. Staked out in sketchy area, even cops will throw down on me because they don’t know what I'm doing. One time, we went to collect this guy’s things from the apartment he shared with his wife—they were separating and she had changed the locks. He technically still lived there, so we called a locksmith and were legally able to get back in there. The wife called her uncle and he came down with his gun out, threatening me, crazy sh*t like that. People get crazed. But usually it doesn't directly involve you.

What do films and television shows get wrong about being a PI?

One of the things they do in movies and TV is have guys who are working on just one case at a time, and that never happens. You don’t go out and work on a single case for weeks and months without taking other business. I’ve seen some good PI movies, The Late Show, Chinatown. The other big difference is, the things you see in films do happen to private detectives, but they’re shrinking down maybe 20 years of adventure into an episode, then the next week doing it again. I've had exciting, interesting cases, but I've been doing this for like 30 years. After 30 years, I probably have one good movie worth of experiences.

So, even Chinatown kind of misses the mark?

Chinatown is a good one. I have some Chinatown stories myself. Benny Chin was a PI down in Chinatown in my early years. Everyone knew him, he did debugging (checking for wires in homes and offices) and stuff. Then I heard, “Benny Chin was shot to death in a garage in Chinatown.” Turns out he wasn’t licensed. So I said to the other guy, "can you believe Benny Chin wasn’t licensed?" And he said, "I can imagine he wasn’t. The shit that he did, he would have lost his license anyway. He was doing illegal stuff all the time." That was an eye-opener for me.

What are some pro-tips for trailing people?

There’s a lot of things to do to trail someone on foot. Don’t be the first thing people see when they leave a building, even though you need to see them. You're better off being at an oblique angle. If you follow someone on the subway, you almost never have to be in the same car as the person you are following, but you have to make sure you leave behind them, so they don’t run into you. On foot, it’s really determined by environment. If it’s wide open you can be 100 feet away, but if it's a crowded city block you gotta be like 30 feet away. It’s not really a science. If they turn a corner you need to hustle, of course.

One thing that’s good if you are trailing someone is to have a different look. Wear a jacket, get on the subway with the guy, and then take your jacket off. Keep a baseball cap in your sleeve and when you take your jacket off, put the cap on. It changes your look a little bit, gives you a little confidence.

You have to be careful with what you do. You can’t be driving a cherry red BMW and expect to slip under the radar. The same thing with the way you dress. You also need to blend in, in a way that other people just won’t register you.

What about trailing someone by car?

The same rules pretty much apply as on foot. If someone is on the expressway with no exits for miles at a time, you can keep your distance, because where are they going to go? If you are following them in the city, you kind have to be one car behind them because if the light turns red, and they turn, you’ll lose them—and that's the end of it  Sometimes, I’ll put a hard hat on the dash of my car if I’m waiting somewhere, and people kind of brush it off as a “construction guy, goofing off," and tend not to pay much attention. 

Is it illegal to follow people and record them?

No. It's not illegal. You have to be concerned about the invasion of privacy. If I'm trailing a guy for an insurance company and he says he has a bad back and is out on the street changing his tires, I can videotape it. If he’s in his yard with a high fence, lifting weights, I can’t climb a tree and videotape him. It has to be in plain sight. People have an expectation of privacy, as the law says. Even in someone's apartment, you can’t zoom inside, but if they are standing by their window doing the Jane Fonda workout, it’s possible that could count as plain sight. It depends on the situation.

What kind of obstacles do you run into when you are trailing someone for extended periods?

Recently I trailed a woman from New Jersey. She takes the express bus into the city. I needed to get on that bus. So I took the bus to the city with her, and then she got off to transfer to the crosstown bus, so I did too. I’m in line behind her, and she turns to me and says, “Oh you can go ahead, I’m not getting on because I want my own seat.” Luckily, I had a different outfit and hat, so I ducked back and changed my look. I followed her onto her bus to her workplace.

She goes into a building on Madison. I needed to see what floor she was going to, so I had to get on the elevator with her. Now I’m sweating, because I’m the guy she had talked to on the street before. I look different. But it’s still me, and she could still make the connection. She never noticed. And I found out where she worked, which is what I needed to find out.

What's the future of private eyes? Do you even think there will still be PIs in 10, 20 years?

A lot of the basic stuff like surveillance: "Is the guy working?", "Is he really hurt?", "Is my wife seeing someone else?" That’s not going to change. You still have to be out there following the guy. I don’t think that’s going to change. There’s no replacement for the human element, the decision-making, and the ability to blend into a crowd and make decisions on the spot. I don’t see how that can be taken over by technology.

Have you ever tailed any celebrities?

I trailed Jackie O for a little while for another PI. We were working for a tabloid and they thought she was going to get married again in secret and wanted the scoop. I’ve done other work for, and with, celebrities, but she’s the only one that’s passed on, so I can tell you about it.

What are some of the weirder requests you've gotten?

I had a guy once who thought his wife was having sex with his nephew. Turns out he was right. It was his brother's son. Not too good.

I had another case kinda like that, where a guy ran off with his daughter-in-law and his grandson. It was bizarre.

Do you lose people a lot?

No, actually. I've been doing this for a long time. I'm pretty good.

Wil Fulton is a staff writer for Supercompressor. He'll be following a lot more people now. Follow him @WilFulton.