What It's Like to Be an Undercover FBI Agent

Working as an undercover agent probably ranks as one of the most terrifying and dangerous things you could choose to do with your life. You're thrown into the deep end to infiltrate some of the world's most violent and paranoid criminal organizations and face immense pressure to extract intelligence while not getting brutally murdered. There's also the murky ethical ground you're constantly treading: the fine line between enticing criminals to reveal their most sordid plans and entrapment.

Bob Hamer spent 26 years doing undercover work for the FBI. In various disguises, he writes on his website, he "successfully posed as a drug dealer, contract killer, residential burglar, fence, pedophile, degenerate gambler, international weapons dealer, and white-collar criminal," and was involved in operations against everyone from the Mafia to the pro-pedophile group North American Man/Boy Love Association (NAMBLA).

I first spoke to Bob Hamer while working on a piece about North Korea's role in the international drug trade. The last case of his career was Operation Smoking Dragon, a sting operation that took down a cell of Chinese smugglers who were bringing weapons and counterfeit cigarettes into the United States. At one point during that gig, Hamer was propositioned to help fund a giant meth factory in North Korea.

Hamer's been busy since his retirement, writing books, including ghostwriting one for Oliver North (of Iran Contra fame—Hamer is fairly conservative). He's not what you'd necessarily expect from a grizzled undercover cop who's infiltrated the inner circles of drug cartels, pedophile rings, and weapons smuggling operations. He speaks with a friendly Midwestern twang that's more Fargo than Infernal Affairs, is a big-time Christian, and is generally a very affable guy.

I called him up for a chat to talk about the old days.

VICE: So how did you get into working as an undercover agent for the FBI?
Oliver Hotham: I was looking for excitement, and while I was in training at the FBI academy, a couple of the instructors had done some undercover work, and I thought, That seems interesting and exciting. So I looked for those opportunities once I graduated. I gravitated toward individualism: I sought it out. I'd conduct interviews by myself, and I liked the idea of working undercover and posing as someone else.

How do you begin to infiltrate an organization and work out how to make contact?
It varies with each assignment. In most, I had an informant who'd introduce me—typically, we had somebody that we had arrested and they were "working off a beef," they were cooperating with us in order to lessen their sentence, and they'd introduce me. That made it much easier than it was on several of the cases where I had to infiltrate a group on my own, without the introduction.

How did you get into the character?
As an undercover agent, you have to see the gray—you have to find some goodness in a person in order to be attracted to them. Criminals can smell fear, they can smell hatred, they know when you aren't accepting of their lifestyle. And as an undercover agent, you've gotta understand them in some way, be it the child molester, be it the drug dealer, be it the weapons dealer.

What do you think about the ethics involved in undercover work? There have been allegations of entrapment, particularly in terrorism cases, where defendants feel they have been led on. Do you think that's a problem?
To me, the undercover case is the best investigative tool to put a case together, because particularly when it's an undercover agent—not an informant but an undercover agent—you have a trained law-enforcement officer that knows what it takes to put a case together. There aren't a whole lot of defenses when the bad guy hands me the weapons, when he hands me the drugs, when he's on tape saying that he wants someone killed.

So you don't feel there have been situations where you felt there was a fine line between leading someone on and encouraging someone to do something?
Not in my case. There may have been in others, but I always tried to give them an out in some way. A good example: in Operation Smoking Dragon, we had a female and on more than one occasion I would tell her, "Why don't you go work for a living? If you put this much effort in, you could make money." And she'd say, "No no no, I don't wanna do that, it's more money making this." I think that the good undercover agents that you're gonna find, they give these people the opportunity to back out, because they want [to guard against] the argument that "I was entrapped" or that "He forced me into doing it."

So how did you go about infiltrating NAMBLA?
The actual infiltration was initially very easy: I sent in my $35 [€32] and joined. I began doing an awful lot of research on what it's like to be a "boy lover," as they call themselves. How do they talk, how do they act, what their interests are, that kind of thing.

I started receiving emails from them asking me if I would participate in their pen pal program, where they would send cards and letters to incarcerated members. So I started doing that. I also started writing articles for their magazine, The Bulletin. They began to see me as a true believer.

It actually took a year and a half before they eventually invited me to a face to face meeting—they were very paranoid, the most paranoid group I had ever targeted. I went to my first meeting and then went to a second a year later and it was at the second meeting that things really took off. It took me a long time to even be in a position where they were willing to accept me.

So what happened at the second meeting?
We had gone into it a little more aggressive that we did the first. But within an hour of arriving in Miami, Florida, for the second meeting, I met an individual who was a part-time airline flight attendant and he started talking about—unsolicited—how he would fly overseas using his benefits with American Airlines to have sex with with little boys in Thailand, and he would fly down to Mexico and have sex with boys in Mexico, and starts saying to me, "We should go on a trip to do this."

How did that investigation pan out?
The NAMBLA case resulted in the convictions of eight members of the group's inner circle. Two were Steering Committee members—the group's governing body. We convicted a PhD psychologist, a dentist, an ordained minister, three special education teachers, a physical trainer, and a blue-collar worker.

What was it like readjusting to the world after an assignment like that?
It really was my most difficult case, but not from a safety standpoint—quite frankly, if they had jumped me, I could have taken care of myself. I think I could take on about ten NAMBLA members and probably survive.

But psychologically and emotionally it was hard, but at the same time I was in NAMBLA, I was working Operation Smoking Dragon, so when we took down the NAMBLA case and arrested the eight members of the inner circle, within two or three days I was back with my undercover meetings. They're really wasn't time to decompress.

It probably sounds silly, but it was cathartic to start dealing with an international weapons case after hanging around boy lovers. I only had one undercover cell phone, and so I used to joke, you know, when the phone rang I didn't know whether I loved eight-year-old pubescent boys or I was a macho international weapons dealer.

What was the most dangerous mission the FBI sent you on?
I don't mean to sound glib, but every investigation is dangerous, even the white-collar cases, because they're the ones that are most fearful of prison. But I worked gangs for five years in South Central Los Angeles, I was by myself at midnight in an old beat-up pickup truck purchasing rock cocaine from gang members, which obviously was dangerous.

When you think you got closest to being caught out?
I had friends of mine walk into a half-million dollar heroin deal when I was sitting in the lobby of a hotel. The target of our investigation had just told me minutes earlier that his partner had a gun and "if anything goes wrong, you're the first person we're gonna kill." Within a few minutes of that, this couple that I knew from Cincinnati, Ohio, several thousand miles away from where we were located, a couple that I had lived with for a semester when I was going to school, walked into the lobby of the hotel and saw me.

I kinda signaled to the woman that this wasn't the time for grips and grins, and she could tell by looking at me that this wasn't the ideal opportunity—she knew I was an FBI agent.

What's your impression of the portrayal of undercover cops in TV and movies?
The Departed was way over the top, but I think [Leonardo] DiCaprio did a good job of mentally and emotionally [capturing] what you're going through when you're undercover.

My biggest complaint about Hollywood is that they portray every undercover agent as a womanizer, an alcoholic—they're always going over the line, participating in crimes. In my experiences, the most successful agents I've seen are the ones that are wel- grounded in something: in their religious beliefs, in their moral beliefs, their family, you know? If you're trying to hide your alcohol abuse from your supervisor, if you're trying to hide your womanizing from your wife, you're having trouble focusing on the role you're trying to play.

What's it been like adjusting to civilian life?
I'm bored stiff. I've written five books, but I miss the adrenaline rush. I miss sitting down face to face with a bad guy and convincing him that I'm just as bad as he is, or getting him to admit to me what he wants done and engaging him in a criminal conversation—that's the greatest thrill. That's the hardest thing to overcome, knowing that I can't do this anymore.

This interview has been edited and condensed for clarity.

Follow Oliver Hotham on Twitter.