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Inside Look at Undercover Investigations

by Isaac Peck, Publisher

In today’s day and age, private investigators have a multitude of investigative tools: sophisticated databases, OSINT, surveillance, interviewing witnesses, public records, and the list goes on (and on!).

One of the least discussed and underutilized investigation techniques also happens to be one of the most aggressive tactics available to a PI: undercover investigations.

Undercover investigations are most often associated with law enforcement—i.e. a “sting” involving purchasing drugs, prostitution, and even murder-for-hire comes to mind. However, undercover operations can also be used by PIs in private practice across a wide spectrum of clients and scenarios.

Working PI magazine sat down with Ketwork Investigations LLC, an Alabama-based PI firm that specializes in undercover work, to get the inside scoop on how they deploy this very hands-on, and sometimes risky, investigation technique to get the best results for their clients.

Ketwork is led by Ketrick Kelley, James Hurley, and Tobi Libbra, each with a unique background and skillset—each of whom converged with Working PI for the interview.

Ketwork has successfully deployed undercover operations in a variety of high-stakes, high-profile cases.

Here’s an inside look into this fascinating investigative technique.

Working PI: Tell us about your background(s) in law enforcement. How does that influence your approach to undercover investigation work?

Ketwork (Ketrick): As a retired Special Agent with the FBI, I am well versed in undercover work. While in law enforcement I worked in the following undercover scenarios: conspiracy to commit commercial armed robbery and conspiracy to commit escape in the 1st degree (jail break). I’ve purchased drugs over 1,000 times, I’ve purchased stolen firearms, I’ve bought and sold stolen industrial equipment, I’ve negotiated fraudulent contracts with city officials, I’ve been a hitman, I’ve been a bagman, and I’ve even bribed a judge. I have also worked successful undercover operations against doctors (pill-mill cases) and attorneys.

Most of these stemmed from having a Confidential Informant (CI) introducing me as a confidant of theirs.

In law enforcement, undercover work is often preferable because if we get a defendant that is part of a larger group, he or she will often be offered leniency in exchange for complete cooperation. But having a government agent as a witness is usually better than just sending the defendant back into the lion’s den by themselves. A government agent is well-trained, knows specifically what the attorneys need and what the objectives are. So typically, in law enforcement, that was how an undercover was introduced—someone well-trusted in a criminal organization could vouch for the undercover’s identity in the operation.

Ketwork (James): Similar to Kit, I am also a retired FBI Agent and used undercover techniques throughout my career. My personal undercover work was more “white collar” than Kit’s, but we used the exact same principles. I enjoyed both short and long-term undercover assignments, in the US and abroad. I got to bribe a city councilman, sold fraudulent billing software to restaurants, and went undercover on a number of mortgage fraud and hacking/cyber cases.

One memorable case involved playing a dive-boat captain in Hawaii on a domestic terrorism case. While on another operation in Amsterdam, I was actually arrested by the Dutch military police because they thought I was one of the bad guys. In a case we worked with the Canadians, we had an agent living undercover in a house near the suspect—and the suspect actually confessed and bragged about a murder to our undercover!

I also had the privilege to work at FBI Headquarters in Washington, D.C., in the FBI’s “Clandestine Operations and Undercover Unit.” There, I oversaw FBI undercover operations globally and developed undercover training schools for the FBI and our federal, state and local partners. It was truly amazing to see how undercover techniques are successfully taught and used by law enforcement and intelligence agencies throughout the world!

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Working PI: What makes undercover investigations different? For what kinds of cases would you want to use this approach?

Ketwork (James): It all depends on the information you are seeking…and you’ll never get better evidence than by talking directly with the target. In some cases, you’ll participate alongside them in questionable activities; in others, you just try to get inside their circle and see what you’ll observe and what they’ll say about the truth of what is going on.

Ketwork (Ketrick): In terms of what makes it different, let’s start by defining each of the terms:

Conducted in secret or through the use of subterfuge, as in an investigation or in spying.

Deception used to achieve an end.

This technique can be used in almost all cases if they meet certain criteria. We also have ethical considerations we must look at. We’re always trying to get to the truth of something. Often, this is stuff you won’t get in a deposition. You’re hearing it straight from the target’s mouth. There’s often no way to get the information anywhere else.

Being able to consider each situation thoughtfully has allowed us to use undercover techniques in a variety of different cases. We’ve actually employed this technique in domestic cases. We used it with a case involving serial infidelity. The client wanted us to do an undercover investigation. Before you ask: no, we didn’t sleep with the target. We had other means, but we still had to approach it carefully and plan it out as a team because we knew we were going to have to put the undercover in a situation with unsavory conversations, texts, emails, pictures, etc.

We’ve deployed it in a criminal defense case where our client was accused of an assault and was adamant he did not do it. The client happened to have a lot of money. In that case, through the undercover operation, the target admitted the only reason she was doing it was because a civil attorney told her that if they had a criminal conviction, they could file a civil lawsuit. We helped save our client from both a wrongful criminal conviction and a civil case.

We’ve gone undercover in a Civil RICO case. We’ve done it in contractual disputes—most recently we went undercover on a case involving city officials.

We’ve also gone undercover on worker’s compensation cases. A lot of times, an undercover operation might cost less than surveillance. In the assault case, the target made admissions within 48 minutes. You can be on surveillance for weeks and weeks and not get what you want. With the right undercover op, you might be able to get to the truth faster. Whatever case we’re looking at, we look at the objectives, and we ask what the most efficient and best way to achieve those objectives is. Most of the time an undercover option is a good option, but not every time.

Undercover ops have been used for centuries in military, government, and law enforcement, but they’ve been widely underused or not used in private practice. We see it as a very, very valuable tool in our toolbox.

Working PI: What about recording the conversations and “two-party” states?

Ketwork (James): Since we’re often getting information straight from the horse’s mouth, we always want to get a recording if possible. We have a number of tools, clothing, and devices to capture the sound, but we also have to be mindful of what state we’re working in. In “one-party” states, recording is usually a given since it only requires the knowledge/consent of one party (our undercover). In two-party states, however, we no longer have the blanket authority we had as federal agents to record anybody at any time.

Ketwork (Ketrick): We try to record everything when we’re in a state that allows it. There are more one-party states than two-party states.

If we were doing a job in California, a two-party state, we would go about the investigation in the same way, we just wouldn’t be able to record everything. Our approach is to always gather other information that will corroborate what our testimony would be. If you are the target and you and I are meeting and having a discussion that covers some of the objectives, we can always talk about it again via text messages or email, recapping some of those discussions—that would corroborate my testimony. So, there are other means to capture that, besides a recording.

Working PI: Tell us more about how you prepare for an undercover investigation and plan it out.

Ketwork (Ketrick): For starters, we always work in a team. It’s not just one investigator who puts the plan together and runs off and does the operation by themselves. We plan, surveil, roleplay, and talk through the issues before ever contacting the target.

We start with planning. We have the target(s). Then we establish our objectives and do an extensive social media background scrub to get an idea of who they are, and so on. We will then conduct surveillance and figure out where they are, where they go, and what their normal pattern of behavior is. This allows us to figure out what kind of undercover we need for the role.

Once we have this foundation, we will pick an undercover for the job and start preparing them for the job. When we know where the target is going to be, we’ll send the undercover in prior to the target’s arrival, so they can be meeting with the people the target normally converses with. The undercover understands the first and only objective of that meeting is to get a second meeting. The target arrives and the objective is to get them to trust you. Oftentimes we’ll have the undercover connect with them on social media and build from there.

People like to talk about themselves. We train on ways to get information without seeming obvious. A lot of conversations unfold like this: I tell a story, you tell a story. Sometimes you can spark that conversation by telling a story that’s similar but not as glamorous as the target’s story would be. The target will then tell their story and you can ask follow-up questions to that because now the target has brought up the story. We practice all that with our stories. This helps us get to the meat of the matter and is an indirect way to get the information we need.

There are a number of logistical and ethical considerations. For example, we have to consider how this is going to affect the personal relationships of our undercovers. We also have to consider if the public interest outweighs the undercover scenario. We have a checklist of things that we address as far as ethics. No single case is worth destroying relationships or jeopardizing future endeavors over.

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Working PI: Do clients specifically request undercover? Do you offer it up?

Ketwork (Ketrick): Oftentimes, it is an option we will bring up to the client and then we’ll have a larger discussion around it. We have clients we have done extensive work for and successfully used this technique with in the past, and often they will request it.

Working PI: What are some things PIs need to know about undercover work?

Ketwork (Tobi): As PIs, we have a lot of tools in our toolbox. When to use which tool is the question. It can be fantastic, or it can be a waste of time and resources.

Understanding not only if you can do it, but should you do it, is just as important as the technique itself. Most times, it has to be before the other side is represented. If one side has filed in court, you can assume the other side is represented. In that case, all surreptitious activity is off the table unless your attorney thinks he can argue it was necessary and/or an ongoing thing.

We have a checklist of whether or not a case meets specific criteria. Having a documented process builds legitimacy toward the case and the undercover’s future testimony—that way, we’re not just a random person walking into a bar. We have a process, a plan, and an experienced team backing the undercover up. We try to look at the situation from as many different angles as possible. Ultimately, it’s not what the conversation is or what evidence is gathered, it is whether that evidence is going to be admissible in court. Is this evidence going to be accepted by a juror? It has to be presented in a way they’re going to be able to digest.

PIs must understand this is a super aggressive investigative technique. As PIs, when playing an undercover role, we are often accused of being professional liars. In the context of working undercover, the answer to that is “yes”; that’s exactly what happened! But we have a team of people around the undercover who have helped them shape that assignment. As PIs, our primary objective is to find the truth.

Undercover work is not for everyone. Not everyone wants to do it; not everyone will be able to do it. With that said, building your team, designing your process, and planning your operation is key. Botching an undercover job can ruin the case for your client. We don’t recommend trying this alone. There’s never a time that I’m doing undercover that both Kit and Jim are not 20 feet from me. We do so much preparation and planning, considering safety, the background of the target, and so on. You want to walk into this with a team. Thinking about going undercover or seeing it on television is very different from actually doing it.

Working PI: How does undercover evidence and testimony actually play out in court?

Ketwork (Ketrick): If done correctly, undercover operations typically uncover damaging evidence. Undercover work is an aggressive technique. When there is nothing else for opposing counsel to defend, they will go after the investigator. So be prepared for it to be very adversarial.

In terms of defending your process to opposing counsel and presenting it to a court, the number one thing is to have specific objectives that are outlined. In other words, you must show when you met with the target—it wasn’t just a fishing expedition.

You have to consider how this is going to play with jurors, as well as the judge. There is no question there is an opposing argument for the use of the undercover technique. The undercover is fabricating a story and this character is not real.

That’s why it’s so important to outline the specific objectives so you can explain it to the judge and the jury. Your investigation in a case is multi-dimensional and informed by historical information, text messages, emails, contacts, and witness interviews, along with the evidence that the undercover operation provides.

Oftentimes in litigation, the thing that’s missing—and the thing that can be explained away—is the target’s true intention. An undercover investigator discovers the true intention of the targets. So, your objectives need to be outlined in a contractual way: what the specific objectives are and what we are trying to uncover. Prove or disprove what the intent of the targets was.

Opposing counsel will try to paint it in a light where you’re just on a fishing expedition. You’re a professional liar and they want to paint you like you broke into a house and you’re rummaging around looking for the jewelry and the cash. If you have those specific objectives outlined in advance, and you can show them to a jury or a judge, it answers that back. You can say: we didn’t go outside of those objectives. We didn’t ask them about their personal finances or their sexual preferences outside of the “getting to know you” and the rapport-building small talk. We structured the dialogue based on these particular objectives.

It’s another reason you need an experienced team who is backing you up and has been down the road 1,000 times. They can put controls in place. You don’t want to go into an undercover op with a shotgun—you want a precision weapon. So, you need an oversight piece of it, including discussions before, during, and after.

Sometimes on undercover ops, you have specific objectives—you get in there, the target will say something, your attorney listens to the conversation, and they may want you to explore something else that wasn’t initially outlined. That’s fine, as long as it is documented. You want documentation on what you did, when you did it, and you want to demonstrate you have oversight on this particular operation. It’s very intrusive, but you need this to be credible and palatable to the jury. You need to be well-versed on what entrapment is. A lot of that comes with oversight and roleplaying with the undercovers prior to the operation.

Opposing attorneys will try to blur the lines between the undercover personally and the undercover role. They will try to make assumptions that the undercover’s personal beliefs and thoughts are the same as the character that the undercover is playing. This is a role. Nobody thinks Harrison Ford is a Professor of Archaeology. These aren’t personal thoughts and feelings—this is an undercover investigator playing a role based on the objectives.

Working PI: This is fascinating stuff. Is there anything else you’d like to add?

Ketwork (Ketrick): We are working to put together a training piece for private investigators who may be interested in or are considering this type of work. So look out for announcements on that. Also, if you have a case that justifies this method, we have a team that specializes in this. You can reach out to us at www.ketwork.com.

About the Author
Isaac Peck is the Publisher of Working PI magazine and the President and Senior Broker of OREP.org, a leading provider of E&O insurance for the PI industry. Working PI is the most widely read print magazine for investigators nationwide, reaching over 25,000 PIs. PIs who become OREP Members enjoy an 8-hour CE course at no charge (Visit OREP.org/PI-Members for details). Reach Isaac by email at isaac@orep.org or by phone at (888) 347-5273. CA License #4116465.

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