Q & A With A Real Undercover Operative– Part II

If you missed yesterday’s post, Q & A With A Real Undercover Operator – Part I, you really should go back and read it to get the most from this interview. You can find it here, or click on the title above. Reminder: please no reblogging unless you revert your followers to the original, as permission was only granted for this site. Full disclaimer on Part I.

While you’re reading this interview (including Part I & III) I want you to notice his ‘voice’– his word choices and sentence structure. I did very little editing so this could shine through. It gives us an extra advantage when creating characters of this type. In our lives it’s not likely we’d ever come across an Undercover Operative, and if we did we’d never know it. So take advantage of this.

Okay, here we go…

How do you go about convincing someone to confess? I would think this must be handled with finesse. Most people probably aren’t willing to reveal their darkest secrets, especially murder. So when playing ‘Mr. Big’ or one of his ‘gang’ members, what do you say that makes a killer want to open up and tell you the whole story, or where the bodies are buried?  

This is my favourite part– the psychology of persuasion.  Doing an undercover operation is like creating acts in a play.  In fact, we even call each act or exposure to the target a scenario.  The goal of each scenario is to develop rapport and credibility.  This leads to trust and eventually a confession.  But, the other part that is important is ‘pressure.’  Under stress or pressure, people will react without deep thought– it’s referred to as peripheral thinking.  Someone under pressure will react without fully evaluating the information or consequences.

This is a real murder file:  In the disappearance of a woman who was presumed deceased (no body) I was primary UC on a suspect who was believed to have been last seen with the woman.  At some point during the file, the suspect and I were out of town doing a scenario.  I had a cover story of being a smuggler– bringing contraband, liquor and cigarettes, over the border.  The target had not revealed to me anything about the murder at this point, other than being questioned by the police.  When we were approaching a City, driving in a rural area, he told me that if I ever needed to bury a body he knew a good place.  So, I made note of where he mentioned this on the drive.

A month later we designed a scenario were we (UC Team) drove out in this area again and met a contact that I was dropping contraband off to in exchange for cash.  We had a concealed video camera watching the target’s reaction as I drove in this area.  We noticed upon review of the video (I actually also noticed by watching him) that he leaned forward and looked down a road toward the river (while we were driving in this area).  His reaction was strange and he seemed concerned and happy at the same time.

This made me believe that he had possibly disposed of her body in the river.  So, I designed a scenario where I was driving with the target and we were cued listening to a news radio station.  I had the head of the homicide unit give a news release saying that the police were going to search this area of the river for the missing woman (creating pressure/stress).  Depending on the target’s reaction (if positive), I would then signal the team to have the head of homicide call the target on his cell phone and say that they had new evidence and needed to talk to him immediately (again, pressure…).

The target’s reaction was perfect– he was stressed to the max, swearing and freaking out.  I told him that I had committed some armed robberies in my past and my ‘boss’ (Mr. Big) had hid me so that the heat (from the police) could die down.  But, that he would have to come clean so we knew how what he did could affect our crime group– bring heat on us / our illegal business.  I also said the ‘boss’ was only in town until tonight (more pressure because he had little time to decide), so he better talk now or he would loose his chance.  Well, out it came…

I then set up the meeting with the ‘boss’ (all captured on video) where he graphically described how he killed this woman and dragged her body onto the ice of the river.  Then, picked her up several times and smashed her into the ice until she went through.  I might add that at trial the judge’s face dropped when he watched the video.  The calculated and feelingless look on the target’s face as he bragged about killing her.  I spent 5 ½ months with this guy leading up to the confession.  He was also a potential suspect in the murders of two other women– this led several members of the investigative team to believe he may be a serial killer.  He is currently serving 25 years with no chance of parole– and, also said he would kill me when he gets out.  Lol, get in line…

The best persuasion information I have found, but it’s theory and not specific to undercover work, is Dr. Cilidini– ‘Persuasion and Influencing.’  I have actually taken the theories from this book and designed scenarios in undercover operations and the recruitment of agents and informants in organized crime groups.  And, even taught Influencing courses to the military.

I would imagine keeping the Mr. Big character in check would be crucial in your everyday life. After all, most people don’t want to sit down to dinner with a criminal. So, after a long stretch undercover work did the Mr. Big personality ever slip out at the wrong time? And how did you handle it? 

Not really.  The Mr. Big role is usually very short.  It’s generally near the end of the file, like the above file explanation. Mr. Big is generally brought in for the finale only.  He may be seen a few times through the file by the target, but we (UC team in planning the scenario) would intentionally not let the target have face time with Mr. Big.  It made that finale meeting very important, as the target felt privileged to get an audience with the big man.  This developed respect for Mr. Big with the target, and more easily led to a confession.  As the target would want to impress Mr. Big when he got the chance to meet– they frankly just give more detail that we assumed existed.

This reminds me of a tactic called environment manipulation.  That is, you create or control the environment that you expose the target to.  For example, if the target killed the victim and disposed of their body in the ocean it may at some point benefit the file to take the target ocean fishing.  This may stim conversation that may lead to gaining evidence– an ‘Evidentiary Scenario’.

What can you add so we, crime writers, can make our undercover characters more believable? For instance, what temperament does an undercover operative need to have to be successful? What character traits are necessary and which ones hamper the investigation? 

Undercover members are a different breed.  They have a zest for adventure and definitely have egos– big ones!  Lol.  As I mentioned above– alpha males, risk takers, and most have an edge.  I would also say, that most of the really good ones (there are bad ones) can talk their way out of anything.  To do this you have to be quick thinking and ‘read people’.  Picking up slight body language is imperative– you need to see it coming before it comes.  You need to anticipate a target’s reaction and be two steps ahead.  You would pretty much ‘funnel’ the conversation with a target in the direction you wanted, without the target detecting you’re doing this.

And, very important, you have to be believable!  Trust me, having a gun to your head and being asked to ‘prove your not a cop’ is all about believing it yourself.  You truly have to close your eyes and then open them believing you’re a different person.  It’s acting, but with a twist– in a movie you would get a bad rating from the critics, in a file you could end up with a bullet in your head.  In terms of personalities, I saw them all in UC work, both outgoing and introverted.  In some cases one would out perform the other, but it was mostly dependent upon the target.  And, a good UC who was an introvert could pull off being an extrovert with complete ease.

Traits that hamper a UC operation were UCs that were fearful or not confident.  I recall one UC where I was Primary with a new member on the UC Team taking a secondary role.  At some point a few weeks into the file, the target told me that he didn’t like my secondary UC.  He said, “I just don’t feel comfortable around that guy.”  In looking at the video, I noted that the UC looked scared.  I didn’t pick up on it at the time, but the target certainly did.  We ended up cutting the UC from the Team shortly after– in fact, he admitted it wasn’t his thing.  It’s truly not for everyone, in fact it’s hardly for anyone.

I always got a kick out the new and old UCs.  The new ones (6 month – 2 years) are more like the above– cocky, overly confident, risk takers, and frankly too new to know how much danger they are really in.  The old ones are crusty and confident– with an even bigger ego!  But, the big difference is that they look at the risks differently– they have more to loose (family, kids, etc.) so they don’t take the same chances.  But, the old timers also carry huge skeletons.

I have to say, the results of years of undercover and informant/agent handling makes you look at the world through a different lens.  The results manifest in many ways from what I have seen.  I was involved in numerous Undercover Files and recruited and handled some of the highest levels of Informants/Agents in Organized Crime.  During all this I slept with a gun under my pillow (I seriously did).  Every time I came home from work, I would conduct counter surveillance to ensure I wasn’t followed.  Then, once I got inside I would search my house at gunpoint.  Sleeping was something I dreaded.  More often than not, I would wake up swinging if I heard a slight noise.  I have assaulted my wife and kids from being woken up– they don’t even consider trying to wake me now.

I still struggle with sleeping and probably always will.  Some of the guys I worked with are full-on alcoholics– some have even been kicked out of the force.  Almost all lost their first and second marriages…  And, you truly don’t realize what this work does to you until you’re out for a year(s).  There’s lots more I could say on this, but the reality is that to do this work and be healthy it must be short term.  Long term exposure to the minds of killers makes you more and more confused and lost.

I stopped questioning why killers murdered and just did my job, it helped me to get through.  I just think if you try to understand the why, you will get caught up in an unhealthy cycle, because every time you complete a file you get further away from the answer.  Not sure if that makes sense, but to me I never really got the answers I was looking for.  I felt a sense of accomplishment with every confession, but I also believe that exposure in this type of work is like being exposed to small quantities of radiation.  It doesn’t kill you, but it changes you.  And the damage is irreversible.

What kind of documentation do you need before you can begin a sting operation? Meaning, what kind of warrants, wiretaps, etc., and how do you secure them so they do not become public? 

It depends on the file.  For most all files you need a ‘one party consent.’  This is a document/affidavit that I (a UC) would sign, and it gives permission to record me while in conversation with anyone else, such as the target.  This information can then be used in court proceedings.  A wiretap, or a ‘Part 6’ Authorization is recording conversations without the consent of the target.  So, a target talking on the phone to another target, or a listening device hidden in the target’s car or house, etc.  In most UC homicide files you will likely need both.

A Part 6 Warrant is very difficult to obtain.  You have to prove to a judge that you have exhausted every other investigative avenue.  And that the seriousness of the offense justifies the invasion of privacy for the target.  I have seen documents in excess of 2000 pages.  So, these documents would be created and given to a Judge to review and authorize.  The UC Team would not write the Warrant, it would be the investigative team on the file (i.e. Homicide Detectives).  These documents are very research intensive and require information from multiple police resources:  surveillance observations/notes, statements for witnesses, statements from investigators, CSI forensic evidence, etc.

By securing (preventing disclosure) the Part 6 Authorization, it is done by a Sealing Order.  Essentially, it’s a document that a Judge also has to ‘approve/sign’ which gives the police permission to not disclose to the public or the accused.  It would eventually be unsealed and disclosed.  But, only if:  it will not jeopardize an ongoing investigation– many investigations take a turn into another and by disclosing you could jeopardize the ones that stem off the original;  it doesn’t jeopardize the identity of an informant– many wiretaps have numerous information sources to establish the grounds, including information from confidential human informants– in the courts the identity of these persons is protected (under certain circumstances); and is in the public interest– this is an interesting statement, at times the actions of the police can bring the administration of justice into disrepute (i.e. discredible conduct, etc.).

In cases like this the file would likely not be prosecuted.  In many cases the document is vetted by the Investigative Team (some information is removed or covered up) and disclosed.  So, some information which may be considered sensitive would not be made public, or given to the defence.

I am frankly not an expert on wiretaps, as the investigative team (not the UC team) would create and author the document.

If I was writing a character who knew someone was guilty of murder, but he had nothing but his gut telling him so, how would he go about gaining the evidence he needed to secure the proper warrants? 

This is a tough one to answer.  If you provide me a ‘for instance’, I could tell you how I would start and perhaps were it could lead.  Some of the above tactics and documents may be my starting point.

Okay, let’s say a drug dealer, for instance.

The gut feeling may be a starting point, but in court it has to be evidentiary.  So, if I saw a guy who in my gut I believed was a drug dealer I would have to articulate that he looked like a drug dealer because of similarities I had noticed about him in working files involving drug dealers.  Then, build a prosecutable file. For instance, I then checked his license plate and noted police files where he had been stopped in an area of town known for drug trafficking.  Then, I noted that he is associated to a person who has been convicted of drug trafficking.  And, this led me to conduct surveillance.  And, from the surveillance observations, I developed a UC to purchase drugs from him, etc…

That’s all for today. Tune in tomorrow when we’ll continue this riveting interview. I don’t know if you realize this, but by doing this interview an Undercover Operative risks his life and family’s well-being. That’s why interviews of this type are so rare.
So please, take the time to show him how much we appreciate him and the work he’s done, and that he was willing to sacrifice to help us with our writing. That’s a big ask– one he was incredibly generous to grant.

10 thoughts on “Q & A With A Real Undercover Operative– Part II

  1. Pingback: Power Of StumbleUpon & How-to Add Sharing Button To WordPress.com | Crime Fiction Writer Sue Coletta

  2. My characters are more in the immediate level, i.e. homicide cop, but this is fascinating to read. I can’t express enough my appreciation for the deeply insightful descriptions, and of course for our operative taking the time to “talk” to us. And I kept thinking, “Whoa! A real-life Donnie Brasco!” Such a vicarious thrill. Thank you for making this possible. Incidentally, I bought the book mentioned, since I’m fascinated by persuasion and how some people can play with your mind to get results. To read here how not reading someone correctly can cost you your life, your family, your sanity, that is priceless. Thank you!

    Liked by 1 person

    • I am so glad you enjoyed it. He IS the real Donnie Brasco!! That’s so funny. I never thought of that before. Let me know what you think of the book. I’m interested in reading it myself. If you haven’t already, don’t forget to read part III of this interview to see how it ends. Thanks for stopping by. Hope to see more of you!


  3. Pingback: Q & A With A Real Undercover Operative– Part III | Crime Fiction Writer Sue Coletta

    • I know I sure am! I love his voice so much I’m going to base a character on him. He’s much to good to not follow through. And who wouldn’t love a charismatic, as he says “changed from the life”, kind, generous, intelligent bad-ass? He’s star material!


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