Skip to content Deep Undercover in Organized Crime Sep 23 · 26 min ...more
Deep Undercover in Organized Crime
September 23, 2025 · 26 min
Flashback: He started as an actor in Star Wars. Then he turned to the world of law enforcement. Ray Hassett joins us to talk about a life of service, what it's like to go deep undercover and more.
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Flashback: He started as an actor in Star Wars. Then he turned to the world of law enforcement. Ray Hassett joins us to talk about a life of service, what it's like to go deep undercover and more. ...more Show the full description Show less Flashback: He started as an actor in Star Wars. Then he turned to the world of law enforcement. Ray Hassett joins us to talk about a life of service, what it's like to go deep undercover and more.
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In this video 0:00 Bridging the Gap: Civil Servant and Civilian Perspectives
Bridging the Gap: Civil Servant and Civilian Perspectives 0:00 Guys, we're excited to bring you a special episode of Law Enforcement Today. We have a good friend of the family, guest Ray Hassett. Give them all the background on why we started the show, lieutenant.0:12 We started this show to really bridge the gap between civil servant and civilian, and I think over the past episodes, we've really done what we can do to the greatest extent to present things in0:24 law enforcement that bridge that gap where Kyle brings you the civilian perspective, I bring you the civil servant perspective, and we have an open conversation about things that the regular0:36 media really doesn't cover.0:37 Even when the regular media does pick up on these topics, they typically have a 60 to 90 second story that's not really giving a fair and accurate representation of what's happening in the world of law enforcement. So0:49 today, excited to introduce you all to Ray Hassett. Ray, let's talk a little bit about your background first and foremost. It was not in law enforcement yet. Right? You started off in the world of acting.1:02 Yes. Law enforcement was my second career. First career was as a professional actor. If there are any Star Wars fans out there, 1 of the films I was in was the1:13 Empire Strikes Back, which, I have my own playing card now and, my own action figure out there somewhere. I don't know where it is. But, it it was a great1:25 foundation for, segwaying into law enforcement. Although, when I did come into law enforcement, people said acting and policing is totally opposite. And, I think
1:37 we proved that, them wrong. It's an excellent connector becoming a police officer.
1:43 You know, Shay's been trying to get an action figure of himself for a while with the big cape. Maybe you can make that happen. Once you moved out of the world of acting, let's talk a little bit about your LE
1:55 background.
1:56 So, came in a little bit unique. I had lived abroad. I had lived in a couple of different cultures. I went right into inner city policing. I did
2:08 25 years in New Haven, Haven, Connecticut. Very different environment than the theater world. It was at
2:20 the height of the crack epidemic. So things were extreme, things were dangerous, things were dirty, things were dysfunctional, and I loved every minute of it.
2:32 Probably because of my acting background, I was approached to leave law enforcement. And the the offer was to leave
2:44 law enforcement and be given a different identity and begin embedding in organized crime. Which I really had to take a step
2:56 back to figure whether I wanted to do that because there is no manual that comes with that. I love patrol. I I I loved running and gunning and
3:08 everything that that went with that. To leave that, my new law enforcement family, was a pretty weighty decision I had to make.
3:17 Your background in acting probably prepared you pretty well for that undercover role though, correct?
3:22 It did. But there's a big difference between undercover and deep cover. Deep cover is not for everybody. Deep cover is, you you
3:34 you have no friends and you are you can't think like a cop. You have no friends. Everybody believes that you've left law enforcement. You live feral. You have a handler who wakes you up and
3:46 puts you to bed. You've got to figure stuff out. You have no backup. You have no communication. You got to figure stuff out as as things go on. And once you embed
3:58 into a particular group of people, you develop relationships. And, Deep Cover, I I kind of label that is it's the ultimate ultimate, the
4:10 ultimate deception, of another human being. Because it it never ends until the job ends. And in my case, the job went for 2 years.
4:22 Ray, I've always said that to be in law enforcement, you have to be a little bit screwed up. No disrespect. I mean, how many people are willing to put their life on the line, lose their identity
4:33 to go in and ultimately help other people? So I guess my first question there is, what's your why? Why why would you give up everything to pursue this path?
4:46 It's an interesting question. I've always liked the unknown. I've always liked the challenge. I've I've feel that I've been pretty self disciplined.
4:58 And it was probably the deepest going into the unknown that I had ever done.
5:06 I think in law enforcement, a lot of law enforcement officers go into this job knowing that it is a selfless career. You know, we go into this job for the purpose of
5:18 ensuring public safety, and we do that risking our lives each and every day every time we put on that uniform. For you, I think going into that role,
5:30 from being an actor to being a public servant, I think that speaks to the value of selflessness that you had leaving a career in acting to go on and
5:42 and take a role to help society.
5:46 I I would agree. I think that that coming off 2 years of of experience like that, it it takes quite a while to figure stuff out. And it takes quite a while to
5:58 figure out who you are now that you've been someone else. Ultimately, that that experience, kinda opened my eyes to many things that we
6:10 do in law enforcement. Number 1, post traumatic stress. Number 2, being able to help somebody without making them worse by just kind of taking yourself out of the
6:21 mix, making about that making it about them. And also understanding how the brain works. And understanding when people are in crisis, their brains are working maybe totally opposite
6:34 of the way our brains work because we come in, we're measured, we we we have training, etcetera, and we're often dealing with people who are at the worst moments of their lives. Circling back to deep
6:46 cover, you can't leak anything. By leak, I mean, you can't you can't send a message that you're scared, that you're angry, that you're different because
6:58 people are hyper vigilant. In dealing with people in crisis, they're also hyper vigilant. Their instincts oftentimes are much better than ours. We're coming in off a CAD call. Okay. This is the issue. What's the problem?
7:09 I'm here to fix it. Especially now, we can't fix anything. You can't fix another human being. It takes time to get another human being to comply,
7:22 when things are hot. And so the ability to take yourself out of it, center, radiate some sense of calm and confidence, huge tool.
7:34 I could have used you last week when this guy was a little hot on camera. But, Ray, 1 of the things that you've
7:40 done always hot on camera, baby.
7:41 1 of the things that you've done in law enforcement is you've kinda bridged that gap between walking into a situation and giving orders and training
7:53 officers to walk into a situation and kind of assess what is going on so that the outcome is much better.
7:59 Yes. Can you
8:00 talk to us about that?
8:01 Yes. I can. And I I'm I'm gonna I'm gonna go a little bit macro here. We're we're we've in understanding how the brain works and and helping officers and even civilians
8:14 to be able to reset to be more, connective in their communication. We've studied animals. And in my training, I always bring up the the, the the
8:25 example of a deer. And especially for those who hunt, and you know, I I say if you're hunting a deer for whatever the reason, if you wanna take a picture of it, if you wanna shoot
8:37 it, you wanna kill it for food, etcetera, you're looking to connect with that animal. That animal has greater sense of smell than you, better better or more of a history of trauma,
8:49 faster than you, understands windage, understands space, escape routes, etcetera. If you're trying to connect with that deer, that's find that sweet spot, when was the last time
9:01 that you were screaming at that deer to get on the ground?
9:05 That's a great analogy.
9:07 Guys, I wanna take a second to interject and say if you haven't seen Ray's episode of behind the uniforms, check it out. It was, when we were downstairs in the old whiskey wall. But Ray talks a little bit about his
9:18 background deep undercover and the challenges that he went through, after and in getting out. Ray, now you spend a lot of time using your experience and your background to educate people.
9:29 You're traveling the globe. You're working with everybody from officers to librarians to civilians. What is your hope as we enter into what's quickly becoming a new age in law enforcement?
9:42 I think that that right now, everything is on the table. Race is on the table. Gender is on the table. Politics is on the table. Law enforcement on the table is on the
9:54 table. Everybody's hot. The difference in law enforcement law enforcement is on the menu. People are people are not ready to accept the the suggestions
10:06 that we offer. And the the biggest challenge is retraining police officers to understand that and not take it personally. But again, shifting
10:18 we we read people for threat exceedingly well. We do not read people for behavior. To be able to read people for threat as well as behavior requires
10:29 slowing things down. Understanding that people are driven by emotion. Stop talking so much. We have a history of talking to people. There's a great phrase, a good street
10:41 cop can talk a dog off a meat truck. This is not about talking anything off any truck. It's getting that dog to walk off that meat truck and think it was their idea.
10:53 So there's a part of my background hostage negotiation. What we've done is taken the first principle of negotiation, which is really, hey, it's you're hold up
11:05 in in a in a in a in a in a in a apartment. You've just killed your whole family. You every everything is surrounded. Commands have not worked, you bring in
11:17 the negotiators. From a negotiator's point of view, it's just another Tuesday. So how that applies to the public? Listen, a traffic accident for
11:29 somebody who's never met a cop can be the worst moment of their life. And what are we doing? License registration. You know, you should have backed up. So we're transactional in law. We don't realize that everybody's
11:41 different. Everybody's coming in hot. We're moving meat as cops. This is what we're real good at. My training is stop moving meat. Everybody's different. We start talking about tactical
11:53 empathy, tactical rapport building. Slow it down here. People are looking to connect. And as police officers, librarians, ideal position to connect,
12:05 but you only got about 5 seconds. And if you missed it, you gotta realize you missed it.
12:11 Ray, I dated a crazy woman for a while back in the day, And, I I think that my personality, instead of being 1 to deescalate, often made things worse.
12:23 We've seen in 2019 officers killed in line of duty responding to domestics. What's the takeaway for the civilians like me who could use a little bit of a
12:34 lesson in how to slow things down and how to calm things down?
12:39 I think the first thing you have to do is understand that you have to be present in any situation you walk into, you have to be present. And by that mean I mean
12:51 hundred percent for the first 2 or 3 minutes, hundred percent invested in that person, that conversation, that space. If you're thinking of something else, if you're,
13:03 you know, going over your what you're gonna have for lunch, that person who needs you the most knows that. So they know that they don't have your full attention. And so they're
13:15 starting to stray, you're already multitasking. It's a it's a perfect storm for bad stuff to happen because everybody is just 1 click away from
13:27 going off.
13:29 And, you know, we look at law enforcement when we arrive on scene and we start talking to an individual. I think a lot of us out there have become so ingrained in the mission
13:42 and not as much ingrained into the person that we're dealing with. You know, a lot of times, law enforcement shows up when it it is a crisis situation for that person. But if we show
13:53 up and immediately go to that by the book mentality of I need your license and registration, even though that person is had just had a really bad day, and their
14:05 reaction to us asking them a simple question, we just wanna see your license, registration, and insurance, they may not even conceptualize
14:17 that all they have to do is give us that information so that we can continue doing what we made that traffic stop for. They may just wanna talk to somebody. They may wanna tell us what the problem is in their
14:28 life. And if we don't look at that, we can create a bad situation where all of a sudden, their reaction to a question is now to us,
14:40 them obstructing what we're trying to do when all the reality is is they just wanna talk. And I think I've arrived on scene to talk to individuals, and at the point when I arrived on scene,
14:52 immediately, there's that resistance to doing what I'm asking them to do. And if I took that tactical pause, which I have, and you see that reaction from the person who now realizes, okay.
15:04 This officer is going to listen to me rather than just arrive and bark an order at me.
15:10 Sure.
15:11 That creates such a better atmosphere for me to do my mission of public safety, And I think that's something in law enforcement that we really have to grasp, because we do. We go through all this training, and and we
15:22 understand what we have to do to accomplish our mission. But sometimes we lose that thought of, well, this is a human who has an issue that brought law enforcement here.
15:34 What's the best way I can come about finding a resolution for this individual?
15:39 1 of the things that I've always appreciated about Ray is that he he's able to raise awareness from a variety of different perspectives. So thanks to my time with you, when I'm at
15:51 the carnival with my family, I'm reading body language. When I'm at the airport traveling, I'm reading body language because we are in an age of something that we need to be considering, which is heightened awareness. We
16:02 have concerns over domestic terrorism. Ray, you've got a a widespread of sources, resources, abilities to help people. How can people learn more about you?
16:14 You can go to my website, w w w dot ray hassett dot com. I'm, I'm not on Facebook, and I don't wanna be. So,
16:27 probably through my website.
16:29 Alright. Well, we'll work on the Facebook thing with them. But, Ray, if any final parting thoughts.
16:35 To just to to your point on that traffic stop, we're starting to look at every person based on their last 8 hours,
16:47 their last 5 minutes. So, you know, when when we're walking up to that car, we're we're reading everything for threat. We're not reading
16:59 people, maybe the driver, it it's probably the worst moment of their life. Their kids might be sick. That last time I cleaned my glove box, there was a bunch of stuff in there. There's a lot of stuff that people have to
17:10 go through when we step into their story. So the the kind of sweet spot that we're pushing here is, okay, once there's no threat, before you go transactional
17:22 for your license and registration, you're reading that that person is upset, asking them, hey. You okay? But the way you ask it is is in a human way. So the
17:34 biggest thing that we're pushing here is to remind police officers that empathy is a tremendous currency to get people to connect with you. I already know you're a cop when you stop me. I already know it. I can see
17:46 it. I know the drill, but I'm I'm feeling I'm not feeling relieved. And the thing that we have to remember that probably 90 percent of the population has never had a police contact. The only
17:57 police contact they have is to get dinged or to get scolded or lectured. We need to take another look at that because that's those are the important teach teachable moments. Yeah. I
18:09 understand I'm getting fined, but how could I have done this a little bit differently? So taking that time to make us back to human is a tremendous, tremendous rebrand of
18:21 our of our business.
18:22 And you said it right. The tactics that we use approaching that situation don't change.
18:27 We still use the
18:28 best tactics. And I think, in law enforcement today, especially in departments that understand that keeping their officers safe from a tactical perspective, and training their officers how to
18:40 approach those situations, they're going to approach that car knowing that they're looking for threats.
18:46 Absolutely.
18:46 Once they get to a point where they've negated any chance of any threat, then having empathy and going into that situation to have a conversation, I I think
18:58 that's gonna put us in a better position to accomplish our mission.
19:03 Well, as far as the driver goes, if you've taken the time listen, we're talking a minute, 2 minutes here. Taking the time to listen to me, that my kids are sick, you know, I apologize, I know he's I messed up. Now, we're
19:14 ready to do business. Mhmm. And I and I if
19:14 you leave me better than you found
19:14 me, And I and I if you leave me better than you found me, that's what I remember. And the next time I meet an officer, I remember you. If you ding me and left me spinning, that's what I
19:26 remember next time I meet a cop.
19:28 If you haven't checked out his episode behind the uniforms, make sure to do so. This show, this series, all of the content that we put out there is entirely to support this community and you. All of the money that comes
19:40 in through LED Unity gets reinvested into telling these stories, so we thank you all so much for sharing. We thank you all for subscribing. We leave you with the names and the faces of the officers killed so far in the
19:52 line of duty in 2019, said to Dave Bray's last call. Thank you all for watching. Thanks for sharing. God bless America.
21:08 I'm sorry. I'm sorry. I'm sorry. That I can't be a
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