Michael Mann and Author Elaine Shannon on the Terrifying New Face of International Crime

From left: Tommy Cindric, Michael Mann, Elaine Shannon, and Lou Milione. Photo: Gary Gershoff/Getty Images

When the filmmaker Michael Mann announced that he was establishing a publishing imprint several years ago, some were perplexed. Why would a director known for his use of cinematic style want to become a literary mogul? With the arrival of Elaine Shannon’s spellbinding true-crime opus Hunting LeRoux this month — the first title from Michael Mann Books — suddenly it all makes sense. Shannon’s investigative book, subtitled “The Inside Story of the DEA Takedown of a Criminal Genius and His Empire,” feels like one of Mann’s movies right from its opening scenes, in which we sit on an airplane watching a sobbing German sniper who’s just been apprehended via an elaborate, internationally coordinated DEA sting operation. That moment is but one small part of the vast tapestry of criminality and police work portrayed in Shannon’s book, which focuses on the rise of Paul LeRoux, a Rhodesian cybersecurity expert who quickly grew from selling prescription meds online to become the head of a vast, shadowy, technologically revolutionary crime empire, with tentacles all over the world. Shannon also follows the efforts of the DEA agents who discovered LeRoux, caught him, and then used him to take down the rest of his network — all through a series of intricate, daring ruses that make The Sting look like an episode of Paw Patrol. I recently sat down with Mann, Shannon, and two of the DEA officials who caught LeRoux: Lou Milione, who led the unit that apprehended the crime lord, and Tommy Cindric, one of the agents who did much of the work of tracking and capturing him.

Elaine, when did you start following the story of Paul LeRoux and why? What drew you to this figure?
Elaine Shannon: I was looking at several figures in the new world of drugs and organized crime, and suddenly, a source of mine said, “You know, I have just been with the most remarkable man. He’s totally revolutionizing what we think of as organized crime.” And I realized: This is new, new, new. LeRoux started out as a cybersecurity guy, brilliant. He is of English heritage. He comes out of this outlaw colony in Rhodesia, and he could fit right in in London. He worked in London, Amsterdam, Seattle, Virginia, Australia. He was working with government ministries, law firms, banks — entities that needed cybersecurity. That was when that whole system was being built, because hackers were coming in and more and more information had to be protected. He has said that he worked for a time at GCHQ, which is like NSA in England. We’ll never be able to prove that, but I can see him, and he’s learning how the engine rooms of the corporate world work — he’s learning how to use that information to blend in and disappear.

And then when he went dark, he went totally dark. He went to the worst corner of the underworld. I see what I call “Middle Earth”: It’s a dark world. It’s spewing money and poison into the world above. It’s causing wars, it’s causing terrorism, it’s causing terrible tragedy. Paul LeRoux is a door into the ratlines into North Korea, the ratlines into Iran, the ratlines into the mercenary world. Through him I can tell you what it’s like to be in this modern world.

Then I found out that when the DEA tracked him, LeRoux was almost invisible. And so the mind of the hunter became compelling, too: How does someone figure out what an incredibly secretive, rich man would want enough to tempt him out of his comfort zone? How does that work?

As a journalist, you touch a lot of stories, and as you touch them and touch them, they melt away and they become very ordinary. Some of them become hardly worth mentioning, some of them become a paragraph, and some of them become a chapter. I thought I had maybe a chapter — but then when I dived in, I realized, No, this is a book. And whenever I hesitated and said, “Well, maybe I’ll do a chapter about something else,” Michael Mann said, “No. This is the whole book. This is all you can handle, this is all the human brain can wrap itself around.”

Michael, at what point did you get involved?
Michael Mann: Elaine sent me a couple pages early on. And two things [about the project] struck me. One was that this guy was a revolutionary. This is a sea change in transnational organized crime, by this genius crime lord. Then, two: the elite secret view of the DEA, and its investigation, pursuit, and apprehension of LeRoux. But it was also the proximity — the proximity to LeRoux, and the proximity to the police story. You were so close, you were in the room. These kinds of procedural things, whether we’re with investigators or with criminals, we see a lot in drama. But this isn’t drama, this is real. You were so close, [it felt like] a film that was happening. So there was an immediate appeal to me.

So are there any plans for you, as a filmmaker, to do something with this?
Mann: Yes, I have plans. Very definitely. That’s it. That’s all I can say.

I’m curious about what Michael Mann Books will encompass. This is the first one, and it’s nonfiction. Next up I believe is the Heat prequel. These are quite different. 
Mann: The vision initially was novels. The first one was gonna be a Heat prequel and sequel, rolled together into one novel by Reed Coleman. But [Hunting LeRoux] was such an arresting story when it came along, that [we said,] “Let’s get this out there. This is really unique as a nonfiction true crime/world crime piece.” There’s a number of other projects. The one after the Heat prequel-sequel is going to be something that was intended to be titled Big Tuna, which is kind of a Who’s Afraid of Virginia Woolf in gangland.

Tommy, I was interested to read when you were younger you basically wanted to be Sonny Crockett from Miami Vice.
Tommy Cindric: Who didn’t? [Laughs.]

Okay, this is true. So, here you are, with a starring role in a real-life version of this kind of story. How do movies and TV compare to the reality?
Cindric: Most movies don’t. I would say in this particular case, we took aspects of movies. How can we create an illusion based on fact? The big joke for me and my partner was — we’d just watched Argo, and we said, “Argo fuck yourself” all the time. Because [CIA officer Tony] Mendez was so out there. He really thought outside the box. Most of the time that doesn’t work. This case it did, because all of the illusions had a very strong factual basis.

In the book, we see the different stages these criminals go through when they get caught. And it is interesting how many of them — even if they’re these big German snipers — just break down crying once they know what’s going on. We’re so used to seeing these stoic figures in movies and TV, but the reality seems to be quite different. 
Shannon: I wanted to show all of these guys as human beings, not as stick figures — because the more you learn about them, the more interesting they are. The first thing I ever heard about this case was the two young men in the plane, which is how the book opens. Here’s a 30-year-old guy and here’s a 26-, 27-year-old guy. And one was supposed to kill the other. Then, suddenly, the roles are reversed, everything’s whirling, and the killer is crying. The young man on the other side of him, knee to knee, is thinking about his life and what the bad guy’s life is gonna be like. But then we go back to the [Afghan-American] DEA agent’s life, and his time in Afghanistan. He’s seen more war than any of us will ever see, because he was in four years of deployment there, and he knows people, and he’s haunted by what that country became when he was gone.

Paul LeRoux. Photo: Hunting LeRoux

We also see that LeRoux himself conceives of himself almost as a cinematic figure. When you’re after someone like that, do you have to play up that angle — appeal to his flair for the dramatic?
Cindric: My thing is always trying to make a connection. Whether it’s with a source, whether it’s with a bad guy, whatever it is. It’s to make that connection and understand them. What their motivation is, what their thought process is.

Michael, that ties in to the idea of what you do as a filmmaker. You have to understand people, and then figure out the next step that character needs to take.
Mann: There’s a similarity of process. What these [DEA] guys are doing is trying to discover what he wants. When you know what he wants, and then if you’re very, very crafty and very, very good — and these guys are — then you can put things out there that can track him. Now he’s on your terms, and he’s moving in a process, and you trap him. Set him up through stings.

In drama, an actor says, “What’s my character’s action in a certain scene? What does he want?” When I’m writing and directing a scene, and in fact a whole movie, I have to know what every single character wants. I have to choreograph what they want to collide with each other. And sometimes what they say they want isn’t really what they want. What they really want is the subtext. And you do that for lots of scenes and lots of acts in the whole movie.

There’s also probably a mutual understanding of process because I kind of use the inverse of police action. They have a perpetrator who’s motivated, that motivation compels him to do something. He commits a crime, he leaves evidence, and he goes on his way. That’s what I’ll invent. What they do is they’re starting with the remains of an event, and trying to work backwards to what motivated this event, and then maybe if you can figure out what motivated this event, you can start to predict his behavior.

Tommy and Lou, you not only had to predict LeRoux’s behavior and capture him, you then kept it totally quiet that he’d been captured, and used him to take down the rest of his network and go even further into the people and organizations he’d been working with.
Lou Milione: There was tremendous investigative urgency. It’s an insulated, very sophisticated network that doesn’t realize he’s in custody. How do you then plumb the depths of what LeRoux knows? If we hadn’t done that, if we’d just done an indictment, announced an indictment, unsealed it, then all the other parts of his network … who knows who else they would have been murdering? Who knows what else would have been going on with Iran and North Korea and everything else?

Cindric: What you had was Western-trained soldiers — Americans, Germans — who were committing murder on behalf of LeRoux and who knows who else that we don’t know. And if we don’t go after them, who does? But I’ll tell you, we really did not expect him to cooperate to the extent that he did when he first got on the plane. We were expecting to work for a confession. It was kinda funny: “Well if you guys are after me, you’re obviously after much bigger things.” Me and my partner were like, “Nah, not really, you’re kind of the prize.” And then he goes, “No, nation-states, gentlemen. Nation-states.” Okay, that’s another level. But that’s when you know you have him.

The book suggests that LeRoux is probably not the only figure who’s out there. What is the next step for somebody like that, after he’s cornered the market on all these other things? Does he move on to governments? And not just failed states. Because we see how connected everything is — can they go and basically buy a first-world government?
Cindric: Here’s what I would say. LeRoux was in bed with the Iranians. He was smart enough to take flawed technology that was out on the open market, and then exploit it to create a guidance system, to be sold to Iran, that was then designed to go on a missile system to overwhelm the Dome in Israel. Could he buy a first-world country? No, but he could buy influence in it.

Milione: Guys like LeRoux, and a number of the other targets that we’ve investigated, they love these ungoverned spaces. The chaos that goes on there, that is how they get empowered, and they certainly have a tremendous corrupting influence on those countries. In a first-world country, influence would probably be about it. That’s where you hope that there’s the rule of law, and fortunately, for whatever you want to criticize or not about our system, we have that.

Mann: Do you guys love chasing them in the ungoverned places?

Milione: One-hundred percent. No doubt. The chaos works for them, but the chaos works better for us because we can blend in. We can move, manipulate, do what we have to do. But there’s also a passion that goes on the other side, because you work with the counterparts, like in Liberia. When I first started going down there, it wasn’t that long after the civil war ended and President [Ellen Johnson] Sirleaf was down there. You can see a nascent stability and peace, and you can see wonderful people, and you can see what eroding the rule of law had done. So then you can work with people who couldn’t be bought.

Doesn’t the LeRoux story prove that the internet itself is one of those ungoverned spaces? It’s a failed state on its own in some ways.
Cindric: I agree. You remember Silk Road, right? LeRoux was Silk Road before Silk Road was cool. These guys were well ahead of the curve. LeRoux was so far ahead of the curve. He identified the ungoverned spaces. He identified the chaos that you’re talking about.

And it’s particularly chilling, because you see the progression of his career, and it seems so smooth. We talk about how the internet flattens borders, brings people together, makes anything possible, and we see a really terrifying side to that as well.
Shannon: The immorality. He started out as a digital nomad, as they’re called in Silicon Valley. He was just this fat guy coding, coding, coding. One day, he saw these yachts and he said, “I want that.” That meant he had to be a billionaire. “How am I gonna do that?” He could have gotten pretty wealthy, because he was being offered a partnership in a cybersecurity firm. But he wanted so much more, and he was born with no conscience at all. None. Has he ever felt guilty about anything?

Cindric: No, I don’t think so.

Shannon: Has he ever felt sorry about anything?

Milione: I think he feels sorry about being caught.

Can you tell me a little bit more about the so-called “Mercenary Facebook”?
Shannon: I heard that phrase from Joe van der Walt, who is a South African security consultant now, but he was South African military intelligence. We were talking about mercenaries. There are quite a lot of them in and around South Africa. When you go to a café there, you see these white guys with big shoulders and big chests, and they’re packing. The mercenaries, as I understand it, communicate by WhatsApp signal. All these encrypted forums, they’re looking for jobs. If you’re a military-trained sniper, you’re looking for gigs where you can use that skill. If you go to the Dubai airport and you go to that Irish bar [McGettigan’s Irish Pub], you see them all. They’re all there, they’re doing their email, exchanging stuff. The whole place is wired by intelligence services, then you see these contractors. I’ve talked to special-operations guys from different countries, and they said, “You know, we’re gonna have a problem, because we’ve got all these guys, they’ve now been in battle. They have good skills, they’re not scared of stuff, and they’re looking for jobs.” We don’t have jobs in the civilian sector that can give them the money and the excitement that they can get in this other world.

Cindric: Look, the underworld out there is looking for the jobs. They’ll know, [the shipping firm] Maersk is hiring, for example. “We need to get on that boat.” “Okay, I need five guys. Put it out there to five of your buddies who were former military guys working ranger battalion, or just general military police, or wherever for whatever country.” Again, the ungoverned country of the internet allows for you to anonymously communicate and create a network of people who are willing to do a number of things.

Elaine, you write about the “reality distortion field” around LeRoux. Which kind of goes both ways. It affects the people around him, but it also affects him. He’s delusional about what he can achieve.
Shannon: I got much of this from Jack [a pseudonymous informant], who was a person who worked for LeRoux for quite a while. LeRoux called him “my golden boy.” Good, well-built seafarer. He was Navy, and he obviously wanted adrenaline and he lifted to Manila. Ended up getting a job with LeRoux who he thought was some sort of tech mogul who had money. And then, as he got seduced into the web, he discovered he was in a big criminal enterprise. I often asked Jack, “Why did you stay there when you realized what he was?” He couldn’t articulate it. The moment that broke the spell was when Jack fell in love with a grown-up woman. He told her everything, and she said, “You have a decision to make. We can have a nice life, or you can be with him and go have his adventures, but he will probably kill you. So you need to decide.” She was beautiful, she was smart, he decided. They went out on the balcony of their rented flat, and they burned all his passports, and then he emailed LeRoux, broke up with him. Then he called the CIA.

That sounds like something out of a Michael Mann movie.
Mann: An old one.

But as I read this book, I also kept thinking about Blackhat. The character of LaRoux feels like the villain in that movie.
Mann: Actually, yeah it does.

Was any of it based on him?
Mann: I had no knowledge of LeRoux at the time of Blackhat. But it was postulating who would be a player, where he would come from, emerging from the opportunity that had been presented by the internet. What excited me about Blackhat, and what’s exciting about this, is that with the internet, [people thought] free information disseminated everywhere simultaneously was gonna make the world better. Well, no, this technology makes everything accessible to everybody, regardless of their intent.

The distinction between the most sophisticated traditional cartel operations that you can imagine out of the ’90s into the aughts, between that and LeRoux, is a quantum leap. It is not an additive increase of capabilities — it is a quantum, quantum step. [Think of] Amado Carrillo Fuentes in the middle of the ’90s or even afterwards. When he died, he was worth like $35 billion. That bought the best counterintel. It bought the best signal-interception equipment you could buy. Management consultants. “What’s the best way for us to compartmentalize ourselves to defeat what the DEA trying to do? What’s the best the way to co-op Mexican military?” All that stuff. Nevertheless, it’s still an industrial enterprise — farm to arms. Someone’s gotta grow the coca leaves, process it, move it. It’s all discoverable, it’s all vulnerable. It’s locked to physical places. It’s dependent upon a fabric of loyalty to keep people in place. Paul LeRoux blows all of that away. There’s nothing. There’s just the man and a bridge chair, and an empty penthouse with a laptop.

Shannon: In order to understand LeRoux, I had to dig into entrepreneurship. The new business world in Silicon Valley. My son, who’s there, said, “You gotta read The Lean Startup.” It’s a wonderful book, and what it tells you is, entrepreneurs hop like water bugs, grasshoppers. First they’re gonna make dog collars, then they’re gonna make tunnels, then they’re gonna go to space, then they’re gonna build apartment buildings. It’s whatever idea sparks their mind, and if they put it together fast, they will do it. Look at Elon Musk, look at Jeff Bezos, look at all of these tech giants. None of them are linear, none of them are rational. It’s just sparks flying out in all directions, and they wait for one to stick, and if it sticks, then they scale up fast. This guy is doing that, but he’s doing it in the dark world. Tommy, you asked LeRoux what he would do if he got out, and he said what? “Sell women”?

Cindric: “Girls. Because the Arabs like girls.” That was what he said. Commodity, it’s all a commodity to him.

This interview has been edited and condensed for clarity.

Michael Mann and Elaine Shannon Talk Hunting LeRoux