Uncovering Deep Cover

In late May, a New York Times investigation revealed that Russia was churning out deep cover operatives from Brazil for years until a CIA tip and sharp Brazilian policework led to their capture and escape. 

But what exactly is “deep cover” and when and how is it best used?

On this episode of Straight from the Shoulder, Jack and Julia chat to uncover: 

• The historic and contemporary motivations and methods behind the latest Russian effort
• The pros and cons of operating under deep cover
• How and if other nations are using deep cover 
• The implications for human intelligence (HUMINT) moving forward

Transcript

Julia

In late May, The New York Times shared a bombshell article detailing how the Russian intelligence services had been systematically churning out deep cover operatives from Brazil for years. The mission of these operatives wasn't to spy on Brazil, but to use their fake and well-established Brazilian identities to gain entry into parts of the world that would have otherwise been impenetrable. In fact, the Brazilians first learned about the Russian spies after receiving a CIA tip that an undercover Russian operative who was traveling on a Brazilian passport was about to start an internship at the International Criminal Court, just as Russia's war crimes were coming under review. Jack, where to even begin? What exactly is deep cover?

Jack

I think this is terminology that's really worth going over at the beginning. For example, the FBI and the CIA use the same word for two different meanings. If you're an FBI agent, you are actually an American FBI officer. When you enter CIA and are in the operational directorate, you're a case officer. The people that you run in the field are agents. The agents are foreigners who are secret sources. 

And then you get to the cover question. So a lot of times you're not undercover- like all the analysts are not undercover unless they're in a special category. But all the case officers are under official cover. That means they have some official affiliation. You have people that are under other government agencies. It's not a secret that State Department and Defense Department have been used and other agencies and commercial have been used. And that's what they call official cover in the case of the business. 

But when someone gets buried the way the Brazilians with false identities. There's an interesting word used for it. It's called illegals. It's the illegal category. And one thing we had in United States was extremely popular, and I liked it myself, was The Americans. And that was talking about illegals in the United States. And part of it's real, I mean, for sure. But the Brazil one is absolutely 100 % authentic. And here is a huge investment in illegals.

Julia

In the case of The Americans, though, Jack, the point of the Russian operatives’ deep cover was to spy on Americans. And this case that The New York Times has revealed seems different in that the Russians who became Brazilians didn't care about what was happening in Brazil at all.

Jack

I think this is a learning moment in the sense that when we think about illegals, they've been written about. I've written about it in my books. There was a famous Colonel Abel who was involved in the stealing of our nuclear secrets and giving them to the Russians. I think his name was Fisher at one point, and he was an artist in Brooklyn, right? But he was a Russian, a true Russian. Abel was handling two of the most famous spies, actually more than two…It was probably most of the spies that were in the Manhattan Project where the United States was trying to develop a nuclear weapon. Russia was able to develop a nuclear bomb because of the information that were provided by Colonel Abel. That's what you think of an illegal. 

Why the Brazilian is so interesting here in the learning moment, because if you're looking at what the Russians are doing, they're going one step further than what they did during the Cold War. What is that one step? Even before we send you to America, we're going to bury you. In other words, there's this cognizance about the power of AI and technology today that makes it so easy to unravel people. So this is very good tradecraft.

Julia

Brazil was a good place for the Russians to do this because the Russians discovered a loophole where essentially in rural areas you could file for a baby just having two signatures. And so these passports were all legitimate. And the other thing about Brazil is that it's a place that has people from all over the world that have come there, a long history of immigration, many skin colors, accents, everybody is in Brazil and is Brazilian. It wouldn’t be unusual if somebody was conducting business abroad or traveling or even had a slight accent? So in some ways, the United States is similar to that.

Jack

One of the hardest things to do in the business is to develop people with that non-official type of illegal cover. And the reason is the risks are so high to them that if they get caught, they will give up one of your most sensitive sources because they'll be handling that sensitive source and they have no protection. And the second part of it is you can't put an American into an illegal situation if he's from Milwaukee and talks about the Brewers, right? I mean, you have to have somebody that has an ability to carry themselves off as a foreign personality and have a legitimate foreign passport. In other words, the idea of how many you can manufacture. I give the Russians credit for producing so many, and the Brazil case is a really good example of mass production.

Julia

One of the funniest parts and sort of most human parts of this case was the text messages that one of these deep cover operatives shared with his wife, who was also a Russian spy but living in a different country. And he kind of expressed his frustration with the whole endeavor. He was waiting for a moment that would make it all worth it, right? Here he is alone, far from his wife, losing his faith in the mission. How do you keep guys like that motivated?

Jack

I think you fail. In other words, this process that they are engaged in, I'd like to see the final results on it. Colonel Abel was an extraordinarily complex man. And you have to have extraordinary dedication to think about, I'm going to go be in the convent or the monastery for 10 years, and then I'm going to come out and be chief of worldwide operations. It's asking way too much. However, if you're a action person, the last thing they want to do is put you in as a knock or an unofficial or an illegal because you will be totally frustrated. So I don't know how they can do that. 

The other side of it is they are developing personal lives. That means they have children. In fact, it was interesting. They even allowed them to have affairs so it looked authentic. God bless the Russians and how they view cover. But my point was their lives get so complicated and all of a sudden, well, now I want you to go to the polling. What wait? I've been in Brazil for 10 years. the chairman of the school board. So I think there's so many things embedded. 

Now, I do want to make a point that I should have made earlier. They have to do it. Why do they have to do it? In so many parts of the world, during the Cold War, it was a hostile environment. The CIA could operate with light cover. They always had to have a heavier degree because we had to support the local governments and we're covering every move they made. So I think they're used to having to work within really deep cover. Now, the problem is because of the social media and AI, everybody has to be sharper.

Julia

Is there also the risk of these spies, given how long and how invested they are in their country of assignment. Do they go native?

Jack

There's a lot of policies that develop in the government that are never written down. It's you know, it's the policy, right? You know the policy of the CIA, if you're to do something, you say, yes, sir, yes, ma'am. Well, it's what they call “kendo”. If you say, well, let's talk about it, then you're going to worst spot in the earth. So the other part of unspoken rules are an American can't stay in the post too long, maybe four years. But then they start to get too identified with the locals. So you bring them back.

The Russians always had a different view. I thought they had a hand up in places like Mexico where they would send people for a couple of years. They'd go to the university and develop Spanish. And part of it might've been budgetary. It's very expensive to move people every three years. But you do run the risk, particularly when there's political issues and there's difficulties between the United States and that country. You can become overly sympathetic to the local proposition. So if you're in Brazil for 10 years, I think that's a really legitimate test.

You should bring them back for vacation at least, and then now you have a cover issue. And I think this was part of one of the problems is they went back for a Olympic game or something, and it actually started to unravel on the cover. And that is you need to refresh them that they belong to a system and the system and the country. So there are a lot of risks.

Julia

What came out of this entire endeavor?

Jack

After all this investment, a lot of them got wrapped up. I mean, there can't be many more of them. And Brazil got a tip from the CIA, which is rightly covered in the press, but they were able, with really good police work, to wrap this up. That was a lot of work, very sophisticated. We're not the only ones who know how to do counterintelligence and how to investigate. And we better watch our step because we've had some embarrassing wrap-ups, as has every major service in modern times because of the inability to have foolproof cover.

Julia

Well, Jack, have you ever come across anybody in deep cover over the course of your career?

Jack

Well, I have. I was in charge of all of them at one point, and they are quite different. There's actually one who came out and is in private sector, and it's quite interesting. He's very much involved in the business sector today, and I know him. He declares himself. He had Iranian cover and citizenship and was able to carry it off, but today he's a public figure. I've known them. 

I had one situation which was extraordinarily painful, if you will. And that was in a foreign country and there was an illegal there who was not declared to me. But that I mean, by agreement, they didn't even want him to have any contact whatsoever with the American embassy. And one day the deputy chief of the mission came in, Jack, and said, you know, guy named Harry Schmidt, I'd never heard of Harry Schmidt. There's something here that you want to look at. And there was indeed, in other words, the illegal had gotten into an automobile accident. A fatal one. And he was out there, no one knew it, no one knew he was affiliated with the United States and so on. But that's how deep he was. And it was only after mortality that I tried to be helpful after the fact. But they live extraordinarily different lives and their personalities have to be different. It'd be hard to get them on a podcast. It wouldn’t be a lot of fun because they can't talk about any of this.

Julia

Or they can talk about everything- and not a lick of it is true. Jack, just to wrap it up, given all of these obstacles and difficulties of deep cover and also the Russian affinity for using it- and you shared some of those historic reasons, who else uses deep cover? Does China use deep cover?

Jack

It's a big investment. You're talking money, time, resources. You have to have a reason. And a lot of times you find expatriates. In other words, I'll just say the Brits or the Germans, they'll have expatriates, right? It's very few. The Russians have done it because they were in a big game with us. The Chinese wouldn't even come out of the embassy, let alone have covered. But what I'm watching with China is they're doing everything we did. In other words, they're looking, they're one by one.

They're picking off every technique that we've used in the spy business during the Cold War, bringing it to the sophisticated level of technology today. So I believe China is probably in this game as well today.

Julia

Given all of what you've mentioned about AI, how easy it is now to learn things over signals and there's all these different communications that can be intercepted. Do you think that Deep Cover is going to have a revival - are people going to be considering it more or less moving forward?

Jack

I think the size of it will be very limited and the size is limited even if you have 300 million people. When you start to qualify, what would put somebody illegally into a system? There's only space for a few. I think if I were able to divine how do you handle them? And I always felt during my career in the agency that we lost an art because during the OSS and the immediate days after the Cold War, we actually had staff agents. That meant that somebody like me, not like me, but somebody who was an Italian but was in the agency with me, but spoke Italian and so on, and could get a second passport, that you would actually bury them. They would go into Italy and that the agent, CIA person would become a member of the, I don't want to pick on Italy, but in the foreign ministry. There was a, one of the ways, if you wanted to invest, instead of taking those people in Brazil and you put them in the Brazilian government, foreign industry. They could go very, very far. 

What I found is it is so hard to do this and find people and to run them in place that I think the world is so complex today. The very best agents, that's the foreigner that's actually in the government, has no roots with the United States, need to be handled very, very carefully. And we may consider in a denied area, you know, what I would call a staff agent, a real American, tested, true blue, but who can live the life in China, live the life in Indonesia or Mexico City and wherever. So I think it is coming back. I think human is coming back. That's spies coming back. You know, we're in the investment world and one of the problems investors are having now is how do you deal with the geopolitical world? And I think what they're finding, there's so much in it, they're almost blinded. And now I see a resurgence.

And you can hear it in the agency. The agency is speaking out boldly that we're under invested. I've been talking about it for years, including, as you know, an op-ed I wrote about what happened with the Hamas attack and where we are with HUMINT. I think it's going to get to the point where some of the really old techniques, the techniques like illegals also find their way back, but they're not to be handled the way they are under Brazil. They really have to be designed to handle that very special agent that they're so few of. You talk dozens when you talk about really good agents. You don't talk hundreds. ⁓

Julia

Thanks, Jack.