Ukraine Report #5: Former CIA Officer David Chasteen

Ken Harbaugh:

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I'm Ken Harbaugh, and this is Burn the Boats, a podcast about big decisions.

As the invasion of Ukraine unfolds, we want to provide timely insights from the experts, so we've launched a series of special unedited episodes separate from our normal content.

Today I'm joined by David Chasteen, a former CIA officer on the covert action staff. While at the agency, David conducted overseas operations, guided human intelligence collection, evaluated foreign threats to computer systems, and provided analysis on cyber issues to the president. David was also a consultant for the Amazon Prime series, Jack Ryan, starring John Krasinski, and the show is heavily influenced by David's experiences. I brought David on today to talk about intelligence collection and cyber warfare as it relates to the war in Ukraine.

David, welcome to Burn the Boats.

David Chasteen:

Thanks Ken. It's nice to be spending some time with you again.

Ken Harbaugh:

I got to tell you, guest prep background research for agency types is not easy. We've had a couple on the show, and you guys cover your tracks well. I'm sure that's because you know things we don't.

David Chasteen:

Yeah. It is one of those things. I think paranoia, it's funny, for a little while I worked with some internet freedom fighter types after I left the agency, and it was interesting. There was a lot of paranoia, and the thing that you learn is that paranoia is a function of ignorance. They're like, "Oh, we think somebody flipped our house or somebody's reading our email." When you're an intelligence officer, you pretty much assume people are reading your email, and you have a general sense of who they are and why they're doing it. So I think you just get used to a level of surveillance that just comes with the territory.

Ken Harbaugh:

What are you doing now? I know your career has run the gamut, and it obviously started in uniform, but you've done some pretty interesting things since. Give us the rundown.

David Chasteen:

Sure. Yeah. After I left the military, defense for a little bit and was undercover at CIA for a while and did those things you talked about. Then came out to San Francisco, worked on a mayoral campaign out here, and then ended up running cyber security ops for the city and was chief information security officer, or CISO, for the police department and then for GoFundMe.com, which is a great website doing great work. After I left GoFundMe, I'm CEO at CipherLoc, which is a micro segmentation encryption software company, cyber security company. I'm also a partner at SideChannel Security, which is a cyber security consulting firm, fractional CISO firm.

Ken Harbaugh:

I want to tap that experience for this conversation on the digital battlefield in Ukraine. We are just seeing image after unforgettable image of the devastation being wrought upon Ukrainian cities by the mass of the Russian army. But there's an invisible war going on at the same time that I think it's being very under-reported. While it does not have the same kinetic impact, it can have devastating effects on life in a modern city. Can you talk about the digital battlefield writ large, and then we'll dive deep into some of the aspects of it.

David Chasteen:

Sure. Yeah. I think ever since Stuxnet, there's been a general sense, I think it started to come out into the public a little bit, that foreign governments have really added cyber warfare as a tool of state craft. We in the business differentiate cyber warfare from cyber intelligence. Cyber intelligence is when you're stealing people's secrets. That's what intelligence officers do, is they find out things you're not supposed to know. Cyber warfare is when you reach out and break things, things that actually have impact in the physical world. You saw that in Iran with the attacks on their nuclear processing capability.

Ken Harbaugh:

That's the Stuxnet reference?

David Chasteen:

That's Stuxnet, that's right. Then you've seen it quite a bit in Ukraine over the last number of years as the, presumably the Russians, have basically tested out their capability to take out power grids using that kind of, it's either called a SCADA attack. SCADA is... the new term is kind of operational technology or OT, but SCADA is the computer systems that control things in the physical world, the train switches, power grids, traffic lights, water supply systems, and things along those lines.

Ken Harbaugh:

You're not just talking about shutting things down inside another country. There are ways to impact infrastructure that have... I don't even know what the term is for it, but the equivalent of a kinetic impact. Things don't just stop working. Things can blow up. Can you give us a sense of the severity that these attacks can reach?

David Chasteen:

Yeah. There was a lot of press about some tests that were done at some of the national laboratories here in the US, where essentially what you can do is you can take a transformer and you can do the equivalent of, imagine flooring it in your car, just revving up to full throttle, throwing it into drive, and then keeping it floored and throwing it immediately back into reverse, and then drive reverse, drive reverse, back and forth. After a while, you're just going to destroy the transmission of the car. It is possible, it's been demonstrated possible, to do that essentially to the power grid, to transformers, where it's not just a function of shutting it off. You're actually destroying that piece of equipment, and if you are savvy about which parts of the grids are the most vulnerable, the most difficult to replace, it's theoretically possible to take out a power grid in the region for months or longer as it takes them time to just complete... Literally, you have to rebuild the grid.

Ken Harbaugh:

Now, in the US, and maybe you are not at liberty to speak to this, so if not, just map this onto Russia. Who is leading these attacks? I know at the unit level, every larger command has a cyber officer, but this is much more organized and focused than that. There are parts of the government dedicated now to offensive cyber warfare. How was that structured, and will that... I want you to help give us a sense of what a priority this has become in the prosecution of a campaign like we're seeing in the Ukraine.

David Chasteen:

Sure. Are you talking about American offensive capabilities or other countries' offensive capabilities?

Ken Harbaugh:

Well, let's talk about American to the extent you can speak to that.

David Chasteen:

Sure. Well, what I would say is that it's probably safe to assume... When I say that, it's become clear to all nation states that this kind of cyber warfare is a tool of state craft. You should assume that the United States has done that math as well, right. There's three things at play here. The first in is going to be the intelligence piece. You've got the CIA who's responsible for human intelligence and all source analysis. Then you have the NSA who's responsible for signals intelligence overall. Then you have DIA, which is defense intelligence, that's focused on stealing secrets that can help war fighters win wars specifically. That would be like, what's the new Russian tank or stealth plan look like. That's more of a DIA mission than a CIA mission. Then of course, each of the uniformed services have their own intelligence capability to support war fighters on the ground.

So first in, it's someone's job to break into the kind of computer system that would do something like that. It's going to be NSA, because it's their job to get into computer systems where they're not supposed to be, and NSA falls under DOD authority, and there's a lot of uniformed folks walking around at NSA. So the job then is to steal stuff, steal information. The more visible piece, of course, when the government, when the US government, uses force in the pursuit of national security policy, it's usually the military. It's DOD. One of the differentiators we use between DOD and intelligence capabilities is we say Title 10 or Title 50, and Title 10 is referenced to the part of the US code that establishes and runs the military. Title 50 does that for the intelligence community.

The thing that we think about with the military is that it's best to think of the military as diplomacy by other means, right? It is a public act using the military as a public act. It's designed to sway opinions. It's designed to change people's minds, and it's designed to be seen. That's why militaries wear uniforms. It is an inherently public act. You want people to understand that it's being done under the auspices of the United States government.

Sometimes you'll want to do things that never get found out. At that point, you're talking about covert action, and that's Title 50. There's only a couple of declassified covert action instances ever. This is generally when the president of the United States says, "I want..." The CIA has sole authority to do this in practice. "I want you to go out and do this thing, which is never going to be found out." So if we're talking about something where it is an intentional diplomatic act against another country, we want them to know that we did it. That is more likely to be carried out under Title 10 authorities, because that's under the military, because that is the thing that is designed to be seen and designed to be public.

So when you think about those things and those capabilities, there's going to be that military aspect of an offensive cyber warfare capability, and that's probably what would be used in a Russia scenario and likely in response to... Frankly, everyone's very surprised at this point that the Russians haven't already launched a pretty serious cyber attack on NATO or the United States. There hasn't been anything substantial so far, and I think we're kind of waiting for that to happen. When that happens, the trick, when you're in a conflict with a nuclear power, is you don't want to escalate. It's always very challenging to find out what is the proportional response. Of course, the most proportional response to a cyber attack would be another cyber attack of the same kind back in the country that did it to you.

If you have to move into a physical attack or something else, then you start to run into accidental escalation, which nobody wants. But what you need to know about these kinds of attacks is you can't just decide... I remember one time I visited a general early on at Air Force Cyber Command, and he's like, "We're looking for a future where we have a hack button and we can push the button and it says hack." It's like, "Oh, bless your heart. It doesn't work like that." This stuff takes years of work in advance to put in the tools necessary to have the effect that you want to have when the time comes. So it's safe to assume that work has already been done so that when the president of the United States says we want to respond in kind, we're able to do that.

Ken Harbaugh:

What do you make of the lack of a massive offensive cyber attack from Russia? Is it really just about their concern over escalation, or is there a capability question?

David Chasteen:

The thing to remember about a cyber attack is you get to do it once, right? The most damaging thing that happened... I know this entirely based on just reading the newspaper like everyone else, but the shadow brokers leak, where I think the assumption is, or the assessment is, it was likely the Russians who did this, but were able to steal a big chunk of the NSA toolkit from contractors and leak it publicly. It was massively damaging, because those toolkits are very difficult to build. These are the vulnerabilities that you know exist in other computer programs that other people rely on for day-to-day work.

Once you make it known that those vulnerabilities exist, Microsoft, these other companies, they patch those vulnerabilities and they don't work anymore. So if the Russians launch a massive SCADA attack in the United States, it'll probably only take us a matter of days to just patch that thing, and then we're not vulnerable to that anymore. So it's a one-time use kind of scenario. It's not like a nuke where you can just keep launching nukes all day long. You get to do that one time, and then you can't do that same trick, and these tricks are very hard to come up with.

Ken Harbaugh:

Are there ways to fire warning shots in that same theater of conflict, if you will? I'm thinking about what appeared to be a take down of USAA, the banking site for military members, recently. Maybe I'm reading too much into that, but are there ways to flex without launching that cyber nuke?

David Chasteen:

Yeah. The trick, the problem is, and we're talking about a distributed denial-of-service attack or a DDoS attack. Those are so common, and any group of... You can rent that capability on the dark web. It's not special to a nation state.

Ken Harbaugh:

Okay.

David Chasteen:

It's not easily attributable to a nation state, and so even if they DDoS'd, I don't know, the IRS or something like that, one, it's temporary. Two, we know how to deal with it. That's not something that's going to be taken seriously. This is the thing. You can't really fire a warning shot with something like a SCADA attack, because let's say we're going to take out the water system or the power grid in Muncie, Indiana, some small place where it's like, that's not that big of a deal. It's my hometown, by the way. But say you go somewhere small. Well, the problem is, military intelligence, law enforcement, are going to swoop in on that area, find out how they did it, and once they find out that vulnerability, will just patch the entire power grid over the next week or so, and then the attack doesn't work. So that's why it's difficult to fire a warning shot in that scenario, because you're really giving up the goods when you do it the first time.

Ken Harbaugh:

One of the things that struck me in the weeks and days leading up to the Russian invasion was the flood of authorized disclosures that were coming out betraying our what seemed like total visibility, into the Russian game plan.

David Chasteen:

Yeah.

Ken Harbaugh:

You have to have mixed feelings about that kind of thing having been on the inside, having been one of the suppliers, at great risk to yourself and your colleagues, of that kind of info. How does your community feel about using your products for public persuasion?

David Chasteen:

I've been out of the CIA since 2014, so I can't speak directly to the feel inside the building. I've had conversations with friends. What I will say is that it feels like the general consensus is this is a win, and it's nice to have a win. There is always this balance when it comes to sources and methods. It's a running joke with CIA. [inaudible 00:17:40] to talk about sources and methods. But I was a collection management officer at CIA, and one of the ways to think about the CIA is, the CIA is basically like a really kind of bad newspaper. We run at a massive loss for a tiny readership who doesn't read 99% of what we write, but every now and then we get a big story that gets it right, and that's what keeps us in business.

The director of operations, you have case officers who are essentially reporters. They have sources, like reporters. They are given assignments by collection management officers who are best thought of as editors. Those case officers go out, collect stories, write those stories in a journalistic format. Then the collection management officers like myself publish those stories and go to our customers and say, "Is this answering the mail for you? Is this useful to you?"

I think at the CIA we like to think of ourselves on the very best day, doing our very best work, we can prevent wars, or we can prevent negative outcomes, because we can give policy makers the heads up in advance to be able to take actions early enough that they can prevent worse outcomes. This is such a glowing example of a win on that front, it's hard to feel too bad about it. I do know I was never a Russia guy. Russia house is famously very closely guarded with its assets for obvious reasons, given the capability of the Russian intelligence services and the [alter chaims 00:19:09] and other kinds of penetrations that the CIA has historically had from big adversaries like the Russians, that they're very hesitant to let the good stuff out, because you recognize that every time you let that out to the public, you put those sources at great risk and their families. But the point of it is to have an impact, is for it to win. I think, from what I've heard and seen in press reporting and from what I've heard from folks, it does seem like ultimately the folks at CIA were able to sit down with policy makers and say, "Okay, let's try this. Let's try to find a way that we can publicize this information widely but still redact enough that we can protect the sources that gave this information to us in the first place." That's a very hard thing to do, but if you get it right, if you get that balance right, you can have a massive impact, and that's definitely what happened here.

Ken Harbaugh:

I think the impact most people are writing about is the impact on the public and the impact on removing from Putin any excuse for a pretense. We knew that they were staging not just military gear, but they were preparing a false flag operation. We let all of this out into the public domain. What is the impact, though, on the Russian intelligence services, on the adversary, when something like that happens? For you, what would it have been like to have your principal geopolitical adversary tell you that they knew your business?

David Chasteen:

In advance. It's interesting. We talk a lot about in the strategic space, third generation warfare is diplomacy by other means. Fourth generation warfare has really become public relations by other means. The point of warfare has always been to change minds, right? Even by the time the third generation warfare and... Sorry, I should probably, for folks who are not Ken and I are both military guys, so we're familiar with these terms. But first generation warfare is I think pre-trench warfare. It's guys lining up and taking turns shooting at each other, like during the American Revolution. Second generation warfare is generally trench style warfare, World War I. Third generation warfare is combined arms, fast maneuver, air support, World War II style warfare. Fourth generation warfare is generally what people think of as insurgencies and especially media savvy insurgencies.

When you're in that third generation warfare space, the job of the allies in World War II was to convince the Germans to surrender. You needed to change their minds so that they believe what we believed, which is that it is time to give up and stop doing what you're doing. Fourth generation warfare is very much about convincing the fence sitters, that is the big chunk of public opinion that is available on the global stage, about who's the good guy in this scenario, convincing enough of those people that you're right, that we're the good guys and the Russians are the bad guys, Ukrainians are the good guys, Russians are the bad guys, that they support, they throw their support, they come off the fence, and they throw their support behind the Ukrainians in this case. That ability for folks to get out and shape the narrative in advance is really the thing that ultimately wins this kind of conflict.

Ken Harbaugh:

One of the biggest challenges we'll face in that regard is penetrating the new firewalls that Putin has thrown up inside his countries to getting the truth. What are your predictions on our ability to do that? Are the Russians willing and innovative enough to get it themselves? Because with VPNs and other things, you can do it, but it's risky and it's hard.

David Chasteen:

It is. It's risky. It's hard. Of course, Voice of America has been doing this since the cold war, shortwave transmissions. We've always had a mission to try and get real news, Western narrative news anyway, into countries where it is trying to be blocked by an autocratic regime. There's experience with this. I think the trick, of course, is, Russia, the internet is always going to be porous. There's always going to be ways around the firewall. It's just a question of what are the consequences for coming around the firewall in that way. It's really been very inspiring to see how many Russians are willing to risk immediately going to jail in order to protest. The courage and bravery of the Russian people needs to be marked in this way, I think, for sure, and they'll continue to try and get the news in that way too. It's going to be possible.

I think the danger of an autocrat, especially one who's savvy like Putin, is I think in the last few election cycles, we've seen the real danger of telling people what they want to hear. I think that, unfortunately, a lot of the Russian people like what Putin is saying, and they have for a long time. They want to hear that version. I think there's a lot of folks in Russia who think that Putin has made Russia great again, which is very much the narrative that he's been spinning for a long time.

So there's always going to be dissidents. There's always going to be people who are savvy enough to look for other narratives and try to find more objective sources of news. Those folks will be informed, but there's also a lot of people who have family in Ukraine, who are talking to those family members in Ukraine, are like, they're showing us right now, and they don't believe it, because they don't want to believe it. They want to believe that the Russians are the good guys and that Ukraine is controlled by Nazis, and it's World War II all over again, and Russia's the good guys again on the global stage. Some people are going to continue to believe that. At least they'll believe it until the consequences of the sanctions start to really massively hit the Russian economy, which is already happening.

Ken Harbaugh:

Well, the consequences of the sanctions and young Russians not coming home. It is really hard to pierce that narrative until the body bags or lack of body bags, since most of them are being thrown in mass graves or cremated before they get there, until the reality of war sets in. But that might take some time. I don't know if you saw this clip from just the other day of Putin addressing a massive stadium with tens of thousands of cheering Russians and Russian flags about the glory of Greater Russia and the nobility of this invasion and the bravery of the Russians defending Russia and liberating Ukraine. The brainwashing was on full display.

David Chasteen:

Yeah. Yeah, that stuff is hard. The reality, of course, no one wants to think they're the bad guys, and I think there's definitely some people that the more you challenge them on the consequences of the things they've done that are wrong, the more they want to double down. There's this thing called backfire effect, where unfortunately, we've learned that debunking doesn't work. When you try to challenge people with the facts that challenge their preexisting closely held positions, they don't actually change their minds. They dig in deeper. For some critical portion of the Russian people, that will probably continue to be the case. But I think you have to hope that the number of people who are persuadable and the number of people who are dissidents, and also, frankly, look, Russia's not a democracy, right? Not really.

Putin's popular, but it's not a real democratic system. It is an oligarchy. I think people have been throwing that term around a little too loosely. But the reality is that after the fall of Soviet Union, Putin led the dismantling and the sale of the Russian state to people who were former intelligence officers, former military officers, who then literally just stole big chunks of the Russian economy, and Putin has done a very good job of coordinating those folks in order to retain in power. The reason why the administration has targeted the oligarchs is they're the actual seat of power in the country, and if enough of them can be convinced that this is not beneficial to them, then that might actually bring some change.

Ken Harbaugh:

I was going to ask you that, and you brought it up in euphemistic terms. The CIA has a pretty mixed record when it comes to targeted assassinations, I would say a pretty appalling record when it comes to targeted assassinations. But what you're really talking about is a regime change in Russia led by those who may calculate they have more to lose by Putin remaining in power than by him continuing to prosecute this war in Ukraine. Is there anything the US can do or shouldn't do to facilitate an outcome like that?

David Chasteen:

Well, one, to be clear, I left the CIA in 2014, so I'm not privy to any sort of covert action that would be aimed in that direction or anything covert action wise aimed at Ukraine or Russian, and obviously wouldn't talk about it if I did know about it. There is I believe still in power, and I'd have to check on this, but I believe under Executive Order 12333, there is still a prohibition on assassinations of heads of state, like what we're talking about there, or actions that would lead to their death. When I was in the CIA, I never saw anyone try to violate that when I was there. It's not to say that it didn't happen and I didn't know about it, but I never saw anyone try to break the law in that way when I was at the CIA.

What I would say is that when it comes to strategic messaging, when it comes to trying to shape the narrative, all you can do is try to influence the people who are in power to make changes. I think it's also probably frankly overestimating, especially when it comes to changing, I think it's overestimating the capability of the American intelligence capability to do something like that even if we wanted to. An autocrat like Putin has probably survived multiple coup attempts just through the normal course of business just by being who he is. So much of when you have an autocrat like that, the purpose of the state is to preserve the regime.

I think it's hard for us as Americans to think about that. We have a purpose of the government that's enshrined in the Constitution, and the government mostly operates pretty much the same way regardless of who gets elected president or who gets elected to Congress even when those people have wildly differing opinions about how the government should work. We saw how much that was true when the Trump to Biden transition.

Autocracies are not built like that. A democracy is a pyramid that is, it's a regular pyramid where the person at the top is held up by a massive infrastructure that mostly operates the same whether the top gets lopped off or not. An autocracy is built like an inverted pyramid. It's built in such a way that everyone who's in a position of real power owes that power and that position to the person who's in charge of that autocracy in such a way that if they're removed, the entire pyramid collapses. If you're an autocrat and you haven't set that up correctly, you don't last very long. Someone else comes along and does it better.

So Putin's very dug in. It'd be very surprising if something like that happens without a lot of people changing their minds about whether or not supporting him is in their best interests overnight. It's a hard one. That's a challenging thing to do. If someone came to me as the executive officer of the covert action staff and said, "Hey, what do you think about trying to do this," that's what I would explain to them. But I think you can change minds over time. Clearly, the Russian government has changed drastically in our lifetimes. It can do it again, and nobody lives forever. At some point Putin will die of natural causes. There will be a transition. It's just a question of when and what it looks like.

Ken Harbaugh:

As a HUMINT collection officer at CIA, did you have a hand in developing or analyzing psych profiles of key figures?

David Chasteen:

Obviously, the CIA, the analytical, DI is the director of intelligence, and they have analysts, and I'm sure those folks... I've heard open press reporting about the use of psychological profiles of senior leadership, but I don't know anything specific about that, about that background and how it works.

Ken Harbaugh:

Our last guest was someone who worked side by side with Putin in St. Petersburg when he was deputy mayor for a while and was in the room with him for key meetings and just provided some fascinating insight into the vastness of that man's ambition. Honestly, we haven't released this episode yet, but he did not see what was coming, but looking back he sees signs of it.

I want you to take us inside Ukraine from the perspective of a covert action officer and the importance of intelligence for the war fighter, for those territorial defense forces for the regular Ukrainian army. I mean, day-to-day, they're just running and gunning, but intelligence is foundational to their ability to succeed. Explain for us.

David Chasteen:

Well, again, there's a key difference. I spent the first half of my career doing foreign intelligence, and I spent the later half of my career doing covert action. They're different things funded with different dollars and kept very separate for very intentional purposes. Intelligence is when the CIA reports the news, and covert action is when the CIA tries to actually make the news by changing world events in that way.

Where it comes to the intelligence piece, I think the overall, and again, I'm not right in on any of this stuff. I've been out since '14, but in general, one of the most valuable things we do to support our allies is provide both strategic and to share strategic and tactical intelligence. That's not just CIA. It's actually a lot of the more useful stuff is coming from the other members of the intelligence community, like the military focused folks, who are specifically charged with helping American war fighters win. Those folks can help our allies win as well and the folks that we're trying to support. That kind of intelligence is just the normal stuff you would expect a military intelligence foundation to do. It's true movements and where are people where, and what are their capabilities and all that stuff, that you're going to do your best to try and prepare them with that sort of thing.

The covert action piece is different. Covert action is, again, it's something that's not designed to ever be public. I think one of the things that's interesting about how much support that the... and really honestly, one of the ways in which Putin really screwed up, in my opinion, is by taking the Donbas and taking the Crimea and then waiting a couple years to take the rest of the country. He both created time for Ukrainian nationalism to build in a way that it had not in a long time, and also created time for NATO and its allies to provide training and equip, to train and equip to the Ukrainian military. You can't just airdrop a bunch of surface-to-air missiles and anti-tank missiles into a conflict and expect them to have an impact. It takes time to train the trainers, train those soldiers how to use those weapons. Over the last couple years, that's been done very publicly, not by CIA, but by the military, the NATO forces, which is a huge part of the reason why things have gone as well as they have for the Ukrainians under this circumstance.

Covert action is when you do that secretly. The secret part is usually, there's three broad categories of covert action. There's trained equip, which is one of the big ones. There's strategic messaging, and then there's disruption, which is where you kill people and break things. Those are the three broad categories the CIA has ever done under those authorities. This is all public knowledge. This is just part of the doctrine of how this is done in the US code and strategy.

But the training equip piece is mostly when we're teaching other militaries to do what we do. So when CIA intelligence services do that, it's the same thing on the intel piece. So that's training intelligence officers how to do intelligence and training special forces how to do their jobs well using modern Western techniques and modern Western technology. You saw that on the overt side in Iraq and Afghanistan, Ken, and you should, generally speaking, if we're working with an ally, it's someone we support and it makes sense, then most presidents are probably going to look at trying to provide that capability to the intelligence and special forces of the folks we're trying to support as well.

Ken Harbaugh:

How quickly can that ramp up? I know we have been supporting the Ukrainians in that respect since at least 2014, probably before, but obviously there's a need for a surge now. Have you seen that happen?

David Chasteen:

Well, I wouldn't know about it if it had.

Ken Harbaugh:

Well, not in this case, but in your experience?

David Chasteen:

In the past.

Ken Harbaugh:

Yeah.

David Chasteen:

I think what happens is, obviously, there's some things you can do quickly. Look, if you just need basic logistics, like beans and bullets and stuff like that, all armies and all folks are ready to take those kinds of things. When it comes to using more advanced capabilities, like the anti-aircraft missiles or the anti-tank missiles, it takes time. You got to train the trainer and get that capability out there. When it comes to training people how to do HUMINT collection and how to do special operations and insurgency tactics and stuff like that, that all takes a while. It takes a long while. Also, it's about building relationships and building trust with people so that they trust that what you're teaching them is even worthwhile and worth using, and that stuff takes time. But again, weirdly, Putin did us a favor by giving a multiyear heads up notice that this was coming, so I would assume that a lot of that work has already been underway.

Ken Harbaugh:

What do you make of these reports of multiple foiled assassination attempts against President Zelenskyy, especially, and this might be just trolling the FSB, but these reports that the Russian internal security service is actually tipping off the Ukrainians that these attacks are coming.

David Chasteen:

That's fascinating, and that's the first I've heard of that. But I do know, it's obvious at this point that the Russians are very fond of assassinations of people that they don't like or that are inconvenient for the Russian regime. That's certainly consistent with what we've seen so far. I will say, it's interesting talking to folks about this. I don't think people understand Ukrainians have family members in Russia and Russians have family members in Ukraine. I'm telling people, "This is like invading Canada." You know what I mean? If you show up for an exercise and it's like, "We're going to invade Saskatchewan," and we're like, "What? Why?" And they're like, "It's controlled by Nazis," and it's like, "I don't think that's right." It would be really upsetting for us to go in and shoot people who have our accents and kind of look like us and looks like just an extension of the United States culturally. That's kind of what's going on in Ukraine.

So when you're asking your troops to do things, and when you're asking intelligence officers to do things that they find morally questionable... It's interesting. I think there's competing schools of thought about why you get defections and why you get spies from other countries who volunteer to come work for you or provide you with intelligence. Some people, like, "Oh, they do it for the money," but I think a lot of times the best sources that you get are people who think that they're on the wrong side of history and they want to have a positive impact, and they realize, "Oh, this thing that we're about to do is a bad thing, and I don't want to be a part of it, and I would rather actually try and stop it." So if you've got SPR officers and then other FSB officers who are aware of these things, and they're like, "You know what? We're not the good guys in this situation, and I actually don't support that," it's not that hard for an intelligence officer to pick up the phone and drop a line to a NATO intelligence service and just let them know what's coming.

Ken Harbaugh:

I'm maybe attributing too much here, but as a collections officer, you were managing assets with those kinds of motivations that you had to understand, right?

David Chasteen:

Well, it would be a little more accurate to say that I was managing the efforts of case officers who were managing assets. I was more like the editor at the newspaper rather than a reporter at the newspaper.

Ken Harbaugh:

Got it.

David Chasteen:

Yeah.

Ken Harbaugh:

You served in the military, as did I, and when you're in uniform, there is a definite mind shift between the wartime military and the peacetime military. When the balloon goes up, there's a change in the way you think about your job. Does that exist at CIA as well? Is there a wartime CIA and a peacetime CIA?

David Chasteen:

Not in my experience. The reality of course is that I joined CIA in '06, so we were at war, and we were at war the whole time we were there. I think what happens is the CIA is often operating in war zones or other places that are critical, where there's some kind of emergency going on all the time. Different offices at CIA are at war sometimes and are not at other times. So if your region is like, "Oh, this is real." If your region's really blowing up, then yeah, there's that general sense of like, okay, if you're on the Syria desk when the Syrian revolution kicks off, suddenly it's like, oh yeah. There is that same kind of focus, where it's like, oh, suddenly what we do is really important, and you get money, you get resources, you get attention suddenly. Your boss is off to the White House to brief the president. So there is that kind of energy and focus for sure when you're in one of those offices and the balloon goes up, as you say.

Ken Harbaugh:

You said a while back that it's nice to have a win every once in a while. I got to believe that's one of the toughest things about that line of work. In the military, your wins are often public and your failures are often covered up. In the CIA, the wins are intentionally not publicized.

David Chasteen:

Yes.

Ken Harbaugh:

How does that affect the morale and the psyche of folks at the CIA when, often years can go by and the only news coming out of Langley is scandal because you can't talk about the wins.

David Chasteen:

Yeah. It can be hard. I will tell you, early in my career, what's interesting is when you're junior and when you're in an area that is maybe not as hot as another area, and that was kind of early in my career, you can look at what you're doing and be like, "This isn't that important. I don't feel like it's worth it. What are we doing here? Maybe we're not very good at this." What happens is in your career is you move around, you move to different offices. As the executive officer on the covert action staff, I suddenly was read into a lot of stuff, a lot of really big stuff. What you find is that what you ultimately learn is that, and hopefully through your career you have enough places where you realize, "Oh, we're actually doing a lot of good here. This is really positive work. We're absolutely earning our keep. This is great."

Hopefully, you have enough of those things where you understand that your impact is actually quite high. We're a very good value for the American taxpayer for how little HUMINT costs. We have a very big impact for the dollar compared to a satellite system or what NSA does. As you get more senior, you get read into more and you see more, and you get a little bit more of behind the scenes in terms of the overall national security process with the rest of our partners, State Department, military, the White House, Congress, that whole thing. I will say that as I progressed in my career,

I started to realize that both intelligence and covert action are a lot like the rest of American domestic and foreign policy. There's a solid third of it that's probably pretty dumb. We probably shouldn't be doing this, but there's either political reasons why we got to try, or you never know where something might pay off. Then that moves you into the second category, which is a solid third of stuff where it's like, I don't know if this is good yet, but it's probably a pretty good investment, and in the future, we might be really glad we made this investment.

I had a friend who was an analyst on, she was an analyst on a farm or agriculture in X region, and it was like this... or the economy in agriculture in this particular region. It was one of those things where she did this job for years. She was dating a friend of mine, and it was completely unimportant. Then one day the right headline came, and she's briefing the president of the United States. It's like, oh, we're really glad we have that person who has that expertise and that thing.

There's another solid third of stuff where it's like, this is an investment in the future. It might be super important. We got to make sure we're smart about this thing. Then there's a last third of stuff where it's just like a home run, where you're like, this is great policy. This is absolutely worth every penny. If the Americans knew we were doing this, they would be so proud of us. Greenpeace would sign off on this, it's such a good idea and absolutely the right thing to do ethically. So obviously, when you get more of the latter category ones, hopefully, over your career, and those things are really satisfying and they feel really good.

Ken Harbaugh:

A lot of the investment in that second third you described, the impact of it does depend, though, on having a president and an executive branch that is willing to listen.

David Chasteen:

Yeah, that's right.

Ken Harbaugh:

And willing to execute in good faith, effectively, not manipulate the intelligence. You have a customer. You don't get to make the decisions really.

David Chasteen:

That's right. That's right. On both sides, both covert action and the intelligence side. It's one of the reasons why the relationship between the director of the CIA and the president of the United States is so critical. We're useless if the president doesn't believe us, doesn't trust us. That is something that is tricky. It's one of the reasons why the CIA, it's so important that the CIA remain nonpartisan, remain apolitical, much like the military, for the same reason. Under our Constitution, if you're going to have that pyramid, where the top can swap out, and the pyramid still works and is stable, you can't have a Republican president who thinks that there's a Democrat CIA or a Democrat military or a Democrat Chairman of the Joint Chiefs of Staff. You got to be nonpartisan.

That's something that is, I'm proud to say the CIA takes extremely seriously, because they know the stakes. They understand the stakes. You spend much time in the White House, you get it. It's like, we've got to still be taken seriously by the next person in here, regardless of their politics. The CIA is a funny place. It's actually very politically diverse. I knew a lot of Republicans and Democrats at CIA, but nobody's dumb. That's one of the special things about the CIA. You're never the smartest guy in the room. There's always some guy or gal who's way smarter than you, and that's one of the special things about working there. Yeah, people take that very seriously, the nonpartisan aspect of it.

Ken Harbaugh:

Last question. We have an upcoming interview in a couple days with someone on the front lines in one of the besieged Ukrainian cities. He's part of the territorial defense forces. What would you say to that person about America's role in this conflict, about our ability to help or not help? Are there any thoughts you'd want to share?

David Chasteen:

Yeah, it's tricky. One of the things I really like about where we are right now... Look, I have a number of colleagues actually on the special forces side, mostly military vets, friends of mine, who are on their way right now to go help in person. Mostly on their way to Poland to help in person, and really proud of those guys. I totally get it. Some of the expressions that those folks are telling me is, "I didn't feel great morally about what we did in Iraq. It was complicated what we did in Afghanistan. It wasn't clean. It wasn't clear cut that we were the good guys when we were doing a lot of what we were doing there, and this is not like that. The Ukrainians are the good guys and the Russians are the bad guys, and I want to help. I don't like bullies, and it's pretty clear who the bullies are in this case," and those folks are on their way.

I think that my friends at the State Department and CIA, in the military, who've been able to help in any way, have been extremely proud that they've been able to play a part in supporting the Ukrainians, who've just been so courageous in all of this, and so are obviously on the right side of history. I haven't seen in my lifetime the American people and Republicans too, friends of mine who are Republican. It's the first time in a long time I've seen Americans on both sides of the aisle agree on what we should be doing, so there's definitely the American people support the Ukrainian people all across the board.

I just saw a Twitter video today of Presidents Clinton and Bush visiting a Ukrainian church here in the United States to express their support for the Ukrainian people. I think we're going to do everything we can. It's tricky, because obviously it doesn't help the Ukrainians to start a nuclear conflict. The Ukrainians do not win in a nuclear conflict. So there's this trick of nobody wants a nuclear armed NATO and a nuclear armed Russia shooting at each other. That is a bad plan and it doesn't help the Ukrainians. So that's the trick, is how do we give them the support they need to defend themselves and to defend their sovereignty while not triggering a nuclear conflict, which is bad for everybody.

So it's nuanced. Like a lot of this stuff, it's complicated, especially when you're working in the intelligence in the national security space. But I think it's clear the American people support the Ukrainian people, and we'll do everything we can that doesn't cause a disaster to make sure they win.

Ken Harbaugh:

Well thanks, David. I agree. Been great having you. Let's do it again.

David Chasteen:

I love it. Thanks, Ken. Great to catch up with you a little bit. It's been too long.

Ken Harbaugh:

Thanks again to David for joining me. You can find him on Twitter @DavidChasteen

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I’m Ken Harbaugh and this is Burn the Boats, a podcast about big decisions.