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Chris Tarbell: FBI Agent Who Took Down Silk Road | Lex Fridman Podcast #340

Chris Tarbell is a former FBI special agent and cybercrime investigation specialist who brought down Ross Ulbricht and Silk Road, and Hector Monsegur (aka Sabu) of LulzSec and Anonymous. Please support this podcast by checking out our sponsors: - True Classic Tees: https://trueclassictees.com/lex and use code LEX to get 25% off - InsideTracker: https://insidetracker.com/lex to get 20% off - ExpressVPN: https://expressvpn.com/lexpod to get 3 months free - BetterHelp: https://betterhelp.com/lex to get 10% off - Blinkist: https://blinkist.com/lex to get 25% off premium EPISODE LINKS: Hacker And The Fed podcast: https://podcasts.apple.com/podcast/hacker-and-the-fed/id1649541362 Naxo: https://naxo.com/who-we-are PODCAST INFO: Podcast website: https://lexfridman.com/podcast Apple Podcasts: https://apple.co/2lwqZIr Spotify: https://spoti.fi/2nEwCF8 RSS: https://lexfridman.com/feed/podcast/ Full episodes playlist: https://www.youtube.com/playlist?list=PLrAXtmErZgOdP_8GztsuKi9nrraNbKKp4 Clips playlist: https://www.youtube.com/playlist?list=PLrAXtmErZgOeciFP3CBCIEElOJeitOr41 OUTLINE: 0:00 - Introduction 1:16 - Silk Road 11:39 - Mass surveillance 15:50 - Operation Onion Peeler 21:06 - Hacker Avunit 31:56 - Ross Ulbricht and Silk Road 44:39 - Edward Snowden 46:44 - NSA surveillance 58:51 - Silk Road murders 1:07:37 - Dark web 1:11:39 - Ross Ulbricht's arrest 1:19:37 - Aaron Swartz 1:22:55 - Donald Trump and the Mar-a-Lago raid 1:26:01 - Tech companies and censorship 1:35:00 - War in Ukraine 1:38:58 - Anonymous and LulzSec 1:49:10 - FBI 1:52:11 - Personal threats 1:57:57 - Hector Monsegur a.k.a Sabu 2:11:07 - Cyber attack threats against civilians 2:27:55 - Most secure operating system 2:31:44 - Cyber war 2:39:38 - Advice for young people 2:44:50 - FBI's credibility 2:53:21 - Love SOCIAL: - Twitter: https://twitter.com/lexfridman - LinkedIn: https://www.linkedin.com/in/lexfridman - Facebook: https://www.facebook.com/lexfridman - Instagram: https://www.instagram.com/lexfridman - Medium: https://medium.com/@lexfridman - Reddit: https://reddit.com/r/lexfridman - Support on Patreon: https://www.patreon.com/lexfridman

Chris TarbellguestLex Fridmanhost
Nov 22, 20222h 56mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:16

    Introduction

    1. CT

      ... you could buy literally whatever else you wanted. You could post things-

    2. LF

      Drugs.

    3. CT

      Drugs. You could buy heroin right from Afghanistan, the good stuff. Uh, hacking tools, you could hack for hire. You could buy murders for hire.

    4. LF

      The following is a conversation with Chris Tarbell, a former FBI special agent and cyber crime specialist who tracked down and arrested Russ Ulbricht, the leader of Silk Road, the billion dollar drug marketplace, and he tracked down and arrested Hector Monsegur, AKA Sabu of LulzSec and Anonymous, which are some of the most influential hacker groups in history. He is co-founder of Naxo, a complex cyber crime investigation firm, and is a co-host of a podcast called The Hacker & the Fed. This conversation gives the perspective of the FBI cyber crime investigator, both the technical and the human story. I would also like to interview people on the other side, the cyber criminals who have been caught and perhaps the cyber criminals who have not been caught and are still out there. This is a Lex Fridman podcast. To support it, please check out our sponsors in the description and now, dear friends, here's Chris Tarbell.

  2. 1:1611:39

    Silk Road

    1. LF

      You are one of the most successful cyber security law enforcement agents of all time. You tracked and brought down Russ Ulbricht, AKA Dread Pirate Roberts who ran Silk Road and, uh, Sabu of LulzSec and Anonymous, who was one of the most influential hackers in the world. So first, can you tell me the story of tracking down Russ Ulbricht and Silk Road? Let's start from the very beginning. And maybe let's start by explaining what is the Silk Road.

    2. CT

      It was really the first, uh, dark market website. Um, you literally could buy anything there. Uh, I'll take that back. You couldn't... there's two things you couldn't buy there. You couldn't buy guns because that was a different website. Uh, and you couldn't buy fake degrees, so no one could become a doctor, um, but you could buy literally whatever else you wanted. You could post things-

    3. LF

      Drugs.

    4. CT

      Drugs. You could buy heroin right from Afghanistan, the good stuff. Uh, hacking tools, you could hack for hire. You could buy murders for hire if you wanted someone killed. Now, so when I was an FBI agent, I had to kinda sell some of these cases and this was a, a big drug case, you know, that's the way people saw Silk Road. So internally to the FBI how I had to sell it, I had to find the worst thing on there that I could possibly find, uh, and I think one time I saw a posting for, uh, baby parts. So let's say that you, you know, had a young child and that needed a liver, you could literally go on there and ask for a six-month-old liver, uh, if you wanted to.

    5. LF

      For, like, surgical operations versus something darker?

    6. CT

      Yeah, I never saw anything that dark as far as people, like, wanting to eat body parts.

    7. LF

      Yeah.

    8. CT

      Um, I did interview a cannibal once when I was in the FBI. That's another crazy story but, uh, but that, that one actually weirded me out.

    9. LF

      So I just watched, uh, Jeffrey Dahmer, uh, documentary on Netflix and it just changed-

    10. CT

      Mm-hmm.

    11. LF

      ... the way I see human beings because it's, uh, it's a por- it's a portrayal of a normal looking person doing, uh, really dark things and doing so not out of a place of insanity seemingly but just because he has almost, like, a fetish for that kind of thing. It's disturbing that people like that are out there. So people like that would then be using Silk Road, not like that necessarily but people of different walks of life would be using Silk Road to primarily... what was the prim- primary thing? Drugs?

    12. CT

      It was primarily drugs and that's where it started, it started off with Russ Ulbricht growing mushrooms out in the wilderness of California and selling 'em but really his was more of a libertarian viewpoint. I mean it was like you choose what you want to do for yourself and do it. And the way Silk Road kind of had the anonymity is it used what's called TOR, the Onion router which is a anonymizing function on, uh, on the deep web. It was actually invented by the US Navy back in the mid 90s or so, um, but it also used cryptocurrency so it was the first time, like, we saw this birth on the internet of mixing cryptocurrency, uh, and a, an IP blocking software so, you know, in cyber crime you go after one, the IP address and trace it through the network or two, you go after the cash and this one kind of blocked both.

    13. LF

      Cash meaning the flow of money?

    14. CT

      Yeah.

    15. LF

      Physical or digital and then, um, IP is the, some kind of identifying thing of the computer.

    16. CT

      It's your telephone number for, on your computer, so yeah, all, all computers have, you know, a unique four octet numbers, you know, so 123.123.123.123 and it, you know, the computer uses DNS or domain name services to, to render that name so if you were looking for, you know, cnn.com, your computer then translates that to that IP address or that telephone number where it can find that information.

    17. LF

      Didn't Silk Road used to have guns in the beginning? Or was that considered to have guns or was... did it naturally emerge and then Russ realized, like, "This is not good."

    18. CT

      It went back and forth, uh, I think there were guns on there and he tried to police it, um, you know, he, uh, he called himself th- the captain of the boat so you had to follow his rules so, you know, I think he took off those posts eventually and he moved guns elsewhere.

    19. LF

      What was the system of censorship that he used? Like of selecting what is okay and not okay? I mean, it's-

    20. CT

      Him alone, he's the captain of the boat.

    21. LF

      Do you know by chance if there was, uh, a lot of debates and criticisms internally amongst the criminals of what is and isn't allowed? I mean it's interesting to see a totally different moral code emerge that's outside the legal code of society.

    22. CT

      We did get the, the server and was able to read all of the chat logs that, what, that happened.

    23. LF

      Okay.

    24. CT

      I mean all the records were there. Um, I don't remember big debates, I mean there was a clear leadership.

    25. LF

      Yeah.

    26. CT

      Uh, and that was the final decision, that was the, the CEO of Silk Road.

    27. LF

      And so primarily it was drugs and primarily out of an ideology of freedom which is, um-If you want to use drugs, you should be able to use drugs.

    28. CT

      You should put in your body what you wanna put in your body.

    29. LF

      And when you were presenting the case of why this should be investigated, uh, you were trying to find, as you mentioned, the worst possible things on there. Is that what you were saying?

    30. CT

      So we had arrested a guy named Jeremy Hammond, and he hid himself. He was a hacker, and hi- this w- when we arrested him, it's the second time he had been arrested for, for hacking. Uh, he used Tor. Um, and so that kind of brought us to a point, um... The FBI has a computer system where you look up things, uh, you know, you look up anything. I could look up your name or, (laughs) or whatever, if you're associated with my case. And we were finding at the time a lot of things in... You know, when you look it up, it- the c- a case would end, be like, "Oh, this is Tor." And just stopped.

  3. 11:3915:50

    Mass surveillance

    1. LF

      the things you were able to do in tracking down information, and we'll get to it, there is some suspicion that this was only possible with, uh, mass surveillance, like with NSA, for example. Uh, first of all, is there any truth to that? And second of all, what do you feel are the pros and cons of mass surveillance?

    2. CT

      There is no truth to that. Uh, and then my feelings on mass surveillance-

    3. LF

      If, if there was, would you tell me?

    4. CT

      Probably not, but... (laughs)

    5. LF

      Yeah. (laughs) I love this conversation so much. (laughs)

    6. CT

      (laughs)

    7. LF

      But what do you feel about...... the, given that you said child porn-

    8. CT

      Sure.

    9. LF

      ... what are the pros and cons of surveillance at a society level?

    10. CT

      I mean, nobody wants to give up their privacy. I say that. I say no one wants to give up their privacy, but I mean, I used to have to get a search warrant to look inside your house.

    11. LF

      Yeah.

    12. CT

      Or I can just log onto your Facebook and you've got pictures of all inside your house and what's going on. I mean, it's not... You know, so people like the idea of not giving up their privacy, um, but they do it anyways. They- they're giving away their freedoms all the time. They're- they're- they're carrying watches that gives out their heartbeat to a wave of companies that are storing that. I mean, what's more personal than your heartbeat?

    13. LF

      So I- I think people en masse really want to protect their privacy, and I would say most people don't really need to protect their privacy, but the case against mass surveillance is that if you want to criticize the government in a very difficult time, you should be able to do it. So when- when you need the freedom, you should have it. So when you wake up one day and realize, "There's something going wrong, wrong with the country I love, I wanna be able to, uh, to help." And that- the- one of the great things about, uh, the United States of America is there's that individual revolutionary spirit, like, so that the- the government doesn't become too powerful, that you can always protest. There's always... The best of the ideal of freedom of speech, you can always say, "Fuck you," to the man. And I think there's a concern of direct or indirect suppression of that through mass surveillance. You might not... Th- is that- that little subtle fear that grows with time, that, uh, why, you know, why bother criticizing the government? "Ah, it's gonna be a headache. I'm gonna get a ticket every time I say something bad," that kind of thing. So it gets out- it can get out of hand. The bureaucracy grows and, uh, the freedoms slip away, is that's the, that's the criticism, right?

    14. CT

      I completely see your point, and I agree with it. I mean, uh, but, I mean, on the other side, people criticize the government of these freedoms, but, I mean, tech companies are... Talk about destroying your privacy and controlling what you can say. I realize they're private platforms a- and you- they can decide what's on their platform. Um, but, you know, they're taking away your freedoms of what you can say, and, you know, we've heard certain- some things where maybe government officials were in line with, uh, with tech companies to take away some of that freedom, and that's... I- I agree with you. That gets scary.

    15. LF

      Yeah, there's something about government that feels, maybe because of the history of human civilization, maybe because tech companies are a new thing, but just knowing the history of abuses of government, it, there's something about government that enables the corrupting nature of power to take hold at scale more than tech companies, at least what we've seen so far.

    16. CT

      You... Yeah. I- I agree. I agree. But, I mean, we haven't had a voice like we've had until recently. I mean, w- anyone that has a Twitter account now can speak and become a- a news article, um, you know. My- my parents didn't have that, didn't have that voice. If they wanted to speak out against the government or do something, they had to go to a protest, or organize a protest, or, you know, do something along those lines. So, you know, we have more of a place to put our voice out now.

    17. LF

      Yeah, it's incredible, but that's why it hurts, and that's why you notice it when certain voices get removed. The President of the United States of America was removed from one such, or all such, platforms, and that hurts.

    18. CT

      Yeah, that's crazy to me. That's insane. That's insane that we- we- we took that away, but...

  4. 15:5021:06

    Operation Onion Peeler

    1. CT

    2. LF

      Let's return to (laughs) to Silk Road and Mossad break. So how did your path with this very difficult, very fascinating case, uh, cross?

    3. CT

      We were looking to open a case against Tor because it was a problem. All the cases were closing, uh, because Tor, so we went on Tor and we- we came up with 26 web different Onion, .onions that we targeted. We were looking for nexuses to hacking 'cause I was on a squad called CY2 and we were, like, the premier, um, squad in New York that was working, uh, uh, criminal cyber intrusions. And so, you know, any website that was offering hackers for hire or, um, hacking tools for free, you know, or- or paid- paid services, uh, you know, like, now we're seeing ransomware as a paid service and phishing as a paid service. Um, anything that offered that, so we opened this case on- on, uh, I think we called it... So you have to name cases. One of the fun thing in the FBI is when you start a case, you get to name it, and you- you would not believe how much time is spent in coming up with the name.

    4. LF

      Yeah.

    5. CT

      Um, you know, case goes by. I think we called this Onion Peeler because of the-

    6. LF

      Nice.

    7. CT

      ... yeah.

    8. LF

      So a little bit of humor, a little bit of wit, and some profundity to the language. Yeah, yeah.

    9. CT

      Yeah.

    10. LF

      'Cause you're gonna have to work with this one for quite a lot, so.

    11. CT

      Yeah, this one had the potential of being a big one, you know, because I think- I think Silk Road was, like, the sixth on the list, uh, uh, for that case, but we all knew that was sort of the golden ring. If you could make the splash that that Onion site was going down, then it would probably get some publicity. A- and that's part of, you know, law enforcement, is getting some publicity out of it that, you know, that makes others think not to do it.

    12. LF

      And we should say that Tor is the name of the project, the browser. What is the Onion technology behind Tor?

    13. CT

      Let's say you wanna go to a .onion site. You'll w- you'll put in the .onion you wanna go to and your computer will build, uh, communications with a Tor relay, uh, which are all publicly available out there. Um, but you'll encrypt it. You'll put a package around, uh, your data, and so it's- it's encrypted, and so n- can't read it. It goes to that- that first relay. That first relay knows about you and then knows about the next relay down the chain. And so it takes your d- data and then encrypts that on the outside and sends it to relay number two. Now, relay number two only knows about relay number one. It doesn't know who you are asking for this, and it goes through there adding those layers on top, layers of encryption till it gets to where it is. That, and then even the Onion server doesn't know, except for the- the relay it came from, who it's talking to. And so it peels back that, gives the information, puts another layer back on. And so it's- it's layers like you're peeling an onion back of, uh, the different relays, and that encryption protects, uh, who the sender is and what information they're sending.

    14. LF

      The more layers there are, the more exponentially difficult it is to decrypt it.

    15. CT

      ... I mean, you get to a place where you don't have to have so many layers because e- e- it doesn't matter anymore, it's mathematically impossible to- (laughs)

    16. LF

      Yeah.

    17. CT

      ... decrypt it, but yeah, um, you know, i- uh, the more relays you have, the slower it is. I mean, that's the one of the big drawbacks o- o- on Tor, is- is how slow it operates.

    18. LF

      So how do you peel the onion? So what- what are the different methodologies for trying to get some information from a cybersecurity perspective on these operations like Silk Road?

    19. CT

      It's very (laughs) difficult. Um, people have come up with different techniques. There, um, there- there's been techniques to put out in the- in the news media a- about how they do it, um, running, like, massive amounts of relays and- and you're controlling those relays, I think. I think somebody tried that once.

    20. LF

      So there's a technical solution. And- and what about social engineering? What about trying to infiltrate the actual humans that are using the- the Silk Road and trying to get in that way?

    21. CT

      Yeah, I mean, I- I definitely could see the- the way of doing that, and in- in this case, uh, in- in our take down, we used that. Um, there was one of my partners, uh, Jared Darig, and he was an HSI investigator, and he had worked his way up to be a system admin on the site. Um, so that did glean quite a bit of information because he was- he was inside and- and talking to, uh, you know, at that time, all we really know it as DPR or Dread Pirate Roberts. Uh, we didn't know who- who that was yet, but- but we had that open communication. Um, you know, and one of the things, you know, the technical aspects on that is there was a Jabber server that was, uh, that's a communication- type of communication server, um, that was being used, and we knew that Ross wi- had his Jabber set to, uh, Pacific time. So we had a pretty good idea what- what part of the- the- we- w- what part of the country he was in.

    22. LF

      I mean, isn't that from- from- from DPR's perspective, from Ross's perspective, isn't that clumsy?

    23. CT

      He wasn't a- a- a- he wasn't a big computer guy.

    24. LF

      Do you notice that aspect of, like, the technical savvy of some of these guys doesn't seem to be quite... why- why weren't they good at this?

    25. CT

      Well, the- the- the real techy savvy ones we don't arrest. We don't get to 'em. We don't find 'em.

    26. LF

      You don't get to them.

    27. CT

      (laughs) (exhales)

    28. LF

      Shout out to the techy, uh, criminals. They're probably watching

  5. 21:0631:56

    Hacker Avunit

    1. LF

      this.

    2. CT

      I mean, yeah, I mean, you were getting the low hanging fruit. I mean, we were getting the ones that can be caught. I mean, th- they, you know- well, I'm sure we'll talk about it, but the Anonymous case, there was a guy named AVUNIT. He's still- I lose sleep over him 'cause I- we didn't catch him. We caught everybody else. We didn't catch him. (laughs) He's good though. (laughs) He pops up too once in a while on the internet and it pisses me off.

    3. LF

      Yeah. What's his name again?

    4. CT

      AVUNIT. Uh, it- uh, that's all I know is it's AVUNIT.

    5. LF

      AVUNIT?

    6. CT

      Yeah, I got a funny story about- about him and what- who people think he is.

    7. LF

      Can I ask you... can we go on that brief tangent?

    8. CT

      Sure. I- I love tangents.

    9. LF

      (laughs) Well, let me ask you, um, since he's probably he or she... do we know it's a he?

    10. CT

      We- we have no idea.

    11. LF

      Okay.

    12. CT

      And that's another funny story about hackers, the he/she issue.

    13. LF

      What's the funny story there?

    14. CT

      Well, one of the guys in LulzSec was a- was a she, was a 17-year-old girl.

    15. LF

      Yeah.

    16. CT

      Uh, and, uh, my source in the case, the ha- the guy Sabu that I- I arrested in part of an- you know, we sat side by side for nine months and l- then took down, you know, the case and all that, he was convinced she was a girl and we said, you know, and he- he was in love with her almost at s- at one point, and turns out to be a 35-year-old guy th- living in England.

    17. LF

      Oh, so he was convinced as a- a- a- (laughs)

    18. CT

      Yes, he was absolutely convinced.

    19. LF

      Based on what exactly? By linguistic, like, human-based linguistic analysis or what?

    20. CT

      She- she, he, uh, whatever, uh, you know, Kayla is what we went- which ended up being like a- a modification of his sister's name, the- where- the real guy's sister's name-

    21. LF

      Got it.

    22. CT

      ... was so good at building the backstory. All these guys, and they're- and it's funny, like, these guys are part of a hacking crew. They social engineer the shit out of each other-

    23. LF

      Yeah.

    24. CT

      ... just to build if one of 'em ever gets caught. They'll convince the everybody else that, you know, they're a Brazilian, uh, you know, ISP owner or something like that, and that's how I'm so powerful.

    25. LF

      Well, yeah, that social engineering aspect is part of living a life of cyber crime or cyber security on the offensive or defensive. So AVUNIT... can I ask you a- also just a- a tangent of a tangent first?

    26. CT

      That's my favorite tangent.

    27. LF

      Okay. Um, is it possible for me to have a podcast conversation with somebody who hasn't been caught yet? And because they have the conversation they still won't be caught? And is that a good idea? Meaning, is there a safe way for a criminal to talk to me on a podcast?

    28. CT

      I would think so. I would think they- that- that someone could... I mean, someone who has been living a double life for- for long enough where you think they're not a criminal, um, I-

    29. LF

      No, no, no, they would have to admit that they- they would say, "I am AVUNIT."

    30. CT

      Oh. Oh, you would wanna have a conversation with AVUNIT?

  6. 31:5644:39

    Ross Ulbricht and Silk Road

    1. LF

      Silk Road, can you speak to the scale of this thing? What, what, uh, just for people who are not familiar, uh, how big was it, um, and w- any other interesting things you understand about its operation when it was active?

    2. CT

      So it was, uh, w- when we finally got looking through the books and (sighs) you know, the- the numbers came out as about $1.2 billion in sales. It's kinda hard with the fluctuation value of bitcoin at the time to come up with a real number, so you kind of pick a daily average, you know, and go across, so...

    3. LF

      Most of the operation was done in, in bitcoin?

    4. CT

      It was all done in bitcoin. You, you couldn't, you had escrow accounts on, you know, you came in and you put money in an escrow account and, you know, it, the transaction wasn't done until the client got the, the drugs or whatever they had bought, um, and then the drug dealers had, had sent it in. There was some talk at the time that, that the cartel was starting to sell on there, um, so that started getting a little hairy there at the end.

    5. LF

      What was your understanding of the relationship between organized crime, like the cartels, and this kind of more ad hoc, new age, uh, market that is the Silk Road?

    6. CT

      I mean, it was all just chatter. It was just, uh, you know, 'cause, like I said, Jared was in the inside, so we saw some of it from the admin sides, and Ross had a lot of private conversations with the different people that he had advised him, um, but no one knew each other. And I mean, the only thing, the only thing that, that they knew were the admins had to send an ID to Ross, had to send a picture of their driver's license or passport, which I always found very strange. Because if you are an admin on a site that sells fake IDs-

    7. LF

      Mm-hmm.

    8. CT

      ... why would you send your real ID? And then why would the guy running the site, who profits from selling fake IDs, believe that it was? But fast-forward-

    9. LF

      Yeah.

    10. CT

      ... tangent, they were all real IDs. All the IDs that we found on Ross' computer as the admins were the real people's IDs.

    11. LF

      What do you make of that?

    12. CT

      Because I don't-

    13. LF

      Just other clumsiness?

    14. CT

      (laughs) Yeah, low-hanging fruit, I guess. I guess that's what it is. I mean, I mean, I would've bought, I mean, even Ross bought fake IDs off the site. He had federal agents knock on his door, um, you know, and then he got a little cocky about it.

    15. LF

      The landscape, the dynamics of trust is fascinating here. So you trust certain ideas or, like, who do you trust in that kind of market? What was y- your understanding of the network of trust?

    16. CT

      I have no idea, anyone trust anybody, you know. I mean, I think Ross had his advisors of trust, but outside of that, I mean, he required people to send their ID for their trust. He, you know, people stole from him, uh, there was, there's open cases of that. Um, it's a criminal world, you can't trust anybody.

    17. LF

      What was his life like, you think?

    18. CT

      Lonely. Can you imagine being trapped in something like that where you're, the, your whole world focused on that and you can't tell people what you do all day?

    19. LF

      Could he have walked away?

    20. CT

      Like, someone else take over or the site just shut down?

    21. LF

      Either one. Just you, put- putting yourself in his shoes, the loneliness, the, the anxiety, the, just the growing immensity of it, so walk away with some kind of financial stability.

    22. CT

      I couldn't have made it past two days. I- I'm not, I'm no- I don't like loneliness, you know. I mean, my, I, if my wife's away, I probably call her 10, 12 times a day.

    23. LF

      Yeah.

    24. CT

      We just talk about things, you know, I just, you know, "Oh, something crossed my mind, I wanna talk about it." And I'm sure she... Before-

    25. LF

      And you like to talk to her, like, honestly about everything? So if you were running Silk Road, (laughs) you w- you wouldn't be able to, like, uh...

    26. CT

      Hopefully, I'd have a little protection. I'd only mention to her when we were in bed, um, to have that marital, uh, connection, but, (laughs) but who knows? I mean, she's gonna question why the Ferrari is outside and...

    27. LF

      (laughs)

    28. CT

      And things like that.

    29. LF

      Yeah. (laughs) Well, I'm sure you can come up with something. Why didn't he walk away? That's another question of why don't criminals walk away in these situations?

    30. CT

      Well, I, I mean, I don't know every criminal mind, and some do. I mean, A.B. Unit walked away. I mean, d- not to go back...

  7. 44:3946:44

    Edward Snowden

    1. LF

      it's, it's not out of the realm of possibility.

    2. CT

      Yeah. I mean, I've been asked before, who, you know, who... Does he get out of prison first or does Snowden come back into America and... I, I don't know. I have no idea.

    3. LF

      Snowden just became a Russian citizen.

    4. CT

      I saw that, and that's, yeah. I've heard a lot of good, weird theories about that one.

    5. LF

      Well, actually, uh, on another tangent, let me ask you, do you think Snowden is, um, a good or a bad person?

    6. CT

      A bad person.

    7. LF

      Can you make the case that he's a bad person?

    8. CT

      There's ways of being a whistleblower, and, and there, there's, there's rules set up on how to do that. Um, he, he didn't follow those rules. I mean, they, they... You know, I'm red, white, and blue, so I'm pretty, you know, as a federal government-

    9. LF

      So you think his actions were anti-American?

    10. CT

      I think the results of his actions were anti-American. I don't know if his actions were anti-American.

    11. LF

      Do you think he could have anticipated the, the negative consequences of that, his action?

    12. CT

      Yes.

    13. LF

      Should we judge him by the consequences or the ideals of the intent of his actions?

    14. CT

      I think we all get to judge him by, based on our own beliefs, but I believe what he did was wrong.

    15. LF

      Can you steel man the case that he's actually, uh, a good person and good for this country, for the United States of America, uh, as a flag bearer for the whistleblowers, the check on the power of government?

    16. CT

      Yeah. I mean, I'm not big government type guy, you know. So, uh, even, that sounds weird coming from a government guy for so many years. Um, but there's rules in place for a reason. I mean, he put, you know, some of our best capabilities, um, he made them publicly available. Um, it really kind of set us back in the, and this isn't my world at all, but the offensive side of cyber security.

    17. LF

      Right. So he revealed stuff that he didn't need to reveal in order to make the point.

    18. CT

      Correct.

    19. LF

      The... So, so you, if you can imagine a world where he leaked stuff that revealed the mass surveillance efforts and not reveal other stuff.

  8. 46:4458:51

    NSA surveillance

    1. LF

    2. CT

      Yeah.

    3. LF

      Like is the, is the mass surveillance... I mean, that's the thing that, uh... Of course there's, in the interpretation of that, there's fear mongering, but at the core, that was a real shock to people, that, um, it's possible for a government to collect data at scale.

    4. CT

      It's surprising to me that people are that shocked by it. (laughs)

    5. LF

      Well, there's conspiracies, and then there's like actual, uh, evidence that that is happening.

    6. CT

      Yeah.

    7. LF

      I mean, it's a, it's a real-... There's a lot of reality that people ignore. But when it hits you in the face, you realize, holy shit, we're living in a new world. This is, this is the new reality, and we have to deal with that reality. Just like you work in cyber security, I think it really hasn't hit most people how fucked we all are in terms of cyber security. Okay, let me rephrase that.

    8. CT

      (laughs)

    9. LF

      How many dangers there are in a digital world, how much under attack we all are, and how more intense the attacks are getting, and how difficult the defense is, and how important it is, and how much we should value it, and all the different things we should do it at the small and large scale to defend. Like most people really haven't woken up. They think about privacy from tech companies. They don't think about attacks, cy- cyber attacks.

    10. CT

      People don't think they're a target, and it's a, that message has, definitely has to get out there. I mean, you know, if you have a voice, you're a target. If the place you work, you might be a target, you know. Your husband might work at some place, you know, and they, because now people are working from home, so they're gonna target, you know, target you to get access to his network in order to get in.

    11. LF

      Well, in that same way, the idea that the US government or any government could be doing mass surveillance on its citizens is, um, is one that was a wake-up call. Because you could imagine the ways in which that could, um, be a, like you could abuse the power of that to control us as a, for political reasons and purposes.

    12. CT

      Absolutely. You know, you could abuse it. I, I think during the part of the Snowden leak, we saw the two NSA guys were, uh, monitoring like their girlfriends.

    13. LF

      Yeah.

    14. CT

      And there's rules in place for that. Those people should be punished for abusing that. But how else are we going to hear about, you know, terrorists that are in the country talking about birthday cakes? Uh, and you know, that was a case where that, that was the trip word that, that, you know, we're gonna go bomb New York City's subway.

    15. LF

      Yeah. It's complicated, but it just feels like there should be some balance of transparency. There should be a check on that power. 'Cause like you, you know, in the name of the war on terror-You, you can sort of, uh, sacrifice... There is a trade-off between security and freedom, uh, but it just feels like there's a giant slippery slope on the sacrificing of freedom in the name of security.

    16. CT

      It's, I, I hear you. And, and, (sighs) you know, we, we live in a world where... Well, I live in a world where I had to tell you exactly how... When I arrested someone, I had to write a, a 50-page document of how I arrested you, uh, and all the probable cause I have against you and all that. Well, you know, bad guys are reading that. They're reading how I caught you and they're changing the way they're doing things. They're changing their MO. Um, you know, they're doing it to be more secure. If, you know, we tell people how we're monitoring, you know, how, what we're surveilling, we're gonna lose that. I mean, the, the, the terrorists are just gonna go a different way. And, and I'm not trying to... I, again, I'm not big government. I'm not trying to say that, you know, it's cool that, that, that we're monitoring, the US government's monitoring everything. Um, you know, big tech's monitoring everything. They're, they're just monetizing it versus, uh, possibly using it against you.

    17. LF

      But there is a balance, and those 50 pages, they have a lot of value. Um, and they make your job harder, but they prevent you from abusing the power of the job.

    18. CT

      Yeah.

    19. LF

      There's a balance.

    20. CT

      Yeah.

    21. LF

      That's a tricky balance. So the chat logs in Iceland gave you evidence, uh, of the heroin and all the, the large-scale tsar-level, uh, drug trading. Uh, what else did it give you in terms of the, how to catch...

    22. CT

      It gave us infrastructure. So the Onion name was actually running on a server in France. So if you, like... And it only communicated through a, a back channel, a VPN, um, to connect to the Iceland server. Um, there was a, um, Bitcoin, like, in a vault server that was also in Iceland, and I think that was so that the admins couldn't get into the Bitcoins, the other admins that were hired to work on the site. So you could get into the site, but you couldn't touch the money. Only Ross had access to that. And then, you know, another, another big mistake on Ross's part is he had the backups for everything at a data center in Philadelphia. Don't put your infrastructure in the United States. (laughs) I mean, again, let's not make a playbook, but, you know...

    23. LF

      Well, I think these are low-hanging fruit that people of competence would know already. Uh-

    24. CT

      Yeah, I, I agree.

    25. LF

      ... but it's interesting that he wasn't competent enough to make... So he was incompetent in certain ways.

    26. CT

      Yeah, I don't, I don't think he was a mastermind of setting up an, an infrastructure that would protect his, uh, his, his online business because, you know, keeping chat logs, keeping a diary, putting infrastructure where it shouldn't be, um, bad decisions.

    27. LF

      How did you figure out that he's in San Francisco?

    28. CT

      (inhales deeply) So we had that part with Jared, that he was on the West Coast, and then-

    29. LF

      Who, again, is Jared?

    30. CT

      Jared Dehughian was a, he was a partner, um, in, uh... He, he was a DHS agent, um, worked for HSI, Homeland Security Investigations, in Chicago. Uh, he started his Silk Road investigation because he was working at O'Hare and a weird package came in. Um, come to find out, he traced it back to Silk Road. So he, he, he started working a Silk Road investigation long before I started my case, and he made his way up undercover all the way to be an admin on Silk Road. Um, so he... I was talking to Ross on a Jabber server, the, a private Jabber server, private chat communication server, and, uh, we noticed that Ross's, um, time zone on that Jabber server was set to the West Coast. So we, we had Pacific Time on there, so we had a, a region, one twenty-fourth of the world was covered, uh, of where we thought he might be.

  9. 58:511:07:37

    Silk Road murders

    1. CT

      people will argue back and forth that there was never murders on Silk Road. When we were doing the investigation, to us, there were six murders. Um, so there, there was... The way we see him, saw him at the time was Ross ordered people to be murdered. Um, you know, somebody's... people stole from him and all that. It was sort of an evolution from, "Oh, man, I can't deal with this. I can't do it. It's too much," to the last one was like the guy said, uh, "Well, he's got three roommates." Uh, and it's like, "Oh, we'll kill them too."

    2. LF

      Was that ever proven in court?

    3. CT

      No.

    4. LF

      Just part of murder?

    5. CT

      And it's... The, the murders never went forward because there was some, uh, some, some stuff, problems in that case. So, there was a separate case in Baltimore, uh, that they had been working on for a lot longer. And so, you know, during the investigation, that caused a bunch of problems because now we have multiple federal agencies case against the same thing.

    6. LF

      How do you decide not to push forward the, the, the, the murder investigations?

    7. CT

      So, there was a de-confliction meeting that happened in DC. Um, I didn't happen to go to that meeting, but Jared went. This is before I ever knew Jared. And, um, we have like, um, televisions where we can just sit in a room and s- sit in on the meeting, um, but it's all, you know, secured network and all that so we can talk openly about, uh, secure things. Um, and we sat in on the meeting, and people just kept saying the term "sweat equity." "I've got sweat equity," meaning that they had worked on the case for so long that they deserve to take him down. Um, and th- by this time, you know, no one knew about us, but we told them at the meeting that, well, we had found the server and we have a copy of it and we have the infrastructure. Um, and, and these guys had just had communications, undercovers. Um, they didn't really know what was going on. And this wasn't my first de-confliction meeting. We had a huge de-confliction meeting during, um, during the Anonymous case.

    8. LF

      What's a de-confliction meeting?

    9. CT

      Agents within your agency or other, other federal agencies have an open, uh, investigation that if you expose your case or took down your case would hurt their case or the other way.

    10. LF

      Oh, so you kinda have a... It's, it's like the rival gangs meet at the table in a smoke-filled room and, uh-

    11. CT

      Less bullets at the end, but yes (laughs) .

    12. LF

      Yes (laughs) . Oh, boy, with the sweat equity.

    13. CT

      Yeah. So-

    14. LF

      I mean, there's c- careers at stake, right?

    15. CT

      I hate s-

    16. LF

      Yeah. You hate that idea?

    17. CT

      Yeah. I mean, why would you... why is that at stake? Just because you've worked on it long enough, longer than I have, that means you get... you, you, you did better?

    18. LF

      Yeah.

    19. CT

      That's, that's insane to me, the, the... that's rewarding bad behavior.

    20. LF

      And so, that one of... the part of the sweat equity discussion was about murder and this was, "Here's a chance to actually bust them, be... given the data you have from Iceland," and all that kind of stuff. So why...

    21. CT

      Well, they wanted us just to turn the data over to them.

    22. LF

      To them?

    23. CT

      Yeah.

    24. LF

      So that-

    25. CT

      Thanks, thanks for getting this this far. Here it is. I mean, it came to the point where they sent us like, they, they had a picture of what they thought Ross was and it was an internet meme.... it really was a meme. It was a, it was a photo that we could look up. Like, it- it was insane.

    26. LF

      All right, so there's, uh, different degrees of competence all across the world between different people. Yes. Okay. Uh, does part of you regret, because you pushed forward the- the heroin and the drug trade, but never got to the murder discussion?

    27. CT

      I mean, the only regretting is that- that the internet doesn't seem to understand. Like, they- they- they just kind of blow that part off, that- that he literally paid people to have people murdered. It didn't result in a murder, and I thank God no one resulted in a murder.

    28. LF

      But that's where his mind was.

    29. CT

      His mind and where he wrote in his diary was that, "I had people killed and here's the money." He paid it. He- he paid a large amount of bitcoins, uh, to- for that murder. So- those murders-

    30. LF

      So he didn't just even think about it, he actually took action, but the murders never happened. He took action by paying the money.

  10. 1:07:371:11:39

    Dark web

    1. LF

      What else can you say about this complicated world that has grown of the dark web?

    2. CT

      ... I don't understand it. I- I- like, it would have been a, a, something for me. I- I thought, I thought it was gonna collapse, but, I mean, i- it's just gotten bigger in what's going on out there. Now, I'm really surprised in- in, that it hasn't grown into other networks, or people haven't developed other networks, but, but Tor is.

    3. LF

      You mean like instead of Tor?

    4. CT

      Yeah. Yeah. Tor's still the main one out there. I mean, there's some, there's a few others, and I'm not gonna put an advertisement out for them-

    5. LF

      Yes.

    6. CT

      ... but, uh, but, you know, uh, I thought that market would have grown.

    7. LF

      Yeah, my sense was, when I interacted with Tor, it was that there's huge usability issues. But that's for, like, legal activity.

    8. CT

      Yeah.

    9. LF

      'Cause like if you care about privacy, it's just not as good of a browser. Like, uh, it's to- to- to- to look at stuff.

    10. CT

      No, it's way too slow.

    11. LF

      It's way too slow.

    12. CT

      It's way too slow. But I mean, you can't even, like... I know some people use it to, like, view movies. Like Netflix, you can only view certain movies in certain countries. You can use it for that, but it's- it's too slow even for that, so.

    13. LF

      Were you ever able to hold in your mind the landscape of the dark web? Like, what- what's going on out there? It's just, like, to me as a human being, it's just difficult to understand the digital world. Like, these anonymous usernames, like doing anonymous activity, it's just, it's hard to, um... What am I trying to say? It's hard to visualize it in the way I can visualize, like I've been reading a lot about Hitler. I can visualize meetings between people, military strategy, uh, deciding on, uh, certain evil atrocities, all that kind of stuff. I can visualize the people. There's agreements, hands- handshakes, p- stuff signed, groups built. Like, in the digital space, like with bots, with anonymity, any one human can be multiple people. Uh, it just-

    14. CT

      Yeah, it's all lies. It's all lies.

    15. LF

      Like, yeah, it feels like I can't trust anything.

    16. CT

      No, you can't. You honestly can't. And, like, you can talk to two different people and it's the same person. Like- like, there's so many different... You know, Hector had so many different identities online, that, you know, uh, of things that- that, you know, the- the lies to each other. He lied to people inside his group, uh, just to use another name to spy on, make sure what they, you know, weren't talking shit behind his back, or weren't doing anything. Um, it's all lies. And- and people that can keep all those lies straight, it's unbelievable to me.

    17. LF

      Ross Ulbricht represents the very early days of that. That's why the- the competence wasn't there. Just imagine how good the people are now, the kids that grow up.

    18. CT

      Oh, they've learned from his- his mistakes.

    19. LF

      Just the extreme competence. Did you see how good people are at video games? Like, the level of, uh, play, in terms of video games. Like, I- I used to think I sucked.

    20. CT

      (laughs)

    21. LF

      And now I'm not even, like, I'm not even in-in the, like, consideration of calling myself shitty at video games. I'm not even, I'm like nonexistent. I'm like, uh, the mold.

    22. CT

      Yeah, I stopped playing because it's so embarrassing.

    23. LF

      It's embarrassing.

    24. CT

      It's like wrestling with your kid and he finally beats you.

    25. LF

      (laughs)

    26. CT

      He's like, "Well, fuck that, I'm not wrestling my kid any- ever again."

    27. LF

      And in some sense, hacking, uh, at its best and its worst, is a kind of game. And you can get exceptionally good at that kinda game.

    28. CT

      And you get the accolations, uh, of it. I mean, there- there's, you know, there's power that comes along if you have success. Uh, look at the kid that- that was hacking into Uber in Rockstar Games. He put it out there that he was doing it. I mean, he used the name, um, whatever hacked into Uber was his, uh, screen name.

    29. LF

      Mm-hmm.

    30. CT

      He was very proud of it. I mean, one, building evidence against himself, uh, but, you know, th- like, he wanted that slap on the back, like, "Look at what a great hacker you are."

  11. 1:11:391:19:37

    Ross Ulbricht's arrest

    1. CT

      Russ was a little bit older. Um, I think, I'm- Russ truly is a libertarian. He was l- truly had his beliefs that- that he could provide the gateway for other people to live that libertarian lifestyle, and put in their body what they want. Uh, I- I don't think that was a- a front or a lie.

    2. LF

      What- what's the difference between, uh, DPR and Russ? You said, like, "I have never met Russ until... I only had those two, uh, t- two days of worth of interaction."

    3. CT

      Yeah.

    4. LF

      It's just, it's just interesting, given how long you've chased him, and then having met him. What was the difference to you as a human being?

    5. CT

      He- he was a human being. He was, he was, you know, he was an actual person. He was nervous when I- when we arrested him. Um, so one of the things that- that I- I learned through my law enforcement career is, if I'm gonna be the case agent, I'm gonna be the one in charge of, you know, dealing with this person, I'm not putting handcuffs on him. Someone else is gonna do that. Like, I'm gonna be there to help him. Uh, you know, I'm your conduit to help. And so, you know, right after someone's arrested, you obviously you have to pat them down for weapons to make sure for everybody's safety, but then I just put my hand on their chest. Just feel their heart, feel their breathing. You're gonna... It- it's, I'm sure it's the scariest day.

    6. LF

      Yeah.

    7. CT

      But then to have that human contact kind of settles people down, and you can kinda like, "Let's start thinking about this. I'm gonna tell you, you know, I'm gonna be open and honest with you." You know, there's a lot of cops out there, and federal agents cops, that just go to the hard ass tactic. You don't get very far with that. You don't get very far being a mean asshole to somebody, you know. Be compassionate, be human, uh, and it's gonna go a lot further.

    8. LF

      So given everything he's done, you were still able to have compassion for him?

    9. CT

      Yeah. We took him to the jail, and we- we... So, he- it was after hours, so he didn't get to see a judge that day, so he stuck, we stuck him in the San Francisco jail. Um, I hadn't slept for about four days because I was dealing with the people in Iceland, bosses in DC, bosses in New York. So, I, and I was in San Francisco, so timeframe, like- like the Iceland people were calling me when I was supposed to be sleeping. It was insane. But...... I still went out that night while Ross sat in jail and bought him breakfast. I said, "What do you want for breakfast? I'll have a nice breakfast for you." 'Cause we picked him up in the morning and took him over to the FBI to do the, the FBI booking, the fingerprints and all that. And, and I got him breakfast. I mean, and he don't get paid back for that sort of thing. I'm not looking, but like, for that, out of my own-

    10. LF

      D- did he make special requests for breakfast?

    11. CT

      Yeah. He asked for c- certain things.

    12. LF

      What, can you m- mention? Or is that top secret FBI?

    13. CT

      Uh, that's not top secret. I, I, I think he wanted some granola bars. (laughs)

    14. LF

      (laughs)

    15. CT

      Like, and, and, and, you know, but, but-

    16. LF

      Yeah.

    17. CT

      ... I mean, he already had lawyered up. So, we, you know, which is his right. He can do that. So, I, I knew we weren't gonna work together, you know, like I did with Hector. Um, but, I mean, this was this guy's-

    18. LF

      So most of the conves-

    19. CT

      ... last day.

    20. LF

      ... most of the conversations have to be done with lawyers?

    21. CT

      From that point on, I can't question him-

    22. LF

      Yeah.

    23. CT

      ... when he asks for a lawyer. Um, or if I did, it wouldn't be used against him.

Episode duration: 2:56:02

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