Darknet Diaries – Episode 99: The Spy

Host: Jack Rhysider
Air Date: August 17, 2021

Overview

In “The Spy,” Jack Rhysider delves into a real-world tale of modern espionage involving private intelligence firms, famous journalists, and spy-versus-spy tactics in New York City. The episode follows Igor, a Ukrainian immigrant turned private investigator, who unwittingly finds himself working for nefarious clients—including Black Cube, a notorious Israeli intelligence firm—spying on prominent reporters and cybersecurity researchers. The story escalates into an elaborate sting operation, with both sides deploying intricate surveillance, ultimately unraveling the concealed web of corporate and criminal intrigue behind these operations.

Key Discussion Points & Insights

1. Introduction to Tradecraft and Espionage

• Jack sets the stage with classic spy “tradecraft” examples, such as using shoelaces to convey hidden messages.
• Quote:

  “I love a good spy story. It's so intriguing for me to think that someone among us might not be who we think they are.” (Jack, 00:00)

2. Meet Igor: Private Investigator in NYC

• Jack is contacted on Twitter by Igor, offering his surveillance skills.
• Igor describes his day-to-day work: conducting insurance fraud surveillance in Queens, New York.
• Details of typical surveillance tactics: working with partners, covering shifts, and waiting patiently for targets to emerge.
• Quote:

  “Sitting in cars, watching people and buildings. That's what he does all day and sometimes all night. He sees a lot.” (Jack, 06:30)

3. Enter Black Cube

• Igor recounts doing subcontract surveillance jobs for Black Cube, an Israeli intelligence company known for employing ex-Mossad agents and conducting high-level business and political espionage.
• Initially, Igor is unaware he’s really working for Black Cube, since the jobs are contracted via his boss, Roman Haken.
• Quote:

  “We were doing different types of jobs for them, all involving some form of surveillance. And at some point, they assigned us to follow Ronan Farrow and Jodi Kantor.” (Igor, 08:26)

4. The Harvey Weinstein-Ronan Farrow Black Cube Operation

• Igor begins noticing his targets are high-profile journalists: Ronan Farrow and Jodi Kantor.
• Black Cube deploys a social engineering geolocation attack: sending spam texts to Ronan Farrow, which, upon engagement, retrieves Farrow's location.
• Igor reads Farrow’s articles and slowly realizes his surveillance ties into Farrow’s exposure of Harvey Weinstein and Black Cube itself.
• Upon confirmation from his boss, Igor discovers he’s helping Harvey Weinstein’s efforts to discredit journalists and suppress sexual harassment stories.
• Igor, disturbed by the job, attempts to alert law enforcement and ultimately flips, secretly informing Farrow about Black Cube’s surveillance.
• Quote:

  “I felt very uneasy being sent to do surveillance on journalists...these are publications that I respect.” (Igor, 11:58)
  “I decided to call Ronan Farrow. So I contacted Farrow and we met up. And I said, hey, I've been following Jodi Kantor. I was assigned to follow you.” (Igor, 13:29)
  “To be assigned to spy on Ronan Farrow, but then completely flip and actually call Ronan to tell him that you're spying on him. That must have been some meeting.” (Jack, 13:49)

5. New Target: Citizen Lab and John Scott-Railton

• Black Cube’s scope broadens. Igor is roped into spying on John Scott-Railton (JSR) of Citizen Lab, who investigates abusive spyware developers like NSO Group.
• Black Cube operatives attempt to target JSR by inventing a bogus persona (“Michel Lambert”) and trying to lure JSR into a recording trap—hoping he’ll say something compromising or damaging about Citizen Lab.
• JSR, catching on, sets up counter-surveillance and enlists Rafael Satter from the Associated Press to help ambush “Michel.”
• Quote:

  “This person is obviously coming under a false pretense, and they may be coming with the objective of...harming me, harming my colleagues' reputations.” (JSR, 25:27)

6. The Sting Operation at the Restaurant

• JSR prepares a covert camera in his necktie and arrives at a prearranged meeting with “Michel” at a swanky NYC restaurant.
• Rafael Satter and an AP videographer covertly document the encounter from a nearby table.
• “Michel” tries various tactics, including small talk in French, crude attempts to elicit racist remarks, and persistent questioning about Citizen Lab. He relies on cue cards coded by color for questions.
• JSR quickly realizes the operative is bumbling and his cover is thin.
• After about 90 minutes, Satter confronts “Michel” on camera about his fake identity and company, precipitating the operative’s panicked attempt to escape.
• Memorable Moment:

  “There's almost like a yakety sax moment as he's being followed around by me, by the cameraman, by Satter asking him all these questions...He finally spots an open door...and that's the last we see of this guy.” (JSR, 44:08)

7. Aftermath: The Unmasking of Black Cube’s “Bumbling Spy”

• Igor, outside, captures surveillance photos of everyone involved, all while still thinking he's working for Black Cube.
• He later forwards these to Farrow, who identifies everyone for him, completing the circle of spy versus spy.
• Investigative journalism reveals “Michel” to be Aharon Almog-Assouline, a former Israeli intelligence officer.
• Black Cube attempts to distance itself from any illegal actions, blaming the New York subcontractors for unlawful data collection.
• Igor’s decision to refuse a polygraph severs his relationship with the surveillance firm.
• Quote:

  “They had this concept that they believed journalists would pay for a story or pay a source to be a source. So whatever I told him, I said, listen, they didn't pay me anything. I'm worthless.” (Igor, 63:25)

8. Themes and Reflections

• Journalism & Whistleblowing: Igor’s personal ethics ultimately lead him to become a whistleblower, switching sides in the battle between press freedom and corporate espionage.
• Surveillance Techniques: Both sides employ classic and modern tradecraft—tinted car windows, phone-based geolocation traps, covert audio and video, and misdirection.
• Spy Culture vs. Modern Reality: The episode exposes the messy and often amateurish reality of private intelligence work.
• Emotional Fallout:

  “I had spent years of my life working with victims of spyware...What this moment gave me was a bit of a sense of what that feels like to be in a city and to not know whether someone is following you.” (JSR, 72:34)

Notable Quotes & Timestamps

• “I love a good spy story. It's so intriguing for me to think that someone among us might not be who we think they are.” (Jack, 00:00)
• “I felt very uneasy being sent to do surveillance on journalists...these are publications that I respect.” (Igor, 11:58)
• “To be assigned to spy on Ronan Farrow, but then completely flip and actually call Ronan to tell him that you're spying on him. That must have been some meeting.” (Jack, 13:49)
• “There's almost like a yakety sax moment as he's being followed around by me, by the cameraman, by Satter asking him all these questions...” (JSR, 44:08)
• “They had this concept that they believed journalists would pay for a story or pay a source to be a source. So whatever I told him, I said, listen, they didn't pay me anything. I'm worthless.” (Igor, 63:25)
• “What this moment gave me was a bit of a sense of what that feels like to be in a city and to not know whether someone is following you, to have the sense that there's a well-resourced entity that's trying to dig up dirt on you...” (JSR, 72:34)

Timestamps for Important Segments

• Spy Tradecraft & Introduction (00:00–03:00)
• Igor’s Life as a Private Eye (05:01–06:53)
• Black Cube’s Involvement & Targeting Journalists (07:04–11:09)
• Igor Flips, Becomes Whistleblower (13:29–14:48)
• The John Scott-Railton Operation Setup (16:28–20:00)
• Restaurant Sting & Confrontation (25:27–44:43)
• Aftermath, Unmasking, and Black Cube’s Response (59:15–62:42)
• Reflections on Surveillance and Its Toll (68:35–73:51)

Memorable Moments

• JSR assembling a DIY video necktie from hotel gadgets (26:24)
• The chaotic, slapstick ending to the restaurant sting as “Michel” flees (44:08)
• Igor’s meticulous tactics for spotting counter-surveillance in NYC (51:17)
• Both spies and journalists ending up in the same photographs, unraveling the web of watchers and watched

Tone & Language Notes

Jack’s narration maintains a tone of awe and curiosity, mixed with the dry wit characteristic of Darknet Diaries. Igor brings a streetwise, world-weary candor (“Are you seriously, are you a spy? And then, look, it has his name tag...”). JSR delivers careful, analytical insights tinged with a sense of personal violation and resolve.

Conclusion & Teaser

The episode concludes with unresolved questions about the true masterminds and motivations behind these espionage operations—hinting at ties to NSO Group, a subject for the following episode. Jack’s parting words echo both admiration for those under pressure to do the right thing, and the chilling atmosphere of being hunted on digital and physical frontiers.

For more on this tale, check out Ronan Farrow’s podcast “Catch and Kill,” and stay tuned for part two, as Jack digs into the NSO Group—the world’s most infamous spyware company.