The 404 Media Podcast
Episode: Inside the Biggest Sting Operation Ever (with Michael Bobbitt)
Date: December 1, 2025
Host: Joseph Cox (404 Media)
Guest: Mike Bobbitt (Former FBI Agent, Stationed at The Hague during ANOM Operation)
Episode Overview
This episode dives deep into the FBI’s unprecedented sting operation: Operation Trojan Shield, commonly known as the ANOM operation. Host Joseph Cox interviews Michael Bobbitt, a former FBI agent stationed in The Hague, who played a pivotal role in relaying intelligence between the San Diego field office and Dutch authorities. The discussion offers unparalleled behind-the-scenes insight into how the FBI ran a tech company to surveil organized criminals globally, the intricate collaboration with European counterparts, and the operation’s far-reaching implications for law enforcement and organized crime.
Key Discussion Points & Insights
1. Setting the Scene: Encrypted Communications and Global Crime
- Encryption Evolution: Organized criminals' communication methods evolved from pagers and burner phones to highly customized encrypted devices with removed cameras, microphones, and GPS.
- Joseph Cox (00:58): "Drug traffickers, hitmen, money launderers, they use these devices ... camera removed, microphone as well, the GPS functionality ... the idea is that this is a device I can securely communicate with my fellow drug traffickers ..."
- Phantom Secure and Market Vacuum: After the takedown of Phantom Secure, a market for new encrypted devices emerged, leading to opportunities for law enforcement infiltration.
2. The Birth of ANOM and Operation Trojan Shield
- ANOM Origins: A Phantom Secure/Sky vendor offered the FBI a new encrypted phone platform, aiming for sentence reductions in exchange.
- FBI’s Approach: Rather than backdooring an existing system, the FBI ran ANOM itself, designing organic growth and global outreach while maintaining a covert backdoor for intelligence gathering.
3. Mike Bobbitt’s Journey in the FBI
- Career Path: From university uncertainty to FBI agent via Deloitte, with assignments across Houston (cartels), Budapest (Russian organized crime), Thailand, and Denver (diverse violations).
- Mike Bobbitt (07:56): "We were addressing some of the most prolific Colombian cartels and Mexican cartels. ... ended up dismantling the Gulf Cartel ..."
- The Hague Assignment: Applied for and secured a competitive international assignment, working as assistant legal attaché in the Netherlands on organized crime and encrypted communications.
- Mike Bobbitt (10:20): "This was a position I applied for and then was given ... for the specific purpose of working organized crime. That would be dark web matters, encrypted communications..."
4. The Secret: Learning About ANOM
- Initial Ambiguity: Bobbitt received intelligence from San Diego without knowing the tech’s exact source, suspecting a prolific human source at first.
- Mike Bobbitt (13:37): "At first I suspected it was through a human source. ... then it became apparent to me that it was technical collection ... I had never heard the name Anom."
- Dutch Collaboration: As the information flow increased and broadened, the necessity for trust and secrecy within partnerships became paramount.
5. Operational Mechanics: Passing Critical Intel
- The Workflows: Information about impending crimes (drug shipments, kidnappings, life threats) was relayed from the FBI to Dutch tactical teams.
- Mike Bobbitt (15:42): "They were calling me, as you say, and saying, by the way, there is a drug shipment coming in. Two days from now, it will arrive into the Netherlands ..."
- Balancing Act: Ensuring operational success without revealing that ANOM was compromised: tactical teams often received limited details to conceal the phone’s role in alerting law enforcement.
- Mike Bobbitt (19:21): "You provide instructions ... lead them to believe that maybe there was a tracker on the car ... plant the notion that somebody's brother ... may have called the police ..."
6. Law Enforcement Tactics and Security
- Letting Drugs Walk: Strategically allowing shipments to proceed into different jurisdictions to dispel suspicion and preserve the intelligence platform.
- Immediate Action: In high-risk situations, such as labs near daycares, authorities intervened regardless.
7. The Criminal Landscape Unveiled
- Unexpected Scale: The operation revealed the vastness of high-level organized crime networks; the number of major players exceeded all prior estimates.
- Mike Bobbitt (23:50): "We have no idea just how many high level criminal groups were out there. ... They need communication devices desperately to ... plan and execute ... drug trafficking, murder for hire, money laundering, corruption..."
- Estimate Tripled: Law enforcement’s understanding of criminal underworld size and influence multiplied due to ANOM, Encrochat, and Sky operations.
- Mike Bobbitt (26:18): "...the math had to change because no one expected those numbers to show up. ... The number of attempted murders were amazing."
8. Scaling Up: Europol’s Role and International Collaboration
- Bringing in Europol: COVID-19 hindered plans to bring international partners to San Diego, prompting the creation of an operational task force within Europol.
- Mike Bobbitt (27:57): "We needed ... a very surgical, close hold way to share very specific information among a very small group. ... So, we ... put this together into an operational task force."
- Day-to-Day at Europol: Despite pandemic constraints, teams from 17 countries collaborated in real-time, expediting complex cross-border actions.
- Mike Bobbitt (33:15): "All these countries ... in one long hall with offices on the sides where we had long tables ... you had this amazing exchange ... things that are worked out over weeks and months ... happening on the floor of Europol."
9. The Grand Finale: Takedown Day
- Preparation: Legal (“MLAT”) hurdles were circumvented by pre-approving evidence transfers so countries could execute warrants simultaneously.
- Mike Bobbitt (39:08): "...basically write the MLATs for those countries from DOJ's perspective ... so that DOJ ... would be pre approved and we just have to provide ... info on takedown day."
- Execution: As the "sun moved across the globe," arrests, searches, and seizures unfolded in a meticulously-coordinated sequence.
- Mike Bobbitt (43:01): "Australians and the Kiwis would kick off first and then ... Europe ... The Dutch ... were going to be targeting ... six or seven high priority targets ... invited us to their operations center."
- Scale: Over 11,000 law enforcement officers involved, over 1000 arrests, tons of narcotics seized, and hundreds of threats to life mitigated.
10. Aftermath and Global Fallout
- Legal Challenges: Mixed court rulings on the admissibility of ANOM evidence, generally favorable but not universal.
- Enduring Impact: The operation shattered trust in dedicated criminal encrypted communications, forcing criminal innovation and continued law enforcement adaptation.
- Mike Bobbitt (47:08): "I do believe that ANAM and Operation Trojan Shield, the work that FBI San Diego did, had massive impact on this. ... It'll continue to erode that trust and make them shift ... towards logistical inconvenience. It'll slow them down a little bit."
Notable Quotes & Moments
-
On the criminal need for communications:
"They need communication devices desperately. They need means to plan and execute their drug trafficking, murder for hire, money laundering, corruption, everything that we found."
— Mike Bobbitt (23:50) -
On managing operational secrecy:
"You lay them, you layer them together so that you can plant doubt in their head. They already want to believe that this platform is not able to be compromised."
— Mike Bobbitt (19:21) -
Anecdote on Takedown Day:
"They just mailed [the speeding ticket] to me at the embassy and I had to pay it. I was like, oh, you're welcome."
— Mike Bobbitt (44:09) -
On law enforcement’s cat-and-mouse future:
"Will they find the new thing? I don't know what that will be. Smoke signals? I don't know. But yeah, they'll find something new. They'll always innovate and then hopefully ... law enforcement ... will innovate as well."
— Mike Bobbitt (48:00)
Timestamps for Key Segments
- Intro & Context about Encrypted Phones – 00:00-05:30
- Intro to Guest & ANOM’s Genesis – 06:07-08:30
- Mike Bobbitt’s FBI Journey – 08:30-11:20
- Learning About ANOM – 13:16-14:52
- Passing Actionable Intelligence – 15:42-19:21
- Operational Tension and Tradeoffs – 18:20-22:23
- How Big Was the Criminal Network? – 23:50-26:18
- Europol and International Coordination – 27:57-36:38
- Inside Europol’s Coordination Hubs – 32:18-36:38
- Scaling Up, Takedown Planning – 38:10-41:00
- Takedown Day & Aftershocks – 43:01-45:32
- Legal Fallout & Reflections – 45:32-49:31
- End Reflection on Law Enforcement and Criminal Innovation – 47:08-49:31
Conclusion
Through remarkable personal anecdotes and detailed operational breakdowns, this episode delivers a gripping account of the most technologically ambitious sting in FBI history. Michael Bobbitt’s frontline experiences illuminate the unprecedented logistical, technical, and human challenges that made Trojan Shield a landmark case. The legacy: a warning shot to criminals and a fresh playbook for global law enforcement.