Chris Simmons: Former Spycatcher Breaks Down Spy Interrogation Techniques

One of Chris Simmons’ cases still haunts him - that of Ana Belén Montes, an American-Cuban double agent and DIA analyst who is the focus of Simmons’ memoir Castro’s Nemesis (2022).

Spycatcher Chris Simmons grew up in Washington, D.C. in a house brimming with secrets. Both of his parents worked for FBI director J. Edgar Hoover, his father in fingerprinting and his mother as one of Hoover’s stenographers. 

Chris Simmons, Defence Intelligence Agency spycatcher

Simmons would flip through the scrapbooks as a child, reading letters of commendation and asking questions about the FBI chief who oversaw the Bureau for almost 50 years. Hoover practically lived at work seven days a week, but Chris’ mother kept her counsel: “She’d never say anything but the one comment they both agreed on was, ‘No man should ever have that much power again.’” 

It was an intriguing scrap of intel for a budding young analyst and Simmons was soon drawn to work for the US government himself, first as an Army officer and later as a counterintelligence expert for the US Defence Intelligence Agency (DIA) coaxing information out of terrorists and double agents - spying on spies.

While it takes a particular skill and mindset to excel as a spycatcher, Simmons relished the sensitive work. He’d spend most of his counterintelligence career operating in small groups and sharing information only with those inside his trusted circle. 

Spy training

Simmons’ introduction to the world of spying came on a career day during military training. “Two guys got up there in suits and they said, ‘We are counterintelligence Special Agents. Our job is to identify, neutralize, or destroy other spy services.’ And my hand could not go up fast enough. I didn’t care where they assigned me. That’s what I wanted to do.”

His first assignment was at a training detachment at Fort Meade, Maryland in the late ‘80s where he was thrown into the deep end learning everything from counter-signal intelligence to running a field office and surveillance training. From there he began heading counterintelligence investigations.

Within two-and-a-half years, his team had identified more than 50 potential spies at the tail end of the Cold War and Simmons was ready for a new challenge: the DIA was looking for an intelligence officer to specialize in Latin America. 

Chris Simmonds, Defence Intelligence Agency spycatcher
Chris Simmons (right) is a top US spokesman on Cuban intelligence


Chris Simmons: Former Spycatcher Breaks Down Spy Interrogation Techniques

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One of Chris Simmons’ cases still haunts him - that of Ana Belén Montes, an American-Cuban double agent and DIA analyst who is the focus of Simmons’ memoir Castro’s Nemesis (2022).

Spycatcher Chris Simmons grew up in Washington, D.C. in a house brimming with secrets. Both of his parents worked for FBI director J. Edgar Hoover, his father in fingerprinting and his mother as one of Hoover’s stenographers. 

Chris Simmons, Defence Intelligence Agency spycatcher

Simmons would flip through the scrapbooks as a child, reading letters of commendation and asking questions about the FBI chief who oversaw the Bureau for almost 50 years. Hoover practically lived at work seven days a week, but Chris’ mother kept her counsel: “She’d never say anything but the one comment they both agreed on was, ‘No man should ever have that much power again.’” 

It was an intriguing scrap of intel for a budding young analyst and Simmons was soon drawn to work for the US government himself, first as an Army officer and later as a counterintelligence expert for the US Defence Intelligence Agency (DIA) coaxing information out of terrorists and double agents - spying on spies.

While it takes a particular skill and mindset to excel as a spycatcher, Simmons relished the sensitive work. He’d spend most of his counterintelligence career operating in small groups and sharing information only with those inside his trusted circle. 

Spy training

Simmons’ introduction to the world of spying came on a career day during military training. “Two guys got up there in suits and they said, ‘We are counterintelligence Special Agents. Our job is to identify, neutralize, or destroy other spy services.’ And my hand could not go up fast enough. I didn’t care where they assigned me. That’s what I wanted to do.”

His first assignment was at a training detachment at Fort Meade, Maryland in the late ‘80s where he was thrown into the deep end learning everything from counter-signal intelligence to running a field office and surveillance training. From there he began heading counterintelligence investigations.

Within two-and-a-half years, his team had identified more than 50 potential spies at the tail end of the Cold War and Simmons was ready for a new challenge: the DIA was looking for an intelligence officer to specialize in Latin America. 

Chris Simmonds, Defence Intelligence Agency spycatcher
Chris Simmons (right) is a top US spokesman on Cuban intelligence


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Spy interrogation techniques

So how does a professional spycatcher interrogate a suspect? Although Simmons served in Iraq, he doesn’t believe in so-called ‘enhanced interrogation’ techniques: “Going physical never works.” he said. “Interrogation doesn’t go on in a cell. It goes on in the mind.”

“The idea is that it is human chess,” Simmons said, adding that the first rule of human nature is that self-interest trumps all. “And that’s the key to whether you’re interrogating people or just working on relationships.”

Simmons focuses on finding out what his subjects hold dear. “With terrorists, it’s finding that one thing they are willing to trade the world for because everybody has it. It may be another person. It may be their ego.” 

“Everyone has something they hold important, something they’ll give everything for. Once you find that, you’re in.” 

Chris Simmons has ruined the careers of dozens of double agents
Chris Simmons: The first rule of human nature is that self-interest trumps all.

Mirror imaging, observation, and ‘tells’

So what do you do once you’re ‘in’?

Observe the interviewee’s behavior, non-verbal body language, and speech to get a baseline for the type of person they are.

Start mimicking their gestures occasionally. If they cross their legs or arms, copy their strategic gestures from time to time so they see themselves in you. “You’re a reflection of them.”

Pay attention to a few ‘tells’ that reveal if they are being truthful or not. 

  • If someone is lying to you, they will often appeal to a higher power along the lines of “I swear to God” or “I swear on my mother’s grave” in the opening phrase.
  • Also, listen carefully if you hear the phrase “To tell the truth…” because they’re likely about to lie. 
  • Watch their face and gestures. Are they tense? 
  • Listen to what they’re saying. Are they inconsistent? 
  • Keep an eye on their body language. 
  • Pick apart their story and wait to catch any hesitations. People sometimes memorize their stories and aren’t prepared to deviate from the script. 


The Puppetmaster & spycatcher

The ex-US Army paratrooper has crippled the careers of dozens of double agents throughout his time in the Army and DIA, along the way earning his nickname ‘The Puppetmaster’, the spycatcher with a knack for getting information from anyone. 

One of Simmons’ cases still haunts him, however - that of Ana Belén Montes, an American-Cuban double agent and a colleague, a DIA analyst who spied for Cuba for 17 years.

Montes, the focus of Simmons’ memoir Castro’s Nemesis (2022), was arrested in 2001 in the weeks after 9/11. She was on the verge of gaining access to classified information about America’s planned invasion of Afghanistan. Simmons wanted to see her imprisoned for life or even sentenced to death, but he was satisfied with her 25-year sentence.

“Our expression was a kill is a kill - whether you ended their service career or revoked their clearance. As long as they were out of the game it was a success, but putting people in prison always felt a little bit better.”

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