Befriend and betray A look inside the world of a former female undercover agent

On Insight’s episode, Life Undercover, Jennifer and other former undercover operatives talk about the moral and ethical dilemmas of living a double life. Watch on Tuesday, August 3 at 8:30pm on SBS or On Demand.

*Jennifer had always wanted to be a police officer, but it wouldn’t have occurred to her that knowledge of cows, curtains and astrology would one day help her infiltrate drug syndicates and make her one of NSW’s most in-demand undercover operatives.

Starting at just 21 years of age, as the only female undercover officer in her squad, Jennifer’s job involved mingling with dangerous criminals, mainly drug dealers. Her goal: to befriend, and later arrest them.

Compared to her male counterparts, Jennifer said she took a more personal approach to her job and spent more time getting to know her targets.

“I really came to know the targets and the families, and I really formed a relationship with [them],” Jennifer told Insight.

“I was invited to their homes. I was invited to christenings, birthday parties of their kids.”

*Jennifer pictured in her days as a police officer and undercover agent.

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To gain their trust, Jennifer would speak to her targets about mundane or obscure topics.

“I could talk about cows. I had an interest in cows. I've got an interest in astrology and star signs,” Jennifer said.

“Because I was a female, the target would be asking me questions like, ‘What do you think of these cushions? What do you think about the colour of these curtains?'

“And being a female, it wasn't too difficult for me to ask, ‘Oh, how many bedrooms have you got here?', which was gaining intelligence for a later arrest… I would be looking where the bathrooms are, where they might be able to dispose of the drugs.”

...I'm sort of liking these people and forming a friendship with them, and I know my job is to set them up and they're going to be arrested.

But what started out as deception and manipulating criminals to gain their trust, would sometimes develop into “deep friendships” and empathy for some of her targets.

“I empathised a lot when I knew that they were going to be arrested and possibly gaoled. I did empathise with the people in the family that it may affect, the wife and the children,” Jennifer said, adding that one of the most challenging aspects of her job was weighing up the greater good of her work, with its inherent deception and betrayal of people she considered friends.

“I remember speaking to my supervisor when I was having a bit of conflict and thinking I'm sort of liking these people and forming a friendship with them, and I know my job is to set them up and they're going to be arrested,” Jennifer said. “I remember he said to me, ‘You have to decide what side of the fence you're on’.”

For 13 years, Jennifer remained on the undercover policing side of the fence, but the nature of her work â€" including contracts on her life â€" took a heavy mental toll that later led to a diagnosis of PTSD.

“I still get teary,” Jennifer said about leaving the police force. “I miss it, I miss it.”

*Name has been changed to protect the identity of the source.

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