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This podcast contains dramatic reenactments and content that may be considered unsuitable for younger audiences.

Listener discretion is advised.

John Zip Connolly.

Special agent for the federal bureau of investigation. For more than 20 years he was a prince of the city in Boston.

A dashing, swaggering figure almost a legend for his handling of organized crime informants.

Zip Connolly was so well respected that in 1985 he made a training video for the FBI Training Academy in Quantico, Virginia.

He instructed agents in training how to handle mobster informants.

One of my rules, one of the many I try to keep in mind and be mindful of what I'm contacting them is they want to meet and expect to meet an FBI agent.

They don't expect a professional individual. They don't expect to meet another wise guy, gangster, amrabah.

So I always have maintained that we shouldn't be trying to as agents trying to out gangster or gangster for instance.

Never try to out gangster a gangster. But that's exactly what Zip Connolly tried to do.

He violated every one of the rules he laid out in the FBI training video for the agents to be.

He should be in the driver's seat with these people.

They're either going to rule you or you're going to rule them. And if they're ruling you're wasting your time in a bureau's time and you could put yourself in the bureau in a very melancholy situation.

And now Zip finds himself in the most melancholy of situations. At the age of 79 he's serving what amounts to a life sentence in a Florida state prison after being convicted of murder in a gangland hit in Miami in 1982.

He's not scheduled for release until 2039 when he will be 99 years old.

They're criminals and we're professionals. They expect us to be professionals and we expect them to be criminals.

And I don't think we can ever lose sight of who we are and who we're working for. We should always be mindful of that when we're dealing with informants.

And they act criminals and they have a different mindset totally than we do.

And you're going to get friendly with them and you're going to like them and along the way and this is going to be certain friendships that develop out of these things.

But you never can forget who you work for and the fact that you're an FBI agent and early on in that relationship you have to establish with him that you have rules and regulations.

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