'Operation Family Secrets': Inside the FBI takedown that shattered the Chicago Outfit

CHICAGO - It has been called the most important mob prosecution in U.S. history.

Twenty years ago this month, the federal government filed charges against more than a dozen top leaders of the Chicago Outfit, involving nearly two dozen murders that had gone unsolved for decades. They called the case "Operation Family Secrets."

What we know:

The Chicago Outfit had a hold on the city for decades, with influence in the courts, the police department, and at City Hall. But that all changed when the son of a powerful mob boss grew frustrated that his father would never change his ways.

Frank Calabrese Jr. went to the library in the federal prison where he was doing time with his father and typed out a cry for help to the FBI.

"I feel like it was a different life," said Calabrese Jr. during a recent interview for the 20th anniversary of the Family Secrets indictment. "Sometimes I feel it was like a nightmare that it really didn't happen, that I'm just talking about some story."

Calabrese Jr. was raised to be a mobster. His father, Frank Calabrese Sr., ran the Chicago Outfit's notorious Chinatown crew. Frank Sr.’s brother, Nick Calabrese, was a trusted mob soldier responsible for at least fourteen hits.

"The difference between me and my uncle is as soon as he got in this life, he was ordered to kill," said Calabrese Jr. "And once he was in, he could not get out."

The backstory:

In 1998, Calabrese Jr. was serving time with his father at the federal prison in Milan, Michigan, for illegal juice loans and racketeering.

"I'll never sit up there and tell you I'm a victim. I did a lot of bad things in my life at one time that I'm embarrassed of today."

The younger Calabrese said he wanted to turn his life around. But he said it became clear his father had other ideas.

"It came to the point where I realized he is never going to let me out of this and he's never going to lose control of me, and I have to do something. And the choices that I had were to wait till he gets on the street, finish this with him. He's good at killing. I'd probably be dead or he's dead and I might be in jail. The other one was getting the government to help."

After considering his options, Calabrese Jr. went to the prison library and typed out a letter for help to the FBI, writing, "I feel I have to help you keep this sick man locked up forever."

Calabrese Jr. said it was a gut-wrenching decision.

"I knew the day that I did that letter that my life was going to change forever. It wasn't about prison. It was about me and my dad. And the hardest thing I ever did to this day is go against my own father."

When the letter arrived at the Organized Crime Division of the FBI, agents weren’t sure it was real.

"That letter was extremely important to the organized crime squad," said Michael Maseth, a former Chicago FBI agent who was assigned to the Organized Crime Unit in the late '90s. "There was a lot of excitement, but there was a lot of secrecy associated with it."

Maseth was among the agents who set up top secret meetings with Calabrese Jr. at the Michigan prison, eventually giving him a recording device hidden inside a pair of headphones and setting up an undercover surveillance system in the prison's visiting area.

"There were gang members there, all in the area of the yard. And so had they seen that he was wearing a wire, it would not have gone very well for him."

Calabrese Jr. knew his life was on the line.

"If (my father) catches me, I'm dead. And if anybody else catches me there, I am dead."

In long conversations recorded in the prison yard, Calabrese Sr. opened up to his son about unsolved mob murders going back decades, including the assassination of mob hit man William Dauber and his wife in 1980, and the car bombing of businessman Michael Cagnoni in 1981.

"The amount of information on those recordings was phenomenal," said Maseth. "We were astounded at how Frank Calabrese would talk about the homicides that he was involved in. Just the amount of information he was providing, the detail."

Dig deeper:

Around the same time, FBI agents approached Nick Calabrese, who was serving time inside another federal prison. The agents told Nick they had newly obtained DNA evidence from a bloody glove left at the scene of a mob hit on the Northwest Side years earlier. Nick Calabrese had killed Outfit enforcer John Fecarotta but hurt himself during a struggle for the gun.

After initially clamming up, "Nick had had enough and realized that I'm not going to stand up for my brother," said Maseth. "He's a horrible person and I'm going to, I'm doing it."

Calabrese Jr. said he had no idea his uncle was also turning on Calabrese Sr.

"That's when my uncle started cooperating. And he was the one who really took down the whole mob."

Maseth said Nick Calabrese broke the case wide open.

"Telling us about one murder after the next, and the members of organized crime who were involved in it. And that's when we realized that we had to expand our investigation ten to twenty-fold."

That also includes the infamous execution of mob brothers Anthony and Michael Spilotro, whose bodies were found buried in an Indiana cornfield in 1986. The murders were portrayed in the 1995 mob movie Casino. Nick Calabrese revealed for the first time that the Spilotros had been killed in a home in the northwest suburbs, then buried in a shallow grave in Indiana.

"Nick Calabrese had quite a bit of insight about that because he said he was there," said Chicago mobologist John Binder.

After a seven-year investigation, the Family Secrets case exploded into the public with sweeping charges against not just Calabrese Sr. but the longtime leaders of several other Outfit street crews.

What's next:

In part two of our look back at the historic case, we'll revisit that dramatic trial, examine what happened to the key players, and ask whether the Chicago Outfit still has a pulse.

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