'Operation Family Secrets': Former Chicago mobster reflects on life after testifying against his father

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 mob, Outfit. It involved nearly two dozen murders that had gone unsolved for decades. They called the case "Operation Family Secrets."

On Tuesday, FOX 32's Dane Placko talked to the ex-mobster who wore a wire against his father and triggered the FBI investigation. Tonight, we look back at the historic trial and its aftermath.

"I know I had to finish what I started. Because if he gets on the street, I'm done or he's dead. And one of us is locked up forever," said Frank Calabrese Jr.

The backstory:

In April 2005, following a seven-year investigation and the surprise cooperation of Frank Calabrese Jr. and his uncle, mob hitman Nick Calabrese, federal prosecutors filed a 43-page racketeering indictment against 14 Chicago mobsters and associates responsible for 18 murders going back to the 1960s.

Calabrese Jr. says he doesn't regret wearing a wire on his father.

"The hardest thing I ever did in my life. I loved my dad. I did not love his ways, but it's my father," he said.

In addition to his father, Frank Calabrese Sr., the feds charged top Outfit leaders James "Little Jimmy" Marcello, Paul "The Indian" Schiro, and Joey "The Clown" Lombardo, who disappeared as the indictment was filed before being discovered hiding in a basement in Elmwood Park several months later.

"It was by far the most committed team I've ever had the opportunity and the privilege working with," said Markus Funk.

Funk was part of the "dream team" of federal prosecutors at the 2007 trial, which featured a colorful cast of defendants, witnesses and defense attorneys.

"I mean, every day, things expected and unexpected happened," Funk said. "It was drama filled. I mean, every day. And we were always aware that the public was there in large part to see the mobsters, right?"

At one point, as Funk grilled Calabrese Sr. on the witness stand, jurors heard the mobster whisper that Funk was a dead man.

"I think the legacy of the trial is, in part, that it was the first time in Chicago we ever had a made member of the mob convicted of murder. And in fact, we had many murders," Funk said.

Dig deeper:

The trial lasted nearly two months, with prosecutors calling 125 witnesses and presenting over 200 pieces of evidence.

And with the smoking gun first-hand testimony of star witnesses Calabrese Jr. and Nick Calabrese, the jury returned guilty counts on all charges, sending Calabrese Sr., Lombardo and Marcello to prison for life.

"I think that's the legacy of this case, to not only take down the entire organization, but also to remember that there's victims. And those victims’ families, they will live with this forever," said Michael Maseth, a former Chicago FBI agent.

Those victims' families also received restitution after the FBI found $1.7 million in stolen loot hidden behind a family portrait in the basement of Calabrese Sr.’s Oak Brook home.

Both Calabrese Sr. and Lombardo have since died behind bars.

Marcello is now 81 and remains at the federal supermax prison in Colorado.

Schiro was released from federal custody in 2022.

As for Nick Calabrese, despite 14 murders, he received a short sentence in return for his cooperation and spent his final years a free man.

"He did pass on a couple years ago, naturally, with his family. So he had a heavy heart. He had a hard time sleeping at night. He had some ailments that were caused by the stress of it and what you've done," said Calabrese Jr.

"The victims were very upset with the sentence that Nick got and the fact he died a free man," Funk added. "He lived up to every part of his deal. He testified to dozens of criminal acts and murders the government had no idea about, frankly, before he began talking. And so, he did what we expected and more and we held up to our side of the deal."

Local perspective:

"As far as I'm concerned, the Chicago Outfit still exists, but it's a very reduced form of what it once was," said John Binder.

Binder, a Chicago mobologist, says the Outfit was badly damaged by Family Secrets but also by the fact the government has legalized much of their old business model: bookmaking, gambling, loan-sharking and drugs.

"Basically, legalization has been killing them. So much of what they did for years and liked to do because it's profitable has gone away because they've legalized any number of things," Binder said.

"Kind of crazy, payday loans. That was one of our biggest things, loan-sharking. The only difference now is there's no violence. But you sign your life over so they just take it from you the easy way," Calabrese Jr.

So, is the Chicago Outfit still alive?

"There’s certainly evidence that the mob is not even close to full strength anymore in the way that they once were. But they also are not dead. In other words, the story of the mob demise is premature and they're still very much active," Funk said.

What's next:

"Operation Family Secrets" was the most successful mob trial in Chicago's history.

Now, two decades after the case that brought down the mob's old guard, Calabrese Jr. spends much of his time in Las Vegas, telling his spellbinding life story as a lecturer at the Mob Museum.

We asked Calabrese Jr. after 20 years, why does he think people are still fascinated by this story?

"I speak to a lot of people, and there's a lot, because this is a family story, Dane. It's not about me getting up and telling you who got killed, who ordered it, who's the boss. This is about what this life does to your family. And at the museum here, I think I found my niche and it's going great," Calabrese Jr. responded. "And you know who I answer to today? My two kids and my grandson. That's my life now."

There have been books written about the "Family Secrets" case, but remarkably, given the Shakespearean family drama at the center of the story, there hasn't yet been a movie.

Calabrese Jr. said there's still plenty of interest and that he hopes to be able to make an announcement soon.

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