He wanted out of mob life, so he turned on his father

Frank Calabrese Jr. slipped the gloves over his hands to conceal his fingerprints and began typing.

The click-clack, click-clack, click-clack of the old Smith Corona manual typewriter rang in his ears.

“I am sending this letter in total confidentiality. IT is very important that you show or talk to nobody about this letter except who you have to,” the Chicago mobster wrote from the library of a federal prison in Milan, Michigan. “The less people that know I am contacting you the more I can and will help and be able to help you.”

It was July 1998. By then, he was in his late 30s and had been in prison for eight months with his father, Frank Calabrese Sr., both locked away for their roles in a loan shark scheme.

The younger Calabrese wanted out of the mob life for good. His father kept trying to pull him back in.

To get out, he would have to cooperate with the FBI — and turn on his own father, a violent mobster and a central figure of the Chicago Outfit, which at the time, according to the FBI, had been operating in the city for more than four decades.

Calabrese Jr.’s letter ends: “This is no game. I feel I have to help you keep this sick man locked up forever.”

What he couldn’t have known then was that this letter to the Chicago FBI field office would trigger Operation Family Secrets, one of the most successful organized crime investigations in the FBI’s history.

The investigation spanned 40 years of crimes, led to the indictment of the Chicago Outfit as a criminal enterprise and closed the books on 18 unsolved murders — including that of Las Vegas mob legend Anthony “The Ant” Spilotro.

“Sometimes in life, you got to make a decision even if all your choices suck,” Calabrese Jr. said last month during a sit-down interview with the Las Vegas Review-Journal. “I thought about killing him when we got out, but he would kill me first. Only other thing I could come up with was the worst thing you could do in my neighborhood: Be a rat. Be a snitch.”

Today, the former gangster, now 59, has settled down in a suburb outside of Chicago, making an honest living as an author and a motivational speaker, a career that brought him to Las Vegas last month for a speaking engagement at — fittingly — the Mob Museum downtown. The event was held for graduates of the local FBI’s Citizens Academy.

Operation Family Secrets

Michael Maseth was 27 when he graduated from the FBI Academy in June 1998, and he soon crossed paths with Calabrese Jr., when work on Operation Family Secrets began.

“Operation Family Secrets really started with the murder of John ‘Big Stoop’ Fecarotta, which happened Sept. 14, 1986,” Maseth said at the Mob Museum, standing alongside Calabrese Jr. The two have kept in touch over the years.

During the FBI’s first few prison visits at the start of the investigation, Calabrese Jr. went into great detail about the Fecarotta murder, which would eventually lead agents to Calabrese Jr.’s uncle, Nick, the man who had carried out the crime.

When Maseth later paid Nick Calabrese a visit, to his surprise, the man agreed to cooperate with authorities.

“Without Nick Calabrese coming forward, this case would have never come forward, and all of those victims, their families wouldn’t have known what actually happened to their family,” Maseth said.

Fecarotta was an accomplished hit man for the Chicago Outfit who had been stealing money from the Calabrese family, according to Maseth.

When the family found out, Calabrese Jr. and his uncle settled on killing him together. It would mark Calabrese Jr.’s first murder.

But after extensive planning, Calabrese Jr. told the agents, his uncle decided to carry out the killing alone.

“I don’t want you to cross that line with your dad or the mob,” Calabrese Jr. recalls his uncle telling him. “You cross that line, there’s no going back.”

Calabrese Jr. now considers this night a “turning point” for him.

“He really saved my life that night,” he said of his uncle.

‘His savior and his crucifier’

From there, Calabrese Jr. eventually agreed to wear a live wire in prison to allow FBI agents to listen in on his conversations with his father.

“After thinking about it for a while, I knew my dad would manipulate me if I didn’t get it in his own words,” Calabrese Jr. said during the Mob Museum event.

Calabrese Jr. knew his father better than anyone else. So he had a plan: Convince the man that he wanted to get back into the mob life, and pit his father against his uncle Nick.

And it worked.

“I got my dad so mad at my uncle, he just started talking like crazy about all these murders,” Calabrese Jr. said.

The way Maseth puts it, “Nick was a hot button topic for Frank Sr. It was like a treasure trove of information awaiting us.”

Though the evidence gathering was going well, the process took a toll on Calabrese Jr.

“Am I doing the right thing? This is my dad,” he would ask himself. “While I was in these conversations I felt like his savior and his crucifier.”

Sometimes, he recalled, he’d sneak back to his cell and cry. But Calabrese Jr. knew his father would never leave the Chicago Outfit, and if he wasn’t put away for life, Calabrese Jr. would never be free of the mob, either.

When Maseth approached Nick Calabrese about the information he had learned from his own nephew, the FBI agent recalled, Nick Calabrese began “to rattle off about the 14 people that he killed.”

“We had no idea,” Maseth said. “We’re the FBI, and we’re good at what we do, but this guy was able to hide in plain sight and commit 14 homicides.”

The trial

A 43-page indictment came in April 2005 and accused 14 members of the Chicago mob of crimes including murder, obstruction of justice and extortion.

Calabrese Sr., along with four other defendants, went to trial in Chicago between June and September 2007. The government had more than 600 exhibits and called more than 100 witnesses, including both Calabrese Jr. and his uncle.

All five defendants were found guilty.

It was the hardest thing Calabrese Jr. has ever had to do, he said last month — scarier, even, than sending the letter.

After one week of testifying on the stand, he said, he left the courtroom crying.

“In my heart, it felt that I had just seen my dad for the last time alive,” he said. “And it was. It was the last time I ever saw him.”

Calabrese Sr. died in December 2012 at a federal prison in North Carolina, according to the FBI. He was 75.

Of the remaining defendants, six pleaded guilty, two died prior to the trial and one was “too ill” to stand trial, according to the FBI.

Until Operation Family Secrets, the June 1986 murders of Spilotro and his brother, Michael, in Illinois had been unsolved for more than a decade.

Anthony Spilotro was an “enforcer” for the Chicago Outfit, sent to Las Vegas to protect the enterprise’s casino profits. The FBI estimates he was behind nearly two dozen killings in Nevada and Illinois.

His trouble with the Outfit began when news spread of his apparent affair with the wife of a mob associate, Lefty Rosenthal, according to Maseth.

The brothers were lured to Bensenville, Illinois, with the promise of a promotion for Anthony Spilotro and a guarantee that his brother would be made a member of the Chicago Outfit.

During the trial, Nick Calabrese testified that once the Spilotro brothers had arrived at a home in Bensenville, he and 10 other Outfit members beat and strangled the pair.

Breaking the cycle

The one-page letter that would effectively dismantle the Chicago Outfit was 20 years in the making, according to Calabrese Jr.

Growing up, he idolized his father. To this day, he believes that his father was a good one — at least when he was younger.

“I loved my dad. He was good to me. I felt safe, and I felt loved in our home,” he told the Review-Journal. “If my dad told me that a black wall was green, and to me it looked black, if my dad says it’s green, it’s green.”

As he got older, though, Calabrese Jr. noticed a change in his dad. He was more violent, paranoid.

The first time his father told him he had killed someone, Calabrese Jr. was in his early 20s. By then, he already had two young kids of his own.

It was time to get out, he had decided. But it wasn’t until his father tried to kill him, in spring 1995, that Calabrese Jr. truly believed his father was an evil man.

“I was so heartbroken that I could never trust my own dad again,” he said. “The one man that I idolized, that I would have followed through the gates of hell, I couldn’t trust anymore. I felt my life falling apart.”

That heartbreak, though, helped end a vicious cycle that too often felt unbreakable to Calabrese Jr. when he was younger.

“Myself, my brother and my Uncle Nick, we broke this cycle,” he said. “I lived my life, and now I’m giving my kids a chance at life.”

Contact Rio Lacanlale at rlacanlale@reviewjournal.com or 702-383-0381. Follow @riolacanlale on Twitter. Review-Journal podcast producer Reed Redmond contributed to this report.