Excerpt from Frank Calabrese Jr's 'Operation Family Secrets'

I set myself up in the corner of the prison library at the Federal Correctional

Institution in Milan, Michigan, and banged out the letter to FBI Special

Agent Thomas Bourgeois on a cranky old Smith-Corona manual typewriter. My mobster father, Frank Calabrese, Sr. — who was serving time with me in FCI Milan — had taught me to be decisive. So when I typed the letter, my mind was made up.

I didn't touch the paper directly. I used my winter gloves to handle the sheet and held the envelope with a Kleenex so as not to leave any fingerprints. The moment I mailed the letter on July 27, 1998, I knew I had crossed the line. Cooperating with the FBI meant not only that I would give up my father, but that I would have to implicate my uncle Nick for the murder of a Chicago Outfit mobster named John "Big Stoop" Fecarotta. Giving up my uncle was the hardest part.

When I reread the letter one last time, I asked myself, What kind of son puts his father away for life? The Federal Bureau of Prisons had dealt me a cruel blow by sticking me in the same prison as my dad. It had become increasingly clear that his vow to "step away" from the Outfit after we both served our time was an empty promise.

"I feel I have to help you keep this sick man locked up forever," I wrote in my letter.

Due to legal and safety concerns, it was five months before Agent Thomas Bourgeois arranged a visit to meet with me at FCI Milan. He came alone in the early winter of 1998. In 1997 the FBI and Chicago federal prosecutors had convicted the Calabrese crew, netting my father, Uncle Nick, my younger brother Kurt, and me on juice loans. Bourgeois seemed confused and wanted to know what I wanted.

I'm sure Bourgeois also wondered the same thing I had: What kind of son wants to put his father away for life? Maybe he thought I was lying. Perhaps I had gotten into an argument and, like most cons, was looking to get my sentence reduced. Yet in our ensuing conversation, I told Tom that I wasn't asking for much in return.

I just didn't want to lose any of my time served, and I wanted a transfer out of FCI Milan once my mission was accomplished. By imprisoning us on racketeering charges, the Feds thought that they had broken up the notorious Calabrese South Side crew. In reality they had barely scratched the surface. I alerted Bourgeois that I was not looking to break up the mob. I had one purpose: to help the FBI keep my father locked up forever so that he could get the psychological help he needed. The FBI didn't know the half of his issues or his other crimes.

When asked by Bourgeois if I would wear a wire out on the prison yard, I promptly replied no. I would work with the FBI, but I would only give them intelligence, useful information they could use, and with the understanding that nobody would know I was cooperating, and I would not testify in open court. Outfit guys like my dad called that "dry beefing." Frank Calabrese, Sr., was one of the Outfit's most cunning criminals and had been a successful crew chief and solid earner for the Chicago mob for thirty years.

He could smell an FBI informant a mile away. If he hadn't talked about his criminal life in the past, why would he do so now?

I searched my soul to make sure I wasn't doing this out of spite or because Dad had reneged on taking care of me and Kurt financially in exchange for doing time. This couldn't be about money! After Agent Bourgeois's first interview with me at Milan, he reported back to Mitch Mars, an Assistant U.S. Attorney and Chief of the Chicago Organized Crime Section. Mars wanted to know if there was enough to present the case to a grand jury and gather a bigger, more inclusive case against "the Outfit," Chicago's multitentacled organized crime syndicate, which dated back to the days of "Big Jim" Colosimo and Al Capone.

As I lay in my cell bunk, I thought about my refusal to wear a wire. Suppose I gave the Feds information, but my father got lucky and walked? I'd be screwed, Uncle Nick would be stuck on death row, and after my dad's sentence ran out he would bounce right back out on the streets to continue his juice loan business and murderous ways.

What if what I was doing was wrong? How could I live with myself? I loved my dad dearly, and I love him to this day. But I was repulsed by the violence and his controlling ways. I had to decide between doing nothing and cooperating with the Feds, two choices I hated.


I knew that if I did nothing, my father and I would have to settle our differences out on the street. One of us would end up dead, while the other would rot in prison. I would be incriminating myself, and I didn't want an immunity deal. If I needed to do more time to keep my dad locked up forever, so be it. After I sent the letter, I was determined to finish what I started. I contacted Agent Bourgeois one more time to tell him I had changed my mind. I would wear the wire after all. All the deception my father had taught me I was now going to use on him.

My father's own words would become his worst enemy.