Family Secrets: The Case That Crippled the Chicago Mob

Family Secrets: The Case That Crippled the Chicago Mob

by Jeff Coen


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Family Secrets: The Case That Crippled the Chicago Mob by Jeff Coen

Even in Chicago, a city steeped in mob history and legend, the Family Secrets case was a true spectacle when it made it to court in 2007. A top mob boss, a reputed consigliere, and other high-profile members of the Chicago Outfit were accused in a total of eighteen gangland killings, revealing organized crime’s ruthless grip on the city throughout the 1960s, 1970s, and 1980s.
            Painting a vivid picture of murder, courtroom drama, family loyalties and disloyalties, journalist Jeff Coen accurately portrays the Chicago Outfit’s cold-blooded—and sometimes incompetent—killers and their crimes in the case that brought them down. In 1998 Frank Calabrese Jr. volunteered to wear a wire to gather evidence against his father, a vicious loan shark who strangled most of his victims with a rope before slitting their throats to ensure they were dead. Frank Jr. went after his uncle Nick as well, a calculating but sometimes bumbling hit man who would become one of the highest-ranking turncoats in mob history, admitting he helped strangle, stab, shoot, and bomb victims who got in the mob’s way, and turning evidence against his brother Frank.
            The Chicago courtroom took on the look and feel of a movie set as Chicago’s most colorful mobsters and their equally flamboyant attorneys paraded through and performed: James “Jimmy Light” Marcello, the acting head of the Chicago mob; Joey “the Clown” Lombardo, one of Chicago’s most eccentric mobsters; Paul “the Indian” Schiro; and a former Chicago police officer, Anthony “Twan” Doyle, among others.
            Re-creating events from court transcripts, police records, interviews, and notes taken day after day as the story unfolded in court, Coen provides a riveting wide-angle view and one of the best accounts on record of the inner workings of the Chicago syndicate and its control over the city’s streets.

Product Details

ISBN-13: 9781569765456
Publisher: Chicago Review Press, Incorporated
Publication date: 09/01/2010
Pages: 432
Sales rank: 782,691
Product dimensions: 6.00(w) x 8.90(h) x 1.00(d)

About the Author

Jeff Coen has been a reporter on the Chicago Tribune's political enterprise team since 2010, covering a variety of issues. He was present in the courtroom throughout the Family Secrets trial, and his pieces on the case were featured in a popular series in the Chicago Tribune.

New York-based actor Matthew Boston has over thirty years of professional experience working in theater, film, television, and voice-over. He received his training from the Mason Gross School of the Arts, Shakespeare & Company, and the Lee Strasberg Institute.

Read an Excerpt

Family Secrets

The Case That Crippled the Chicago Mob

By Jeff Coen

Chicago Review Press Incorporated

Copyright © 2009 Jeff Coen
All rights reserved.
ISBN: 978-1-56976-545-6



Taking a life was like a riddle to be solved or a puzzle to be slowly pieced together, and by 1986, Nick Calabrese was a pretty patient guy.

He was hardly the bruising movie version of the mob hit man, some beefcake with a machine gun and a chiseled jaw who bursts into a restaurant in a pinstriped suit to flatten someone, sending plates of ravioli and a checkered tablecloth flying. There was no swagger or bravado about him. You could walk toward him on the street and pass by without a second thought or glance.

He had an everyman appearance to be sure, but many would have been wiser not to be fooled. Nick was a deadly and cool technician. He would stalk his victims, trailing them and learning as he watched them move. Sometimes his hit squads would lurk for weeks, looking for the best way to strike and then escape detection.

Follow the target long enough and a pattern would emerge; eventually a weak spot in his daily routine could be recognized and then efficiently exploited. There was almost always a time when the victim's guard would be down or he could be found in an opportune spot. Trickery and deceit were preferred to the daylight ambush. Making a good kill was about guile and cunning and surprise, and not always blasting in and then out if need be. Finding the right angle or lure usually made all of that unnecessary.

The idea, of course, was not to get caught. So the Chicago Outfit liked to take its victims to secret places, such as garages or basements, closed businesses, or empty buildings. Its killers appeared like phantoms and vanished quickly.

For the least accessible victims, maybe a bomb was the answer, as the Outfit took every step to try to keep the advantage. Men like Nick were responsible for figuring out how the killing should be accomplished and then doing what had to be done and disappearing — though sometimes they would stop for coffee when they were through. There was no bragging and no returning to the scene of the crime to take it in.

Most of the time it was only later that the sinister handiwork would turn up: a body in a gulley or stuffed mostly naked in a trunk, tied up and contorted with a gaping wound to the neck.

In many ways that layer of mystery was better when the goal was keeping Chicago's criminal underworld in line, sending a constant threatening chill over the streets. For some the threat of being killed was always there and felt as if it could come from any direction. That was good business for the mob, keeping Outfit associates and customers alike looking over their shoulder. Break the Outfit's rules or don't pay who you're supposed to pay, and that could be it. The next time anyone sees you, there's a group of cops standing over your corpse, with flashes going off while your picture is taken for the file.

Bosses in the Chicago Outfit marked many for death to protect the organization, sometimes from a witness who might talk to the feds and sometimes to punish a member who stepped out of line or brought too much heat. Sometimes it was just to make a bloody example out of an enemy, and Nick was among the trusted few called upon to do the ugliest of jobs.

Nick was a weapon, although a mostly reluctant one.

He had allowed himself to begin down the dark path, never having the courage to make it all stop. He had been in the navy and had held real jobs. He'd been a union ironworker and had a family. None of that had involved digging holes or lying in wait for the unwary with a rope or a gun.

Maybe he could have found the courage to tell them he was through. But once in the Outfit, there was no deciding to quit, no retirement parties, no turning away and deciding you'd had enough. He'd wanted to run, but where was he supposed to go? There was really only one way out — death — and Nick was afraid of that consequence.

It was an oppressive fear, a fear that had a name and a face that stayed with him — as close as a brother.

It was Frank Calabrese Sr., a successful Outfit loan shark, who had started Nick's slow sink into the Chicago syndicate. It had been almost harmless at first, after all. Nick would help Frank Sr., a member of the mob's Chinatown street crew, make sense of scrawled loan notes and betting slips. He would collect envelopes and track what debtors owed, parking out of sight and walking to meet them where he could take their tribute. He would help run sports bookmaking and hold his brother's many agents accountable. It was a way for Nick to make a little extra cash, above and beyond what he could make doing his legitimate work.

The quiet Nick was a paper-and-numbers guy — at least at the beginning — not a vicious killer.

In 1970, the first time he watched his brother plunge a knife into someone's throat, he wet himself he was so scared. It was dark and his pants were grimy with the dirt of the South Side construction site where they would hide the body in a small pit, so neither his brother nor his brother's henchman had noticed.

He had started as the ride-along, the spare hand.

But some sixteen years later, he was the kind of soldier those in command of the Outfit valued, no matter his reasons for being a part of it. He asked no questions and caused no trouble, a trait appreciated by the harsh men in charge. They needed to give an order and have it carried out with merciless determination. Nick was given a job, and in a Chicago lunch-bucket kind of way, it got done. He would return with a quick word or make a coded phone call where he talked about having soup or something, and the mob's business could go on. His brother passed an order from the bosses, and Nick was in, fearing what might lie in store for him if he said no. There were mobsters with more bluster, intense men who would yell and threaten and instill fear, but it's the quiet ones you never see coming.

That's not to say that things always went perfectly when Nick was told to take a life. Sometimes the adrenaline would kick in too strong and force mistakes. When the heart raced too fast, it could be hard to stay focused. In the dark, with a begging, struggling victim, things could get confusing quickly.

There was the time Nick helped kill another mobster lured from a neighborhood club, placing the beaten, strangled, and stabbed man in his car and leaving it parked on a residential street. When it was over, his street crew's capo, or captain, had demanded that the body and the car be burned, so Nick went back and doused the man's corpse in Zippo lighter fluid in the backseat and lit it. But in his haste he left all the windows rolled up and snuffed out the flames when he shut the car door. Only a fresh snow covered that error, at least for a few weeks.

And there was the time in Phoenix Nick had pulled a grand jury witness into a van and shot him in the head. It had taken two trips to Arizona and weeks of careful planning to finally execute him, but one of his guns clumsily fell into the tarp on the floor of the van as he rolled up the body to dispose of it.

Nick had been far from home for that hit, traveling on the nastiest kind of business. But a member of the Chicago mob finding himself that many states away for a killing was not an outlandish idea at the time. The Outfit that he worked for in the 1970s and 1980s was a ruthless organization of extraordinary reach, a hidden evil at the pinnacle of its strength. Its bosses ruled an empire of gambling that stretched to Las Vegas and made untold millions through extortion and high-interest "juice loans." Nick's brother alone had hundreds of thousands of dollars on the street at a time, ordering his minions out to make collections.

Their Chicago was a dense mass of rail and truck yards, warehouses, insular neighborhoods, grit, steel, and vice, and the mob drained it wherever it could. Outfit muscle collected street taxes and protection money from porn shops and legitimate businesses alike, and the syndicate held sway over everything from trucking to strip clubs. The city's lifeblood — money — flowed under the Outfit's watchful eye.

Unlike La Cosa Nostra, the fractured Mafia of the East Coast, organized crime in Chicago had been unified for much of the century, since the days of the infamous boss Al Capone. He had molded the factions into a singular, menacing organism that would go on to thrive in the 1940s under Paul "the Waiter" Ricca. Instead of tearing itself apart through infighting, the Outfit acted as a united force for decades under one "Old Man," a shadow mayor of sorts.

With Chicago under its thumb, the Outfit began to concentrate on expansion, tapping into vast labor union pension funds that it used to build glittering casinos — which it then skimmed — in the Nevada desert.

At home in Chicago, both the businessman who couldn't get a legitimate loan from the bank and a sucker needing to cover a mounting gambling tab would find themselves accepting Outfit loans that required interest payments of 5 percent per week. A pornographer wanting to open a city sex shop was wise to get permission from the Outfit and then give it a cut to avoid facing its wrath. Burglars were expected to pay a percentage, too, and in some neighborhoods even a hot-dog stand would require a blessing before it could open.

The Outfit's influence seeped into the Chicago Police Department, corrupting street cops who looked the other way or, worse, warned the mob when the police were moving against its interests. One officer who became a chief of detectives was even found to be running a massive jewelry-theft ring with a nod from Chicago bosses. And in 1977 the mob bought an acquittal in a murder case in court in Cook County, crossing a barrier that few believed could be breached.

The Chicago Outfit of the day included six street crews around the city and suburbs: Elmwood Park, Melrose Park, Chinatown, Grand Avenue, Rush Street, and Chicago Heights. But they weren't so much geographic territories as seats of power. Nick and Frank's Chinatown organization, also known as the Twenty-Sixth Street crew, had gambling agents as far away as Rockford, sixty miles northwest of Chicago. The crews were made up of handfuls of individuals working closely to make money, which was passed up the chain and into the Outfit's hierarchy. Crew members worked bookmaking rings together, gave out juice loans, and collected extortion payments. And when necessary, they became murder squads.

Nick knew them all and had threatened, bombed, and killed with many.

There was Johnny "Bananas" DiFronzo, later known as "No Nose," in Elmwood Park. Vince Solano and Frankie Belmonte of the Rush Street crew, and Al Pilotto in Chicago Heights. There was Joey "the Clown" Lombardo, a gangster known for his humor and eccentricity, leading the Grand Avenue crew on Chicago's North Side, and there was James "Jimmy Light" Marcello in Melrose Park, a crew that had Sam "Wings" Carlisi as its capo.

Yet another group of mobsters had banded together under Joe Ferriola into what became known as the Wild Bunch, including feared hit man Harry Aleman, Gerald Scarpelli, and William "Butch" Petrocelli.

And at the top of the entire food chain were "Number One" and "Number Two," boss Joey "Doves" Aiuppa and his second in command, Jackie Cerone. They demanded absolute loyalty and could impose their will with just a look or a gesture.

But of more immediate concern for Nick was the capo of the Chinatown crew on the South Side. Angelo "the Hook" LaPietra was in command, and Nick's brother Frank Sr. and his juice operation were among his chief moneymakers. The crew had the reputation of being the Chicago mob's real enforcers, the arm that leaders went to when others weren't able to get a killing done. They were the worst of the worst, men who took pride in their refusal to give up on a stubborn job even where others had failed.

In some years Nick found himself bringing LaPietra's cut of the crew's action to the capo's garage in the Italian stronghold of Bridgeport, on the South Side, where Nick and his brother had come to be connected to the Outfit. Nick would stuff the cash in a barbecue mitt hanging on the wall — sometimes $20,000 at a time — flipping it over so the thumb would alert LaPietra that his payment was there.

Frank Sr. had been plugged into the Outfit years before Nick, beginning as an auto thief in the chop shop business and eventually moving into making juice loans. He was a bit of a natural, and his success eventually was noticed by LaPietra, who didn't get his menacing nickname "the Hook" for nothing. Frank soon was whistled in, or summoned, for a meeting and was told in no uncertain terms that he would work with the mob. Even though the brothers had grown up with immigrant parents in the West Side Italian neighborhood around Grand and Ogden avenues — known as "the Patch" — with Frank Sr. the eldest of seven children and Nick smack in the middle, they found themselves key members of the South Side crew.

In later years when LaPietra was headed to prison, he informed the Calabreses that his brother, Jimmy LaPietra, would take over as capo, muttering in Italian in a restaurant meeting and letting the Calabreses know he was handing over daily control.

In fact, in the days before September 14, 1986, it was "Brother Jimmy" who had given the order for Nick to kill his next victim. A simple "Go ahead" was all that had been said after Frank Sr. had taken his grievances about the target to mob leaders.

Soon Nick was driving a stolen blue four-door Buick that Sunday evening on the Northwest Side, taking the car, which he'd lifted from a suburban train station, to a bowling alley to meet up with his friend, fellow hit man John Fecarotta. Nick had stolen some license plates from another car and put them on the Buick himself. Like many Outfit "work cars," the Buick would be used solely to commit a crime and then promptly dumped.

Fecarotta, a mobster known as "Big Stoop," had been with Nick on jobs a number of times, including the killings of the mob's leader in Las Vegas, Anthony "the Ant" Spilotro, and his brother Michael, which for a time would be one of the city's most notorious unsolved gangland slayings. The Spilotros had been lured to their deaths with promises of promotions in the organization, killed, and buried in an Indiana cornfield.

But as it turned out, Fecarotta wouldn't be helping Nick this time.

Outfit bosses had become displeased with Fecarotta's seemingly endless money problems, and he had made the very serious misstep of leaving the Arizona killing before it had been completed. On that trip Fecarotta had also taken a gambling excursion, and when he'd won $2,000 at a Bullhead City casino, he had asked Nick to sign paperwork for the winnings when they were supposed to be keeping a low profile. His fate was sealed when he became involved in a dispute over a juice customer with the forever-plotting Frank Sr., the kind of loan shark who wasn't accustomed to letting such things slide.

The man who had been making payments on his Outfit debt to Frank Sr. was suddenly told to start coming up with Fecarotta's house payment instead. So it wasn't long after the money dried up that Frank Sr. paid a visit. He pulled the debtor close and held a knife near his crotch, telling him it would probably be best for him if he settled with the Calabreses before listening to that idiot Fecarotta. The man quickly agreed with the angry loan shark and his blade, and the bully of Chinatown released his hold without doing any long-term damage.

Fecarotta knew he was on bad paper with Frank Sr. and those above him, so he had been "on point," or alert, in the weeks leading up to the Sunday bowling alley meeting with Nick, his old pal.

Catching another hit man unaware would be difficult enough and would take a very clever ruse for Nick, but a hit man who already feared that his time had come and that he was going to get hurt was an especially hard target. There had been too many disputes with Frank Sr. and other mobsters, like John "Johnny Apes" Monteleone, for either of them to get close to Fecarotta. It would take Nick and his relationship with his trusting friend to put Fecarotta at ease and catch him in a weak moment. Fecarotta, a seasoned hit man, would expect a lot of things, but not that Nick would be the one to take him out.

So with the trap set, Nick watched from his stolen car as Fecarotta was dropped off near their meeting point. But Nick didn't drive up right away. Appearing instantly might make Fecarotta think Nick had been eyeing him, activating the suspicious hit man's intuitive sense that he was in some kind of danger. Instead, Nick drove around the block, relaxing the energy around the situation and waiting to make sure that the person who had dropped Fecarotta off was gone before he approached. It was better to let things develop at a normal pace and keep the situation from feeling forced.

After pulling up, Nick parked and slid over into the passenger's seat.

Fecarotta's skills as a wheelman in this kind of Outfit work were widely known and respected, so he would have expected to drive. Fecarotta had been told that he and Nick would go together from the meeting to an alley near Austin Boulevard and Belmont Avenue on the Northwest Side. In the alley was the back door of the offices of a dentist who did union work, the story went, and the dentist had to be sent a fiery message from the mob.


Excerpted from Family Secrets by Jeff Coen. Copyright © 2009 Jeff Coen. Excerpted by permission of Chicago Review Press Incorporated.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Table of Contents


Author's Note,
1 A Killing Between Friends,
2 The Surprise Letter,
"We gotta put somebody in a hole",
3 Witness of a Lifetime,
"Don't make any plans",
4 United States vs. the Chicago Outfit,
"You do it",
5 This Is Not The Sopranos,
6 Testimony and Tapes,
"This is a robbery",
7 Alva and Emma,
"Strangers in the Night",
8 A Son Against His Father,
9 Nick,
10 A Killer Tells His Tale,
11 Explosion on the Tollway,
"If I give up my brothers",
12 From Cicero to Las Vegas,
13 One and Two,
14 The Beak, the Oven, and the Dentist,
15 Joey,
16 Cross-examination,
17 Frank Sr.,
18 Twan,
19 Closing Arguments,
20 End of a Trial, End of an Era,
Key Figures,

What People are Saying About This

Scott Lassar

An inside look at the Chicago Mob and the extraordinary prosecution that devastated it. (Scott Lassar, former U.S. attorney and former editor in chief of the Journal of Criminal Law and Criminology at Northwestern Law School)

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