by: Matthias McCarn
Chicago’s Organized Crime Roots
Al Capone once said, “Some call it racketeering. I call it a business.” While most people are familiar with Chicago and New York mobsters such as Capone, Gambino, and Gotti, what citizens in the United States would become to know as “La Cosa Nostra” actually started in New Orleans’ 2nd District back in 1869. The Sicilian immigrants came into the US through New Orleans’ major sea port. From there they became influential in NY, and then ultimately within other major cities such as Chicago, Kansas City, and Miami. Decades later, the well-known “Five Families” (Gambino, Lucchese, Genovese, Bonanno, and Colombo) had established themselves in New York, but they all had their start from the “5-Points Gang.” Led by Anotonio Vaccaerlli (also known as Paul Kelly), the 5-Points Gang recruited and groomed gangsters such as Jonny Torrio and the famous Al Capone. Eventually Capone moved east to Chicago and became notorious for his bootlegging and illegal manufacturing during prohibition and rose to prominence as a result of waging wars against the Irish Mob. These wars ultimately ended in a stalemate with the St. Valentine’s Day massacre in 1929. With that stalemate, the Irish moved into controlling Chicago through politics and law, while the Italians continued their organized crime endeavors. Yet, an unlikely partnership developed between the two former adversaries, and the Italians used their notorious influence in the form of lucrative payouts in order to leverage city business licenses, permits, and contracts, as well as influence local police, attorneys, and judges. Fast forward to the 1960s, and the Chicago Outfit controlled the Teamsters Union, started funding Las Vegas hotel ventures, and even used their connections to influence national politics. La Cosa Nostra definitely became a force to be reckoned with.
A 2005 article in the Chicago Tribune states, “The Chicago Crime Commission counts 1,111 Chicago-area [Mob-related] slayings since 1919, but only 14 have ended in murder convictions.” Chicago, aka the “windy city,” a term coined for its blowhard politicians rather than the wind off Lake Michigan, has a long history of violence tied to organized crime. And with millions of tons of concrete foundations being poured for skyscrapers over the last century as well as the convenience of being located next to one of the largest fresh-water lakes in the world, it’s very easy to make a body disappear. Or, for those mobsters who wanted to make a point, they would often use a car bomb or leave a body in the trunk of a car and park it on Lower Wacker Drive, one of the busiest streets in the country. But whether a body was found or not, secrets were almost always kept and those responsible stayed in the shadows.
Throughout most the 20th Century, no one dared go against the Outfit, thereby guaranteeing its secrets would go to the grave. But with the passage of the Racketeer Influenced and Corrupt Organizations (RICO) Act in 1970, advances in surveillance technologies used by the Feds, and the ever-increasing use of security cameras everywhere, the Outfit had to adjust their criminal operations to stay further out of reach from the eyes and ears of Law Enforcement. They began to operate more secretly under the veneer of legitimate businesses, using their power and influence to steer lucrative construction and distribution contracts to Mob-owned businesses. Whether they got their money via fraud, extortion, illegal gambling, or contracts secured through threats or bribery, the only thing that mattered was getting paid. And any threat to those payments was met with swift violence. Yet, as a new millennium approached, things were about to change. The Outfit’s powerful control over the city would come to be threatened far more by internal forces, rather than external.
Family Secrets Investigation
In July of 1998 the FBI opened a typed, one-page note that simply read: “I am sending you this letter in total confidentiality. […] IT [sic] is very important that you show or talk to nobody about this letter except who you have to. The less people that know I am contacting you the more I can and will help and be able to help you.” The letter came from Frank Calabrese Jr., the son of Cicero, Illinois Mob boss Frank Calabrese Sr., and was sent in an effort to let the Feds know that Frank Jr., incarcerated since 1997, had decided to flip and was intent on cooperating with federal investigators. This cooperation on behalf of Frank Jr. stemmed from Frank’s personal vendetta against his father’s abuse, the latest of which resulted in Frank Jr. staring down the barrel of a gun after accusing Frank Jr. of stealing hundreds of thousands of dollars from him. Sitting in jail and allowing the past to steep made Frank Jr. believe that his father truly didn’t love him and was actually quite capable of killing him, even in jail. According to Frank Jr., this made him decide to open up to the FBI.
Ultimately, this move by Frank Jr. would lead his uncle, Nicholas Calabrese (known for protecting Frank Jr. through the years), to also opening up to the Feds. Together, the two veteran mobsters would drop a veritable treasure of Mob-related information straight into the hands of federal investigators. But perhaps most importantly, Frank Jr. could shed light on the violent rule of the Chicago Mob from the perspective of an insider who not only knew all the key players, but also the roles and responsibilities of those individuals. The Feds jumped at the opportunity to work with Frank Jr., and on Valentine’s Day 1999, 70 years to the day after the stalemate between Irish and Italian criminal forces, Frank Jr. began to secretly tape conversations for the FBI while the two would walk around the prison yard. The sum of this evidence would lead to a huge federal investigation code-named “Operation Family Secrets.” Ultimately, this investigation would lead to the largest and most prominent Mob trial since Al Capone, the Family Secrets trial. And on April 25, 2005, the Department of Justice released a ground-breaking press announcement regarding this investigation that named 14 defendants being indicted for “alleged organized crime activities” including 18 Mob murders and one attempted murder.
The resulting Family Secrets trial included over 200 pieces of evidence collected over decades of investigations, as well as testimony from 125 different witnesses. Of the initial 14 defendants, two died before trial from natural causes, one was deemed too sick to stand trial, six pleaded guilty, and the remaining five went on to be found guilty with sentences ranging from 12 years for racketeering to life imprisonment for multiple murders. According to the FBI, Operation Family Secrets was one of the most successful organized crime investigations in their history of law enforcement. It not only shed light on some of the darkest secrets of the Outfit’s internal operations, but also went on to solve multiple homicides, many of which had been unsolved for decades. Besides providing closure to victims’ family members, it also removed several acting Outfit bosses and permanently changed their influence over the city. While the Outfit wasn’t completely destroyed, it will never again operate with impunity anywhere near their heyday of the 20th century.