OPERATION FAMILY SECRETS: How Chicago’s Historic Investigation Gave Closure to the Authors of “DEADLY ASSOCIATES.”

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Al Capone

On July 27, 1998, an anonymous letter was sent to the FBI. Not only
would this letter indict the notorious organized crime syndicate, the Chicago
Outfit, but it would go on to spur one of the most historic trials in U.S. history, the
“Family Secrets” trial. This trial would include two hundred pieces
of evidence, testimony from one hundred twenty-five witnesses, and eventually, eleven guilty verdicts.

One of these defendants, Joey “the clown” Lombardo, would face
multiple convictions of racketeering and serial murder. The day he was
sentenced to life imprisonment, Joey stood in the middle of the courtroom,
stone-faced. Behind him in the crowd sat two grown men, whose faces vaguely
resembled someone Joey used to know. Someone he had shot and left to die in a puddle
of blood.

That someone was Danny Seifert, and the two grown men were Danny’s
sons. They had seen their father shot down, watched him die, and went adrift
into their lives wondering if they would ever find justice. Eventually, they
went seeking it. And in that courtroom, on the day that Joey “the
clown” Lombardo was sentenced to life, these two grown men found it.

The Chicago Outfit

Before Chicago, there was New Orleans. The famed “La Cosa Nostra,” with its strong ties to Sicily, ran its first corrupt mob deal through New Orleans’ 2nd District way back in 1869. Because of the easy access into the U.S. through New Orleans’s seaport, Sicilian immigrants flooded into the city, bringing with them their mobster roots of the old country.

Decades later, the well-known “Five Families” – Gambino, Lucchese, Genovese, Bonanno, and Colombo – had established themselves in New York, with criss-crossing ties to each other through 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 Al Capone.  Eventually, Capone moved east to Chicago, becoming notorious for his bootlegging and illegal manufacturing. It was during prohibition that Capone rose to prominence along side other brutal mob families, like, the Irish Mob.

The mob wars between the Irish and Italians, ultimately, climaxed with the St. Valentine’s Day massacre in 1929.  With no clear winner to the famed bloody massacre, the Irish chose to push for more elite positions in Chicago. Soon they were occupying some of the most prestigious positions in politics and law, while the Italians continued on with organized crime endeavors.

Soon, the Irish and the Italians began to do business with each other after seeing the mutual benefit to the  unification of their powerful organizations. The result was a deep corruption across Chicago’s upper divisions of politics, banking, and law. The Irish used their positions for benefit of bribery payouts, and the Italians used their notorious influence to leverage underground dealings. Soon these payouts would secure city business licenses, permits and contracts for Italian Mob, which made for easy access to money laundering and racketeering schemes. By the time Capone was at his height of power criminal and corrupt enterprises poisoned the police, the courts, the business world, and the local population, who were looking for handouts or protection.

The eventual merging of the “Chicago Outfit” and the Teamsters Union seemed inevitable, and in early 1960 Chicago would have to deal with the effects of the Union as legally organized and locally recognized entity, which controlled everything from local labor and wages to the judicial departments to the local drug trade. And as the scale of the Chicago Outfit’s business endeavors became larger, the money began to be more traceable. How does an organized criminal enterprise secure enough monies to fund a Las Vegas hotel? The FBI was determined to find out.


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 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.

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Throughout most the 20th Century, no one dared go against the Chicago 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 Chicago Outfit had to adjust their criminal operations to stay further out-of-reach from the long arm of the Law.

Come early 1970’s, the Chicago Outfit 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. Any threat to those payments were met with swift violence.  Yet, as a new millennium approached, things were about to change: the Chicago Outfit would find themselves threatened 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 Chicago Mob boss Frank Calabrese Sr. Frank Jr., incarcerated since 1997, had decided to flip on his father and the entire Chicago Mob family.

Frank Jr.’s intention to cooperate seemed to be about wanting a shorter sentence, but in reality, Frank Jr. desire to flip on his own father stemmed from a personal vendetta against his father. Frank Sr. had been abusive to Frank Jr., so much so, that the last episode of abusive rage had ended with Frank Jr. staring down the barrel of a gun his own father’s gun. After contemplating the ins-and-outs of his father’s abusive, murderous rage, Frank Jr. decided to protect himself and petitioned the FBI to consider him their new singing canary.

Ultimately, Frank Jr.’s flip would lead his uncle, Nicholas Calabrese, to also opening up to the Feds.  Together, the two veteran mobsters would drop troves of Mob-related information straight into the hands of federal investigators.  But perhaps more importantly, Frank Jr.’s cooperation shed light on the violent rule of the Chicago Mob. His perspective was that of an insider who not only knew all the key players, but also their roles and responsibilities.

On April 25, 2005, the Department of Justice released a ground-breaking press announcement regarding this investigation that named fourteen defendants being indicted for “alleged organized crime activities;” including, eighteen Mob-related murders and one attempted murder. The investigation would be code-named “Operation Family Secrets,” and would ultimately lead to the largest trial in U.S. history – both, in its scope and depth.

The Verdict

The resulting Family Secrets trial included over two hundred pieces of evidence, which were collected over decades of investigations, as well as, testimony from one hundred and twenty-five different witnesses.  Of the initial fourteen defendants, eleven were convicted and given sentences ranging from twelve years to life imprisonment.

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 Chicago Outfit’s internal operations, but it also went on to solve multiple homicides, many of which had remained unsolved for decades – including, the murder of Danny Seifert. The conviction and sentencing of their father’s killer, Joey Lombardo, in the Family Secrets trial provided closure to Seifert family. And, while the Chicago Outfit wasn’t completely destroyed, it will never again operate with so much unbridled impunity.

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