Mark’s Mob Corner: Operation Family Secrets, Part 1

Operation Family Secrets was a federal investigation into the alleged criminal activities of the Chicago Outfit, a branch of the Italian-American mafia whose origins dated back to the days of Prohibition and Al Capone. The investigation lasted from 1998 until 2005, when federal indictments were issued to four made members of the Outfit, as well as a number of associates also implicated in the organization’s crimes. The indictments charged the defendants with a number of offenses, including interstate racketeering, murder, illegal gambling, bookmaking, and extortion, among other, lesser charges. The case turned out to be a home run for federal prosecutors, and while it didn’t cripple the current leadership structure of the Outfit, it was still a loud and clear warning to remaining members of the organization that the government would continue to relentlessly pursue members of organized crime in the city of Chicago.


The Chicago Outfit has existed in some form or fashion since nearly the turn of the twentieth century. The Black Hand extortion gangs of the 1900’s had evolved into the bootlegging gangs of the 1920’s, which were in turn consolidated by Johnny Torrio and his successor, Al Capone. From there, the Outfit spread its tentacles into every racket it could get its hands on, from extortion and juice loans to labor manipulation and political bribery. As the century progressed, the Outfit’s power and influence spread throughout much of the Midwest, even stretching to Las Vegas and California. However, Operation Strawman, the federal investigation into Vegas casino skimming, was a major blow to the Outfit, imprisoning its upper echelon and leaving the Outfit scrambling to pick up the pieces. Additionally, the introduction and enforcement of RICO, the federal racketeering act, put many more Outfit members behind bars. As the twenty-first century dawned, the mafia in American was on the run, but the federal government was not ready to apply the brakes just yet. One more hard hit and the whole structure just might go tumbling down.

The Outfit’s final shove just may have been initiated with a letter. In June of 1998, Frank Calabrese, Jr., Outfit associate and son of notorious loan shark and namesake, Frank Calabrese, Sr., had written a letter from prison addressed to the FBI asking to cooperate with them in keeping his father behind bars – for good. Frank Sr. and Jr., along with Sr.’s brother, Nick, were already imprisoned after being charged with operating an extortion and loan sharking crew out of Chicago’s South Side, and all had been sentenced to serve out varying terms in federal prison. Jr.’s relationship with his father had always been strained; he felt as if he had been forced into the “life” and was often verbally and physically abused by his father. Consequently, Frank Jr. became addicted to cocaine and in the early 90’s stole several hundred thousand dollars from his father to support the habit as well as to invest in various ill-fated business ventures. When Sr. found out he was furious. A substantial portion of the money was owed to Sr.’s superiors in the Outfit and now Sr. would have to pay them out of his own pocket. Sr. confronted his son about the missing money, slapping him and pointing a gun in his face, which caused Jr. to break down and beg for help and forgiveness.

Frank Calabrese, Jr.
Frank Calabrese, Jr.

Jr. was tired of this abuse and angry at his father for raising him in such a criminal atmosphere and for not allowing him to grow up under “normal” circumstances. By writing this letter and requesting to cooperate with the FBI, Frank, Jr. aimed to get back at his father and attempt to turn his own life around for good. The FBI was very interested in Frank, Jr.’s request and even more interested once he claimed he could garner information from his father on several unsolved murders. Frank, Jr. agreed to wear a wire while conversing with his father while both were imprisoned, but getting useful information from Sr. would not be easy. He often spoke in code and never used real names when describing his crimes to Jr. However, Jr.’s association with his father’s crew allowed him to learn some information, particularly concerning the unsolved murder of former Outfit member “Big” John Fecarotta. Around the time of the murder, Jr. had retrieved a gun from a storm drain for his uncle, Nick, and also revealed to the FBI that Nick had injured his arm around the same time as the hit on “Big” John. Using this fresh information, the FBI began pulling evidence from the Chicago P.D.’s evidence room, including a blood-stained pair of gloves found near the crime scene.

Meanwhile, in February 1999, Frank Jr. had begun secretly recording his father using a tiny microphone installed in a set of headphones which Jr. wore around his neck. Sr. was apparently using the time with his son in prison to mend their relationship, mentoring him and telling him the history of the Outfit and of some of his experiences as a member, including a ceremony involving a pricked finger and a burning holy card, “just like in The Godfather”. Jr. also picked his father’s brain on past Outfit members, particularly ones who had met an early death, hoping to glean information to feed to his government handlers. Seeing a son eager to listen, Sr. was more than happy to oblige, although he made sure to stick with the code-names he had developed for his victims. Over the next few months, Sr. was recorded effectively admitting to participating in over a half dozen murders. By the time of Jr’s release from prison in early 2000, the FBI had gathered a wealth of information on murders dating back three decades. Although Frank Sr. had spoken mostly in code, investigators, with the help of Frank Jr., had nevertheless managed to piece together solid information on a number of murders, including Fecarotta’s. Sr. had unwittingly corroborated Jr.’s claim that Nick had injured himself during the hit; while struggling with Fecarotta, Frank Sr. stated, Nick had shot across his body at his intended victim, shooting through his own forearm in the process. Additionally, Sr. had revealed his suspicions concerning other Outfit members, including Jimmy “Poker” DiForti and his brother, Nick. His suspicions concerning his brother would soon be confirmed.

Frank Calabrese, Sr.

Frank Jr. also tipped the FBI off concerning his father’s other visitors in prison, Anthony “Twan” Doyle and Michael Ricci, two Chicago police officers who were also on the payroll of the Outfit. Acting on the tip, the FBI installed a tiny microphone in the visiting room’s surveillance camera to record Sr.’s talks with the crooked lawmen. Doyle and Ricci acted as intermediaries between Sr. and the outside, often relaying messages between him and his crew in the South Side, as well as collecting juice loans and extortion payments while Sr. was away. Doyle revealed to Sr. that the FBI had removed from the Chicago police department’s evidence room a pair of gloves from the Fecarotta murder scene and also indicated that the case may be restarted in federal court sometime in the near future. Frank Sr. saw this as support of his suspicions concerning “Poker” DiForti, who was currently under indictment for a 1988 murder and may be cooperating to save his skin. Sr. also instructed Doyle to “check in” on Nick and to determine if he was still holding up behind bars. The two crooked cops would gather their information from James “Jimmy Light” Marcello, an Outfit powerhouse currently incarcerated with Nick at the federal prison in Milan, MI.

Visting room surveillance footage still of Frank Calabrese, Sr. (right) speaking with rogue Chicago lawmen Anthony Doyle (left) and Michael Ricci (center)

Nick was holding up relatively well – at least until the DNA test. Prior to that, Nick had grown friendly with Marcello during their incarceration, voicing his displeasure at the treatment he received at his brother Frank’s hands and expressing his desire to transfer to another crew once he was released from prison in 2002. Marcello extended Nick an invitation to join his crew and even offered to pay a stipend to Nick’s wife on the outside, amounting to $4,000 dollars a month. Marcello also had an ulterior motive for this: he had received through the grapevine Frank’s message concerning his misgivings about Nick and hoped that the payment would keep Nick on the right side of the fence. One morning, Nick was called to the prison’s medical ward where his mouth was swabbed for DNA by two federal agents. In addition, both arms were x-rayed and photographed, a particularly ominous sign. Nick was rightfully nervous as he was released back to his cell.

Not long after his impromptu examination, Nick was visited again by the same two agents. They informed him that his outlook was bleak and that his best option now would be to start cooperating. Nick rejected their request, stating that he would do nothing until his daughter’s graduation in June of 1999 and even then he needed to confer with his lawyer before doing anything else. Rebuffed, the agents left but in January of 2000, Nick’s attorney was informed that his DNA matched that collected from the gloves found at the Fecarotta crime scene. In late 2001, the FBI informed Nick through his attorney that if he agreed to cooperate, his statements would not be used against him in court. Finally, Nick agreed to meet with agents in January of 2002.

Nicholas Calabrese

The Chicago Outfit had never had a made man testify against one of their own in its entire existence, and Nicholas Calabrese was now agreeing to be the first. Harboring his own resentment towards Frank Sr., Nick agreed to assist prosecutors in attaining convictions on his brother, who had driven the getaway car for Fecarotta’s murder. However, in order to be granted immunity, Nick needed to give the feds information on all crimes of which he had knowledge, regardless of whether or not he had personally participated in them. By the time he was done disclosing this information, Nick had blown the doors wide open, ceding information on not just the Fecarotta murder, but eighteen other unsolved gangland murders committed by Nick, his brother, or other Outfit members. Operation Family Secrets had taken on a whole new importance.


Written by Mark

A gentleman and a scholar.

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