The Chicago Mafia

Down But Not Out

A Roman Catholic priest and former prison chaplain who ministered to Chicago mob boss Frank Calabrese, Sr., was indicted earlier this month for illegally passing jailhouse messages from Calabrese and plotting with his associates on the outside—a sobering reminder of how deeply organized crime can reach into the community, even from behind bars.

“Members of the mob will go to almost any lengths to carry out their criminal activity,” said Special Agent Ted McNamara, a veteran investigator who supervises the La Cosa Nostra (LCN) organized crime squad in our Chicago Field Office.

Calabrese, Sr., was sentenced to life in prison in 2009 for his role in 18 gangland slayings in the Chicago area dating back to 1970. His arrest—along with 13 others—was part of one of the most successful organized crime cases in FBI history, an eight-year investigation called Operation Family Secrets.

Because of the Family Secrets case—in which Calabrese’s son testified against him—“the Chicago mob does not have the power and influence it once had,” McNamara said. “But the mob still operates, and its members still represent a potentially serious criminal threat.”

Unlike New York’s infamous Five Families, the Chicago mob consists of only one family, often referred to as the “Outfit.” It is organized under a variety of crews that engage in various criminal activities. A portion of the crews’ illegal gains goes to the Outfit’s top bosses.

“New York gets most of the attention regarding LCN,” McNamara said, “but historically, going back to the days of Al Capone, Chicago LCN has always been a player, particularly in places like Las Vegas.”

Unlike their New York counterparts, the Outfit has traditionally stayed away from drug trafficking, preferring instead crimes such as loan-sharking and online gambling operations, and capitalizing on other profitable vices. One of the reasons it is so difficult to completely stamp out mob activity, McNamara said, is that over time the crews have insinuated themselves into unions and legitimate businesses.

“Typically they get into running restaurants and other legal businesses that they can use to hide money gained from their illicit activities,” McNamara explained. “Over the years the Outfit has learned that killing people brings too much heat from law enforcement. Today they might not even beat up a businessman who doesn’t pay back a debt,” he added. Instead, they take a piece of his business, and then, over time, exercise more and more control over the company.

The Family Secrets case, which began in 1999 and resulted in the indictment of 14 subjects in 2005 for racketeering and murder, dealt a crushing blow to the Chicago mob. “Our goal now,” McNamara said, “is to keep them from gaining strength again. We’ve got them down and we’ve got to keep them down.”

He noted that some of the mobsters currently in jail as a result of numerous prosecutions will be getting out in the next few years, and they will be under pressure to start making money again for the Outfit’s top bosses.

 “As long as there is money to be made from criminal activity,” McNamara said, “these guys will never stop. So we need to continue to be vigilant and take the long view. The work we do on the LCN squad requires a lot of patience.”