When Family Secrets Include Murder: The Letter That Decimated The Chicago Outfit

"I have to help you keep this sick man locked up forever." --Frank Calabrese Junior

Defendants in the Family Secrets trial at a hearing
Family Secrets trial (source: NPR)

The investigation that decimated the Chicago Outfit began when a letter dated July 27, 1998, reached the FBI's Chicago headquarters.

“I am sending you this letter in total confidentiality," it began. "It 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 message had been sent from the federal correctional facility in Milan, Michigan. The writer was Frank Calabrese Junior, a son of Frank (Frankie Breeze) Calabrese Senior, an especially vicious member of the Chicago organized crime family known as the Outfit.

The letter spawned a seven-year investigation that went back to the 1970s. The original indictment named 14 defendants and included 18 previously unsolved murders; it culminated with five on trial, guilty verdicts, and life sentences, including for James Marcello, the reputed one-time front boss of the Chicago mob. ("Marcello's expression didn't change as U.S. District Judge James Zagel sentenced him to life behind bars. Marcello was believed to be the highest-ranking mobster felled by the ... Family Secrets mob conspiracy trial, and he was held responsible for its marquee murder ," the murder of the Spilotro brothers.)

"We dubbed it “Operation Family Secrets,” and it’s one of our most successful organized crime investigations ever," as the FBI says on its website.

But that was the end; in the beginning, when the letter first arrived, both the FBI and federal prosecutors were baffled. Frank Jr wanted to flip; that part was clear as crystal. But why he wanted to flip, that was the part that didn't make sense. The Fed's and the FBI were under the (mistaken) impression that they had already smashed the Calabrese crew apart. (They came very close to ignoring the letter, it seems. Imagine if they had...)

Frankie Breeze was once "the mob's top loan shark in Chicago." From the late 1970s until 1992, Frank Calabrese Sr.'s crew made hundreds of loans at interest rates as high as 10 percent a week. They raked in more than $2.6 million by government estimates, according to Assistant U.S. Atty. Mitchell Mars. Frankie Breeze used about 80 bank accounts to conceal the assets from his loan-sharking business.

Back in 1995, the Fed's had broken up the operation. SAC Bourgeois had led the FBI probe that culminated in the grand jury  indictment of nine, including Frank Sr., his brother Nick, Frank Jr., and another of Frank Sr.’s sons, Kurt. In addition to running a massive loan shark operation, the Calabreses were also accused of appropriating the auto repair business of a customer, who had then became an informant. (The crew even got a service contract with a large car dealership and  began overbilling.)

The Calabreses had pleaded guilty. Frank Sr. got nearly 10 years in prison, Nick got nearly six years, and Frank Jr., was given nearly five years.

Federal prosecutors and the FBI had moved on. Then the letter from Milan arrived....

Law enforcement would come to understand Frank's motives for writing the letter. At the time, Frank Jr. was in his mid-30s and had determined that he wanted out of organized crime; he also came to the conclusion that his father was an unrepentant, irredeemable criminal and a multiple murderer who belonged in a cage for the rest of his life.

Frank Jr. had gone through a cocaine addiction  and once stole several hundred thousand dollars from his father. Frank Sr. had held a gun to his son’s face and threatened to kill him. The son’s bitterness leaped exponentially after that and resulted in the letter. Frank Jr. has written a book in which he provides great detail, Operation Family Secrets: How a Mobster's Son and the FBI Brought Down Chicago's Murderous Crime Family

It was five months before Agent Thomas Bourgeois finally visited Frank Jr. at FCI Milan, in the early winter of 1998. Eventually the game plan was developed, with Frank Jr ultimately agreeing to wear a wire and talk to his father in the prison yard.

Frank discussed his strategy for recording his father. "I didn't push anything," he said."(M)y father [had] taught me two ways to get a guy to talk: Either feed him a lot of liquor or get him mad. So we didn't have any liquor in jail, so I got my father mad. And the premise was that we were working on our relationship. So all this stuff he was talking about really wasn't forced."

Frank Sr. directly implicated himself on tape by admitting his part in several murders "in great detail."

The FBI noted that once they had the recordings of The Breeze copping to murders, they were able to attain authorization to record conversations between Frank Sr. and certain visitors at the prison. (Frank Sr. continued to run business from FCI Milan.)

From those initial recordings, the FBI was able to collect enough information and corroborate it with evidence, to build an iron-clad case against the senior Calabrese for the 1986 murder of mobster John Fecarotta in Chicago. The evidence also clearly implicated Calabrese’s brother, Nicholas W. Calabrese. Nick was imprisoned with Marcello and would ultimately flip with Frank Jr. and hammer the last nail in.

When Frank Jr. wrote the letter, Frank Sr. was in his 60s.

In Family Secrets: The Case That Crippled the Chicago Mob, Jeff Coen wrote that  despite Calabrese's age, "anger could still bring an intense glare to his face."

This photo of Family Secrets Tour Chicago is courtesy of TripAdvisor.

Frank Sr. "was largely uneducated as far as traditional schooling went and could barely read. What he did have were street smarts and a head for numbers. And he was a good student of the human animal—able to read people and manipulate them."

Frank Jr. closely resembled his father and had learned a great deal from him -- you could say that Frank Jr. never would've had the audacity to pull off what he pulled off without having Frankie Breeze as his tutor.