Calabrese died on Christmas at the Butner Federal Correctional Complex, where he had been serving a life sentence, according to a spokesman for the Bureau of Prisons. He was 75.
Calabrese, one of Chicago’s most feared mobsters, was convicted in 2007 during the Operation Family Secrets trial.
A federal jury held Calabrese and two other aging mobsters -- Joseph "Joey the Clown" Lombardo and James Marcello -- responsible for 10 murders after a trial that exposed the seedy inner workings of organized crime in Chicago.
Calabrese, a portly, bearded loan shark who according to witnesses doubled as a hit man, was found responsible for seven mob murders. Witnesses, including his brother Nicholas Calabrese, said he strangled victims with a rope, then cut their throats to make sure they were dead.
Marcello, described by prosecutors as a top leader of the Chicago Outfit, was held responsible for the June 1986 murder of Tony "The Ant" Spilotro, the Chicago mob's longtime man in Las Vegas and the inspiration for the Joe Pesci character in the movie "Casino."
The Family Secrets trial was the biggest organized crime case in Chicago in years. The defendants were convicted of operating the Chicago Outfit as a racketeering enterprise.
They allegedly squeezed "street tax," similar to protection money, out of businesses, ran sports bookmaking and video poker operations as well as engaged in loan sharking. And they allegedly killed many of those who they feared might spill mob secrets to the government -- or already were doing so.
The cases went unsolved for decades.
The Family Secrets trial was the biggest organized crime case in Chicago in years. The defendants were convicted of operating the Chicago Outfit as a racketeering enterprise.
They allegedly squeezed "street tax," similar to protection money, out of businesses, ran sports bookmaking and video poker operations as well as engaged in loan sharking. And they allegedly killed many of those who they feared might spill mob secrets to the government -- or already were doing so.
The cases went unsolved for decades.
Calabrese’s attorney in the Family Secrets trial, Joseph “Shark” Lopez, said Calabrese had been in ill health.
“Last I spoke with him a little over a year ago, he was a sick man,” Lopez said. “He was on about 17 different medications. But always a strong-willed individual.”
After spending hundreds of hours together while Calabrese was on trial, Lopez said the two developed a relationship.
“Sure he was difficult at times because he was used to getting his way, but I only saw one side of him and that was the good side,” Lopez said. “He was a pleasure to deal with and a pleasure to talk to. We’d talk about cooking, restaurants, history, you name it.”
“He was quick-witted, smart and street-savvy,” Lopez said. “Always very upbeat; nothing could keep Frank down.”
Lopez said Calabrese was very religious, making his Christmas day death feel “odd.”
“He always talked about how much he loved spending Christmas with his family. It was his favorite holiday of the year,” he said.
Lopez said he thinks there will be mixed feelings in Chicago about Calabrese’s death.
“I’m sure there are some people really sad and some people really happy,” Lopez said. “I’m sad for his family.”
Frank Coconate, a friend of the family, said he heard about the death through Calabrese's wife.
"I’m a little shook up about it,’’ said Coconate, 54, who took vacations to Florida with his wife and Calabrese and often dined with him. “It’s a family tragedy."
Coconate said Calabrese had heart problems, and had broken his hip in the shower about a month ago.
Coconate remembered Calabrese as a “unique individual’’ with a temper that would flare up unexpectedly, even during dinners out with his family.
"If he heard something, if you shot your mouth off, you’d be having dinner and he’d ask you to come outside and he’d crack you in the head," Coconate said. "He was a throwback gangster. He would fight with his fists and was strong as a bull. But that’s the business they’re are in.
"He was a great manipulator," he said, recalling recent allegations that Calabrese persuaded a priest to act as a messenger for him. "He was very charming. That’s what made him dangerous.’’
He said the last real communication he’d received from Calabrese was a 19-page letter from prison. In recent years, there were just brief messages through other people. “He’d say, 'How's it going? How’s your wife?' He’d say keep an eye on his son. He didn’t want him him to get hurt."
Coconate said Calabrese was in isolation in prison, and only Calabrese's wife and his lawyer were allowed to see him about every month. “It’s pretty sad. But whatever he was, nobody should be treated like that. An animal should not be treated that way."
Coconate was in the news himself in 2005 when he was fired from his city job in Chicago. He was later reinstated after contending he was dismissed because of his frequent criticism of the Daley administration.
Calabrese's body was taken to the medical examiner's office, where it was to be examined, according to Kevin Gerity, autopsy manager for the office.
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