Calabrese, 75, was stricken by an apparent cardiac seizure on Tuesday while serving a life sentence at a federal prison in Butner, NC according to his longtime Chicago attorney Joe "the Shark" Lopez.
"Christmas was his favorite holiday" recalled Lopez on Wednesday after learning of his client's passing. The mob boss had been in ill health.
The mob killer, known in mob circles as "the Breeze," was characterized as bloodthirsty and unforgiving by many of those who encountered him. He personally had a hand in more than a dozen gangland murders during his long and violent career according to federal investigators.
Calabrese Sr. had been pursued by law enforcement and prosecutors for decades, since his rise through the Outfit ranks to the upper crust of organized crime.
"He was a very smart man on the street. He flew under the radar. He ran a very tight ship," his son Frank Calabrese Jr. said.
He died imprisoned with no hope of ever seeing freedom after being convicted as the central figure in the government's 2007 "Family Secrets" case.
Fourteen members of the Chicago mob were indicted for a variety of crimes, including 18 murders and one attempted murder. Two other Outfit defendants were sentenced to life behind bars besides Calabrese: Joey "the Clown" Lombardo and James "Jimmy the Man" Marcello.
The keys to the landmark case that spelled the end of Frank Sr. were his two closest relatives: brother Nick, a mob enforcer and assassin; and son Frank Jr., who found a conscience while serving a prison term and turned on his father.
The beginning of the end for Frank Sr. was in 1997 when he was sent to prison with Nick and Frank Jr. on a series of racketeering charges. Facing a substantial prison sentence, son Frank Jr. typed a letter to the FBI, offering to help bring down his father's gangland empire.
"I didn't want immunity. I didn't want any kind of deal" said Jr. on numerous occasions. Calabrese Jr., who claimed he was manipulated and abused, said he only wanted to "keep my father locked up."
In court testimony-and later in a book-Frank Jr. said his father was dangerous and should never be free.
He wore a wire while spending time with his dad at the federal pen in Milan, Michigan. The tapes caught Frank Sr. admitting to the murders and rackets that the feds had suspected he committed, but could never pin on him.
"Prior to going to prison, he tried to kill me," Jr. said. "The decision I had to make was to keep him locked up. He wasn't going to change his ways. And this wasn't something I decided overnight."
Jr. testified against his father during the Family Secrets trial in Chicago. The son's cooperation proved to be an incentive for the brother, Nick, to become a government witness as well. Nick Calabrese was an eyeball witness-and participant in-many of the mob murders that Frank Sr. committed during more than three decades. Most of them remained open until the Family Secrets case resolved them.
Among the last public words that Calabrese Sr. uttered were in a courtroom threat against the federal prosecutor who would send him to prison. "You are a f---ing dead man" Calabrese mouthed to Asst. U.S. Attorney T. Markus Funk. There was never any violence executed against Funk, but Calabrese did spend his final years in prison isolation because of the threat.
Following an autopsy, standard in any prison death, Calabrese will be turned over to his family, left splintered and scattered by the mob case.
The date of death on his tombstone will be December 25, 2012.
"He loved Christmas" said attorney Joe Lopez. "The family would get together and eat, drink and be merry. Nick would bring the kids. Frank loved the social interaction with the family."
"In the end, he tried to change his life around," Lopez said. "He became very religious and would read the Bible, and he tried to make up for all his past misdeeds."
Whether or not Calabrese Sr. died a different man, Calabrese Jr. said he sees significance in his father's Christmas Day passing.
"I truly feel that today my father is in heaven," he said. "And I do believe that he's looking over my shoulder now."
With Frank "the Breeze" Calabrese gone, the family and "the Family" will go on...with one less ghost of Christmas past.