Artifact Spotlight: Frank Calabrese Sr.’s handmade dictionary

“PRISON: IS WARE I AM AT,” reads an entry in the handmade dictionary of Frank Calabrese Sr., former boss of the Chicago Outfit’s 26^th Street/Chinatown crew. Calabrese was serving a life sentence at the Butner Federal Correctional Complex in North Carolina. He had been placed in a strict form of solitary confinement, called Special Administrative Measures (SAMs), usually reserved for terrorists to prevent any communication with the outside world. “Your mind can start playing games,” said his son Frank Calabrese Jr., “so he wanted to keep his mind crisp.”

Frank Sr. was not resigned to spending the rest of his life in prison. He was gearing up to write a letter to Attorney General Eric Holder to gain his freedom. “And that’s where those dictionaries come in, too,” Frank Jr. said, “because he always wants to make sure he has the right word to manipulate you.”

This dictionary is not your standard Merriam-Webster. Frank Sr.’s dictionary typically gives context over definitions, such as “ORGANIZED = CRIME” and “BURIED = THE BODYS.” The all-caps writing style reflects his unremediated dyslexia, which stemmed from an extended hospital stay (“SCARLET = FEVER”) that prevented him from attending grammar school.

Frank Sr. had been in prison since 1997, when he, his brother, Nick, and his two sons, Kurt and Frank Jr., were convicted on RICO charges for their “juice loans,” or loansharking, business. He was sentenced to 114 months in prison, with the others serving lesser sentences. As the least involved, Kurt might have received a slap on the wrist if he had fought the charges. But Frank Sr., a master manipulator, guilted him into accepting a plea bargain to spare his father a potential 60-year sentence. He also promised that Frank Jr.’s $150,000 fine would be on his tab, a promise he had no intention of keeping.

Most of the Calabrese crew’s earnings came from loansharking, extortion and illegal gambling, but behind the scenes it had another, more sinister role: It was the Chicago Outfit’s go-to hit squad.

In 1986, Frank Jr., who had been involved with the crew for 10 years, volunteered to carry out his first hit on John “Big Stoop” Fecarotta. Instead, he was saved by his Uncle Nick, who had already been involved in more than a dozen murders. Nick stepped in and killed Fecarotta on his own, accidentally shooting himself in the arm and dropping a pair of bloody gloves on the street in the process.

A few months into his sentence, Frank Jr. was transferred to FCI Milan, the same Michigan prison where his father was serving his sentence. The two reconnected, and Frank Sr. assured his son that his life in the Outfit was in the past. But soon it was clear to Frank Jr. that his father had no intention of reforming or leaving the Outfit behind. This was a man who once held a gun to his son’s head and said, “I’d rather have you dead than disobey me.” If his father were ever freed from prison, Frank Jr. believed he would once again lose control of his life and be in danger. Something had to change.

Operation Family Secrets

Frank Jr. secretly wrote a letter to the FBI and offered to cooperate, not for a reduction in his sentence but to ensure that his father would spend the rest of his days behind bars. The FBI convinced him to wear a wire when speaking with his father in the prison yard. This risky gambit paid off with a heap of evidence tying Frank Sr. and his crew to more than a dozen murders.

The FBI also recorded a visit between Frank Sr. and two Chicago cops discussing a plan to get rid of a crucial piece of evidence: Nick’s bloody gloves. Now knowing the significance of this piece of evidence, the FBI took DNA from the gloves, which tied Nick to the Fecarotta murder. Nick, still in prison and out of options, decided to cooperate.

With Nick’s testimony and Frank Jr.’s recorded conversations with his father, the FBI had what it needed to make a strong case. Dubbed “Operation Family Secrets,” the investigation and subsequent trial crippled the Chicago Outfit. With evidence linking Outfit members to 18 murders, high-ranking members Joey “The Clown” Lombardo and James “Little Jimmy” Marcello received life sentences, and Frank Calabrese Sr. received multiple life sentences plus 25 years.

Frank Sr.’s dictionary makes clear his opinion of the outcome: “CORRUPT = JUDGE IS BAD,” and “VERDICT = THE JUDGE GAVE WAS WRONG.”

Prison life

“My dad’s mindset, which I have too, is if there’s any positive in the situation, you focus on that positive. Don’t focus on the negative. It’s not going to change,” Frank Jr. said. “For him, it was trying to get back out on the street, and that’s what kept him alive for a lot of years.” His father would do whatever he could, futile as it may be, to escape his fate. His letter to Eric Holder was just one avenue.

His strict limit on communicating with others while under SAMs (one of 42 federal inmates at the time with the restriction) proved the toughest obstacle for his plan, however. “You’re locked down 24/7 and in the cell by yourself. No interaction with any inmates,” Frank Jr. said, “If the guards go to the cell, they have to go in groups of two, so they can’t be compromised by the inmate.” Meals are delivered via a conveyer belt and a series of doors. “The only one who can go in this cell is a man of God, and he can go alone.”

And that’s how the Reverend Eugene Klein, a prison chaplain, was charged with violating the special restrictions by delivering notes that Frank Sr. passed through his food slot. Klein was recruited to help Calabrese Sr. steal a Stradivarius violin, which he believed to have belonged to Liberace, hidden in the walls of a Wisconsin vacation home. Calabrese’s two unnamed conspirators valued the violin at $26 million, based on a Discovery Channel program. The violin, probably received as a “juice loan” payment, was never found. In a 2010 search of Frank Sr.’s Oak Brook, Illinois, home, federal agents did find paperwork appraising the instrument as a 1764 creation by Giuseppe Antonio Artalli, not Stradivari.

Unfortunately for him, the clock was running out. Frank Calabrese Sr. died in 2012 on Christmas Day. “Last I spoke with him a little over a year ago, he was a sick man,” Joseph Lopez, his attorney, told the Chicago Tribune. “He was on about 17 different medications. But always a strong-willed individual.”

After Frank Sr. died, Frank Jr. received all of his father’s personal effects, including the handmade dictionary. Frank donated many of these items and documents from the trial to The Mob Museum in 2023.