Friends of mine: Philip Tolomeo
A Chicago police detective walked into The Nest, an old Outfit nightclub, looking for a shooting suspect.
The cop found his suspect -- he just hadn't been accused yet of committing any murders.
It was March of 1958 on the city's Northwest Side, and the lounge was packed to hear singer Tony Smith and his band play some trendy new rock 'n' roll dance music.
Working the midnight shift, Detective James Jack, who now lives in Palatine, and his partner Frank Czech walked in around 2 a.m. looking for a guy they knew hung at the joint. Jack, as he tells it, stepped between two guys to look up and down the bar.
One of the guys next to him swiveled around in his chair and asked him, "What the [expletive] are you looking at?"
"Nothing much," Jack answered.
With that, the guy punched Jack square in the mouth, sending him reeling against the wall. His attacker had a few inches and pounds on Jack, but the detective, a former Gold Gloves boxer, recovered and grabbed the man in a head lock.
Another guy jumped Jack's partner, but the big detective threw him aside like a doll. A police officer who happened to be standing down the bar came to help, they identified themselves as police, and together they wrestled the two hotheads outside and into a police car -- the Tony Smith band playing without skipping a note.
The perpetrator turned out to be none other than Frank Calabrese Sr., then 20. At the time, he was on parole for auto theft.
As they drove to the police station, Jack recalls, Calabrese kept saying, "I didn't know you were a cop."
"I said if I were a normal person, you and your cronies would have killed me and laughed all the way home," Jack said. "He was an animal."
As it turned out, Calabrese was not wanted in the shooting Jack was investigating, and the detective never recalls Calabrese being convicted for punching him. Federal investigators, Jack said, were more interested in bigger cases than a bar fight.
Calabrese's attorney, Joseph Lopez, noted his client was only 20 and "just getting started," but suspected there must be more to the story, saying his client treated police with respect. "I find that hard to believe," Lopez said. "He's not a bully. Something else must've happened."
In recent years, Calabrese has been in prison after pleading guilty to taking part in a long-running juice loan extortion scheme. Now, Calabrese is ready to stand trial on charges of murder and racketeering with 13 other alleged members of the Chicago Syndicate.
Calabrese was far from Jack's only run-in with the mob. His first police partner was Philip Tolomeo, who used to make Jack wait in the car while he met with cronies at a mob hangout, before leaving the force, joining witness protection and getting convicted with Calabrese.
Ironically, Jack also once arrested one of the victims of an alleged Calabrese hit. Jack arrested John Fecarotta for sticking a gun in the mouth of a parking attendant at O'Hare International Airport in 1965. Fecarotta was found shot dead in an alley in 1986.
Jack has long since retired from the force, but he plans to attend the mob trial, which will be presided over by Judge James Zagel, who once worked with Jack on the Illinois Criminal Justice Information Council 25 years ago. Jack says he wants to see some of his old combatants.
"I want to see how they act now, compared to how feisty they were in their younger days, when they didn't care who they got involved in altercations with," he said. "Let the jury throw the dice, and let justice prevail."
Thanks to Robert McCoppin
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