Chicago mobster and reputed hit man Anthony (Tough Tony) Calabrese died of cancer recently in a federal prison in Indiana. The 57-year old Calabrese was suspected by authorities of being the triggerman in two unsolved Outfit murders, but incarcerated on an armed robbery conviction. A plea to his trial judge for a medical release earlier this year failed and a clemency request based on his condition sent to the White House was rejected in April.

Calabrese was found guilty at a 2008 trial of sticking up three businesses — a leather shop, a butcher shop and a tattoo parlor — and sentenced to 62 years behind bars. The FBI fingers him as the shooter in the Thanksgiving Day 2001 gangland slaying of notorious Outfit lieutenant, Anthony (Tony the Hatchet) Chiaramonti and as part of the conspiracy to murder Chinatown mobster Ronnie Jarrett two years before that.

Court records from his armed robbery case show Calabrese ordering the hammering of the hands of the owner of the tattoo parlor he robbed (revenge for tattooing the underage daughter of a mob superior of his) and beating up a member of his heist team for being disloyal. Prior to his arrest, Calabrese owned an auto body shop and reported to leaders of the Outfit’s Cicero crew.

Calabrese’s right-hand man Bobby Cooper was the star witness at Calabrese’s trial. While talk of his mob ties were barred from the court proceedings by the judge, Cooper told the FBI that he drove the getaway car on the Chiaramonti hit where Calabrese shot Tony the Hatchet to death inside the vestibule of a fast food fried chicken place. He tipped the feds off to rumors of Calabrese being the shooter in the Jarrett murder, too.

Tony Chiaramonti, 67, got caught in a power struggle within the Cicero crew, pitting the early 1990s regime, which he belonged to, versus the crew’s New Millennium leadership headed by future Outfit street boss Michael (Fat Mike) Sarno and upset Elmwood Park crew heavyweight Rudy (The Chin) Fratto by swindling a nephew of Fratto’s in a join business venture. Sarno and Chiaramonti were locking horns over video poker machine routes in the years after Chiaramonti was released from a prison sentence for racketeering.

An FBI surveillance unit witnessed Chiaramonti get into a shoving match with infamous Outfit hit man Francis (Frank the German) Schweihs outside a Cicero pancake house in the days before he was slain. Schweihs had been sent to “reel” Tony the Hatchet in, per sources close to the situation, and keep him from continuing to make waves.

Cooper admits to driving Calabrese to a Brown’s Chicken & Pasta location in Lyons Township, Illinois on the evening of November 20, 2001 and seeing Calabrese chase Chiaramonti from the parking lot into the restaurant foyer before gunning him down. Minutes earlier, Chiaramonti had arrived at the fast food outlet, fresh from his Thanksgiving meal, in his brand-new black-colored BMW sedan.

Ronnie Jarrett, 55, was angered by being passed over for a Chinatown crew leadership post in the wake of longtime capo Angelo (The Hook) LaPietra’s death and angered Outfit bosses by openly trafficking in narcotics. He was shot five times outside his Bridgeport home on the morning of December 23, 1999, as he was getting into his car to drive to the funeral of fellow Chinatown crew member Charles (Guy) Bills, and died in the hospital just over a month later.

In the 1970s and early 1980s, Jarrett sometimes filled in as part of a mob enforcement subunit given many of the Chicago mafia’s most difficult hit assignments dubbed the Wild Bunch. His murderer was traveling in a mover’s truck found ablaze in a nearby parking lot that same day.

Calabrese’s viciousness was on full display in the following excerpt from an FBI wire being worn by an associate of his that he and Cooper threatened to kill and stomped with steel-toed boots in the office of his auto detailing business (Tony C’s First Impressions in Alsip, Illinois) for a perceived slight and the belief that he might be informing for the government.

Calabrese: Ya know any of this stupid little shit that you see around here, you keep your mouth shut about? I mean, you understand what will happen if you don’t, right?

Victim: Tony, come on, do I look like I want to end up dead?

Cooper: Nobody said that.

Victim: I know the seriousness of what goes on here, I ain’t stupid.

Calabrese: There ain’t nothing serious going on. But when people get in trouble, sometimes the fucking make shit up. I don’t want you making anything up, that’s all. I fucking bust my balls here every day, all day long. I got enough problems. I don’t need nobody starting rumors or any fucking shit like that.

Cooper: Where you living at these days, pal?

Victim: In a hotel.

Cooper: Which hotel?

Victim: Why you guys gotta know that? Is that necessary?

Calabrese: ‘Cause we’re asking.

Victim: Tony, I don’t know if I feel comfortable telling you guys. I don’t feel safe about that.

At this point, Calabrese and Cooper attack the victim and begin stomping him

Calabrese: You disrespectful motherfucker. Fuck you. What did you just say, you fuck? Fuck you!

Victim: I’m sorry Tony. I’m sorry. I’m sorry. I didn’t mean it.

Calabrese: Go fuck yourself you cocksucker. Motherfucker. Your an ungrateful motherfucker, you know that. I did everything for you. I put food on your plate and you’re going to act like this towards me?

Victim: I’m sorry, Tony. I said, I’m sorry. I’ll never disrespect you again, I swear.

Calabrese: You’re a punk ass bitch. Bobby, get his ass back up, so I can look him in the eye. You wanna feel safe? I’m gonna give you something to feel safe about. This is the last time I’m going to tell you. Remember what happens, motherfucker.

Victim: I will, I promise.

Calabrese: Let me tell you something. If anything happens around here. If anything happens to me, if I see one fucking cop, one fucking fed. I swear, we’re going to fucking kill you. You can take that to the fucking bank.

According to sources in law enforcement, Calabrese was “made” into the Chicago mob by Fat Mike Sarno as reward for his two high-profile hits and as part of a group of Cicero crew loyalists Sarno built his powerbase around. These same sources claim, Calabrese was sponsored for induction by Sarno’s then-No. 2 in charge, James (Jimmy I) Inendino, another former Wild Bunch member and reputedly the current crew chief in Cicero.

Today, Sarno, 61, is eight years into a 25-year prison stint for extortion. He’s considered one of the top suspects in the 2006 disappearance and murder of Outfit underboss Anthony (Little Tony) Zizzo, who like Tony Chiaramonti, was a Cicero crew stalwart of the “old guard” feuding with Sarno over video-poker machine routes.

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