In the months leading up to his alleged murdering of a well-known Chicago mob figure, reputed Outfit hit man Anthony (Tough Tony) Calabrese organized and ordered three armed robberies that proved to be his downfall. His entire crew of subordinates responsible for carrying out the stick ups turned against him and testified for the government at his 2008 trial.

The 58-year old Calabrese was found guilty and sentenced to 62 years in federal prison. The string of robberies spanned April to September 2001. According to his former right-hand man, Bobby Cooper, in November of that year, Calabrese gunned down disgruntled mob lieutenant Anthony (Tony the Hatchet) Chiaramonti in the vestibule of a fast-food fried chicken restaurant as Cooper waited in a getaway van in the parking lot. Cooper was the star witness against Calabrese in court seven years later.

Both Calabrese and Chiaramonti were part of the Chicago mafia’s Cicero crew. Tony the Hatchet, as feared as they came in Outfit circles for decades, based his activities out of Melrose Park.

Per court records, Calabrese planned the trio of armed robberies from his car-detailing business, Tony C’s First Impressions Auto Spa in Alsip, Illinois. The first job took place on April 13, 2001 and the target was The Leather Connection, a leather goods shop where Calabrese had an inside source employed at the store. His crew for the job included Cooper, Sean Smith, Walter Polino and Marcus Baker. Smith and Cooper entered the store brandishing guns and herded the store’s owners into a storage room. Calabrese then came into the premises and watched as Cooper duct-taped their arms behinds their backs. Polino acted as the getaway driver and Baker as a lookout. They walked away with a rented van full of leather jackets and $10,000 in cash. Like Cooper, Smith, Baker and Polino all eventually flipped on their boss.

On July 24, 2001, Calabrese targeted the Metamorphous Tattoo Parlor in Lockport, Illinois, tasked by an Outfit superior to teach the recently-opened parlor’s owner a lesson. The owner had tattooed a mob leader’s underage daughter without proper authorization. Calabrese tapped a crew member of his named Ed Frank with organizing the heist, which would also serve as a cold-blooded assault. Frank recruited his drug dealer Marty Flores and Flores in turn brought his associates, Juan Mirelez and Efrain Formes, on board.

Flores, Mirelez and Fromes did the actual job. They collected a box of zip ties from Calabrese’s nephew that afternoon and headed to the tattoo parlor. Once inside, Flores brandished a pistol, provided to him by Calabrese, and ordered all the employees and customers on the floor. Mirelez and Fromes grabbed the owner, Mike Farell and they took him into his office and proceeded to beat and stomp him. Flores then took a hammer he had brought and, per Calabrese’s instructions, broke both of Farell’s hands. While Mirelez and Fromes removed the shop’s expensive tattoo machinery and emptied the safe, Flores pistol whipped Farell and instructed him to shut his parlor down and “get the fuck out of Lockport for good.” Flores, Mirelez and Fromes each joined Team USA in the coming years.

By September, Calabrese got wind of a butcher shop in Maywood, Illinois which an inside source of his told him kept a lot of cash on hand. He, Frank and another crew member, Ricky Dawson rushed into Morris’ Meat Packing on September 23, 2001 and Calabrese stuck his gun in the owner’s face and demanded all the money he had on hand. Dawson’s friend Dave Sims drove the getaway car and acted as the lookout. The owner handed over $15,000 in cash and the group fled. Frank, Dawson and Sims took the stand at Calabrese’s 2008 trial – Frank wore a wire on Tough Tony and survived a savage beat down at the hands of Calabrese and Cooper in the weeks after the final robbery.

Cooper told authorities after he began cooperating that Calabrese killed Tony Chiaramonti on November 20, 2001, chasing him into a Brown’s Chicken & Pasta location in Lyons Township, Illinois on Thanksgiving night and pumping six bullets into his head, neck and torso. Tony the Hatchet had been feuding with Outfit administrators in the years following being released from prison on a racketeering bust. Calabrese was groomed in Chicago mob affairs by current Cicero crew capo James (Jimmy I) Indendino.

As a part of his debriefing wit the feds, Cooper also implicated Calabrese in the Outfit’s Ronnie Jarrett hit two years prior — Jarrett was slain for beefing with his bosses in the Outfit’s Chinatown crew. Both the Chiaramonit and Jarrett murders remain unsolved.

Today, Tough Tony Calabrese is dying of cancer in a Terra Haute, Indiana prison. His attorneys have unsuccessfully argued for a medical release so he can spend his final days as a free man with his family. Last week, President Donald Trump rejected a plea from Calabrese for clemency.

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