Aging Chicago mafia button man Robert (Bobby the Boxer) Salerno is set to taste freedom for the first time in over 20 years in the coming days. The 82-year old Salerno, a former prize fighter, trainer and promoter, as well as an infamous Outfit enforcer, will be released from a low-security federal prison in Arkansas this weekend after serving more two decades of a life prison sentence for racketeering and murder.

Salerno was part of Operation Good Ship Lollipop, targeting Outfit underboss Ernest (Rocky) Infelise’s Cicero crew. Rocky Infelise and Bobby Salerno were found guilty of murdering independent suburban Chicago bookmaker Hal Smith on February 7, 1985.

The Infelise mob crew, headquartered in Cicero, but lording over large swaths of racket territory in Lake and McHenry Counties too, was jokingly referred to amongst Infelise’s inner-circle as the Good Ship Lollipop, an ironical nod to the 1930s Shirley Temple song from the film Bright Eyes. Infelise died of natural causes ten years later in a Massachusetts prison hospital in 2005.

Smith had repeatedly refused to pay the Infelise crew what it deemed an acceptable street tax on his giant sports book and had gotten into a loud public verbal spat with Infelise’s second-in-command, Salvatore (Solly D) DeLaurentis where the pair reportedly threw wads of cash at each other and exchanged ethnic slurs and death threats in an Arlington Heights, Illinois restaurant. Smith’s dead body was found battered, beaten and sliced up, stuffed in the trunk of his Cadillac in the parking lot of the Hilton Hotel in Arlington Heights.

The government’s star witness in Operation Good Ship Lollipop was William (B.J.) Jahoda, an Infelice crew member, DeLaurentis’ longtime driver and the owner of the Long Grove, Illinois home where Smith was executed. Jahoda wired up for the feds and admitted to delivering Smith to his slaughter at Infelise’s behest and watching as a hit team dressed in all-black clothing consisting of Infelise, Salerno, Robert (Bobby the Gabeet) Bellavia and Louis (Louie Tomatoes) Marino converged on and began throttling Smith on the floor of his kitchen.

B.J. Jahoda recorded a cautious Salerno discussing the investigation into Smith’s murder in the late fall of 1989.

Jahoda: “I don’t know if you’re aware of this, but Louie (Marino), Rocky (Infelise) and myself got subpoenas.”

Salerno: “Subpoenas?”

Jahoda: “We got to see a grand jury a week from today …”

Salerno: “Let me see this (grabbing the subpoena, placing his eyeglasses on to read it for himself), wait …, let me look at this”

Jahoda: “And we know what it is, I mean, what its about, don’t we.”

Salerno: “Yeah.”

Jahoda: “And we’re not worried about it? But I don’t think you know this, so I want you to, I want you to know what it involves. Rocky made a very serious mistake that night. He called me from the outside. He told me that Louie had left something there (his glasses and cigar) …”

Salerno: “Yeah, don’t even talk about it. I don’t even want to talk about it.”

Jahoda: “No, I understand that. So, but, but it was picked up on a tape. So that’s why the three of us …”

Salerno: “Don’t even, don’t even, don’t even tell me about it. They ain’t got shit. Don’t talk about it no more.”

Jahoda: “I know that, but I wanted you to know.”

In 1988, an FBI informant implicated Bobby Salerno as a participant in the felony murder of small-time Chicago gangland figure Mike Oliver a decade earlier. Oliver, a Salerno associate who owned an adult book shop in suburban Elk Grove and ran a sports book, was accidentally killed as Salerno and others staged a late-night vandalism of his store in November 1979, his body buried in a mafia graveyard in Darien, Illinois. The vandalism was an extortion attempt, prompted by the shop sharing a street with another mobbed-up adult bookstore.

Salerno went on trial twice in the Good Ship Lollipop case, once with Infelise and the rest of his inner circle in 1992, concluding in a hung jury for him and guilty verdicts for his co-defendants and then again in 1995 when he was finally convicted. At both trials, Bobby the Boxer was represented his son, attorney Alex Salerno.

The elder Salerno trained and promoted fights for heavyweight pro boxers Ernie Terrell and Ernie Shavers. Terrell, the WBA World Heavyweight Champion from 1965-1977, testified as a character witness at Salerno’s second trial.

Of all the main members of the Infelise crew, DeLaurentis, 78, was the first to get out of prison, flying the coup in 2006 – today, he’s considered by authorities the Outfit’s acting boss. Bobby Bellavia, 77, walked free last spring. Louie Marino was sprung in 2014 and died of natural causes back in the winter at the age of 85.

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