Retired Intelligence Detective Gary Jenkins brings you the best in mob history with his unique perception of the mafia. In this episode, we delve into the intriguing life of Charles “Chucky” Nicoletti, a notorious Chicago Outfit hitman known for his involvement in numerous mob hits and his alleged ties to significant events like the JFK assassination. Nicoletti’s background is painted with a turbulent upbringing, including shooting his father in self-defense, leading him to join the infamous 42 Gang alongside other notorious mob figures. His partnership with Milwaukee Phil Alderisio solidified his reputation as a feared hitter in Chicago.

The episode explores Nicoletti’s involvement in high-profile hits, such as targeting the M&M brothers, which involved brutal torture methods made infamous in the movie “Casino.” His cold-hearted demeanor earned him the nickname “Typewriter,” though the moniker’s origin remains a mystery. Nicoletti’s demise came in 1977 when he was ruthlessly gunned down in his Oldsmobile in a suburban parking lot, suspected of being a part of internal mob conflicts as critical figures like Giancana, Richard Cain, and Mad Sam DeStefano faced similar fates.

The narrative weaves through the intricate web of Chicago mob connections, hinting at ties to CIA operations, the JFK assassination, and the plot to kill Castro. The episode speculates on the possible motives behind Nicoletti’s assassination, pointing to shifting allegiances within the Outfit after the deaths of influential figures like Giancana and Ricca. The mysterious circumstances surrounding Nicoletti’s death, coupled with the demise of critical associates, emphasize the dangerous and volatile world of organized crime in Chicago during that era.

Throughout the episode, the host reflects on the broader implications of Nicoletti’s story, urging caution on the roads and highlighting resources for PTSD, addiction, and seeking help. As the podcast delves deep into the underworld of Chicago mob history, the legacy of figures like Chucky Nicoletti serves as a chilling reminder of the ruthless nature of organized crime and its far-reaching consequences.

#chicagooutfit #tonyaccardo #samgiancana #mafia #underboss #organizedcrimegroups

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Transcript

[0:00]

Introduction

[0:00]Well, hey, all you wiretappers out there back here in the studio of Gangland Wire. This is Gary Jenkins, retired Kent City Police intelligence detective, here to bring you another mafia biography. You know, I’ve been doing these short bios to make sure everybody, when we talk about, we mention a name, you know, you have some place to go to say, hey, let’s look back on the website or because there’ll be like the whole transcript will be on the website and the synopsis of what I’m about to say about whatever mobster it is that I’m discussing. So we’re going to go to Chicago Outfit. In the 1960s, there was a man by the name of Charles Chucky Nicoletti, who was questioned by some FBI agents, one of whom was Bill Romer, Bill Romer Jr., who you all know, or a lot of you outfit guys will have heard of Bill Bill Romer, the FBI agent, he wrote several books, and he’s often cussed and discussed about how truthful he is in his books. He probably does use a little literary devices, a little literary license, as we say, to make a story come together and make it a little bit bett...