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