Crook County: The Secret Double Life of a Mafia Hitman
February 25, 2025·4 min
Mark Smerling, host of Crimetown, introduces listeners to Crook County, a new true crime podcast produced by Tenderfoot TV. The show centers on Kyle, a young man who discovered that his father led a secret double life for more than 20 years. By day, Kyle's father Kenny worked as a firefighter paramedic for the Chicago Fire Department, a respectable and trusted profession. By night, Kenny was an enforcer and hitman for the Chicago Outfit, one of America's most storied organized crime organizations. Kenny was recruited into the mob at just 17 years old, beginning his criminal career as a doorman at a mob-run brothel. Over time he rose through the ranks to become one of Chicago's most ruthless assassins, earning the nickname 'The Kid Tequila.' He ran whorehouses and carried out hits, operating in a world of extreme violence while maintaining the facade of a normal family man. Kenny had a wife and two children who, by their own account, had no awareness of his mafia involvement. Family members describe him as someone they completely trusted, making the eventual revelation all the more devastating. The trailer includes audio of Kenny speaking in his own voice, bluntly describing his crimes without apparent remorse. He also references covering up murders committed by corrupt Chicago police officers, suggesting the show's scope extends beyond typical organized crime narratives into law enforcement corruption. A news clip references federal agents and detectives searching a DuPage County junkyard west of Chicago, expecting to find bodies in car trunks — consistent with Chicago mob methods. A criminal defense attorney with nearly 37 years of experience is heard warning about the risks of publicizing this story. Kenny's family members, including his son Kyle, speak about the shock and confusion of learning who their father really was. One voice asks whether Kenny was leaving the house at night to commit crimes while his family slept, unaware. The trailer frames the show as simultaneously a true crime story, a mafia narrative, and a family saga about the wreckage left behind. Kenny himself reflects that he had every opportunity to make different choices and did not. The show is positioned as Kenny's confession to the one person he most owes an explanation — his son Kyle.
