Digest

This podcast features an interview with Kenny "The Kid" Tequila, a former low-level hitman for the Chicago Outfit. He describes his recruitment at age 17 following a difficult childhood and a robbery that brought him to the attention of the mob. Kenny details his over 20 years with the Outfit, focusing on his role in carrying out "hits" and managing what he calls "horror houses," the exact nature of which remains unclear. He emphasizes his low-level position within the organization and his conscious effort to avoid higher-level involvement. The interview also explores the significant impact of his criminal life on his family, with Kenny expressing deep regret for keeping his activities secret from his wife and children. He reveals his remorse and the difficult circumstances that led him to a life of crime. The overall tone is one of reflection and regret, highlighting the complex choices and consequences faced by individuals involved in organized crime.

Outlines

00:11:56

Kenny "The Kid" Tequila's Life and Crimes

Kenny "The Kid" Tequila, a former Chicago Outfit hitman, recounts his life, from a difficult childhood and recruitment at 17 to his low-level role in the mob, including "hits" and managing "horror houses." He expresses regret for his actions and the impact on his family.

00:18:14

The Chicago Outfit and its Impact

Kenny details his two decades with the Chicago Outfit, his low-level role, and his avoidance of higher-level activities. He describes the organization's structure and his specific tasks, emphasizing his desire to maintain a low profile.

00:25:37

Remorse and Family

Kenny discusses the devastating impact of his criminal life on his family, expressing deep regret for keeping his activities secret and the emotional toll it took.

Keywords

Q&A

• How did Kenny "The Kid" Tequila get involved with the Chicago Outfit?

  He was recruited at age 17 after a robbery that impressed members of the Outfit.

• What type of work did Kenny perform for the Outfit?

  He primarily worked as a low-level hitman and ran "horror houses," involving violent criminal activity.

• What was the impact of Kenny's life of crime on his family?

  He kept his criminal activities secret, causing significant emotional distress and regret later in life.

• What is the overall tone and message of Kenny's interview?

  Despite his past, Kenny expresses remorse and regret, highlighting the complex circumstances and difficult choices that shaped his life.

Show Notes