The Underworld Podcast

Episode: Meet The Chicago Outfit's Most Infamous Hitman
Date: April 8, 2025
Host: Danny Gold
Featured Guests: Kurt Calabrese, Anjay Nagpal, Joe "The Shark" Lopez, Damon Charonis, Ray Morelli, Frank Amanti, Marcus Funk

Episode Overview

This episode dives into the brutal and harrowing true story of Kurt Calabrese, son of Frank Calabrese Sr., the notorious hitman of the Chicago Outfit. Through first-hand testimony and detailed narration, the episode explores the chilling realities behind growing up inside America's most feared mob family, the legendary Family Secrets trial, and the corrosive impact of organized crime not just on the city, but within the family itself. There is no glamour here—just an unflinching look at violence, abuse, and betrayal.

Key Discussion Points and Insights

The Chicago Outfit’s Power and History

• [00:57] The show opens with a narration of the Outfit's influence: "The Chicago outfit has ruled Chicago with an iron fist for generations... Al Capone, St. Valentine’s Day massacre, Tony Accardo... The entire city wrapped around their fingers." (Danny Gold)
• Over 3,200 mob hits in Chicago within a century, but only 12 convictions—showcasing their near-untouchable status.

Frank Calabrese Sr.: Mob Hitman and Abusive Father

• [08:03] Kurt reveals the pain of possibly seeing his father for the last time, referencing the terror and isolation imposed by the government: "They put him under a measure called the SAMS measure. It was like you were a terrorist... took his rights away.” (Kurt Calabrese)
• Described as the Outfit's go-to killer, notorious for strangulation and brutality.
• His violence extended into his family, subjecting sons Kurt and Frank Jr. to relentless physical and psychological abuse.

The Family Secrets Trial

• [09:14] Kurt reads a victim statement at his father’s sentencing:

  "At that point, I hated him. I really hated him. But no matter how I feel about him, it's my dad, you know?... He became himself." (Kurt Calabrese)

• Frank Jr. turns informant, wearing a wire in prison and incriminating his father and others, leading to one of the most significant mob takedowns in Chicago history.

Kurt Calabrese’s Painful Coming-of-Age

• [13:31] Kurt shares:

  "One of my father’s favorite sayings were, I’m gonna kick you so hard, you’re gonna walk funny. Would cry myself to sleep at night. I begged to die. I begged not to wake up." (Kurt Calabrese)

• As a teen, constant stress and fear lead Kurt to develop an ulcer by age 15.
• [24:23] Details of their home life:

  "We lived in this room above a garage... It was beautiful... But whenever that door opened, we’d feel it. Everybody would panic." (Kurt Calabrese)

Mob Life and Its Dual Faces

• [14:05] Joe "The Shark" Lopez (Frank Sr.'s defense attorney) describes Frank:

  "He looked like a Wisconsin Cheese salesman—very personable, likable… but he was a maniac. He was not educated, but he was street smart, very cunning, very organized."

• Community members recall the era's strange mix of neighborliness and menace:

  "Elmwood Park was always safe... There was never robberies... because everybody wanted to live there." (Frank Amanti, [18:38])

Lessons in Crime: From Extortion to Murder

• [34:16] Kurt recalls being forced into mob work as a teenager, collecting street tax and handling adult theaters:

  "It was just disgusting... coins all wet... but we knew we really didn’t have much of an option."

• Frank Sr.'s twisted mentorship: demonstrating how to stalk, attack, and kill, turning violence into a perverse family inheritance:

  "He showed me how to stab someone… the look on his face was like he was actually stabbing somebody and killing them." (Kurt Calabrese, [38:39])

The Impact of Betrayal and Family Dynamics

• Frank Jr.’s decision to work with the FBI divides the family and puts Kurt at risk from retribution:

  "I still have to look over my shoulder every day... because there are people out there that are still pissed off at what Junior did." (Kurt Calabrese, [40:01])

Notable Quotes and Memorable Moments

• Kurt Calabrese on reading his victim statement:

  "[Frank Sr.] just, like a light switch, started cut me off, started yelling, 'You better apologize for the lies you tell. You have been treated like a king!'" (Kurt Calabrese, [10:30])

• Defense attorney on Frank Sr.:

  "He could have attempted to strangle me at any time." (Joe 'The Shark' Lopez, [13:27])

• On the duplicity of mob social life:

  "I really enjoyed him. He just was like... Fred McMurray from My Three Sons... He was just generally a really nice guy, you know, asking about our families and how you guys doing." (Ray Morelli, [19:22])

• On Kurt’s psychological torment:

  "I would cry myself to sleep at night, hoping, praying to God. I begged to die... made me feel like there wasn’t a God.” (Kurt Calabrese, [30:03])

• On being drafted into crime:

  "Me and my brother never went alone. He was always with my uncle." (Kurt Calabrese, [34:16])

• On mob upbringing:

  "When my mother and father got divorced, the FBI came to the house and wanted to talk to my mother. And my mother shut the door on them... my loyalty came from my mother, not my father." (Kurt Calabrese, [28:17])

Timestamps for Important Segments

• [00:57] – Overview of the Chicago Outfit and introduction to Frank Calabrese Sr.
• [08:03] – Kurt recalls confronting his father at trial
• [09:14] – Emotional impact of facing Frank Sr. in court
• [13:31] – Details of the Family Secrets trial and Kurt’s abuse
• [14:05] – Joe “The Shark” Lopez on defending Frank Sr.; character insights
• [18:06—19:43] – Neighborhood dynamics in Elmwood Park
• [22:39] – Home life under Frank Sr.’s reign of terror
• [24:23, 26:12] – The psychological and physical toll on Kurt
• [28:48] – Reflections on loyalty and family division
• [32:39] – Prosecutor Marcus Funk on the power and distinction of the Outfit
• [34:16, 35:20] – Kurt’s induction into mob crimes as a teen
• [36:12–38:39] – Frank Sr. instructs Kurt in violence and intimidation
• [39:15] – How Kurt contemplates patricide, family tensions, and ongoing fear

Tone and Style

The episode is unflinching and unsentimental, maintaining a raw and honest tone throughout. Interwoven speaker narration, personal testimony, and outside legal/communal perspective paint a picture that is equal parts crime saga, family tragedy, and cautionary tale.

Summary

This gripping episode pulls back the curtain on mob mythology to reveal the true, harrowing costs of organized crime—for Chicago and, most tragically, for the children born into its grip. Central to this story is Kurt Calabrese: abused son, reluctant mob henchman, and survivor of the Outfit’s most explosive collapse. Through his eyes and the voices of those who circled his family, listeners are confronted with the brutality, betrayal, and scars—visible and invisible—that endure long after the courtroom lights go out.

If you are fascinated by true crime, criminal psychology, and the hidden traumas below the surface of infamous American legends, this episode is not to be missed.

“This story needs to be told, and people need to know what really happened. I’m just setting the record straight with the truth.”
—Kurt Calabrese ([12:48])