Gone South: Episode S4|E21 - "Breaking Into Prison | Part 2" Summary

Introduction

In Episode 21 of Season 4 of Gone South, host Jed Lipinski delves deeper into the enigmatic case of Alex Friedman, a renowned prison reform advocate who orchestrated a daring scheme to infiltrate Nashville's newly constructed downtown detention center. This episode meticulously unpacks Friedman's motivations, actions, and the subsequent investigation that unraveled his intricate plan, offering profound insights into crime, human nature, and the complexities of the Southern criminal landscape.

Background on Alex Friedman

Alex Friedman is not your typical criminal. Born in Massachusetts and later moving to Saudi Arabia due to his father's oil industry career, Friedman spent his teenage years in Nashville, living with his grandmother. His troubled past began early; in 1987, at just 18, he attempted to rob a collectible coin shop by disguising himself with a wig and fake mustache. The robbery escalated when he brandished a gun, firing six shots that missed the store owner, who retaliated by shooting Friedman in the left hand. This first offense resulted in a month of incarceration, followed by probation.

However, frustration led Friedman down a more sinister path. In 1991, still on probation, he executed another heist at a Kroger grocery store, stealing baseball cards. This time, when confronted, Friedman pulled a .22 handgun concealed within a cassette player and fired at the manager before fleeing the scene. The chase ended disastrously when Friedman lost control of his vehicle. Investigators discovered an "escape kit" in his car, comprising ammunition, razor blades, handcuff keys, and a specialized screwdriver for jail locks. This brazen act earned Friedman a nine-year sentence in a private prison managed by Corecivic.

During his imprisonment, Friedman transformed himself into a prison reform advocate, earning the nickname "Einstein" for his intelligence and dedication. Upon his release in 1999, he maintained a spotless record for two decades, working closely with Sheriff Darren Hall during the construction of Nashville's $200 million downtown detention center.

The Incident: Breaking Into the Detention Center

In early January 2020, just days before the jail was set to open, Friedman executed his audacious plan. Disguised as a construction worker, he infiltrated the empty facility, reportedly stealing two keys to the jail. His motives remained unclear, leaving authorities puzzled. Sheriff Darren Hall recounted the incident:

"He started yelling for somebody to open the door, for him to let him out, to unlock the doors. He just wanted out." ([03:06])

Initial suspicions were minimal given Friedman's esteemed position and background. However, the discovery of a concealed gun inside the jail wall quickly escalated the situation. Investigators found multiple escape kits hidden throughout the facility, each containing tools and weapons designed for an elaborate escape or potential assault.

Investigation and Findings

Realizing the gravity of the situation, Sheriff Hall reached out to federal agencies. The FBI, DEA, and Border Patrol arrived equipped with advanced search technology. Despite their efforts, over a dozen escape kits were found, each meticulously placed and identical in their contents:

"There was a razor blade in every one of them. Okay. There were handcuff keys in every one of them. There were security bit screwdrivers in every one of them." ([06:06])

The sophistication of the escape kits and the specific tools designed to breach the detention center's security suggested a well-thought-out plan rather than a spontaneous act. Additionally, a subsequent tip led investigators to a storage unit owned by Friedman, where they uncovered a notarized letter transferring the contents to an individual named Ferris Morone. Further investigation revealed that Friedman had relocated a significant number of storage crates to Morone's ex-wife's garage, hinting at a larger conspiracy.

Monte McCoyne's Revelations

Monte McCoyne, Friedman's ex-girlfriend and former collaborator, provided crucial insights into Friedman's dual nature. As she recounted to Sheriff Hall:

"He was a Mensa registered genius, a gifted writer and a brilliant legal mind... But he had a darker side... He exhibited violent tendencies." ([17:52])

McCoyne revealed that their relationship involved a consensual BDSM dynamic, where Friedman exerted physical dominance. She speculated that the breakup might have triggered Friedman's desperate actions to secure his return to prison, aligning with his purported "retirement plan."

Furthermore, McCoyne disclosed that Friedman had previously attempted to conceal a gun within the hospital ceiling of the same facility during his incarceration in the 90s, hinting at a long-standing obsession with prison environments.

Trial and Conviction

Friedman's trial, delayed by the COVID-19 pandemic, commenced in July 2022 and concluded swiftly within four days. The evidence was overwhelming, leading to his conviction for hiding firearms and other contraband within the detention center walls during its construction. Despite Friedman’s attempt to rationalize his actions in a seven-page letter, citing past trauma from being raped in prison—a claim not corroborated by Sheriff Hall—the court found him guilty, sentencing him to 40 years in prison.

Sheriff Hall expressed skepticism towards Friedman's explanations:

"I don't believe that core civic, quite frankly, was his real issue... He doesn't want to take responsibility for having shot at a man six times and served an armed robbery sentence." ([27:09])

Conclusion and Insights

The case of Alex Friedman underscores the intricate interplay between personal trauma, mental instability, and premeditated criminality. Sheriff Hall theorized that Friedman’s actions were driven by an internal desire to return to prison, rather than a genuine plan to attack or defend himself within the detention center:

"I believe deep down he had internally planned to do something that was going to get him there." ([28:51])

Lieutenant Thomas Conrad added another layer to the narrative, suggesting that Friedman sought recognition:

"I think Alex wanted for the world to know his name... all about people knowing who Alex is." ([30:12])

Ultimately, Friedman's meticulous planning and ultimate failure to execute his scheme shed light on the complexities of criminal motives and the challenges faced by law enforcement in deciphering them. The delayed opening of Nashville's downtown detention center not only highlighted the financial repercussions—costing the city approximately $3.5 million—but also emphasized the unpredictable nature of criminal behavior.

Notable Quotes

• Sheriff Darren Hall on Friedman's initial intrusion:

  "He just wanted out." ([03:06])

• Lieutenant Thomas Conrad on the discovery of escape kits:

  "We started going to the other hot spots... I think it was a day or two later that we went up to medical and sure enough, here's two more." ([04:36])

• Monte McCoyne on Friedman's character:

  "He was a Mensa registered genius, a gifted writer and a brilliant legal mind... But he had a darker side." ([17:52])

• Friedman's letter to the judge:

  "People are complicated and people are flawed and I am no exception." ([26:00])

• Sheriff Hall's final thoughts:

  "I just believe this was something way more diabolical than, you know, somebody that wants to make a name for himself." ([28:01])

Final Thoughts

"Gone South" Episode S4|E21 masterfully navigates the labyrinthine story of Alex Friedman, blending investigative journalism with compelling storytelling. Through meticulous research and firsthand accounts, Jed Lipinski paints a vivid picture of a man whose actions defy conventional understanding, prompting listeners to ponder the deeper motivations that drive individuals to commit extraordinary acts of crime.

For more gripping true crime stories rooted in the Southern experience, subscribe to Gone South on the Audacy app or your preferred podcast platform.