Gone South: S4|E20 - Breaking Into Prison | Part 1

Episode Release Date: February 26, 2025
Host: Jed Lipinski
Podcast Series: Gone South by Audacy Podcasts

Introduction to the Case

In the twentieth episode of the fourth season, titled "Breaking Into Prison | Part 1," host Jed Lipinski delves into a gripping true crime story centered around the newly constructed Downtown Detention Center (DDC) in Nashville. The episode meticulously unpacks the series of events leading up to an audacious security breach, highlighting the complexities of modern prison security and the enigmatic figure behind the attempted intrusion.

The Opening of the Downtown Detention Center

December 2019:
The DDC, a $200 million state-of-the-art facility, was poised to replace the dilapidated old jail plagued by overcrowding and poor conditions. The new center featured advanced plumbing, surveillance technology, and a specialized mental health unit with 64 beds. The urgency to operationalize the DDC was palpable, as over 200 high-risk inmates were temporarily housed elsewhere, costing taxpayers approximately $26,000 daily (00:00).

Lieutenant Thomas Conrad, overseeing the jail's opening, emphasized the critical nature of the preparations:

“We were preparing to get the building occupied right after the holidays, so we were just preparing everything.”
[00:03:52]

Corey Witkus, the episode’s narrator, elaborated on the extensive security measures in place, including surveillance testing and emergency drills (04:00).

Discovery of the Missing Keys

A few days post-Christmas, Conrad discovered an anomaly in the key control room:

“I noticed that one of the key rings was not horseshoe shaped. ... We were two keys short.”
[04:30:07]

Conrad suspected a possible misplacement or breakage but initially dismissed the idea of theft (05:09). However, upon reviewing surveillance footage, he identified a construction worker replacing the standard key ring with a non-standard one, resulting in two missing keys (05:55).

Introduction of Sheriff Darren Hall

During the discovery, Sheriff Darren Hall, who had invested significant effort into the jail's construction, was on vacation in Pensacola. Upon being notified, he found the situation alarming yet struggled to reconcile the missing keys with the fact that the facility was not yet operational (07:34).

The Mysterious Construction Worker

Conrad's investigation revealed that the construction worker, later identified as Alex Friedman, had been visiting the DDC regularly for months. Distinguished by his yellow hard hat, fluorescent vest, purple gloves, and constant white painter's mask, Friedman's behavior raised suspicions:

“The whole idea of them being stolen did not go through my mind.”
[05:39]
“He couldn't see it. It was perfectly replaced.”
[22:02]

Despite heightened alerts and specific instructions to trap any return attempts by Friedman at the loading dock, he evaded capture until January 4th, when Corey Witkus encountered him personally in the jail's front lobby (09:25).

The Attempted Intrusion

Against protocol, Witkus engaged Friedman directly instead of redirecting him. This decision allowed for a controlled attempt to secure Friedman within the facility:

“I knew instantly.”
[09:42]

Leading Friedman through the jail unnoticed, Witkus eventually locked him in the sally port, a secured entryway. However, Friedman began to exhibit threatening behavior, holding bolt cutters and attempting to dispose of incriminating evidence—a business card and torn paper (15:37).

Sheriff Hall's reaction upon learning Friedman's true identity:

“I knew everything changed at the...”
[27:31]

It was revealed that Friedman was not just any construction worker but a prominent prison reform advocate with deep connections, including ties to Bernie Sanders' campaign and familial links to Ben Bernanke, former Federal Reserve Chairman (17:28).

Uncovering Hidden Elements Within the Jail

Investigations into Friedman's activities within the DDC uncovered several "hot spots," areas where Friedman spent excessive time, such as the infirmary’s holding cell and the visitation booth. Notably, in the visitation booth, Friedman manipulated the infrastructure:

“It was perfectly matched... but I just... moved it an inch or so.”
[22:29]

Further exploration revealed that Friedman had concealed tools and potentially more dangerous items behind walls, indicating a predetermined plan to exploit the jail's infrastructure.

Climactic Revelation: The Hidden Gun

While Sheriff Hall was fulfilling his duties in Washington, D.C., he received alarming information about a gun found hidden within the visitation booth's wall. This discovery not only intensified the investigation but also raised critical questions about Friedman's true intentions within the DDC.

“If you saw him at any point, you were to send that video clip... who you were looking for.”
[20:18]

Key Characters

• Lieutenant Thomas Conrad: Tasked with overseeing the DDC's security preparations, Conrad was the first to identify the missing keys and initiate the investigation into Friedman's activities.

• Sheriff Darren Hall: A seasoned sheriff deeply involved in the DDC's construction, Hall's discovery of Friedman's true identity added a personal and professional stake to the unfolding mystery.

• Corey Witkus: Serving as the security supervisor, Witkus's decision to engage Friedman directly played a pivotal role in attempting to contain the situation.

• Alex Friedman: A respected prison reform advocate whose unexpected transformation into a clandestine intruder forms the crux of the episode's suspense.

Insights and Conclusions

This episode of Gone South masterfully intertwines themes of trust, security, and the unforeseen vulnerabilities within newly established institutions. The revelation that a prominent figure like Friedman could orchestrate such a breach challenges preconceived notions about safety and integrity in correctional facilities.

Through meticulous storytelling and compelling firsthand accounts, Jed Lipinski not only narrates a riveting crime story but also prompts listeners to reflect on the intricate dynamics between reform advocates and law enforcement, and the thin line that sometimes separates valor from deception.

As the episode concludes, listeners are left anticipating the subsequent developments, particularly concerning Friedman's ultimate objectives and the broader implications for the DDC's operations.

Notable Quotes:

• Lieutenant Thomas Conrad:
  “We were preparing to get the building occupied right after the holidays, so we were just preparing everything.”
  [00:03:52]

• Sheriff Darren Hall:
  “I get back to the office. Contacted the police department, contacted the FBI, local and the DA and just said, hey, look, guys, I'd like for you guys to take on this.”
  [24:55]

• Corey Witkus:
  “That could be something. I don't want to screw up the chain of custody for all this stuff.”
  [22:47]

Stay Tuned:

The episode concludes with Cliffhanger moments, setting the stage for "Part 2," where the full scope of Friedman's plans and the potential consequences for the DDC will be unveiled.

Connect with Gone South:

For more detailed discussions, story tips, or feedback, listeners are encouraged to reach out via email at gonesouthpodcastmail.com and follow the podcast on Facebook, TikTok, and Instagram @GONE_SOUTHPodcast. Bonus content is available through their newsletter on Substack.

Gone South is an Audacy original podcast, created, written, and narrated by Jed Lipinski. The production team includes executive producers Jenna Weiss Berman, Matty Sprung Kaiser, Tom Lipinski, Lloyd Lockridge, and Jed himself, with story editors Tom Lipinski, Maddy Sprunkheiser, and Joel Lovell.