S4|E21: Breaking Into Prison | Part 2

Summary

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.

Transcript

[Jake Brennan]

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[Jed Lipinski]

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[Sheriff Darren Hall]

He started yelling for somebody to open the door, for him to let him out, to unlock the doors. He just wanted out.

[Jed Lipinski]

He was disguised as a construction worker, and jail staff believed he'd stolen two keys to the jail.

[Lieutenant Thomas Conrad]

And the Chief of Corrections immediately instantly said his name and then said it again. Is that Alex Friedman?

[Jed Lipinski]

But Friedman wasn't some random criminal. He was a well known prison reform advocate who'd worked closely with the sheriff during the jail's construction. His motives for wearing a disguise and taking keys to an empty jail were unknown. Friedman was arrested for attempted burglary and quickly bonded out. In the meantime, investigators searched an area of the jail where cameras captured Friedman working. That's when they discovered he'd hidden a gun inside the wall. Sheriff Darren hall was introducing Trump's new attorney general in D.C. when he learned about the gun. But investigators had found more than that. The gun was in a bag. And the bag also contained 10 rounds of ammunition, razor blades, handcuff keys, and a special screwdriver that could open most locks in the jail. They called it an escape kit. As soon as the sheriff got back to Nashville, he got some more disturbing news. After finding the gun in the jail's visitation booth, the investigators had started searching other parts of the jail. Lieutenant Thomas Conrad was one of them.

[Lieutenant Thomas Conrad]

We started going to the other hot spots, if you want to call it that, where he spent so much time. I think it was a day or two later that we went up to medical and sure enough, here's two more.

[Jed Lipinski]

That made three guns Friedman had hidden in the walls. At that point, the sheriff asked the feds for help.

[Sheriff Darren Hall]

I would get in touch with the FBI and our relationship in D.C. and said, look, I don't know what I'm asking for. We have a 400,000 square foot building, brand new, that we believe there are guns and weapons in all sorts of corners.

[Jed Lipinski]

As it turned out, a bunch of federal agencies, including the FBI, DEA and Border Patrol, were all headed to Quantic that weekend for some kind of search training seminar. Hall asked if they could stop in Nashville on the way.

[Sheriff Darren Hall]

I was just begging, but we get on the phones and say, look, guys, we have a fertile training ground for you to come and learn how to search. You know, anything you need we'll make it happen.

[Jed Lipinski]

Within days, Nashville's downtown detention center was swarming with federal agents wielding $40,000 pieces of sophisticated search equipment.

[Sheriff Darren Hall]

I don't know how it really works, but it's basically testing the temperature of the wall and the variations in that temperature of the items that are in there. And so scan these sections and if it was varying degrees of temperature, that would tell us there's something in there that's obscure or different. And we got to a point where we felt like we had scanned and screened and searched every piece of the building.

[Jed Lipinski]

In all, they found escape kits in over a dozen different hotspots Friedman visited.

[Lieutenant Thomas Conrad]

There was a razor blade in every one of them. Okay. There was handcuff keys in every one of them. There were security bit screwdrivers in every one of them.

[Jed Lipinski]

The jail used special tamper resistant screws, and the screwdrivers in the kit were designed to unscrew them. Some of the packets also contained prison officer uniforms, tactical gear, and even cash. What did you think at that time his intention might have been?

[Lieutenant Thomas Conrad]

My opinion at the time was this was something way more diabolical than, you know, somebody that wants to make a name for himself.

[Jed Lipinski]

As these discoveries were being made, Friedman was walking around Nashville a free man awaiting trial on burglary charges. Sheriff hall urged the district attorney to indict him and get him back in custody before he fled. In the meantime, Hall's office started digging into Alex Friedman's past to try to answer a simple what was he trying to do? I'm Jed Lipinski. This is gone south. One of the reasons Alex Friedman became a prison reform advocate was that he'd done time in prison himself. Sheriff hall knew that in the 90s, Alex had served a nine year sentence for attempted robbery. But he was hazy on the details, and he knew almost nothing about his background.

[Sheriff Darren Hall]

We have a woman in our Office named Melinda McDowell who does primarily research and data analysis for us. Probably the best investigator in the whole city, to be honest with you. She was fantastic. And one of the things that I knew was, can you go figure out more about him as a person? I mean, it's really what we needed. What is, you know, what all is going on with him. And so when you say that to her, she's gonna go as far back as she could. And she discovered many, many, many more things than even the criminal investigators did about him.

[Jed Lipinski]

According to Melinda's report, Friedman was born in Massachusetts, but his family later moved to Saudi Arabia, where his dad worked in the oil industry As a Teenager, he returned to the US and lived with his grandmother in Nashville. He spent a few years at the Tennessee Preparatory School, which sounds fancy, but was actually a state run institution for neglected or disadvantaged kids. It was after high school that things started getting strange. In the Tennessean newspaper archives, Melinda learned that his first major arrest was in 1987, when Friedman was 18. He attempted to rob a coin purse, a shop that sold collectible coins, while wearing a wig and a fake mustache. When the store's owner confronted him, Friedman pulled out a gun and fired six shots, missing every single one. But the owner didn't miss. He shot Friedman once, hitting him in the left hand. Friedman was arrested and jailed for a month. But since it was his first offense and he was the only one injured, he was given probation and released.

[Sheriff Darren Hall]

That arrest didn't do much to him. He was right back out in the streets, and it surely didn't scare him straight. It surely didn't get his attention in the way you would want.

[Jed Lipinski]

What got him sent to prison happened four years later in 1991, and it showed some of the hallmarks of his Future Crimes. Around 7 at night, Friedman, then 21 and still on probation, walked into a Kroger's grocery store and stole a few cartons of baseball cards. Once again, the store manager confronted him. This time, Friedman cooperated. He followed him to the security office. Then suddenly, he pulled a gun on him, ran out of the store and sped out of the parking lot. Store employees jumped in their cars and chased after him, with Nashville PD close behind. The chase ended when Friedman lost control and crashed. What stuck out in Hall's mind is what cops found in the car. As a detective told the Tennessean, Friedman had hollowed out a cassette player to conceal a.22 handgun loaded with Teflon bullets designed to pierce body armor. They also found a handcuff key taped to the back of his belt, another key that could open a police shotgun rack in a patrol car, and a pen modified into a knife. Sheriff hall was so puzzled by the details that he tracked down the retired detective who'd arrested Friedman.

[Sheriff Darren Hall]

He said, I was in law enforcement 30 years. It was the most bizarre arrest I ever had.

[Jed Lipinski]

The crime earned Friedman a nine year sentence. He served it at a private prison run by the Corrections Corporation of America, later known as Corecivic. According to the Tennessean, he buried himself in legal research and prison reform advocacy. In 1996, while still locked up, he sued Corecivic for violating his civil rights and won, collecting $6,000 by the time he was released in 1999, other inmates had nicknamed him Einstein. Friedman had stayed out of trouble for 20 years. He was the picture of a reformed inmate. But he was now headed back to jail, possibly for good. On February 18th of 2020, a week after the feds found the escape kits in the walls, Friedman was indicted on vandalism charges, specifically for impersonating a construction worker and concealing weapons and tools inside the jail. But he wasn't arrested. Instead, he was ordered to report to the DA's office the next day.

[Sheriff Darren Hall]

I didn't like that idea at all. I think he's a prime suspect for running and doing a lot of things. Well, he was scheduled to return himself in at 9 o'clock in the morning. And trust me, I was watching the watch and at 9am There was no Alex. At 10am no Alex. 11, 12, 1. And I was convinced he was gone. And I believe about nine that night, some 12 hours later, they were able to talk him into coming in. And I remember getting out of bed myself and driving down there to watch him be booked. I wanted to make sure it happened this time.

[Jed Lipinski]

The bond was set at $2.5 million, the largest hall had seen in his 40 years in law enforcement. That same day, he held a press conference to let the public know what Alex Friedman was accused of.

[Sheriff Darren Hall]

Last night, at approximately 9:30, Alex Friedman was booked into the Davidson County Jail on a class A felony vandalism charge with a $2.5 million bond. The bond amount in this case, of course.

[Jed Lipinski]

Hall and the rest of the sheriff's office had no idea why Alex Friedman had hidden guns and escape kits in an empty jail. Investigators struggled to find anyone close to Friedman who was willing to talk about him. That's when they got a call from his ex girlfriend.

[Monte McCoyne]

I told him everything that I knew that I could possibly know because I realized at that point how dangerous he really had been. It's a fascinating story. I think it's kind of been under reported. I'm surprised it has not made national news for the insanity of it.

[Jed Lipinski]

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[Margo Gray]

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[Unknown]

The higher ups are concerned about one.

[Jake Brennan]

Thing, and that is avoiding scandal.

[Margo Gray]

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[Monte McCoyne]

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[Jed Lipinski]

In the history of academia.

[Margo Gray]

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[Jed Lipinski]

A chancellor having a pornographic double life is an extremely rare case.

[Margo Gray]

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[Jed Lipinski]

Monte McCoyne was at her home in Nashville when she saw Sheriff Hall's press conf. She watched in disbelief as the sheriff ticked off the items Alex Friedman was alleged to have stashed behind the walls of the new downtown detention center.

[Monte McCoyne]

When I heard in Sheriff Hall's press conference that there were guns involved in this episode, I felt like I needed to share what I knew. And that's what made me reach out to law enforcement because my blood absolutely ran cold, I called Crime Stoppers, I called the sheriff's office, I called the police department and I told them at that point, you know my entire story.

[Jed Lipinski]

Sheriff hall spoke with McCoyne personally while his chief of staff Took notes after an hour on the phone. He was convinced that she knew Friedman as well as anyone. A native Nashvillian, McCoyne said she'd met Friedman in 2010, about a decade after his release from prison.

[Monte McCoyne]

Back in the day, we did not have Tinder and I met Alex on Craigslist. We started dating and ultimately I was romantically involved with him for about five years now. In that time, I also started working with him professionally and I worked with him for three years following the breakup.

[Jed Lipinski]

During those years, McCoyne told the sheriff that she was deeply involved in Friedman's everyday activities. Friedman was the associate director of the Human Rights Defense center at the time, a non profit that worked on prison reform, and McCoyne was his right hand person. She traveled with him, managed his schedule, and wrote a column for his monthly newsletter. She even went undercover for him once or twice.

[Monte McCoyne]

There were some correction officers at the Metro jail that were selling arts and crafts that the prisoners had made. Made. That's against the law. And he had me go to a flea market with a recorder in my bra and purchase these items.

[Jed Lipinski]

McCoyne had a deep respect for Friedman. He was a Mensa registered genius, she said, as well as a gifted writer and a brilliant legal mind who crisscrossed the country on consulting gigs. When the HBO series Orange is the New Black added a new storyline about private prisons, McCoyne said they called Friedman for advice. But there was a darker side to Alex friedman that only McCoyne saw. In their relationship, he exhibited what McCoyne described as violent tendencies.

[Monte McCoyne]

I know you're recording me right now, and I want to be very delicate. We had a BDSM relationship. Fifty Shades of Grey would have been a nursery rhyme compared to the types of things that we did together. It was completely consensual. But basically, if Alex wanted to have sex with me at knifepoint, I allowed him to. If he wanted to beat me to bruising, I allowed him to. But I believe that when we broke up, he lost the healthiest outlet that he had for those types of things that he was compelled to do.

[Jed Lipinski]

But it wasn't just his behavior with McCoyne that convinced her Friedman had hidden those guns inside the jail. Years earlier, he claimed to have done something similar.

[Monte McCoyne]

Alex told me that when he was incarcerated in the Metro jail in the 90s that he had arranged for a gun to be planted in the ceiling of the hospital and that he had attempted suicide twice in an attempt to get to that gun.

[Jed Lipinski]

As far as McCoyne knew, Friedman never retrieved the gun hidden in the hospital. If one was planted there at all. But when she learned about his arrest during the sheriff's press conference, she worried he might try to fake suicide again and get the gun for real. McCoyne told the sheriff that Friedman had never mentioned any plan to stash guns in the downtown detention center. But he had said something else that now struck her as prescient.

[Monte McCoyne]

He had told me repeatedly enough times that I thought it was a running joke that his retirement plan was to go back to prison. I just never thought, who would want to go back to prison? I mean, why would that not be a joke? He had been incarcerated in the 90s from age 18 to age 29. And part of me believes that he grew up in prison as a young man, and part of him just wanted to go home.

[Jed Lipinski]

Of all the things McCoyne told Sheriff hall, it was that one line. Prison was his retirement plan that stayed with him. Did Friedman really feel more comfortable in prison and plan to commit a crime that would put him there for life? If so, why plant guns and escape kits in the local jail that sounded like he wanted to break out of prison, not retire there? As hall was mulling this over, the sheriff's office received another tip. This one came from an anonymous source, and it sent hall and his staff in a new direction. The tipster suggested they check out a storage unit Friedman owned on Tampa Drive, about 20 minutes from downtown. When the cops arrived, the unit was mostly empty, but they did find a notarized letter stating that in the event of Friedman's death, the storage unit should be transferred to a man named Ferris Morone. Investigators called Marone. He directed them to his estranged ex wife. From what he'd heard, Friedman had moved a bunch of storage crates into her garage the day he turned himself in. Friedman's case was already the strangest of Sheriff Hall's career, but it was about to get even stranger. Wow. What's up? I just bought and financed a car through Carvana in minutes.

[Margo Gray]

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[Jed Lipinski]

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[Sheriff Darren Hall]

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[Jed Lipinski]

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[Monte McCoyne]

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[Jed Lipinski]

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[Margo Gray]

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[Jed Lipinski]

The quest to understand Alex Friedman's motives was not the only thing occupying the Davidson County Sheriff's office in March 2020. On March 3, a severe tornado hit Nashville head on, killing five, injuring over 200 and causing $1.5 billion in damages. Nine days later, the governor of Tennessee declared a state of emergency due to the outbreak of a respiratory virus called COVID 19. And yet, for Sheriff Hall, a devastating tornado and a global pandemic barely registered compared to his twin obsessions opening the new jail and unraveling the mystery of Alex Friedman. Hall had just sent half his staff home when he learned that Friedman had moved a bunch of storage crates into the garage of a friend's ex wife. On March 20, his office got a warrant to search it. When investigators walked in, they found 15 black plastic crates with yellow lids labeled legal files.

[Sheriff Darren Hall]

You know, it was taped on the very top of these crates. Legal files. I knew that was Alex Friedman's joke. I mean, he believes he can stop you from looking at his stuff. He'd been in jails and prisons and if you write that in jail or prison, a lot of times you believe it's protected from anyone looking at it. That's why he did it. He also locked them.

[Jed Lipinski]

Investigators ripped open the crates. What they saw shocked them.

[Sheriff Darren Hall]

You know, every type of weapon you can imagine, from handguns to assault weapons to I think a grenade launcher is in there. Every type of ammunition, body armor, every badge of every, you know, law enforcement agency I can think of and stacked in an orderly way in an organized method. And to me, it's ready to go.

[Jed Lipinski]

The sheriff was at a loss for words. He'd initially assumed that Friedman was a lone actor hiding weapons in the jail for his own benefit. Now he suspected Friedman had a grander design. The discovery of the weapons led to yet another charge against him. Possession of a firearm by a convicted felon. Due to his prior convictions, Friedman faced a minimum of 25 years in prison. Friedman's trial was initially set for 2020, but the pandemic pushed it back to July 2022. It lasted just four days. The jury deliberated for an hour before finding him guilty of hiding firearms and other contraband in the walls of the downtown detention center during its construction. Until now, Friedman had remained silent about his motivations. No one knew what he was thinking. But as the sentencing approached, he wrote a seven page letter to the judge attempting to explain. People are complicated and people are flawed and I am no exception, friedman wrote in the opening paragraph. He called his behavior irrational and didn't expect others who had not shared his life experience to understand. He quoted Russian author Alexander Solzhenitsyn, who'd exposed the horrors of Stalin era prison camps, writing, how can you expect a man who's warm to understand a man who's cold? Then he got to the point. Friedman wrote that after his first arrest in 1987, he'd been raped in jail. It happened at the criminal justice center, he wrote, the same jail that was later torn down and replaced by the downtown detention center. The trauma haunted him for decades, he wrote, adding, I resolved that should I ever be jailed again and subjected to the same sexual abuse, I would have the resources to escape or defend myself. He called hiding weapons and escape items in the prison part of his contingency plan. Sheriff hall didn't buy it. When I asked him why, he gave a few reasons. First, he thinks Alex Friedman is a liar.

[Sheriff Darren Hall]

Alex went on a 10 year crusade to find fault with everybody and everything. 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. After he got out of that and failed probation, he never accepted he did any of that wrong.

[Jed Lipinski]

Second, hall said Friedman had not reported the assault at the time. And as far as hall could tell, he'd never mentioned it to anyone, including Monte McCoyne.

[Sheriff Darren Hall]

None of them have ever heard of that case before. He had never said it publicly. He had never talked about in any environment he'd ever been in.

[Jed Lipinski]

Finally, if Friedman was merely trying to defend himself against bad guys, why go through the trouble of hiding cash and prison officer uniforms in the wall.

[Sheriff Darren Hall]

You would never do that if you were worried about being raped. I mean, let's be honest, none of that makes any sense at all.

[Jed Lipinski]

To hall, it all pointed not to an irrational trauma response, but to a larger premeditated plan. The judge agreed. I don't believe it, he said at the sentencing, adding that Friedman's behavior showed tons and tons of intent. He gave 53 year old Alex Friedman 40 years. Nashville's downtown detention center eventually opened. It now houses more than 700 inmates and employs a staff of 300. Sheriff hall estimates that the delayed opening caused by Friedman's misdeeds cost the city about $3.5 million. When I asked hall what he thought Friedman planned to do, he admitted he didn't really know. But he did offer a theory.

[Sheriff Darren Hall]

I take what Monty McCoyne said. You know, going back to prison is my retirement home. And I believe deep down he had internally planned to do something that was going to get him there.

[Jed Lipinski]

Once he was back in prison, hall believed he was going to use those hidden guns not to defend himself, but to harm innocent, unarmed men and women.

[Sheriff Darren Hall]

If you ask someone on the streets, they don't realize we don't carry guns inside the jail, right? No jail, a prison in America, has a gun in it. Nowhere. I mean, that's the worst thing you could ever, ever, ever happen. Who knew that? Alex Friedman. And so when you have an armed person inside, it's fish in a barrel. You don't have any protection.

[Jed Lipinski]

As for the assault weapons and tactical gear in those crates, hall thinks Friedman had a plan for that too.

[Sheriff Darren Hall]

There's 20 plus boxes of equipment out there that could do all sorts of damage. He's never going to get that into the jail. That's never going to happen. But once he comes out, if he has a group, and he was in a pretty dark group out there, and I'm talking about underground stuff, maybe that was who he was going to reach to on the day before he needed them to come.

[Jed Lipinski]

In the end, of course, Friedman never realized his plan. Whatever it was, he was foiled by the staff of the downtown detention center, starting with Lieutenant Conrad, the man who discovered the missing keys. He has a theory too.

[Lieutenant Thomas Conrad]

I just believe this, that there was going to be a showdown. I believe Alex was prepared for the showdown. And I think Alex wanted for the world to know his name. Bottom line, I think this whole multi year kind of planning and positioning was all about people knowing who Alex is. And he fails to realize everybody forgets about those people.

[Jed Lipinski]

If you have information, story tips or feedback you'd like to share with the Gone south team, please email [e-mail] that's gone southpodcastmail.com and for bonus content you can follow us on Facebook, TikTok and Instagram. On South Podcast, you can also sign up for our newsletter on substack. Gone south with Jed Lipinski Gone south is an Odyssey original podcast. It's created, written and narrated by me, Jed Lipinski. Our executive producers are Jenna Weiss Berman, Maddie Sprung Keyser, Tom Lipinski, Lloyd Lockridge and me. Our story editors are Tom Lipinski, Maddy Sprung Keyser and Joel Lovell. Gone south is edited by Chris Basil and Perry Crowell. It's mixed and mastered by Chris Basil. Production support from Ian Mont and Sean Cherry. Special thanks to J.D. crowley, Leah Reese, Dennis, Maura Curran, Josefina Francis, Kurt Courtney and Hilary Schuff.

[Sheriff Darren Hall]

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