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Jed Lipinski
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Jed Lipinski
On the morning of May 16th of this year, New Orleans journalist Mike Pearlstein learned that an undetermined number of inmates had escaped from the local jail.
Mike Pearlstein
It was earlier this morning, around 8:30am local time, that these missing inmates were discovered.
Michelle Woodfork
This was during a routine headcount and.
Mike Pearlstein
It wasn't immediately clear how many were.
Susan Hudson
They started my day, my office, that is, by sending me to the jail just to find out what was going on, what was behind this alert of some kind of escape. But we were all in the dark at that point.
Jed Lipinski
Mike is an investigative reporter for WWL Louisiana, the CBS local news affiliate in New Orleans. He's been covering the city's criminal justice system for over 30 years, everything from arrests and court trials to wrongful convictions and exonerations. During that time, he's also covered a number of jail escapes.
Susan Hudson
When you hear about jail escapes, it happens. It's not common, but somebody will break out of a jail, maybe two people, walk away from a work release or something or escape during a transport. But as I started working some sources and gathering some information, and at this point we're just on the sidewalk outside of the jail waiting for the sheriff and her team to appear to give us the official account of what was going on, I heard eight to 11 inmates escape from the jail at some unspecified hour. And that right there was enough to sound off plenty of alarms.
Mike Pearlstein
An update on breaking news In New Orleans, Louisiana, the Orleans Justice center is on lockdown after 11 inmates escaped this morning.
Jed Lipinski
The Orleans justice center, formerly known as the Orleans Parish Prison has been under a federal consent decree since 2013. I moved to New Orleans that year, and I remember thinking, what's a consent decree? Basically, it means the jail was such a mess, so rife with abuse, violence and neglect, that the federal government had to step in and make sure things improved. And yet the complaints continued. Overcrowding, understaffing, faulty locks, backed up toilets. The prison escape, in other words, was just the latest scandal in a long line of them. But if the number of escapees was accurate, it would rival all the scandals that came before it.
Susan Hudson
So we were on high alert. And when the sheriff and her team emerged, I believe they were still uncertain of the exact number of inmates who escaped. That actually set up even further alarms that the jail doesn't even know how many people escaped, but they were in the process of doing a head count and the place was on lockdown. But within the course, I would say of the next hour, we got it pinned down to 10 inmates escaped.
Jed Lipinski
Back at the newsroom, Mike and his team did a quick search for comparable escapes in recent American history. They didn't find any more. Alarming still was the fact that the vast majority of inmates at the OJC have been accused of violent crimes. Ten of them were now loose on the streets of New Orleans.
Susan Hudson
And we immediately set to try to find out, of course, all of the details of what went where, how, but most importantly, who are they, what were they in there for? And then immediate law enforcement efforts to launch a manhunt and try to find them.
Jed Lipinski
I'm Jed Lipinski. This is Gone South. As an investigative reporter, Mike Pearlstein is used to reporting out stories for weeks or even months and publishing the results as multi part series or documentaries. But the day of the prison escape, developments were happening so fast that he was ushered onto the set to deliver what the TV news business calls wall to wall coverage. He ended up standing at the anchor's desk for six hours straight.
Susan Hudson
There are times on say, election night or even fun stories like Mardi Gras, you know, anchors kill a lot of time standing there, you know, repeating things or thinking of interesting, fun things to say. But this was a dramatic development, like literally every 10, 15 minutes or at least on the half hour that we were able to report new information. Very fluid. First we started getting a partial list of names, and we saw that some of them had been accused of very serious crimes, including a couple waiting trial for murder one, who had been convicted of not one, but two murders and two additional manslaughter counts, so killed four people so as you might imagine, you know, the alarm that these people were freshly free escaping from the jail did send off some, you know, alarms in the community.
Jed Lipinski
Mike soon got word that the FBI, the U.S. marshals and the state police had joined local authorities in the manhunt. The sheriff's office released mugshots of all ten escapees. Crime stoppers. The anonymous tip line offered a cash reward for any information leading to their capture. Tips flooded in.
Susan Hudson
We quickly heard of one arrest. Right away, within a few hours, one of the escapees in the French Quarter didn't get very far. There was a false report. We had to, you know, debunk a few things. There was a report of a second arrest that turned out not to be true.
Jed Lipinski
The escape happened at an inconvenient time for the Orleans Parish Sheriff, Susan Hudson. A former attorney from Houston, Hudson had served for 11 years as the independent police monitor for the New Orleans Police Department. She made history in 2022 as the first female sheriff of Orleans Parish and the first black female sheriff in Louisiana. But her time in office had already stirred up controversy. In 2023, for instance, she was blasted for spending 20 grand in public funds on high end hotels for her senior staff during Mardi Gras. 2025 is an election year, and when her opponents learned about the jailbreak, they pounced.
Mike Pearlstein
I've been saying since my campaign launch that what happens inside the jail definitely impacts what goes on in our communities. And today is a prime example of that.
Jed Lipinski
That's Michelle Woodfork, the NOPD's former interim police chief and a strong contender in the sheriff's race. She called the escape a major administrative and operational breakdown.
Mike Pearlstein
You know, this is just another incident that shows the incompetence in the leadership at the Orleans Parish Justice Center.
Jed Lipinski
WWL brought Mike Pearlstein on set to talk about the repercussions for a sheriff who was already in hot water. But then another bombshell dropped.
Susan Hudson
We do have a photograph that we'll be showing shortly of. There it is. The hole in the jail wall where this escape initially occurred. That hole, you see, we were able to obtain a photograph that was leaked of a hole in a cell that had been broken through behind a toilet and sink fixture. The hole had written over it, scrawled, handwritten, too easy lol.
Jed Lipinski
In what Mike described as an on brand detail for a viral New Orleans news story. The escapees had misspelled the word too as T o rather than T o o. It was a classic image, but Mike made sure it was legit before posting it.
Susan Hudson
Online, you always have to, you know, verify, is this real? Where did it come from? So I immediately got into the scramble mode to verify that that's the real deal. That's the hole. That's where they broke through. Too easy. Lol.
Jed Lipinski
The photo went viral almost immediately. Not long after that, the sheriff's office, perhaps anticipating other leaks, decided to release more photos of the hole in the wall. And what was behind wasn't just the.
Susan Hudson
Removal of a toilet and sink fixture, but some rebar that had been cut through. Clean cut as one of the jail officials called it. So clearly this was signs of, you know, far more elaborate than just a panicked, you know, punching through a wall. Somebody had to saw through some rebar. And once those pictures were released, we then got video released by the sheriff's office which showed several things that were very alarming to actually see. And one was inmates jimmying a jail cell door. We saw the video of inmates crying that thing open. And then the most, I guess, dramatic of all were a video camera from inside the jail of the inmates running and jumping off of a loading dock. So that would be leaving the jail building itself. And you hear about jail escapes, you hear about maybe one, two or three. But to see 10 guys in various prison clothing flying off of a loading dock, jumping onto the ground below. One of them tumbled and fell and rolled and immediately began sprinting.
Jed Lipinski
WWL quickly got the video online. They played it in a continuous loop, which made it seem like hundreds of inmates were piling out of the jail. National outlets picked it up soon after.
Mike Pearlstein
The Orleans Parish Sheriff's Office releasing this new surveillance video where you can actually see the inmates escaping from the detention facility overnight.
Jed Lipinski
Authorities are now operating a third video showed the same inmates crossing Interstate 10 in the middle of the night as traffic swerved around them. The videos were timestamped. They enabled Mike and the WWL team to put together a rough timeline of events. The inmates appeared to be jimmying the cell door at around 12.30am they were seen running across i10 about a half hour later. And yet Mike hadn't heard about the escape until 8:30 that morning. The public didn't learn about it until a few hours later. Mike concluded the escapees had gotten an eight hour head start. All of this was disturbing, to say the least. What made it more so was the fact that the jail was relatively new. It opened in 2015 and was advertised as being state of the art. It also practices what's known in correction circles as direct observation.
Susan Hudson
Direct observation means every pod, which contains about 60 inmates, you know, in a pod, it's supposed to be supervised directly and at least by cameras at all times, 24 hours with a bed check headcount every half hour on the half hour. So of course, immediately the questions were raised. Okay, how did nobody see this at 12:30 jimming the door or one o' clock when they're breaking through the hole and running across the interstate, much less 8 in the morning and much less the NOPD and federal authorities really not hearing about it in full detail until after 10:30.
Jed Lipinski
Sheriff Susan Hudson remained noticeably quiet through the early hours of the ordeal. But that afternoon she provided the first tentative explanation for the crisis.
Susan Hudson
The sheriff initially did provide some detail that there was supposed to be a deputy in the pod watching, but that person had left to get a bite to eat at that time when the escape is happening. So beyond that major problem, then the question of what happened to all the bet checks after that person is getting something to eat, not watching the pod.
Jed Lipinski
Still, the sheriff assured the public that three jail employees, including a staff supervisor, had already been suspended for allegedly aiding and abetting the escapees. She didn't give reasons or release their names, but the fact remained, by the end of the first day, only three of the 10 inmates who'd escaped had been caught. And things were about to get even stranger.
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Jed Lipinski
It didn't take long for the New Orleans jailbreak to become a major national news story. The FBI and the U.S. marshals, the agency responsible for finding and arresting fugitives, took the lead. Reporter Mike Pearlstein had written plenty of stories about the marshals before and he held them in high regard.
Susan Hudson
Obviously the marshals, they're working, you know, last known addresses and the jail itself, going through the jail phone calls. Who might these people have been in contact with? And boy do they know their stuff. And we did get I think two additional arrests pretty quickly and then it was a little quiet. We were expecting even with an eight hour head start, you know, more information about more captures, at least more quickly and eventually between the crime stoppers the FBI, the reward I think at first got bumped up to $20,000 and that's a pretty high amount. That's a bounty.
Jed Lipinski
Around the same time the sheriff's office announced that they'd arrested their first jail employee, a 33 year old maintenance worker named Sterling Williams.
Susan Hudson
And he was accused of turning off the water to the plumbing so that moving that toilet and breaking through that hole Obviously wouldn't create flooding. And he got arrested and accused, although he had a robust defense. In fact, in his police report, he had been interviewed by state police and nopd, and he said that he had been threatened by two of the inmates with being shanked, being stabbed with a, you know, crude kind of prison knife if he did not turn that water off.
Jed Lipinski
Mike soon got his hands on the maintenance workers police report. In it, he named the two escaped inmates who'd threatened to shank him as Derek Groves and Antoine Massey. Both men were still at large, and the maintenance worker suggested they were the ringleaders of the operation. Mike began calling sources to understand more about them.
Susan Hudson
You know, pretty interesting stories on each of those. Antoine Massey had escaped those four previous times, twice from jails, once as a juvenile, once as an adult, as well as twice previously. He cut off an electronic ankle bracelet. So here we have a Houdini, you know, multiple time escapee, clearly savvy, street wise.
Jed Lipinski
At the time of the escape, Antwan Massey was being held at the OJC on a number of serious charges. Kidnapping, rape, domestic violence and motor vehicle theft. Then there was Derrick Groves.
Susan Hudson
He probably had the most serious rap sheet. He had been put on trial and convicted of two, in fact, a double murder, two counts of second degree murder, which carries in Louisiana a mandatory life sentence. So you could kind of hit label him as a desperado with nothing to lose, already looking at getting transferred to the penitentiary to serve out two life sentences. But he was awaiting sentencing, formal sentencing on that, as well as two counts of manslaughter that he pled guilty to. So he was considered potentially quite dangerous.
Jed Lipinski
As he looked into Derrick Groves background, Mike came upon a detail that stopped him cold. You may remember a recent episode we did about Len Davis, the corrupt New Orleans cop who back in 1994 orchestrated the murder of a 32 year old woman for filing a complaint against him. That woman's name was Kim Groves. As Mike discovered, Derrick Groves was Kim Groves grandson. This fact hit Mike particularly hard because he'd covered the Len Davis case as a reporter for the Times Picayune.
Susan Hudson
I was at the newspaper and I was kind of a younger, like a junior reporter riding with a senior reporter. When we went to pick up that indictment of Len Davis and he's driving, I'm reading, and it was jaw dropping to read the details in that indictment of Len Davis in the Kim Groves killing. If you're a reporter in a place like New Orleans long enough, you know, some stories kind of double back in unpredictable ways. And now to be covering Derrick Groves, the grandson of Kim Groves. Clearly much hardship suffered by that family, but now he's probably the most wanted person in New Orleans, maybe Louisiana.
Jed Lipinski
By May 26, 10 days after the escape, 13 people had been arrested for aiding the escapees. In addition to the maintenance worker, the accomplices included multiple family members, a girlfriend, and another inmate inside the jail. Authorities had also captured eight of the 10 escapees, everyone except for Groves and Massey. Most were apprehended locally, including one inmate who was found hiding under a car in the French Quarter. Another was arrested in Baton Rouge. Only two had managed to make it out of state, but we heard of.
Susan Hudson
Sightings, you know, in Natchez, Mississippi. There was a tip that led them to Texas. They ended up in a car chase outside of Houston in which the Texas authorities caught two of the inmates together in Texas.
Jed Lipinski
Mike says the capture of those two inmates in Texas broke the long standing pattern of prison escapees and wanted men from New Orleans staying close to home.
Susan Hudson
We've had a few people cut off ankle bracelets or walk away from work. Details less frequently break out of the jail. But it's amazing to me that they're almost always found within a few square mile radius of the jail or their house. If anyone ever crosses state lines, it's like, pretty remarkable and rare.
Jed Lipinski
Still, there are exceptions. One of them was a man named Gennaro Arthur, known on the streets as Meatball. Meatball was an enforcer for the notorious Glenn Metz gang in New Orleans back in the 1980s and 90s. He was suspected of being involved in up to 70 murders, including the 1990 Earhart Expressway ambush in which he was accused of killing three members of a rival gang with a machine gun. The incident triggered a manhunt for Meatball, not unlike the manhunt for the OJC escapees.
Susan Hudson
And he stayed on the lam for years before they found him under an assumed name, working as a dishwasher at a restaurant. The most modest possible life surprised everybody up in Seattle that knew him. But he eventually came to justice.
Jed Lipinski
And yet, despite the joint efforts of the FBI, the U.S. marshals, state police, and local law enforcement, the supposed ringleaders, Derrick Groves and Antwan Massey, remained at large. Crime Stoppers raised its reward to $50,000 for any information leading to an arrest. More tips poured in. It wasn't until June 2 that Antwon Massey finally appeared, not in public, but on Instagram.
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Jed Lipinski
There are conflicting reports about when the Antwan Massey video first appeared on Instagram, but Mike Pearlstein first became aware of it on June 2, 17 days after the escape. In the video, Massie, who is 32 with three symmetrically placed face tattoos, sits on a stool in what looks like a sparsely furnished kitchen. He explains that he was being held at the Orleans justice center for the last eight months on car theft and domestic abuse charges, but he insists he's being wrongfully prosecuted. They're trying to give me life for something I didn't do, he says, and holds up an affidavit that, according to him, proves he's innocent of the domestic violence charge. His accuser admitted she'd made it up, he says, to get back at him for seeing another woman.
Antwan Massey
Okay, she did this right, saying all allegations against me is false. And she even saying it, you know, she let us know the truth that I never did it to her, I never hit her, I was nowhere around her, nothing. She got mad and thought that I was dealing with another woman. That's why she did what she did to me, you know what I'm saying?
Jed Lipinski
As for the escape, Massie says he's innocent of that, too. He didn't technically escape from the jail, he says, so much as he was let out.
Antwan Massey
These things that I broke out. I didn't break out, I was let out.
Jed Lipinski
Massie goes on to appeal to several public figures, including Lil Wayne, Donald Trump and Kim Kardashian, asking for help with his case. He admits that he'd been a troublemaker as a kid, but he's not the same person today.
Antwan Massey
That is not who I am. I have a 3 year old son, I have an 18 year old daughter that graduated yesterday. At the end of the day that people don't understand that. They see that I'm on the day. So I have a heart. People that know me know that at the end of the day, I am a good person.
Jed Lipinski
The video was brazen, but it was also heartfelt and sad. A desperate plea by a young black man from a city where black men make up around 81% of the jail population, but only 26% of the city overall. It struck a nerve. MSNBC's TikTok version alone got tens of thousands of likes and hundreds of comments, sparking conversations about Louisiana's criminal justice system, which for years had the highest incarceration rate in the world. But for law enforcement and the media, the biggest question about the video was where had he filmed it?
Susan Hudson
I mean, I speculated from the beginning, like, okay, the first thing they're going to look at is metadata. The second thing they're going to look at is what do we recognize inside this location where he's shooting his video? And sure enough, they had been there before.
Jed Lipinski
U.S. marshals eventually determined the video was filmed in a private residence in New Orleans, the home of someone associated with Massey.
Susan Hudson
And they descended on that house full force and came up empty, except they found some of the clothes that Massey was wearing when he shot the video. So it was almost like a catch me if you can situation.
Jed Lipinski
Mike wrote a story about the video. Like many people, he found it kind of funny that Massey claimed to have been let out of prison.
Susan Hudson
Everyone had to shake their head when he's saying, I didn't escape, I was let out. Well, there could have been a red carpet and a guard holding the door for him. It's still an escape under any legal definition of escape. You walked out of that jail, buddy, and you're not here now. You have escaped. Semantics, perhaps, but obviously it raises questions about the dynamics of who might have helped on the inside. How they got through the whole removal of the toilet, cutting through rebar. How much help did they in fact have?
Jed Lipinski
It does sound crazy that an escaped inmate facing a life sentence would claim he was simply let out. And yet in New Orleans, such things aren't unprecedented. In April of 2013, under the previous sheriff, a video surfaced showing all sorts of illegal activity inside the old jail, the Orleans Parish Prison, or OPP for short. The video became known as OPP Gone Wild, it featured inmates shooting heroin, drinking alcohol, and even brandishing a loaded handgun.
Susan Hudson
And once they finally got to the bottom of OPPO Gone Wild, it turned out that one of the inmates was in fact being let out on a near nightly basis and carousing the city. There was even video of him in the French Quarter getting contraband. Gun, drugs, money, booze. He would return to the jail, share his contraband with cellmates, and there's video of it.
Jed Lipinski
As I said earlier, I recorded this interview with Mike on June 6, 12 days before this episode aired and three weeks after the escape. While it's still an active and developing story, by the time we spoke, the news had slowed to a trickle. Partly, Mike thought, because authorities were keeping whatever leads they had under wraps.
Susan Hudson
Law enforcement tends to, especially when it's in the hands of the feds, they clamp down, you know, pretty tightly on information simply because it's clear that these two remaining escapees are getting some help. If they do have a promising lead, they probably want to keep that to themselves so that they can do their surveillance work, their sources, contacts, make their move with some Stealth.
Jed Lipinski
It's now June 17, the day before this episode aired. Authorities have yet to capture Derrick Groves and Antwan Massey, who've now been on the run for a total of 32 days. They could be anywhere by now, but according to Mike, the cops believe both men are still hiding in or near New Orleans.
Susan Hudson
So in New Orleans, in the news business, as you know, you have to suspend your disbelief and just leave open the possibility that anything and everything could happen.
Jed Lipinski
If you have information, story tips, or feedback you'd like to share with the Gone south team, please email us at gone south podcastmail.com that's gone southpodcastmail.com and for bonus content, you can follow us on Facebook, TikTok and Instagram @ Gone 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, Maddy Sprung Kaiser, Tom Lipinski, Lloyd Lockridge, and me. Our story editors are Tom Lipinski, Maddie Sprunkheiser and Joel Lovell. Gone south is edited by Chris Basel and Perry Crowell. It's mixed and mastered by Chris Basel. Production support from Ian Mont and Sean Cherry. Special thanks to J.D. crowley, Leah Rees, Dennis, Maura Curran, Josephina Francis, Kurt Courtney and Hilary Schuff.
Michelle Woodfork
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Gone South: S4|E35 - The New Orleans Prison Break
Introduction
In this gripping episode of Gone South, host Jed Lipinski delves into one of New Orleans’ most alarming criminal events: the massive prison break at the Orleans Justice Center. Through meticulous reporting and firsthand accounts, the episode unveils the intricate details of the escape, the ensuing manhunt, and the broader implications for the city’s criminal justice system.
The Escape
The story begins on the morning of May 16th, when Mike Pearlstein, an investigative reporter for WWL Louisiana, receives startling news: an undetermined number of inmates have escaped from the Orleans Justice Center (OJC).
During a routine headcount, it became evident that inmates had vanished, prompting immediate concern and confusion among law enforcement officials.
Immediate Reactions and News Coverage
As news of the escape spread, the OJC went into lockdown. The facility, formerly known as Orleans Parish Prison, has been under a federal consent decree since 2013 due to longstanding issues such as overcrowding and understaffing.
Jed Lipinski provides context on the OJC’s troubled history:
Mike’s team conducted a swift investigation, determining that ten inmates had successfully escaped, most accused of violent crimes. This revelation heightened community fears about public safety.
Sheriff Susan Hudson and Controversies
The Orleans Parish Sheriff, Susan Hudson, a former attorney from Houston and the first female sheriff of Orleans Parish, found herself under intense scrutiny following the escape. Her administration had already faced criticism, notably for spending public funds on high-end hotels during Mardi Gras.
Amid the chaos, it became clear that the escape had significant political repercussions, especially with the upcoming election year.
The Manhunt Intensifies
The Federal Bureau of Investigation (FBI), U.S. Marshals, and state police joined local authorities in the urgent manhunt for the escapees. Law enforcement agencies released mugshots and increased the reward for information leading to the capture of the fugitives.
Despite these efforts, initial attempts to apprehend the escapees were met with limited success. Within hours, only a fraction of the inmates had been captured, heightening concerns about the effectiveness of the manhunt.
The Capture of Escapees and Aides
By May 26, ten days post-escape, thirteen individuals had been arrested for aiding the escapees. Sterling Williams, a maintenance worker at OJC, was among those detained. Williams claimed he was coerced into turning off the water to facilitate the escape, asserting that he was threatened by inmates Derek Groves and Antoine Massey.
Moreover, eight of the ten escapees had been captured, with Derrick Groves and Antwan Massey remaining at large. Their backgrounds revealed a dangerous profile, with Groves awaiting sentencing for multiple counts of murder and manslaughter.
The Story of Derrick Groves and Antwan Massey
Mike’s investigation into the remaining fugitives uncovered a personal connection to a past case he had reported on—the Len Davis scandal. Derrick Groves, one of the escapees, is the grandson of Kim Groves, a victim of police corruption orchestrated by Davis in 1994.
Antwan Massey, another fugitive, had a history of multiple escapes and was charged with serious crimes, including kidnapping and rape. His repeated escapes highlighted significant vulnerabilities within the OJC’s security systems.
Antwan Massey's Instagram Plea
On June 2, seventeen days after the escape, Antwan Massey surfaced on Instagram, posting a heartfelt plea claiming wrongful prosecution and appealing for public support.
The video resonated widely, garnering tens of thousands of likes and sparking discussions about Louisiana’s high incarceration rates and systemic issues within the criminal justice system.
Implications on New Orleans' Criminal Justice
Massey’s plea brought to light broader issues, including racial disparities in incarceration. In New Orleans, black men constitute about 81% of the jail population but only 26% of the city’s overall population, highlighting systemic inequalities.
Comparison with Past Events
The OJC’s recent escape draws parallels to the infamous 2013 "OPP Gone Wild" incident, where an inmate exploited the facility’s poor security to engage in illegal activities openly. This history underscores persistent security failures despite federal oversight.
Current Status and Conclusion
As of June 17, the day before the episode aired, Derrick Groves and Antwan Massey remained at large after 32 days on the run. Authorities believe they are still hiding in or near New Orleans, though the extensive manhunt continues to receive no substantial breakthroughs.
Jed Lipinski closes the episode by reflecting on the ongoing challenges facing New Orleans’ criminal justice system and the enduring impact of such high-profile escapes on community trust and safety.
Notable Quotes
Mike Pearlstein [07:36]: "I've been saying since my campaign launch that what happens inside the jail definitely impacts what goes on in our communities."
Susan Hudson [12:07]: "Direct observation means every pod... is supposed to be supervised directly and at least by cameras at all times, 24 hours with a bed check headcount every half hour on the half hour."
Antwan Massey [25:34]: "She got mad and thought that I was dealing with another woman. That's why she did what she did to me, you know what I'm saying?"
Conclusion
This episode of Gone South meticulously unpacks the complexities surrounding the New Orleans prison break, highlighting systemic flaws, personal tragedies, and the relentless pursuit of justice. Through comprehensive reporting and poignant narratives, Jed Lipinski offers listeners a profound understanding of the interplay between crime, community, and human nature in the Southern United States.