A jailbreak, a massive manhunt and a push to fix New Orleans’ broken lockup
The 10 men broke out of a New Orleans jail in an escape straight out of Hollywood. Now, with one escapee still on the run, the city is again grappling with how to fix a troubled jail system.
NEW ORLEANS – They waited until after midnight to make their move.
As nearly 1,400 inmates at the sprawling New Orleans jail slept, 10 men slipped quietly from their metal bunks. A worker monitoring their tier by surveillance camera went on break.
By 12:22 a.m., several inmates in orange and white prison clothing were forcing open the door of an empty cell.
An audacious escape plan was unfolding.
But to reach freedom on this muggy Louisiana night, everything would have to go right.
They would have to wrench a toilet from the wall to open a passage. Get past steel bars. Climb a wall tipped with barbed wire.
All without being spotted in a jail that bristled with 900 surveillance cameras.
About an hour later, the men — some facing charges for violent crimes including second-degree murder — were scrambling across an interstate highway before disappearing into the city just a few miles from Bourbon Street.
All that was left was a drawing of a face, its tongue sticking out, above the misspelled but taunting phrase, “To Easy LoL,” scrawled above a rectangular hole in the cell wall.
The May 16 jailbreak at the Orleans Justice Center marked one of America’s largest and most brazen escapes in recent memory – one seemingly straight out of Hollywood.
It prompted a costly manhunt that gripped the city. It sent prosecutors and victims fleeing for safety. It fueled political fallout. And it would highlight dangerous conditions in the city’s jail, setting off a fresh round of soul-searching over New Orleans’ troubled history of incarceration.
How, many in the city wondered, could they have broken out of a jail that was nine years old? How would police catch 10 scattered fugitives? And would the debacle bring change to a jail that had seemingly failed to turn the page on the city’s long-struggling lockups?
But those answers would all come later.
As the sun rose on the Big Easy that morning, no one at the jail – at least not jail leaders – had any idea the prisoners were missing.
Delayed discovery fuels fear
Orleans Parish District Attorney Jason Williams' phone started pinging the next morning at his office, which has windows looking toward the nearby jail.
“Is it true that there was some sort of jailbreak?” a reporter's text message asked.
Not far away, New Orleans Police Chief Anne Kirkpatrick was in a meeting around 10:30 a.m. when she heard. “We quickly kind of looked at each other and said, ‘Let’s verify this,’” she said.
The news set off a scramble to learn what had happened.
A routine morning headcount had been conducted by the Orleans Parish Sheriff’s Office, which runs the Orleans Justice Center jail. Not long after 8:30 a.m., jail staff realized that at least several inmates were missing.
The facility went on lockdown. A frantic internal search began. Guards checked passageways, crawlspaces and housing units. Not long after, the sheriff’s office notified the U.S. Marshals Service.
Amid reviews of surveillance footage, it ultimately became apparent that 10 men had escaped.
By the time the first absences were discovered, the men had more than a 7-hour head start, which would fuel sharp criticism and anger across the city.
“Do not engage or approach these subjects,” Sheriff Susan Hutson said at a news conference on the steps of the jail later that morning.
Most of the fugitives were awaiting court proceedings or trials, like most other inmates. The youngest was 19. The oldest was 42.
There was Antoine Massey, 33, who stood out for his face tattoos of chess pieces and was in jail on charges of domestic abuse involving strangulation and theft of a motor vehicle. He was called a “Houdini” in a local report because of past instances of slipping out of ankle monitors and other Louisiana lockups.
There was Leo Tate Sr., 31, facing charges including burglary and drug possession, and Jermaine Donald, 42, facing charges including second-degree murder. Lenton Vanburen, 26, was arrested on charges of second-degree murder and armed robbery.
And there was Derrick Groves, 27, convicted of second-degree murder and attempted second-degree murder in connection with a shooting during Mardi Gras in 2018. It was a difficult case that had to be tried twice and included witness intimidation, the DA said.
Groves also had a link to the city’s dark history of police corruption: In 1996, a corrupt patrol officer who led a drug ring was convicted of ordering the killing of his grandmother, Kim Groves, after she filed a police brutality report, local media reported.
Fearing retaliation, two prosecutors who had worked on Groves’ case prepared to leave town with their families. Some witnesses and victims' families were also relocated with the help of prosecutors. A relative of 21-year-old Byron Jackson, killed in the shooting, went to stay with his girlfriend in another part of town, saying he feared for his safety.
The city suddenly seemed way too small.
“There's one degree of separation in New Orleans,” Williams said. “And so if there's someone you're looking for to cause them harm, you're going to see them.”
As news spread, one group of conventioneers contacted city tourism officials. They were connected with local police, who were beefing up their presence in the city.
Some residents cited New Orleans’ resilience during tough times – think Hurricane Katrina or after 14 were killed this year after a man drove a speeding truck into New Year’s Day revelers on Bourbon Street – and took it in stride.
“There’s some concern for our safety because they are dangerous criminals. But it’s not like we’re going to stop living our lives,” said Tess Gonzales, manager of Daisy Mae’s Southern Fried Chicken & Breakfast.
It wasn’t long before some were selling T-shirts emblazoned with the phrase, “To Easy LoL" as it took off across social media.
Others who live close to the jail were downright frightened.
In a New Orleans neighborhood about a mile from the jail, an area dotted with wood-frame homes on stilts with peeling paint, corner stores and small churches, Lakisha Catchings, a mother of eight, said the dangers were keeping her family indoors.
“It's scary,” said the 44-year-old, who grew increasingly angry that the escape put her family in harm's way.
“How did they let this happen?” Catchings asked as she stood near her front door, a welcome sign hanging to one side.
‘Shawshank Redemption on a much bigger scale’
For law enforcement, the clock was running.
In Baton Rouge, 80 miles to the west, the Louisiana State Police quickly mustered a 200-member multi-agency task force to search for the fugitives. Louisiana Attorney General Liz Murrill launched an investigation.
New Orleans police also jumped into action, aiding the search while posting patrol cars at schools and safeguarding victims, witnesses and judges connected to the criminal cases of the inmates.
Authorities hoped it wouldn’t take long. The escape was already a black eye for the jail, generating national headlines as one of the largest in recent memory. And some in the local criminal justice community worried about the fallout from an extended search.
Future witnesses or victims critical to criminal cases “may have second thoughts about cooperating with law enforcement if they believe that the system isn't capable of preventing people that they may be identifying from escaping,” said Rafael Goyeneche, the head of the city’s Metropolitan Crime Commission.
The men had fled the jail with no money, phones, food, transportation or changes of clothing. So there was a good chance some would turn to people they knew for help.
Investigators raced to check jail phone logs to see who might have known ahead of time. They searched out relatives and friends who might know their whereabouts. Police turned to a private network of facial recognition cameras whose use had been under review.
Rewards for tips leading to their capture were announced. They would eventually grow to $50,000 each.
“We understand that some of you might be reporting a friend, a loved one, a relative and albeit not easy, it is critical to your safety and the safety of the public that you report them,” Jonathan Tapp, head of the FBI office in New Orleans, said at a news conference.
But getting some residents to cooperate was complicated by distrust linked to the city’s past history of police abuses – including corruption and unconstitutional arrests that led to years of federal oversight. On top of that, the city’s lockups had historically been places known for violence.
Some residents, as a result, might be “reluctant to participate in an investigation like this,” said Stella Cziment, a former defense attorney who is now an independent police monitor.
Officials expressed confidence. And experts said that typically more than 90% of the nation’s roughly 2,000 inmates who escape each year are recaptured.
But Goyeneche said such escapes are most common during a work or medical release, rather than busting through jail walls and taking time to scrawl a mocking message.
“It was too easy,” he said. “This was ‘Shawshank Redemption’ on a much bigger scale.”
Escapees seek aid and cover
On the morning of the escape, two of the men were seen walking in black hoodies and jeans near Hustler Hollywood on Bourbon Street in the French Quarter, a popular destination for tourists.
Such clues led investigators to believe many were still in town in the days after the breakout.
Anthony Cangelosi, an adjunct professor at John Jay College of Criminal Justice and a former U.S. Marshal and Secret Service agent, said that those with a larger network of resources were likely to last the longest.
For some, that included friends or family members.
Vanburen allegedly got help from one person in driving him to a relative’s home and helping him contact family, while another person offered him a hiding place in a vacant apartment, the Associated Press reported.
Others turned to people they knew for money and rides. Some covered their tracks including by using internet phone service.
Within 24 hours of the escape, however, police had zeroed in on several fugitives.
After a foot chase in the French Quarter, police recaptured Kendell Myles after finding him hiding under a car parked near the swanky Hotel Monteleone, which boasts a seafood restaurant and a heated rooftop pool.
Dkanen Dennis was detained while staying in a house in an eastern city neighborhood.
And by that evening, a tip led authorities just down the street where Catchings and her family were hunkered down and some residents were afraid to talk to reporters for fear of retaliation.
Ron Wicker, who lives with his father in the home they’ve owned and lived in since the 1940s, watched as a flood of unmarked police cars descended on the house next door around 7:30 p.m. as the sun set on his threadbare street.
He saw escapee Robert Moody, 21, wearing camouflage pants, hauled back into custody, where he had been held on drug and weapon charges. It was both a relief and a reminder more could be hiding nearby.
“I couldn’t believe he was next door,” Wicker said.
Others, however, would prove more difficult to find.
Details of the escape emerge
Four days after the escape, Hutson wore a white uniform shirt with a gold sheriff's star as she sat in a New Orleans city council hearing room filled with TV news cameras.
With the city on edge, intense scrutiny had fallen on the sheriff, who had suspended her reelection campaign to seek a second term but not heeded calls to resign.
Louisiana Gov. Jeff Landry had already said the jailbreak demonstrated a systemic failure. Jean-Paul Morrell, a city council member, said people were “terrified, upset and angry.” Now the council wanted to hear how inmates had pulled off the escape.
Hutson and her top staffers said there were procedural failures and apparent “wrongdoing” by some inside the jail, and was compounded by security gaps stemming from poor infrastructure, overcrowding and inadequate staffing.
She took full responsibility, calling the escape “deeply troubling," and vowed to correct lapses.
At the time of the escape, no deputy was assigned to the pod. A civilian worker stationed at a module where cameras can be viewed had briefly stepped away for food. At times, short staffing meant there was no one to cover for such breaks.
Goyeneche said staff are supposed to do physical checks and that lights in observation booths should indicate if cells are locked.
Hutson's office said that by 12:43 a.m., multiple inmates entered the cell door they’d jarred open earlier.
Before they could pull off the sink-toilet unit affixed to the wall, they needed the water turned off to avoid flooding. Jail maintenance worker Sterling Williams was arrested, accused of aiding the escape by turning off the water. His lawyer said he did so because of a clogged toilet, not to aid in the escape.
In addition, three employees were suspended pending an investigation, Hutson's office said, without detailing why.
Behind the sink, at least one steel bar appeared to have been cut using a tool. Orleans Parish Chief of Corrections Jeworski Mallett said breaching the wall near the toilets would not have been possible without outside assistance.
By around 1 a.m., the inmates had climbed through the hole, one by one, and had passed through a loading dock door. They hustled down a secure perimeter road toward a part of the facility that's under construction. The jail is building a mental health annex next door.
By 1:19 a.m., they scaled a fence with barbed wire, using blankets to avoid injury. A traffic camera then captured the inmates dashing across Interstate 10 into a neighborhood where investigators later found discarded prison clothing.
How much help the escapees got from the inside was still under investigation. But Hutson said the escape showed that underfunding had left the jail vulnerable.
The jail needed $13 million for security and infrastructure upgrades, she said. Her office cited inadequate equipment such as aging cameras, faulty locks and jail infrastructure that has faced heavy damage from a growing population of inmates.
Then there were the staffing shortages. Staff could safely manage 800 inmates but instead were supervising 1,400, many charged with violent crimes.
“We need to harden this facility right now, not next month,” Hutson said.
Some on the council pushed back, questioning whether the city's nearly $65 million in annual funding for the jail was being mismanaged.
Outside of the council chambers, critics saw it as a simple failure to ensure jail staff were doing what they should.
“That wasn't a spontaneous escape. That was something that was planned. And they were able to plan it because they recognized that there were flaws in the Sheriff's Office not following their own protocols,” Goyeneche said.
Escape resurfaces historic jail problems
With the manhunt still in full swing and jail problems in the public spotlight, New Orleans resident Ricky Peterson knew some of the problems were nothing new.
When he was briefly locked up shortly after the jail opened nearly a decade ago, he said, inmates had already figured out a way to jam up the locks with tissue.
“It’s not hard to do,” he said.
The Orleans Justice Center, designed with rows of reflective glass, was opened in 2015. Many hoped it would turn the page on the notorious conditions at the former Orleans Parish Prison, known for years as an overcrowded and dangerous jail.
In 2009 – a few years after Hurricane Katrina swamped the city’s complex of crumbling lockups — a Justice Department report found inadequate staffing, supervision, mental and medical health services and sanitation.
It cited an inability to keep inmates safe and instances of “calculated abuse” by deputies who would beat prisoners.
Three years later, a Southern Poverty Law Center lawsuit alleged that “rapes, sexual assaults, and beatings are commonplace.” It alleged that people with mental health struggles were going untreated.
“As hellholes go, there are few worse places in America than the Orleans Parish Prison,” Mother Jones wrote in 2012 in a story about the suit.
Video footage around that time showed inmates, with no apparent supervision, using drugs, drinking, gambling with cash and even holding a gun.
The conditions led to federal court oversight and efforts to overhaul policies and reduce violence, with the Justice Department citing “physical and sexual assaults, inadequate medical care, and risks of suicide and mental health decompensation.”
After spending roughly $150 million to build what was considered state-of-the-art at the time, problems didn’t evaporate. In recent years, federal monitors have cited “extremely inadequate” staffing levels and lax supervision.
In October 2024, the monitors found night shift guards performed only 7% of the security checks indicated on their logs. Assigned staff left units unattended for meal breaks. Deputies faced inmate harassment.
Inmate violence was at an "all-time high” with prisoners making weapons, including by prying metal sheeting from windows or sinks in the janitor closets. Some inmates roamed freely, refused to follow staff orders and extorted fellow prisoners.
A lack of effective random searches led to the presence of pills and narcotics. Inmates were often observed smoking illegal substances.
In 2024, the mother of inmate Terry Carter, who struggled with mental illness, filed a lawsuit after her son died from a drug overdose in the facility in 2023. The suit alleged he had previously overdosed while incarcerated and accused the jail of “failure to stop or even reduce the flow of contraband.”
Two weeks before the May 16 escape, two other inmates allegedly tried to escape through the ceiling of the same pod, local media reported.
“Too often the failure to follow policy is blamed on the lack of staff or training,” the monitors wrote in one report. “Neither is an acceptable excuse.”
Despite the jail’s troubles, Peterson said he believes the 10-man escape would have been extremely difficult to pull off without some help.
“I immediately thought, inside job,” he said.
Captures grow including outside accomplices
In a flat stretch of east Texas on May 26, a white SUV sped down a two-lane road more than 300 miles from New Orleans.
More than a dozen police cars, sirens wailing, were on its tail.
The vehicle made quick turns, hoping to shake the pursuing line of cruisers.
State police finally stopped the car on a rural road outside of Huntsville, north of Houston. Officers with weapons raised surrounded the SUV and demanded the passengers get out.
"I'm not opening, are you kidding me?" one passenger said before officers got him out of the vehicle and put him into handcuffs, according to police video footage.
It marked the capture of Leo Tate Sr. and Jermaine Donald. Tate, wearing orange prison clothing and cuffs, was flown back to Louisiana on a state police aircraft.
By that time, police had arrested eight escapees and sent most to the Louisiana State Penitentiary at Angola.
Gary Price had been captured after neighbors said had been hiding at a vacant home in east New Orleans.
Lenton Vanburen Jr. got picked up while sitting on a bench in a Baton Rouge shopping center.
Corey Boyd was captured while hiding in an apartment by a SWAT team. Later, Corvanntay Baptiste, 38, was accused of hiding Boyd and feeding him while he was in hiding.
She was among a growing number of arrests of people who aided them, many held on bonds $1 million or higher, with some facing charges of accessory after the fact.
Authorities reportedly staked out and searched the New Orleans home of Massey’s sister but didn’t locate him. The alleged victim of Massey’s abuse was also arrested and charged with acting as a principal to an aggravated escape and obstructing justice.
As May drew closer to its end, there were just two inmates left to capture.
“Antoine and Derrick — you are NEXT!” Landry, who announced an independent investigation into the escape, wrote on social media.
But they needed more tips, especially from friends and family. On May 29, authorities increased the tip reward to $50,000.
“Soon as we get one lead, they relocate to somewhere else, whether that’s a home or businesses,” Louisiana State Police Superintendent Col. Robert Hodges said.
He didn’t believe the fugitives had the resources to cross international borders.
Investigators also knew their support was likely centered in or around New Orleans.
"They're tired,” Hodges said. “They're looking over their shoulder.”
Escape fuels political fights, calls for change
Nearly three weeks later, the escapes were proving a wake-up call for change.
Several state agencies were conducting audits expected to result in recommended changes in jail policy, staffing and facility upgrades.
And the jail was working on new measures – including more security checks, a second perimeter fence, lock improvements and reducing crowding with transfers.
“The only good that can come from anything like this is to figure out what went wrong and make the changes that reduce the potential for this happening again,” Goyeneche said.
But the search for longer-term solutions also came amid growing political fallout.
Landry, the Republican governor, blamed jail crowding on progressive elected officials in New Orleans. Hutson accused the district attorney of “personal animus and political campaigning” in light of his support for a rival candidate in the upcoming sheriff’s race.
Some city leaders clashed with the sheriff’s office, blaming mismanagement rather than a lack of funding.
Morrell, the city council member, said former jail employees told him there were thousands of languishing work orders and that jail keys weren’t always collected from former employees. The sheriff’s office called the allegation “misinformation.”
“Maybe you don’t need to have the 'Shawshank Redemption' digging a hole to escape," Morrell said in a social media video. "Maybe he didn’t need to hire or scare a maintenance worker into doing it when any employee could walk out with the keys."
Murrill, Louisiana’s attorney general, suggested funding to “keep up with the wear and tear on this building.” Others called for pay increases for new deputies who make about $18 an hour.
Some residents such as Caliegh Flynn noted the city already spends a significant portion of the city’s budget on public safety amid competing needs of schools and city infrastructure.
Sarah Omojola, director of the Vera Institute of Justice in New Orleans, hoped a desire to reduce the cost of incarceration would lead the state to rethink a pullback last year of money-saving 2017 criminal justice reforms such as shortening sentences and expanding parole.
While Louisiana’s legislature toughened penalties after crime rose during the pandemic, crime is now down in New Orleans, police said.
Freddie King III, a city council member, said it was important to delve into root causes, noting that some escapees had previously been in the juvenile system.
“Are we doing enough as a society, as a city, to ensure that our young, specifically Black men, don’t end up in jail?” he said. “We’re not spending enough money where it truly belongs.”
A potential break, a receding threat
The man with his face tattooed with chess pieces sat on a stool in front of a nondescript kitchen, looking directly at a camera and proclaiming his innocence.
It was early June, and Massey – still on the run – took to social media to deny he was the mastermind behind the jail break.
"I didn’t break out. I was let out,” he said.
Asking for help from a litany of celebrities, including President Donald Trump, he said he fled because he was innocent of his charges of domestic abuse involving strangulation.
A day after the video was posted, police raided a house where the video might have been filmed. It was just three miles from jail, NOLA.com reported. He wasn’t there.
“Turn yourself in and you’ll be able to have your day in court,” Landry said at a news conference.
Massey’s grandfather, Lee Taylor, told CBS that he was worried for his grandson, who is a father to a 17-year-old daughter and a 4-year-old son.
"I haven't slept,” he said. “I haven't been eating, and I've lost 15 pounds.”
By that point, the effort to recapture had cost $500,000 for the city government alone. The Louisiana legislature set aside $1.8 million for expenses related to the manhunt, according to news reports.
Another potential break came on June 9, when U.S. Marshals Service arrested Darriana Burton, 28, and accused her of aiding in Groves' escape. She was believed to be Groves' girlfriend, the attorney general's office said in a statement, and had formerly worked at the jail.
Murrill said in a television interview that while the threat to the public has been reduced with the captures, the two remaining escapees were still “dangerous ” to witnesses in their cases and the community in general.
As the days in June started ticking by, the escapees who remained on the lam were not putting a noticeable dent in tourism or scheduled conventions, local officials said. The escapees fell out of the daily news headlines.
Kirkpatrick, the New Orleans police chief, said at least one of the escapees may still be in the New Orleans metro area.
And she was right.
On June 27, six weeks after the escape, Hutson personally got a tip about Massey's whereabouts. Authorities were soon surrounding a home in a New Orleans neighborhood, one about two miles from the jail.
Massey came out and gave up peacefully.
Hutson and Kirkpatrick "had a moment" together as they talked on the phone to plan a news conference. The relief was palpable, Hutson recalled.
But there was still one left.
In her neighborhood, not far from the jail, Alayciea “Lacy” Favaroth, 34, who has a teenage daughter, said she saw her neighbor’s home raided by a SWAT team. She lives in the same block as Massey’s sister, who was taken into custody.
Favaroth said the ordeal was pushing her to search for a new place to live where she feels safer.
“I really can’t believe it’s been that long. It's crazy that they really are still out there. And you just don't know where,” she said. “This definitely is going down in history.”
When the jailbreak’s final chapter is written, it may become the latest in New Orleans’ tumultuous history, she said, one that has fueled the city’s famous resilience.
And maybe, one that brings change along with it.
Contributing: Paste BN staff
This story has been updated to reflect the June 27 capture of fugitive Antoine Massey.