2 escapees from the New Orleans jailbreak remain at large. One has a lot of experience being on the run

More than a week after 10 prisoners conducted a daring escape out a bathroom wall in a New Orleans jail, two inmates remain on the run, prompting an intensified search across state lines. (Orleans Parish Sheriff's Office/AP via CNN Newsource)

More than a week after 10 prisoners conducted a daring escape out a cell wall in a New Orleans jail, two inmates remain on the run, prompting an intensified search across state lines.

Authorities on Monday captured three escapees: Lenton Vanburen Jr., Leo Tate and Jermaine Donald. Tate and Donald were the first of the escaped inmates to be found outside Louisiana. They were arrested in Texas after what the Huntsville Police Department described as a high-speed chase involving multiple law enforcement agencies.

Now with eight escapees recaptured, the manhunt continues for the two remaining inmates –– Antoine Massey and Derrick Groves –– both of whom should be considered armed and dangerous, authorities say.

Here’s what we know about them.

An experienced fugitive

Antoine Massey is no stranger to breakouts. The 33-year-old has a history of escapes dating back to 2007, when he broke out of a New Orleans juvenile detention center after being arrested for armed robbery and aggravated assault, according to nola.com.

A broken lock at the center allowed Massey, then 15, and five other juveniles to access metal shackles, which they used to shatter a window and escape, nola.com reported. The teen stayed on the run for more than two weeks before authorities found him on an interstate in east New Orleans.

Two years later, Massey faced a charge of attempted simple escape in Orleans Parish, according to online court records. CNN reached out to the parish sheriff’s office for more details about the circumstances around the charge.

At 27, Massey and another inmate broke out of a detention center in northern Louisiana in broad daylight by cutting and slipping under a chain-link fence in the exercise yard, Chief James Mardis of the Morehouse Parish Sheriff’s Office told CNN last week. The two men were believed to have been picked up by a vehicle with Texas tags that was seen in the area. Massey was caught in Texas later that day.

Massey has also twice cut off electronic ankle monitors, according to Matt Dennis, an employee with the company that operates the monitors who spoke to CNN affiliate WDSU. Court records from late 2023 alleged Massey had “tampered and/or removed the court-ordered GPS monitor.”

Dennis told CNN affiliate WVUE he was “astonished” that someone with Massey’s history of escape was being held on the first floor of the New Orleans jail.

“There isn’t an ounce of this man’s history that doesn’t say ‘escape’,” Dennis said.

Chief Mardis, who shared details of the inmate’s 2019 escape, said it was no shock to learn of the current breakout: “It didn’t surprise me, because (Massey) was known for that.”

It’s still unclear how big of a role Massey may have played in planning this month’s jailbreak, which the Orleans Parish sheriff has described as a “coordinated effort.”

The 10 inmates escaped through a hole in the wall behind a metal toilet in a handicapped cell. The escapees appear to have scrawled “To Easy Lol” on the cell wall. The jailbreak has been blamed on a combination of faulty locks, stolen blankets and possible help from inside the jail.

As of Tuesday morning, it is believed that at least 13 people helped the 10 escaped inmates – either before or after the May 16 jailbreak. The growing number of arrests provides new insight into just how elaborate and far-reaching the planned jailbreak may have been.

Sterling Williams, a maintenance worker who turned off the water to the toilet, is charged with aiding the escape. Massey purportedly threatened to shank Williams if he did not turn off the water, according to an affidavit, but Williams’ attorney later said that one of the jail’s deputies asked Williams to fix the toilet because it was overflowing.

“Yes, someone said they would shank him … (but) they didn’t say it in a particularly threatening manner. They said it more as an aside,” Michael Kennedy, the attorney for Williams, told the Associated Press.

Kennedy argues Williams was only doing his job and that jail officials are “trying to use him as a scapegoat to minimize their own embarrassment” over the breakout.

Convicted killer in 2018 Mardi Gras murders

The other escaped inmate who’s still at large is 27-year-old Derrick Groves, who was being held at the New Orleans jail after being convicted near the end of last year in the killing of two people on Mardi Gras day in 2018.

Groves was found to be one of the gunmen who opened fire with AK-47-style assault rifles “on what should have been a joyous Mardi Gras family gathering,” the district attorney’s office said.

Groves was found guilty of two charges of second-degree murder and two charges of attempted second-degree murder, charges that carry a life sentence, according to the district attorney.

Groves’ aunt, Jasmine Groves, told CNN affiliate WDSU that she wants her nephew to turn himself in and that she hopes deadly force will not be used against him. She said she’s seen police cars and helicopters around her and other family members’ homes since the breakout.

‘Their circle is tightening’

Authorities have “a lot of leads” and are getting tips from the community, Orleans Parish District Attorney Jason Williams told CNN’s Jake Tapper on Tuesday.

“My office, the digital forensics team, has been scouring through hours and hours of jail calls using some AI software to figure out who they were in contact with the night before, hours before, to figure out where they may have been heading,” Williams said. “Their circle is tightening, as people who are assisting are being arrested.”

He added that the investigation into the jailbreak is ongoing and essential.

“It’s vitally important that we catch these fugitives, whether it’s Arkansas, whether it’s Louisiana. But it’s also critically important that we know how they got out and who helped them get out, and we can’t wait until they’re in custody to do that,” Williams said.

Williams had previously said he feared for the safety of his staff and others, and on Tuesday called for added security around the city courthouse for jurors and potential witnesses.

“This is going to absolutely have a ripple effect on other witnesses, other jurors, and we want to make sure that they realize that there’s adequate protection at a courthouse when they come to testify and do their service.”

Other manhunts that made the headlines

As Massey and Groves near two weeks on the run, here’s a list of other high-profile escapes that made headlines:

• Alcatraz: On June 11, 1962, three prisoners – Frank Morris and brothers Clarence and John Anglin, all in their 30s – shimmied with a homemade raft through hidden holes in their cell walls, climbed through a ventilation duct onto the roof and bolted from the Alcatraz Island fortress into the freezing, choppy waters of San Francisco Bay. While Morris and the Anglin brothers were never found, fans of outlaw drama – and some of the prisoners’ own family members – are convinced they actually made it to shore and lived their lives hidden from justice and the public eye.
• “El Chapo”: Despite the reportedly cushy conditions at Mexico’s Puente Grande prison, drug cartel boss Joaquin “El Chapo” Guzman Loera in 2001 escaped from the prison in a laundry cart, with 12 years left in his sentence. Guzman remained on the run until 2014, when he was captured at a hotel in the Pacific beach town of Mazatlan. A year later, however, he had broken out of a maximum-security prison again, authorities announced. This time, he used a mile-long tunnel for escape. It took nearly six months for investigators to find him again at a hideaway in the coastal city of Los Mochis in January 2016. He was later convicted for running an industrial-scale drug smuggling operation and is now serving his sentence at a maximum-security prison in Florence, Colorado.
• A “special relationship: Corrections official Vicky White and prisoner Casey White fled a detention facility in Lauderdale County, Alabama, on April 29, 2022. They were finally captured by authorities on Monday, May 9, in Evansville, Indiana. In those 11 days, the guard and the prisoner, who had formed a “special relationship” at the Lauderdale detention facility, travelled more than 200 miles through at least four states, with tens of thousands of dollars in cash to pay for clothes, wigs, hotel rooms and several vehicles. Officers took Casey White into custody, while Vicky White died from what investigators believed to be a self-inflicted gunshot wound. Casey White was booked back into the William E. Donaldson Correctional Facility in Bessemer – the same prison where he had been held at the start of 2022.
• Long time on the lam: According to Guinness World Records, the longest recorded escape by a recaptured prisoner was that of Leonard T. Fristoe, 77, who escaped from the Nevada State Prison, Carson City, Nevada, USA on December 15, 1923. Leonard was turned in by his son on November 15, 1969, in Compton, California. By then Leonard had lived nearly 46 years in freedom under the name of Claude R. Willis. His crime was killing two sheriff’s deputies in 1920, the organization on all things record-breaking said.
• Ted Bundy: Serial killer Bundy was arrested for the final time on February 15, 1978. He had been previously arrested on murder charges in Colorado but escaped from custody, before being captured in Aspen a few days later. Months later, Bundy escaped again, prompting a nationwide manhunt. While a fugitive in Florida, he killed two college students and a 12-year-old girl. Six weeks after escaping, Bundy was apprehended for a third and final time in Pensacola in a stolen car. He was convicted on three counts of murder, sentenced to death in the electric chair and executed on January 24, 1989.

Written by Karina Tsui, Matt Rehbein, Chris Lau, CNN