2 jailbreaks. 3 men still on the run. What we know about the circumstances of each escape

By Chris Boyette, Holly Yan, CNN

(CNN) — A police chief-turned-murderer-and-rapist, a repeat escapee and a double murderer are still nowhere to be found after two high-profile jailbreaks keep communities on edge and law enforcement on alert.

As much as these stories have in common, the circumstances behind their escapes, where they may be hiding and what they might hope to do on the outside are very different.

Grant Hardin, 56, escaped from a state prison in Calico Rock, a remote city in northern Arkansas, on May 25. Formerly the police chief of a nearby small town, Hardin was serving decades-long sentences for murder and rape.

Derrick Groves, 27, and Antoine Massey, 32, are the last two fugitives on the run after they and eight other inmates broke out of the Orleans Justice Center in New Orleans on May 16.

Groves, 27, was convicted of murdering two men on Mardi Gras in 2018. Massey, 32, was charged with domestic abuse involving strangulation and theft of a motor vehicle. He started escaping custody at age 15.

The eight other fugitives have been caught, mostly in New Orleans. But now, several states are involved in the manhunt for Massey and Groves.

In both manhunts, hundreds of local, state and federal authorities joined in the search.

And both manhunts now face the reality that the longer these men remain on the loose, the harder it may be to ever find them. Most inmates who escape get caught within 48 hours, and after 48 hours, it’s more difficult to capture escapees, CNN Senior Law Enforcement Analyst Charles Ramsey told CNN.

Former FBI Deputy Director Andrew McCabe agreed. “The longer this goes, and the further away they can get, the better chance they have of staying out there for a while,” said McCabe, a CNN senior law enforcement analyst.

Elaborate escape plans

Hardin escaped the North Central Unit prison in Calico Rock around 2:55 p.m. on May 25, the state’s Department of Corrections said.

A surveillance image from the time of the escape appears to show Hardin wearing black pants, a black T-shirt and a black baseball cap, as well as an additional item that looks like a bulletproof vest, which the department called “a makeshift outfit designed to mimic law enforcement.” But the department made clear it was not standard-issue clothing for inmates or correctional officers, so they are also investigating how he got it.

Authorities believe he exited through a sally port, a controlled and secure entry point found in places such as prisons, the Stone County Sheriff’s Office said.

Authorities discovered Hardin was missing during a routine count about 15 to 20 minutes after he left, but an investigation into the timeline of events is still being conducted, corrections spokesperson Rand Champion said.

In Louisiana, 10 inmates used hair clippers, stolen blankets and bad infrastructure to ultimately escape a New Orleans jail by squeezing through a small hole cut into the wall behind a metal toilet. They left a message taunting corrections officers on the wall on the way out. “To Easy LoL,” it read.

Arkansas authorities say it was raining “fairly significantly” at the time of Hardin’s escape, giving him a small advantage against his pursuers despite his absence being detected no more than 20 minutes after he broke out, but the men in New Orleans got a much larger head start.

Staff at the Orleans Justice Center did not notice the 10 inmates had escaped until more than 7 hours after the jailbreak, and did not alert the public until even later.

Possible help from the outside

Officials are still digging into how Hardin escaped, what methods he used and whether anyone helped him.

By contrast, authorities in Louisiana say the 10 men who escaped from the Orleans Justice Center received help from at least 14 people – including friends, family members and a maintenance worker at the jail.

Some of those suspected accomplices are now held on bonds of over $1 million and face felony charges, according to The Associated Press.

Authorities face challenging searches

Authorities believe Hardin is still in the general area near the prison, according to Champion but the fugitive’s knowledge of the land and familiarity with law enforcement tactics are helping him stay out of custody.

“There’s caves, there’s barns, there’s abandoned cars, there’s abandoned sheds, there’s residences … It’s not a flat, open area,” Champion said, plus the area where police are searching is one of the most cave-dense in the state.

Hardin grew up in midwest Arkansas, which has similar terrain, giving him another advantage, Champion added.

“I can imagine that the entrance area of a cave could be a useful place to hide,” Matt Covington, an associate professor in the Department of Geosciences at the University of Arkansas, told CNN. “There is often water present. There are boulders to hide under or small crawlways and side passages,” he added.

Officials have been using all resources at their disposal, including dogs, drones and aircraft, among other methods, Champion said, but rain and fog have affected the effectiveness of those resources and with a background in law enforcement, authorities worry Hardin could remain a step ahead of them.

“Obviously, if you have a law enforcement background, you’ve had specialized training, you’ve had a familiarity of the tactics that are going to be used,” Champion said.

In Louisiana, the other eight other fugitives who escaped with Massey and Groves have already been caught. The five youngest escapees were all captured within a few days in New Orleans. But two of the most recent arrests were in Texas, emphasizing the need for a multistate search.

As for Massey and Groves, “We are currently at an impasse on figuring out where these two are,” Deputy US Marshal Brian Fair told CNN last week.

“They can be here locally or can be anywhere in the United States at this point.”

The escapees have received help from friends and family who provided food, cash, transportation and places to rest and hide, according to court documents.

Louisiana Attorney General Liz Murrill had a stern warning for anyone considering helping the fugitives:

“If you help the remaining escaped inmates, you will be prosecuted,” she said. “The more help they get, the more charges there will be. Period.”

What comes next?

Groves was found guilty of two counts of second-degree murder and two counts of attempted second-degree murder, charges carrying a life sentence, Orleans Parish District Attorney Jason Williams said.

Given Groves’ potential jail time and Massey’s long track record of escaping custody – previously escaping a New Orleans juvenile detention center and twice cutting off electronic ankle monitors, according to reports – it is likely the fugitives’ main goal is avoiding going back to prison, though authorities have “a lot of leads” and are getting tips from the community, according to Williams.

“They absolutely could be moving to other areas. I alerted my colleagues in the states surrounding Louisiana immediately after the jailbreak to be on alert and to notify their law enforcement partners that these individuals could be coming to their states,” Murrill said.

Hardin’s motives may be more complex, considering his close ties to the small town of Gateway, where he was briefly the chief of police, less than a three-hour drive from the prison where he escaped.

“To know that he is out on the loose is very scary,” Cheryl Tillman said.

Hardin pleaded guilty to first-degree murder for the death of Tillman’s brother, James Appleton, in February 2017, according to court documents.

Now Gateway’s mayor, Tillman was on the city council when Hardin was dismissed from the police department.

“I’m sure the people here in Gateway are worried about him breaking out of prison after what he’s done,” she said.

The FBI announced a reward of up to $20,000 for information leading to Hardin’s arrest.

“What we would ask – in this area, especially – please be cognizant. Please be aware. Be alert of your surroundings,” Champion said.

Officials announced $50,000 in reward money for anyone with information leading to the arrest of either Massey or Groves. The combined $100,000 offered comes from Crimestoppers Greater New Orleans, the FBI and other agencies.

“We need everyone’s help,” Louisiana State Police Superintendent Col. Robert Hodges said. “If you’re listening, and you’re in another state and you have a tip … please contact us.”

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