10 Jaw-Dropping Prison Escapes Involving Helicopters

There have been a surprising number of prison escapes involving helicopters. And an even more surprising number of those attempts have actually succeeded! Of course, for those of us of a certain age, Escape from Alcatraz comes to mind as the classic story in the prison break discourse. Others may also point to Shawshank Redemption as the legendary arc in this prison-break realm. But sometimes, prisoners don’t have the time or patience to tunnel through a wall for months or years to leave behind their captors. Sometimes, they’ve gotta get going ASAP!

In this list, we’ll take a look at ten shocking prison escapes involving helicopters. These prisoners (and the unlikely helicopter pilots pushed into service for their ends) chose the most daring, obvious, and loudest way to get out of prison. And you’ll be gobsmacked at how often some of these breaks actually worked out in their favor!

Related: 10 Bold Escapes from Island Prisons

10 Joel David Kaplan

Joel David Kaplan was a New York businessman who had been arrested for murder in Mexico in 1962. He was eventually jailed for the crime in Mexico City’s notorious Santa Martha Acatitla prison in the Iztapalapa borough of the capital district. But he wasn’t down to stay in prison for very long as he didn’t agree with the Mexican authorities’ handling of his allegations and prison sentence. His wife, Judy, hated that her husband was languishing in a brutal prison far south of the border.

So she got the means together to arrange for a helicopter to be flown straight into the prison yard. On August 19, 1971, she hired a helicopter pilot to land in the middle of the Santa Martha Acatitla prison yard. When the helicopter got there, Kaplan and his cellmate, a Venezuelan convicted counterfeiter named Carlos Antonio Contreras Castro, rushed up to it and immediately boarded it.

At first, guards thought that the helicopter was there to signal an official visit from a dignitary or a politician. So they didn’t do anything to stop the helicopter or shoot at the prisoners. The chopper then rose from the yard in mere seconds, with Kaplan and Castro aboard and not a single shot fired. From there, both men were flown to Texas.

Then, in different planes, Kaplan was flown on to California while Castro bid him adieu and flew south to Guatemala. The Mexican government was pissed at the incident, but interestingly, they never initiated extradition proceedings against Kaplan. In turn, he wrote a book about his escape, appropriately titled The 10-Second Jailbreak. Four years later, in 1975, that book even became an action movie starring Charles Bronson and Robert Duvall!^[1]

9 Garrett Brock Trapnell

Garrett Brock Trapnell was in prison after attempting to hijack a plane, and he wasn’t happy about it. So, in the early part of 1978, he convinced his friend on the outside, a woman named Barbara Ann Oswald, to help him escape from prison. Their idea was simple, really: They needed Barbara to hijack a helicopter, convince the pilot to fly it to USP Marion in Illinois, where Trapnell was incarcerated, and pick him up and leave forever.

On May 24, 1978, Barbara did just that. She hijacked a charter helicopter in St. Louis and demanded at gunpoint that the pilot, Allen Barklage, fly to USP Marion. Well, Barklage did it, but he had a trick up his sleeve. A tough and aggressive Vietnam War veteran, Barklage wasn’t down with being told what to do. So, when he finally landed the helicopter, he managed to wrestle away Oswald’s gun. Then, he shot and killed her.

That thwarted any chance Trapnell had of escaping. He and Martin J. McNally, another inmate at the prison who had also been involved in Trapnell’s earlier 1972 hijacking that got them locked up in the first place, were stuck behind bars. But amazingly, the story doesn’t end there!

In December 1978, seven months after Barbara was killed in her thwarted helicopter prison escape attempt, her 17-year-old daughter Robin Oswald hijacked TWA Flight 541. She claimed she had dynamite strapped to her body, and she was willing to detonate it if Trapnell wasn’t released from prison.

FBI negotiators were eventually able to secure the release of the plane’s passengers and arrest her before Trapnell could be released, though. When officials moved in to arrest Robin, they discovered that she merely had railroad flares and a doorbell. Maybe she should have tried the helicopter route!^[2]

8 Giles Arseneault

On May 7, 1981, Giles Arseneault was in Orsainville Prison in Quebec City, Canada. There, he was awaiting extradition to California to face a murder charge. But his 25-year-old girlfriend, Marina Paquet, thought that he was innocent—and she didn’t want to see him go to the United States and possibly be jailed for life. So, she did what any (not) sane person would do.

Paquet grabbed a sawed-off shotgun, went down to the airport, found a helicopter, and pointed the weapon at the pilot. The pilot in question was a man named Brian Jenner, and his bird was a powerful and reliable Jet Ranger helicopter. She told him to fly straight for Orsainville Prison, where she was going to pick up Arseneault and run off into the sunset.

Jenner was wise about how he encountered the situation, though—wiser than Paquet was ready for. He first feigned a panic attack to buy himself time to think up a deviation and get her to sympathize with him a bit. Then, when they finally got airborne, Jenner started putting the chopper through rough mid-air maneuvers. It made Paquet sick, for one, and it also made her doubt whether the helicopter was in good working order. He told her they couldn’t make it to the prison, and instead, they’d have to turn around and go back to the airport to land.

That’s just what they did, except the entire time this was happening, Jenner had his finger very subtly pressed onto the intercom button. In that way, it was transferring his and Paquet’s entire conversation back to the air traffic controllers at the airport. She told him of her motives and plans, and they secretly heard every single word.

As soon as the helicopter touched down back at the airport, Paquet got off and figured she was home free from the thwarted escape attempt. She wasn’t, though; cops swooped in immediately and arrested her.^[3]

7 James Rodney Leonard

On December 19, 1985, a convicted murderer named James Rodney Leonard escaped from the Perry Correctional Institution in Pelzer, South Carolina. He was with two other inmates—William Douglas Ballew and Jesse Glenn Smith—when the three were visited on the prison grounds by a helicopter. The chopper had been hijacked by a woman who was armed with a gun, and she’d ordered the pilot to fly down into the prison’s yard to pick up Leonard.

Ballew and Smith used the opportunity to join the escape as well. In fact, two other prisoners also tried to jump on the helicopter. However, the pilot convinced them that the bird was simply too overloaded and wouldn’t be able to take off again. As it turned out, the chopper barely made it over the prison wall and past the fence with the five people on it.

As the escape was happening, the prisoners used the hijacker’s gun to shoot back at guards who had rushed in to try to prevent the escape. One guard was shot in the mouth and wounded in the rush of bullets. The helicopter actually did make it out of the prison—but just barely.

Then, it flew to a getaway car four miles away. There, the prisoners and the hijacker left the helicopter, got into the car, and drove off. A statewide manhunt was immediately initiated. Four days later, on December 23, all three prisoners and the hijacker were caught by cops in nearby Camden County, Georgia.^[4]

6 Michel Vaujour

In 1985, Michel Vaujour was sentenced to serve 28 years in prison in Paris, France, after being convicted of attempted murder and armed robbery. Before he even was sentenced, though, he was already planning his escape. And his wife Nadine was right there with him, thinking about springing the convict free. On May 26, 1986, at Prison de la Santé in Paris, that’s exactly what they did.

That morning, Vaujour managed to get rumors going inside the prison that several inmates had bombs and grenades and were threatening to detonate them. The scary reports surged through the jail and quickly got back to the guards. Alarmed just as they should have been, the guards sped off in large numbers to figure out which prisoners had these supposed weapons and how they might prevent a catastrophe.

Simultaneously, Vaujour and another inmate named Pierre Hernandez had plotted out their escape plan. They intended to go up to the roof and catch the landing helicopter. Hernandez ended up backing out at the last minute, but Vaujour carried on with his plan. He climbed the stairs, snuck out of the inmate rooming spaces, and crept onto the prison’s roof. There, he met Nadine in the waiting chopper, and they flew off together to a getaway car on an athletic field not far from the prison.

Pretty amazing that the escape attempt worked so well, right? Well, it could have maybe turned into a long-term thing for Michel and Nadine, but they were caught just three days later… after committing a pair of bank robberies in Paris.

So, not only did the couple not leave the city and go far away like they probably should have, but they immediately started taking high-risk chances with brazen robberies just as soon as Michel was sprung free. Ah, well. Freedom may have lasted just about 72 hours in his case, but at least it gave the world an absolutely insane story to remember forever, right?^[5]

5 Ronald McIntosh & Samantha Lopez

It was a Romeo & Juliet story for the modern era… except it also involved two prisons, two prisoners, and a hijacked helicopter. On October 28, 1986, a man named Ronald J. McIntosh simply walked away from a minimum security prison where he’d been serving some time on a low-level charge. He laid low for a week, and nobody really inquired much about him or where he was.

Then, the proverbial heat began to rise on November 5. That day, he hijacked a helicopter and flew it to Federal Correctional Institution Dublin in Northern California. Waiting inside that prison was a woman named Samantha Lopez. She had been incarcerated after being convicted of a 1981 bank robbery in Georgia. She was the love of McIntosh’s life, though, and the duo desperately needed to be together.

McIntosh managed to get the helicopter to fly into the yard at FCI Dublin. There, they picked up Lopez and flew right back out. The duo then landed nearby and ran away to safety. For the next ten days, they lived quietly even as cops frantically began searching for them.

Then, on November 15, they were arrested at a California shopping mall. They had been in a jewelry store buying wedding rings for each other. Cops had been watching the bank accounts associated with the couple, and when McIntosh wrote a check at the mall to pay for the rings, they swooped in and arrested the pair.

McIntosh was eventually sentenced to 25 years in prison for his role in the daring helicopter escape. And Lopez was given five additional years on her 50-year sentence for the aforementioned bank robbery. But this story ends sweetly, we suppose. As the duo were being walked to prison vans and driven to separate prisons following their convictions, McIntosh managed to lean out of the window of his car and yell “I love you” to Lopez. True love knows no bounds, or (prison) walls—or helicopter hurdles, we suppose.^[6]

4 Bellaïche, Esposito, & Cipollari

On November 23, 1986, a helicopter was hijacked by two armed men on the outskirts of the Italian city of Rome. Then, the men forced the pilot to fly into the courtyard of the Prigione di Rebibbia prison in Rome. Once the helicopter got there, it lowered down into the maximum security yard and hovered less than three feet off the ground.

More than fifty inmates were out in the yard exercising at the time. As the hijackers opened fire on guards and laid enough cover for the daring escape, three men rushed up to the helicopter to board it. The men were André Bellaïche, Gianluigi Esposito, and Luciano Cipollari.

Bellaïche was a Frenchman who’d been convicted of murder and bank robbery. Esposito was an arms smuggler who had sold guns and ammunition to Italian terrorist groups. And Cipollari was also a murderer who’d been extradited from France over a slaying in Rome a year before.

Cipollari slipped and fell while getting up to the helicopter, and he wasn’t able to escape. But the other two men were flown directly to a nearby soccer field, where they landed in the middle of a game. The soccer players were shocked to see the men jump out, run onto the street, go up to a person sitting in a car, and hijack the vehicle. They fled Italy altogether over the next three weeks. Still, on December 13, authorities were able to track them down and return them to prison.^[7]

3 John Killick

A soft-spoken and mild-mannered Russian-born librarian living in Australia named Lucy Dudko hired a helicopter in Sydney on March 25, 1999. She told the pilot that she wanted to see the sights around Sydney as the city was busy preparing for its turn to host the Olympic Games that next year.

However, once they got into the air, Dudko pulled out a gun. Under the threat of death, she forced pilot Tim Joyce to land the chopper on the grounds of a nearby prison. There, her lover, John Killick, was serving a 28-year sentence for armed robbery. And he was waiting patiently for Dudko, as the two had been planning this daring escape for some time.

Killick jumped into the helicopter while guards on the prison grounds started firing shots. Nobody was hit in the hail of gunfire, though. As the bullets whizzed by, the helicopter took off again. It flew out of the prison’s courtyard and then landed in a nearby park.

There, Killick and Dudko hijacked a taxicab at gunpoint. Over the next six weeks, they were able to somehow elude Australian authorities and remain on the run. But eventually, in May 1999, they were captured and arrested at a tourist park on the outskirts of Sydney.

The case was widely followed in Australian media. Local journalists in Sydney dubbed Dudko as “Red Lucy.” After being tried and convicted of her role in the helicopter prison escape, she was sentenced to the maximum penalty available for her crime: ten years in prison. She was eventually released in 2006 after serving about seven years of that sentence.

As for Killick, he went right back to prison and remained there to serve the rest of his sentence and then some. He was released in 2015—but one of the conditions of his parole is that he doesn’t have any contact with Dudko until his 80th birthday, which was in 2022.^[8]

2 Steven Whitsett

On June 5, 2000, a sex offender named Steven Whitsett hatched a daring helicopter prison escape while serving time at the Martin Treatment Center for Sexually Violent Predators in Martin County, Florida. Just after 1:00 p.m. on the 5th, corrections officers at the facility noticed a helicopter approaching the facility from the south. As cops would later come to learn, it was being piloted by a man named Clifford Burkhart.

Burkhart was a student pilot and a former lover of Whitsett’s who wanted the sexual offender to be released from prison by any means necessary. The helicopter landed inside the prison, Whitsett jumped on board, and the duo started to fly away. But upon trying to leave the facility, Burkhart’s helicopter struck something as it was getting off the ground. It made it out of the perimeter fence but crashed about 100 yards (91 meters) away from the compound.

Whitsett and Burkhard managed to escape unscathed from the low-altitude crash and went on the run. For about the next 26 hours, they were in the wind. Then, on the afternoon of June 6, sheriff’s deputies searched the area’s open outdoor spaces via their own helicopter and found Whitsett and Burkhart hiding out. They were lying low in a canal, standing in place in shoulder-deep water just about 4 miles (6.4 kilometers) east of the prison. Cops swooped in on the ground and arrested both men.

For his escape, as well as weapons charges related to it and his actions afterward, Whitsett was eventually sentenced to 25 more years in prison. In turn, Burkhart was sentenced to seven years of prison time, followed by ten more years of probation. He was eventually released from prison in 2007. As for Whitsett, he was released from prison in 2016 and completed supervised probation of his own in 2018.^[9]

1 Panagiotis Vlastos

On February 24, 2013, two men in Greece chartered a helicopter for a ride. Once up in the air, the passengers produced weapons and demanded that the pilot and technician fly to Trikala Prison to pick up an inmate. At first, the armed passengers lowered a hook in an attempt to rip off the wire fence that surrounded the prison. When that failed, they dropped a rope down into the courtyard and picked up a prisoner named Panagiotis Vlastos.

While Vlastos was climbing up the rope and trying to get into the helicopter, the two armed passengers started firing on guards using AK-47 rifles and Uzi submachine guns. One guard was injured in a watchtower after flying shards of glass struck him in the face. However, he was able to successfully return fire on the helicopter.

During the shootout, Vlastos himself was shot and wounded. The helicopter’s technician was also wounded—an unforeseen injury and an innocent person harmed amid the gun battle. Vlastos briefly managed to climb into the helicopter as it started to fly away, but at some point, he slipped and lost his balance. Just as the helicopter was rising up and out of the prison courtyard, from about 10 feet (3 meters) off the ground, Vlastos fell back down to earth.

Guards grabbed him there and held him down—so close to freedom but so far away. The helicopter was quickly grounded in the prison’s parking lot, and the armed men were eventually taken into custody, too. In the end, officials noted that the hijackers had fired more than 500 bullets from the chopper during the unsuccessful escape attempt. They even had what cops deemed to be improvised explosive devices that they thankfully did not use.^[10]