There have been multiple prison escapes where an inmate escapes by means of a helicopter. One of the earliest instances was the escape of Joel David Kaplan, nicknamed "Man Fan", on August 19, 1971, from the Santa Martha Acatitla in Mexico.[ https://www.la-prensa.com.mx/archivos-secretos/joel-david-kaplan-como-fue-la-fuga-en-helicoptero-de-una-carcel-mexicana-8667313.html Note in Mexican newspaper La Prensa (in Spanish) (Retrieved Monday, June 3, 2024.)] Kaplan was a New York businessman who not only escaped the prison but eventually got out of Mexico and went on to write a book about his experience, The 10-Second Jailbreak.

France has had more recorded helicopter prison escape attempts than any other country, with at least 11. One of the most notable French jail breaks occurred in 1986, when the wife of bank robber Michel Vaujour, Nadine Vaujour, studied for months to learn how to fly a helicopter. Using her newly acquired skills, she rented a white helicopter and flew low over Paris to take her husband from the roof of his fortress prison. Vaujour was later seriously wounded in a shootout with police where he was shot in the head and his wife was arrested.

The record for most helicopter escapes goes to convicted murderer Pascal Payet, who has used helicopters to escape from prisons in 2001, 2003, and most recently 2007.

Another multiple helicopter escapee is Vassilis Palaiokostas, who on February 22, 2009, escaped for the second time from the same prison.

To thwart attempts of this nature, many prisons have taken precautions such as nets or cables strung over open prison courtyards.

This list includes prisoner escapes where a helicopter was used in an attempt to free prisoners from a place of internment, a prison or correctional facility.

Actual attempts

Date Prison name Country Succeeded Escapee(s) DetailsSanta Martha Acatitla Kaplan was a New York businessman who had been arrested for murder in 1962 in Mexico City and was incarcerated at the Santa Martha Acatitla prison in the Iztapalapa borough. Joel's sister, Judy Kaplan, arranged the means to help Kaplan escape, and on the aforementioned date, a helicopter landed in the prison yard. The guards mistakenly thought this was an official visit. In two minutes, Kaplan and his cellmate Contreras, a Venezuelan counterfeiter, were able to board the craft and were piloted away, before any shots were fired. Both men were flown to Texas and then different planes flew Kaplan to California and Contreras to Guatemala. The Mexican government never initiated extradition proceedings against Kaplan. The escape is told in a book, The 10-Second Jailbreak: The Helicopter Escape of Joel David Kaplan. It also inspired the 1975 action movie Breakout, which starred Charles Bronson and Robert Duvall.Mountjoy Jail, Dublin JB O'HaganSeamus TwomeyKevin MallonAn IRA member hijacked a helicopter and forced the pilot to land in the exercise yard of the prison's D Wing at 3:40 p.m. Three prisoners who were also members of the IRA escaped aboard the helicopter. Another prisoner was quoted as saying, "One shamefaced screw apologised to the governor and said he thought it was the new Minister for Defence (Paddy Donegan) arriving. I told him it was our Minister of Defence leaving."

The escape became Republican lore and was immortalized by "The Helicopter Song", which contains the lines "It's up like a bird and over the city. There's three men a'missing I heard the warder say".United States Penitentiary, Marion, Illinois Garrett Brock TrapnellMartin Joseph McNallyJames Kenneth Johnson43-year-old Barbara Ann Oswald hijacked a Saint Louis-based charter helicopter and forced the pilot to land in the prison yard. While landing the aircraft, the pilot, Allen Barklage, who was a Vietnam War veteran, struggled with Oswald and managed to wrestle the gun away from her. Barklage then shot and killed Oswald, thwarting the escape. A few months later Oswald's daughter hijacked TWA Flight 541 in an effort to free Trapnell.Fleury-Mérogis, Essonne, Île-de-France Gérard DupréDaniel Beaumont With the help of Serge Coutel, Dupré and Beaumont succeeded in the first and double helicopter escape of a French prison, in what was regarded as the most secure in the country. The men hijacked a helicopter and its pilot that they rented to fly from Paris to Orléans. The pilot, Claude Fourcade, was taken hostage and was falsely told that they were holding his wife and daughter hostage. The flight landed at Porte d'Orléans.Les évasions françaises en hélicoptère depuis la première en 1981; http://www.helico-fascination.com/flash/1109-les-evasions-francaises-en-helicoptere-depuis-la-premiere-en-1981.htmlOrsainville Prison, Quebec City Marina Paquet (hijacker)Giles Arseneault (prisoner) Paquet held a sawed-off shotgun against the back of the head of Jet Ranger helicopter pilot Brian Jenner. She demanded that he land in the prison courtyard, where her boyfriend (awaiting extradition to California on a murder charge) was set to escape. Jenner feigned a panic attack, put the helicopter through some rough maneuvers and was then able to convince Paquet, in the back seat of the Jet Ranger, to turn over her shotgun and her knife. Jenner then gave her the choice of any landing spot, except the prison. She chose to go back to the airport.

The pilot then explained, in great detail, exactly where they were and where they would be landing on arrival at the Quebec City airport. He added that the police would surely be aware by then, that she had hijacked the helicopter but would not yet be aware that she had given up her arms to the pilot. All the time Jenner was squeezing the transmit button on his cyclic stick and the tower was picking up all the details. The moment they touched down at the airport, the woman left the helicopter but the police, who had been advised of the situation by the control tower, were hiding nearby, and captured Paquet within seconds. Three suspects, all held on drug-importation charges, hired a former SAS soldier, then living in the Philippines, to lift the prisoners from the prison's tennis court to a nearby van fitted with panels to hide them for the 600 kilometre road trip to Sydney, where a yacht was to take them to Manila. The plan was thwarted when Lord Tony Moynihan, himself an exile in the Philippines, informed the Australian Federal Police, who then ran it as a sting operation.

Of the accused, only McMillan and his accountant friend who had visited the prison stood trial. During the hearings, few prosecution witnesses used their real names as they were mostly from Moynihan's former West African MI6 unit. Those on trial were convicted and sentenced.The Sydney Morning Herald; Date: Jan 21, 1983Perry Correctional Institution, Pelzer, South Carolina James Rodney LeonardWilliam Douglas BallewJesse Glenn SmithLeonard, a murderer, Ballew and Smith, who were both armed robbers, fled in a helicopter with a pilot and a woman hijacker with a pistol to a getaway car 4 to 5 miles away. The 3-passenger helicopter was so overloaded with 5 occupants that it barely cleared the fence, while flying away in a hail of gunfire that injured one guard. Two other men attempted to escape as well, but either jumped or were pushed off when the pilot told the escapees that the helicopter could not take off. The three escapees were captured on December 23 in Camden County, Georgia.Cândido Mendes penitentiary, Ilha Grande, Rio de Janeiro José Carlos dos Reis Encina, a.k.a. "Escadinha"Encina, a drug lord, was rescued by José Carlos Gregório, aka "Gordo", who rented the Bell 47 aircraft under the guise of surveying some lands he intended to buy. "Gordo" forced the pilot to land and pick up Encina, who had escaped the prison proper earlier. Encina was recaptured three months later after being shot in a firefight. Prison de la Santé Vaujour had 28 years to serve for attempted murder and armed robbery; this was his fourth escape attempt. He made his way to the roof by threatening guards with a fake pistol and nectarines painted as grenades. On top of the jail he was picked up by his wife Nadine, who had taken helicopter pilot lessons especially for the escape. They landed at a nearby football pitch and fled in a waiting car. Paris-Match published amateur photos of the escape, which was made into a film starring Béatrice Dalle in 1991.Federal Correctional Institution, Dublin, California Ronald J. McIntosh walked away from a minimum security prison on October 28 and then hijacked a helicopter on November 5. He used the helicopter to free Lopez from the prison. Both were later caught on November 15 when they arrived to pick up wedding rings from a California shopping mall. The authorities were monitoring the account McIntosh used to write the check and the police were waiting for them.