The Mammoth Book of Prison Breaks

by Paul Simpson

Sources:

  Daily Richmond Examiner, 11 February 1864: “Escape Of One Hundred And Nine Commissioned Yankee Officers From The Libby Prison”

  Richmond Enquirer, 11 February 1864: “Extraordinary Escape From The Libby Prison”

  Richmond Enquirer, 12 February 1864: “The Recent Escape from the Libby Prison – Recapture of Twenty Two Officers”

  Richmond Enquirer, 13 February 1864: “Recapture Of More Yankee Officers”

  Richmond Examiner, 15 February 1864: “The Re-Captured Yankee Officers”

  Richmond Sentinel, 20 February 1864: “More Capture of Escaped Yankees”

  Harper’s New Monthly Magazine, April 1864: “My Escape from Richmond”

  Moran, Frank E., Famous Adventures and Prison Escapes of the Civil War (The Century Co., 1898)

  National Tribune, 14 May 1885: “Libby Tunnel”

  Civil War Richmond: http://www.mdgorman.com/index.html (An invaluable resource, with all of the contemporary news reports, many of which were referenced for this piece; the ones listed above are those from which specific details and anecdotes were taken.)

  This Room For Rent

  One of the largest mass escapes of the twentieth century occurred in Uruguay over forty years ago when over a hundred members of revolutionary group the Tupamaros tunnelled out of the Punta Carretas federal prison in the capital, Montevideo, leaving behind them a set of cheeky signs to taunt their guards. It was in keeping with the Robin Hood-like roots of the organization – and perhaps there’s a certain appropriateness to the fact that twenty years after the escape, the prison was turned into one of Uruguay’s most prestigious shopping malls. A McDonalds restaurant now resides in the feared prison administration building.

  The Tupamaros were founded in the early 1960s by Raul Sendic, a former law student who had qualified as an attorney, but not quite finished his legal studies during the 1950s. He had become prominent in the Socialist Party of Uruguay, and took a great interest in the plight of the sugar-cane workers, helping to organize them into unions, and arranging marches on Montevideo. Their motto was “Por la tierra y con Sendic” (For the land and with Sendic), a slogan that was ironically left at the prison end of the tunnel that Sendic would organize while within Punta Carreta.

  When the marchers were suppressed by the government forces, Sendic decided that the only way that the workers would receive what they were due was if the government were forced to listen to them. The success of Fidel Castro’s revolution in Cuba inspired Sendic, and a robbery at the Swiss Gun Club in Colonia in 1963 is usually seen as the start of the armed conflict and the birth of the Movimiento de Liberación Nacional Tupamaros. The group was named after Tupac Amaro, the last leader of the Incas in the sixteenth century, who had waged war against the invading Spaniards.

  During the rest of the 1960s, the Tupamaros had a mixed reputation. They were renowned for redistributing food and money to the poor, but they were also responsible for bombings, kidnapping and murder. After a shootout between Tupamaros and the police in 1966, the revolutionaries were arrested or forced to go into hiding, either in Uruguay, or in Cuba, where some of them were trained in military techniques. A state of emergency and martial law was declared in Uruguay in June 1968, and the Tupamaros gained some sympathy from the public since they were fighting the repressive measures.

  In July 1970, the Tupamaros kidnapped Dan Mitrione, an American FBI agent and specialist in torture who was in the country to train the Uruguayan police in interrogation techniques. They offered him in exchange for 150 prisoners, but when the authorities refused, the Tupamaros shot him. This didn’t go down well, particularly as Mitrione was a father of nine.

  Mitrione’s death may have been a direct result of the arrest of Sendic and other Tupamaros leaders on 7 August. “Those captured lost all contact with the others,” Sendic later told the New York Times, “and when the deadline came the group that was left with Mitrione did not know what to do. So they decided to carry out the threat.”

  Sendic and many of his fellow Tupamaros were sent to the Punta Carretas prison, which had been built in the early twentieth century. Conditions there, while not comfortable, certainly weren’t as bad as in some South American prisons. The Tupamaros quickly took control, exerting pressure on the warden to keep things relatively easy (snap inspections of cells were stopped because it made the prisoners nervous, for example), and bribing guards to arrange for food and other items to be brought in. The inmates were allowed to gamble and buy lottery tickets.

  According to Arturo Dubra, one of the key people involved in the tunnel, there never was any doubt that the Tupamaros would escape from Punta Carretas. They considered taking over the prison but that was dismissed because it would have been “very bloody” since they would have had to come in shooting, and deal with the sixty to eighty army soldiers who patrolled the outside walls. When they realized that there was no way to capture it without violence, an alternative was sought.

  The cells were basic, made of eighteen-inch-thick brick blocks, with wood and metal doors, and it didn’t take long before the prisoners discovered that they could remove the bricks between cells by using wires obtained from the woodwork classes to remove the mortar. A throughway between cells was created, and they even managed to create a vertical passage by digging through the floors and ceilings, and putting in a disguised hatch. They got rid of the dust from the mortar down the toilet, or out on the football field where they were allowed to exercise regularly, and replaced the mortar with plaster that had been brought into the prison in bags of “flour”.

  Now all they needed to do was dig a tunnel.

  The Tupamaros in Punta Carretas were encouraged by the escape of women from their ranks who had been held at the Cabildo women’s prison. A year earlier, thirteen of their comrades had walked out of Cabildo after mass; this time thirty-eight women would risk their lives. They planned it carefully: a cypher system of communication was devised based on copies of Don Quixote, using numbers rolled in cigarette papers and pills, and a novel about the Jewish resistance in Warsaw inspired them to check out the local sewer system. On 31 July, the women travelled through a tunnel to the sewers, and from there to a nearby house where they changed and disappeared into the Uruguayan underground, some of them for many years.

  In the lead-up to the escape from Punta Carretas, which was codenamed “El Abuso” (the women’s escape had been known as “Operación Estrella”), plans for the prison were smuggled in, torn up into small pieces and then put in small capsules: some of these were passed orally between wives and husbands when they embraced at visiting time; others had a rather longer passage through the prisoners’ insides! One of the Tupamaros had lived for a time in the sewers, mapping them out, so knew roughly what was beneath the streets beside the prison. Arrangements were made to transfer prisoners whose sentences were coming close to their end into cells on the opposite side of the hallway from where the tunnel would begin. By the time that the escape took place, all of the Tupamaros who would be departing from the prison were therefore on the second and third floors of the prison, with access via the hatch to the ground floor. The cell from which they were going to dig was used by “common” (i.e. non-political) prisoners, and the Tupamaros struck a deal with them to allow use of the cell – the six men could join in the escape.

  Intricate plans were drawn up to deal with the dirt from the tunnel. The men suddenly decided that they were going to become obsessed with hygiene. They got permission to put curtains around the toilets in the cells, and bed skirts on the beds. Linens brought in from outside were sewn up to create bags.

  The tunnel took sixteen days to dig, using modified soap dishes and tools made from bed frames. The digger at the front would loosen the dirt and rocks and pass it back down to another man, who would drag it in a cart to the surface. From there it was put in the bags, and trodden down to remove excess air. These were then hidden behind the curtains in the toilets, or underneath the beds. Dirt was also stored inside an inte
rsecting tunnel that had been built for an escape in 1931 that had never been filled in.

  Air came from a makeshift plastic and cardboard bellows, which pumped air down a tube of taped-together cardboard tubes and rolled-up magazines. Unsurprisingly, it wasn’t that effective, and when the tunnel reached the level of the sewer, a hole was cut through to allow some (albeit fetid) air in from there. (There was no point trying to head out through the sewers: after the women’s escape, the police were patrolling them regularly.)

  The two-foot-square tunnel passed beneath the prison walls, under Solano Garcia street, towards the living room of a house belonging to Billy Rial Castillo, a Mormon missionary, measuring nearly 130 feet in total. Around seven o’clock on the evening of Sunday 5 September, Rial opened the door to find a well-dressed young man standing there. When he asked what he wanted, the man pulled out a pistol and told him, “Stay calm. I am a Tupamaro and we are going to use your house.” At first Rial thought it was a joke, but when he saw a second armed man approaching, he realized it was serious. The Tupamaros went into the living room and knelt down on the floor, listening carefully through a doctor’s stethoscope. At the same time, a Volkswagen van drew up outside the house next door: the six Tupamaros inside took over that house too, brought in a dozen suitcases filled with arms, clothing, money and false papers, and knocked a hole through the adjoining wall into the Rials’ home. Elsewhere in the city, at La Teja, other Tupamaros kicked up a fuss, overturning cars and burning tyres in the street, which drew the police away from the prison area.

  The escape had to take place that night. The truce which the Tupamaros had agreed with the prison governor regarding cell inspections expired the next day, and all of their hard work would have been for nothing. At 10 p.m., as soon as the lights were switched off for the night, the call “Abuso” was passed between the cells. The inmates who were going to escape all started to gather in the end cells, by the mouth of the tunnel. However, around eleven o’clock, one of the common prisoners started to make a fuss, complaining of toothache. The Tupamaros suspected that he was doing it deliberately to draw the guards’ attention, and one of the doctors quickly returned to his cell, since he knew that the guards would come to him for a painkiller. He was able to pass the pill through his cell door hatch and stood carefully to ensure that the guard couldn’t see past him to the disrupted cell walls.

  Even once that had been sorted out, everything didn’t go that smoothly. The tunnel didn’t quite extend far enough: the houses were three feet higher than they had anticipated. Around midnight, the diggers frantically tapped to get their comrades’ attention in the Rial living room, but the sound was so indistinct that the Tupamaros inside the house had to dig up most of the floor trying to find the source of the noise, which had become muffled by the earth between them. Eventually, after hours of increasingly desperate searching, they were able to break through in the right place, although it meant that the escaping prisoners, led by Raul Sendic, had to be hoisted out of the tunnel through a sixteen by twenty inch hole – which caused problems for one inmate who had a deformed arm, and thus had to be pulled up by the other arm.

  By this time, the Tupamaros had a number of hostages to deal with, as well as processing the escapees. Rial’s mother, his girlfriend and a couple of neighbours all came to the house during the evening, and were taken prisoner, although none of them complained about being badly handled by the Tupamaros – in fact, speaking to the press straight after the incident, Rial said they were treated “correctly”.

  As each of the 111 escapees exited the tunnel, they took off their prison jumpsuits, which they left in a pile, and were given a survival kit with the false IDs, a revolver and the equivalent of around ten US dollars. They were then sent through to the neighbouring house where they were divided into groups and taken by trucks and vans to cars waiting around the city. From there they fled into hiding. Because they were running late, one group missed their rendezvous, and the truck driver hid them in his home outside Montevideo overnight, then brought them back into town once fresh arrangements had been made – passing through roadblocks that were checking all outgoing vehicles!

  Shortly after 4 a.m., the last inmate had come through the tunnel, and the Tupamaros released the Rial family. As soon as their captors had left, Billy Rial called the police to alert them that the Tupamaros had escaped from the prison through his house. The police didn’t believe him, but said they’d call the prison to check. To Rial’s disbelief, a few minutes later, the policeman said, “Everything is tranquil at the prison.” Rial went outside his front door, and called up to the guards on the prison walls, “The Tupamaros escaped!” Still there was no reaction. Finally, around 5 a.m., a police truck came to check on Rial’s story, and the guards inside the prison then checked the cells, finding the perforated walls, the bags of dirt under the beds and in the toilets. Notices had been left behind: “This room for rent. Good references required,” ran one. “MLN-Transit Authority – keep left,” was posted at the entrance to the tunnel. “Through the ground with Sendic” was a rewrite of the Tupamaros’ original motto.

  A manhunt was set up, but by that time the Tupamaros had dispersed. Heads rolled quickly. The prison governor resigned before he could be sacked. The government fired Colonel Pascual Cirilo, the director general of the prison service, the next day; he was tried before a military court of honour, although the results were never announced. Both the Interior Minister and the Defence Minister offered their resignations. Many guards and other officials were dismissed following charges of bribery, inefficiency and corruption. Three days later, the Tupamaros issued a press release explaining that as a result of the escapes from both Cabildo and Punta Carretas, they had decided to release one of their key political hostages, the British Ambassador to Uruguay, Geoffrey Jackson, after eight months.

  This helped to rehabilitate the Tupamaros’ reputation with the public, but not with the authorities. Uruguayan President Jorge Pacheco was running in the elections that November on a platform of law and order, and he turned the hunt for them over to the military. While some of the escapees were captured as a result of the arrest two weeks later of one of the five common prisoners who had been allowed to accompany the Tupamaros, many were caught up in the wide net thrown by their pursuers.

  So they promptly decided to escape again. On 12 April 1972, fifteen Tupamaros, as well as ten common criminals, broke out of Punta Carretas through a tunnel that had been dug from the city sewers to a spot beneath the dentist’s office. Around seven o’clock, Jose Mujica Cordano, one of the Tupamaro leaders, and the other twenty-four prisoners filed into the office, apparently needing treatment. Once they had all assembled, they overpowered the dentist and several guards using knives that they had made from spoons. They then lifted a steel grating in the floor, which gave them access to the tunnel dug from the outside by their colleagues.

  To make sure the inmates weren’t followed, the Tupamaros had thoughtfully provided their colleagues with some explosive booby traps which they could leave behind them. The guards following them spotted these in time, and called the Army in to defuse them, but by the time they could proceed down the tunnel, the Tupamaros had reached the sewer system beneath a large residential area, which gave them multiple exit routes. Despite an extensive search of the area by police and the Army, none of them was caught immediately.

  The new president, Juan M. Bordaberry, was angered and embarrassed by this escape, and redoubled the efforts against the Tupamaros. By the end of 1972, the entire Tupamaros leadership was back behind bars, with nine of them held as hostages by the government: if the Tupamaros continued their fight, then the hostages would be killed. Sendic was shot in the face when he was recaptured in September 1972. Only after the fall of the dictatorship in 1985 were the Tupamaros released from prison, and allowed to form a political party. Sendic died of cancer in 1989; other Tupamaros involved in the escape went on to achieve political success, including Arturo Dubra, Fernandez Huidobro and Jos
e Mujica.

  The escape itself was listed for many years as one of the Greatest Jail Breaks in the Guinness Book of World Records.

  Sources:

  Delta Democrat Times, 7 September 1971: “‘Everything calm’ with 111 inmates gone”

  St Petersburg Times, 7 September 1971: “Tupamaros Pull Mass Escape”

  Schenectady Gazette, 13 April 1972: “Tupamaros Free 25 at Uruguay Prison”

  Oxford Companion to Military History

  Latin America News Dispatch, 21 December 2009: “Burying the Past? Former Uruguyan Prison Becomes Shopping Mall”

  RadioAmbulante blog, 31 July 2012: “Escape from Cabildo”

  New York Times, 29 April 1989: “Obituary: Raul Sendic, 64, Founder of Uruguay Rebel Group”

  Northwest Review, 1 January 2007: “The Great Escape”

  Time magazine, 20 September 2007: “The Tupamaros Tunnel Out”

  The Darkest Day

  Described by Oklahoma Governor David Boren as he declared a week-long state-wide period of mourning as “the worst single tragedy in the forty-year history of this outstanding law enforcement agency”, the deaths of three Oklahoma state troopers marked the end of a manhunt for two fugitives who crossed multiple state boundaries. Ten people – including escapees Claude Eugene Dennis and Michael Charles Lancaster – died as a result of the escape from the Oklahoma State Penitentiary (OSP) in April 1978; the town of Caddo has never been the same subsequently.

  The riots at the OSP in 1973 had left millions of dollars’ worth of damage, not all of which had been cleared up by the time of Dennis and Lancaster’s escape five years later. Dennis had been arrested following the discovery of the bodies of John Witt and Mary Litrell in a farmhouse on 31 January 1975 in the small village of Doyle, not far from Marlow, Oklahoma. They were the new tenants of the farm, which had previously been owned by Dennis. Although he tried to claim self-defence, and went through various appeals to try to gain a verdict which would mean a lesser sentence, he was found guilty of first-degree manslaughter and sentenced to fifty years’ imprisonment. He was also found guilty of a separate offence, the second-degree murder of Arthur Lake in Bryan County, Oklahoma; he had in fact originally been picked up by the sheriff’s department investigating this crime, rather than the deaths of Witt and Litrell, and maintained that he had been framed for this crime by the sheriff.