Criminal Justice Degrees Guide

The 8 Most Impressive Prison Breaks in History

Prison breaks loom large in pop culture: they’re in movies, TV series, books, even cartoons. It’s the chaos they cause, more than anything, that makes their stories so riveting. It’s also interesting to note that not all prison breaks are created equal. Some of them are escape attempts by hardened criminals (and these never, ever end well), but quite a few others are rooted in political activism or a desire to break free from imprisonment by an enemy combatant. The most notorious escapes of all time were perpetrated by abused men and women in prison camps who just wanted to fight back. No matter where they fall on the spectrum, these prison breaks were all impressive in their own way.

  1. The Great Escape, March 1944: The story of Stalag Luft III, a German-run POW camp in what is now Poland, was immortalized in the 1963 film The Great Escape, but the real story is even more incredible. In late March of 1944, a coalition of Allied troops banded together to break out of the prison, putting into motion a plan that had been working since early 1943. The men dug three tunnels underneath their cabins that shot out into the German countryside, using wood slats from their beds to shore up the holes as they went. They even installed makeshift air pumps to supply oxygen to the men digging (the tunnels were 30 feet below the surface and stretched out a great length), as well as a series of lights to guide the work. Despite weather setbacks, 76 men were able to escape via the tunnel system on a moonless night in March. Of those, 73 were captured, and 50 were executed. The rest were shipped off to other camps. It remains one of the biggest and most daring POW prison breaks in history, involving 200 planned escapees and more than 600 construction workers.
  2. Alcatraz, June 1962: The fantasies of Michael Bay notwithstanding, nobody ever made it off the Rock alive. There’s only been one possibly successful escape attempt, and it came in June 1962. After three dozen inmates had made 14 unsuccessful attempts, four men — Frank Morris, Allen West, and brothers Clarence and John Anglin — banded together and got closer than anyone else ever had to realizing their freedom. On June 11, Morris and the Anglin brothers escaped through holes they’d cut in the walls of their cells, climbed to the roof, and entered a raft fashioned from prison-issue raincoats and rubber cement. West wasn’t able to get out of his room in time and was left behind by the others, so he returned to his cell and eventually revealed all the details to investigators. (He was subsequently never charged with trying to escape.) Despite an investigation of the area, the men were never found, leading officials to surmise that the men drowned while trying to make it to shore. No one really knows, though.
  3. Maze Prison, September 1983: This is the largest prison escape in British history, and it’s actually known as "the Great Escape" to Irish republicans and others sympathetic to their cause. Her Majesty’s Prison Maze closed in 2000, but the Northern Ireland prison ran for almost 30 years, and the maximum-security prison was mostly devoted to housing inmates related to the constititional battles of Northern Ireland known as the Troubles. The Troubles themselves saw a number of escapes, but the Maze breakout was by far the biggest. On September 25, a pair of prisoners used guns that they’d had smuggled in to take over one of the prison blocks, holding guards hostage to prevent an alarm from being sounded. They stole guard uniforms and eventually worked their way en masse to the gate. A few were eventually stopped, but 35 men breached the perimeter and got out. Some were caught within a day, and over the next two decades, many more would die in paramilitary ops or find themselves caught and returned to prison. By 2003, only two escapees remained at large.
  4. John B. Connally Unit, December 2000: The John B. Connally Unit is a maximum-security prison in Kenedy, Texas, about 60 miles southeast of San Antonio. It’s basically the middle of nowhere. George Rivas, who was 30 at the time, was serving 18 consecutive sentences (each 15-years to life) for kidnapping and burglary he’d committed in El Paso. He became the ringleader of a group that would be known as the Texas Seven when they staged an escape and went on the run. On the morning of December 13, Rivas and the other men physically overpowered 16 other people, including guards, civilian maintenance men, and even three other prisoners not involved with the plan. As their hostages grew, the Seven took their clothes and cash. They made their way down and out to a maintenance truck and drove off. A crime spree followed, ranging from San Antonio up to Dallas and then into Colorado as the men kept running. Tips eventually led to the capture of the runaways, one of whom killed himself before being captured. They were all returned to prison and sentenced to death, and one of them has already been executed.
  5. Sobibor, October 1943: The Polish village of Sobibor was home to a gruesome death camp in World War II. It’s estimated by some sources that more than 200,000 Jewish citizens were executed there during the war. Yet for all its horror, the camp was the site of one of the few successful uprising and prison breaks in the war. On October 14, 1943, a pair of Jewish prisoners managed to kill almost a dozen SS members and a few guards as part of a plan to weaken the camp’s infrastructure and allow an open revolt. The plan originally called for a more stealthy overthrow, but the dead Germans were soon discovered, at which point about half of the camp’s 600 prisoners fled into the forest. Many were soon caught by guard teams or met their fate on nearby minefields, though at least 50 of them outlived the war.
  6. Libby Prison, February 1864: Prison breaks in the Civil War were obviously far different in their planning and execution than those today. Modern prisons have high-quality cameras, multiple lockdown points, and guards with hevay firepower; tech in the mid-19th century was decidedly less capable. For this reason, prison breaks were actually pretty common during the Civil War, though most were smaller than the breakout staged at Virginia’s Libby Prison, a Confederate camp that housed hundreds of Union soldiers. Over time, prisoners tunneled out through a room that had grown infested with rats and padded with straw. By February 9, the tunnel was done, and men crawled through and then sauntered out of the camp. The casual manner and distance fooled the Confederate guards. All told, 109 men escaped, with 48 being recaptured, two drowning in a nearby river, and 59 successfully making it back to Union territory.
  7. Crown Point County Jail, January 1934: John Dillinger was nothing if not bold. He was already an established criminal by the time he and some of his men were caught in late 1933. Dillinger was sent to Indiana and placed in a jail in Crown Point to stand trial for murder and other crimes. Police and officials bragged that the prison was escape-proof, which is pretty much all the invitation Dillinger needed to break out. His lawyer smuggled in a wooden prop gun, and using that, Dillinger was able to get the drop on a pair of guards and get them to release him before they knew the weapon was fake. He stole the sheriff’s car and drove away to Chicago. It was a daring, brash escape that cemented Dillinger’s reputation, but it was also the beginning of the end. He would be dead by July 1934, shot outside a movie theater by federal agents.
  8. Mecklenburg Correctional Center, May 1984: Currently a medium-security facility, Virginia’s Mecklenburg Correctional Center began its life as a maximum-security prison intended to house the worst of the worst, and for a while it was the location of the state’s male death row inmates. In May 1984, six of those death row inmates made a break for it by taking advantage of guards who had grown inattentive. They overpowered guards, took control of the block, and bluffed their way out the gate by claiming to have a bomb. Two of the group, brothers James and Linwood Briley, were doing time after carrying out a killing spree in 1979. The six men parted ways once they crossed into North Carolina, but as is usually the case, they were eventually picked up and pinned down by cops who were actively searching for them. All six men were soon returned to prison, and between fall 1984 and December 1996, they were executed.