There’s an interesting truth about prisons that many people don’t realize: escaping them is incredibly difficult. These facilities are designed to keep people in, with layers of security like guards, walls, and advanced surveillance technology. Despite these challenges, countless inmates attempt to break free every year. However, most of these attempts fail spectacularly. Here are ten of the best examples of prison breaks that went horribly wrong.
The Tunnel to Hell
Richard Matt and David Sweat gained notoriety for their elaborate 2015 escape from the Clinton Correctional Facility. With the help of prison staff who smuggled in chisels and drills hidden in hamburger meat, they meticulously dug a tunnel leading to a drainage pipe. Their escape drew comparisons to “The Shawshank Redemption.” However, unlike the movie, their freedom was short-lived. Matt was shot and killed, while Sweat was captured and faced additional penalties, including a hefty bill for prison repairs.
Dillinger Escape Plan
John Dillinger, a notorious gangster, successfully escaped from prison twice, which significantly impacted his fate. In March 1934, he famously escaped from Lake County Jail using a wooden gun he carved himself. This successful escape, however, led authorities to decide against taking him alive if he were ever caught again. Consequently, in July of the same year, Dillinger was fatally shot outside Chicago’s Biograph Theater, marking a violent end to his life of crime.
Caught White-Handed
In 2013, Kenneth Burnum attempted a daring escape from Hamilton County Jail in Tennessee by impersonating another inmate who was scheduled for release. He signed the paperwork and claimed the other inmate’s belongings, but his plan fell apart when officers noticed a glaring discrepancy: the inmate to be released was Black, while Burnum was White. This simple but critical oversight resulted in Burnum’s capture and an extended prison sentence.
Finally: the Guard’s Cabin
James Edward Russell, serving time at the Olympic Corrections Center in Washington, successfully escaped into the surrounding woods in 2011. Seeking help, he knocked on the door of a nearby cabin to ask to use the phone, but unbeknownst to him, the cabin was rented by a guard from the very facility he had just escaped. Still wearing his prison uniform, Russell was quickly apprehended and transferred to a higher-security prison.
Officer Gravity on the Case
Jessica Boomershine, imprisoned for kidnapping and robbing an elderly man, attempted to escape a holding room in the Prosecutor’s Office by climbing into the ceiling. Unfortunately for her, the ceiling tiles gave way, and she fell directly into a trash can below. This humiliating end to her escape attempt seemed almost poetic, considering her crime.
What a Garbage Plan
Sidney da Cruz and Carlos Pereira tried to escape the Delegacia de Furtos jail in Brazil by hiding in garbage bags during the lunch break. Their plan was foiled when a corrections officer noticed the bags shaking. The officer recounted finding the two inmates disguised as trash bags, proving that remaining still is a key component of pretending to be garbage.
The Daughter Mask
Clauvino da Silva, a leader of a drug trafficking group, attempted to escape from a high-security prison in Brazil by dressing up as his daughter. He wore a mask of her face and her clothes, hoping to walk out the front door during a visitation. The plan was uncovered, and Silva was caught, leading to a humorous scene as guards made him re-don the disguise while they laughed at the absurdity of his failed escape.
Half Ain’t Bad, I Guess
In 1864, 109 Union POWs attempted a massive prison break from the Confederate Libby Prison. While 59 of the escapees made it to Union lines, the remaining 50 faced dire consequences. Two drowned, and most of the rest were transferred to the infamous Andersonville Prison, known for its horrific conditions. This escape attempt highlighted the desperation and dangers faced by prisoners of war during the Civil War.
Ted Bundy… Succeeds
Ted Bundy’s successful escape from prison had tragic consequences. After his escape, Bundy committed more violent crimes, including the murders of two young women. His ability to evade capture for months led to further suffering and cemented his legacy as one of history’s most notorious serial killers.
Can You Escape Alcatraz?
The 1962 Alcatraz escape by Clarence Anglin, John Anglin, and Frank Morris remains one of the most famous and debated prison escape attempts. The inmates meticulously carved holes in their cell walls and slipped out of the building, launching a homemade raft into the San Francisco Bay. The FBI couldn’t confirm whether the men survived the frigid waters, and sightings have been reported over the years, but their fate remains a mystery, adding to the mystique of Alcatraz.
These stories of failed prison breaks remind us of the high stakes and desperate measures some people take in their quest for freedom. From the comical to the tragic, these attempts offer a glimpse into the world of prisons and the human spirit’s unyielding desire for liberty.
Which escape attempt did you find the most unbelievable? Leave your comment below!
