They scaled the walls using makeshift ladders, lowered themselves out of windows using bedsheets, dug elaborate tunnels underneath the prison, and even walked right through its massive front gate. While escapes were not a particularly common occurrence at Eastern State Penitentiary, they did happen. Over the course of the prison’s 142 years of operation, the facility saw more than 100 escape attempts, and at least 59 people managed to make it outside Eastern State’s 30-foot-tall (and at least ten-foot-deep) perimeter walls.
Eastern State Penitentiary received its first prisoner in 1829. Just three years later, it would see its first escape when William Hamilton, who worked as the warden’s waiter, lowered himself from the roof of the front building. Perhaps the most well-known escape attempt came in 1945 when “Slick Willie” Sutton – notorious for robbing banks – along with Clarence Klinedinst – who worked repairing masonry – and 10 other prisoners breached the walls by crawling through a prisoner-dug tunnel that went almost 100 feet underground.
While escape attempts were not a common occurrence, truly successful escapes from the penitentiary were even more unusual. For years, researchers and educators believed that just one person, Leo Callahan, managed to escape Eastern State Penitentiary and evade recapture indefinitely. But with centuries of stories to uncover, we are always making new discoveries. Now, we believe that at least five people escaped Eastern State and remained permanently at large.
Leo Callahan (1923)
Leo Callahan was incarcerated at Eastern State Penitentiary after he was found guilty of assault and battery with intent to kill and sentenced to 18.5 to 24 years. In 1923, Callahan and five other prisoners built a ladder that they used to scale the east wall of the penitentiary after subduing two guards. His five accomplices were all eventually recaptured — including one who made it as far as Honolulu, Hawaii — but Callahan was never found. For years, Eastern State researchers believed Callahan was the only person to ever successfully escape from Eastern State; however, we now know that wasn't the case.
Bernard Teese (1838)
Bernard Teese was two years into a three-year sentence for horse stealing when he escaped on August 27, 1838. Bernard succeeded in opening his cell door and made his escape over the penitentiary’s perimeter wall. In January 1839, the warden noted that: “I have taken much trouble and spent more than $100 in endeavoring to trace and take him, but without the least success.” His records list his method of discharge as “escaped.” In addition, documents like his father’s will, written in 1843, suggest his family members never saw him again.
Patrick Lafferty (1866)
Patrick Lafferty managed to walk right through the front gate. Seven years into a 12-year sentence for second-degree murder at Eastern State Penitentiary, he escaped on November 6, 1866. The warden wrote that Patrick had: “…dressed himself in a suit of clothes belonging to a prisoner…going out on expiration of sentence and was permitted by said Officer Caines to pass out.” The warden dispatched officers to search for Lafferty throughout the city and adjacent districts without success.
James Stewart (1892)
After serving only one week of a four year and 11 months’ sentence for robbery, James Stewart was ordered back to court to receive an additional sentence. After stepping off the trolley car, Stewart broke away from the Warden and an Overseer accompanying him. Newspapers record that he had not been handcuffed and easily outdistanced the officials. The Philadelphia Record reported in May 1893 that he stowed away on a ship bound for England.
Timothy Boyle (1877)
Timothy Boyle worked in the bakery and used that to his advantage when he escaped on December 31, 1877. With the help of two other bakery workers, Boyle concealed himself in an empty cask that was on a wagon leaving the prison. He was nearly two years into a 12-year sentence for second-degree murder. The driver of the wagon returned to the prison and told staff that, upon reaching his destination, he found the rear cask empty and laying open in the wagon. The Philadelphia Inquirer was among the national media outlets that covered the escape, and Boyle’s story continued to make headlines for years to come. Two years after the event, the Harrisburg Daily Independent claimed he “made his escape to Europe.”
We will probably never know what happened to these five individuals who managed to get out of Eastern State Penitentiary and stay out. And as this discovery goes to show, it’s impossible to predict everything we might learn as we continue to research Eastern State’s history and uncover the stories of people who lived and worked here. But one thing’s for certain, our archives will always continue to surprise us!
