Libby Prison escape
The Libby Prison breakout occurred in February 1864 when more than 100 Union prisoners-of-war escaped from Libby Prison, a Confederate detention facility located in Richmond, Virginia. This event stands as one of the most notable and successful prison escapes during the American Civil War.
Under the leadership of Colonel Thomas E. Rose from the 77th Pennsylvania Infantry, inmates dug a tunnel through an area infested with rats—a section largely avoided by Confederate guards. The tunnel emerged adjacent to a warehouse within an empty lot, enabling escapees to slip out through a gate without attracting attention. Libby Prison was thought to be nearly inescapable, which led to reduced guard vigilance and a delay in raising the alarm for almost 12 hours. More than half of those who fled managed to reach Union territory, assisted by their familiarity with the landscape gained during McClellan’s Peninsula Campaign in 1862.
Background
At the onset of the Civil War, Luther Libby ran a maritime supply business from a warehouse corner in Richmond. When Confederate authorities required a facility to detain Union officers, they gave Libby just two days to vacate the premises. Despite this, the original sign "L. Libby & Son, Ship Chandlers" remained visible and lent its name to the prison. The Confederate personnel believed the structure was secure enough that their responsibilities were straightforward.
Location and layout
Libby Prison occupied an entire city block within Richmond. It was bordered on the north by Cary Street and on the south by the James River. The building rose three stories high with a basement exposed on the river-facing side. Confederate troops painted the outer walls white to make any escaping prisoners more visible.
The ground floor contained offices for Confederate guards, while inmates were housed on the second and third floors. The basement was split into three sections: a storage cellar on the west side, a civilian carpenter’s workshop in the center, and an eastern kitchen that had been abandoned. Union prisoners had previously used this kitchen area but it was closed due to flooding and rat infestations; this section became infamously known as "Rat Hell."
Rat Hell
Although most guards and prisoners steered clear of Rat Hell, a small group of Union officers gained access by removing a stove on the first floor and breaking through an adjoining chimney to reach the basement’s eastern portion. This narrow passageway became critical for their tunneling plans.
The floor was layered with about two feet of straw, which posed both difficulties and advantages. The straw concealed soil excavated from the tunnel, helping prisoners hide evidence of digging from both civilians and sentries. Captain I. N. Johnston, who spent considerable time in Rat Hell, described how they packed loose dirt into a deep cavity beneath the straw and then covered it to avoid detection. During daylight hours, workers could hide beneath this straw layer.
One individual remained concealed under the straw to mask ongoing tunneling activities while others moved above ground. Johnston emphasized that without this straw covering, their efforts would have been uncovered early in the process. However, due to the large number of rats inhabiting this straw-strewn area, it earned its harsh nickname Rat Hell. Lieutenant Charles H. Moran recounted the dreadful conditions: "No tongue can tell... how the poor fellows passed among the squealing rats—enduring sickening air, deathly chill, and interminable darkness."
Major A. G. Hamilton, instrumental in organizing the escape effort, underscored obstacles such as inadequate tools and constant rat noises during excavation work. Colonel Thomas E. Rose, who led the breakout, noted that complete darkness sometimes caused confusion among men moving within Rat Hell. Despite these severe conditions—the foul odor, darkness, and infestations—the environment provided effective concealment; Confederate guards seldom entered this area and stayed only briefly due to its repellent nature.
Element of surprise
The tunnelers organized themselves into three relief squads, each consisting of five men. After 17 days of excavation, they emerged into a 50-foot open area east of the prison, surfacing beneath a tobacco storage shed located on the Kerr's Warehouse property. Upon reaching the exit, Colonel Rose proclaimed that the "Underground Railroad to God's Country was open!" On the night of February 9, 1864, the officers slipped out in small groups of two or three, gathering within the warehouse yard before nonchalantly exiting through the main gate.
Though Union officers roaming Richmond’s streets after dark might appear perilous, Confederate guards did not anticipate escapes originating from Libby Prison. This complacency enabled prisoners to exploit patrol boundaries; sentries paid no attention to individuals outside their designated zones unless identified as Union soldiers. The tunnel’s length provided a sufficient buffer for prisoners to enter the city unnoticed.
This protective distance proved so effective that 109 men escaped without interception. Colonel Rose even passed an approaching guard without challenge. Once word spread among inmates, a frantic surge toward the tunnel ensued, with one Confederate sentry mistaking the commotion for spilled coffee.
Precious time
The Confederates’ ignorance extended to their reaction. The Richmond Examiner (February 11, 1864) reported initial suspicions that guards had been bribed; those accused were detained and searched but released after the tunnel's discovery.
Senior officers such as Colonel Harrison C. Hobart managed the flow of escapees before dawn by sealing off the tunnel and replacing bricks to delay detection. Guards began their morning rounds unaware that 109 Union officers had already fled. Multiple roll calls failed to immediately uncover the mass escape, as prisoners had previously employed counting deceptions.
By the morning of February 10, Confederate forces realized what had occurred. Richmond quickly mobilized—dispatching messengers and deploying troops in pursuit—but nearly 17 hours had elapsed since the breakout began. This delay enabled 59 men to reach Union lines safely. The Richmond Enquirer acknowledged that fugitives had "too much the start" for complete recapture. Ultimately, 48 escapees were apprehended and two drowned in the nearby James River.
Prior reconnaissance
Despite Union Commander George B. McClellan’s defeat during the Peninsular Campaign of 1862, his troops acquired valuable intelligence. Their time spent analyzing maps and surveying Virginia’s terrain provided crucial knowledge for prisoners escaping Libby two years later. The Richmond Enquirer suggested that escapees likely headed toward the Peninsula. Lieutenant Moran, who fled under cover of darkness, recalled his prior service under McClellan and navigated using the North Star.
Much like enslaved individuals who followed the North Star to freedom, Union prisoners escaping in 1864 relied on it for guidance. Captain Johnston recounted beginning due north by referencing the North Star and only adjusting course near Confederate encampments.
Leaders
Colonel Rose and Major Hamilton led the breakout effort. Rose, wounded at the Battle of Chickamauga, arrived at Libby Prison on October 1, 1863, immediately dedicating himself to planning an escape. He met Hamilton in the prison’s lower levels, where they collaborated to construct a successful tunnel by February. Fellow prisoners credited Rose with leadership and resolve.
Rose designed access to the basement via a chimney while Hamilton managed tunnel logistics such as dirt disposal and ventilation systems. Despite challenges, their persistence maintained momentum in digging efforts. Lieutenant Moran commended their tireless work ethic, and Lieutenant Colonel Federico Fernández Cavada attributed Rose’s engineering expertise and organizational skills as key factors in their success. Hamilton recognized Rose as the principal leader whose oversight ensured victory.
Although Rose was captured near advancing Union forces at Williamsburg and returned to Libby Prison, Confederate authorities considered him too dangerous to remain imprisoned there. On April 30, 1864, he was exchanged for a Confederate colonel and rejoined the 77th Pennsylvania Infantry, continuing to fight until war’s conclusion.
Effect
Judging the Libby Prison breakout solely by the count of men who reached Union lines fails to capture its wider significance. The incident caused considerable disruption in Richmond and threw Libby Prison into turmoil, significantly lifting the spirits of those still confined. Lieutenant Colonel Cavada recalled moments of levity, including a midnight headcount prompted when a guard mistakenly identified his own shadow as a threat. Even Confederate warden Major Thomas P. Turner appeared unsettled, with Cavada observing his distracted behavior following the escape.
In popular culture
The daring escape served as the basis for Harry P. Mawson’s 1891 Broadway production A Fair Rebel, which prominently featured the dramatic breakout from Libby Prison. In 1914, a silent film adaptation was released, starring Linda Arvidson, Charles Perley, and Dorothy Gish, under the direction of Frank Powell.
This event was also portrayed in the 25th episode of the 1964 television series The Great Adventure (American TV series), and was included in season 2, episode 7 of History's Greatest Escapes with Morgan Freeman (2024).
References
- Cavada, F.F., Libby Life. Pennsylvania: J.B. Lippincott & Co., 1865.
- Hamilton, A. G., Story of the Famous Tunnel Escape from Libby Prison. Chicago: S. S. Boggs, 1893.
- Johnston, I. N., Four Months in Libby. Cincinnati: Methodist Book Concern, 1893.
- Klee, Brue, "Libby Prison," Civil War Times, February 1999.
- Moran, Frank E., Famous Adventures and Prison Escapes of the Civil War. New York: The Century Co., 1898.
- Morgan, Michael, "Breakout from Rat Hell," Civil War Times, October 1999.
- Richmond Examiner, 11 February 1864.
- Rose, Thomas E., “Libby Tunnel,” National Tribune, 14 May 1885.