Of the 109 escapees, 59 succeeded in reaching Union lines, 48 were recaptured, and 2 drowned in the nearby James River.
Escapes were regular occurrences at both Federal and Confederate prisons. John Bray's (First New Jersey Cavalry) account of his own escape from Libby Prsion can be found at the CivilWarSources site.
At the outbreak of the Civil War, Luther Libby was running a ship supply shop from the corner of a large warehouse in Richmond. In need of a new prison for captured Union officers, Confederate soldiers gave Libby 48 hours to evacuate his property.. The sign over the north-west corner reading "L. Libby & Son, Ship Chandlers" was never removed, and consequently the building and prison bore his name. Since the Confederates believed the building inescapable, the staff considered their job relatively easy.
The first floor of Libby Prison housed the various offices of the Confederate guard unit; the second and third floors were partitioned as inmate holding areas. The basement of the prison was divided into three sections. The western end was a storage cellar, the middle section was a carpenter’s shop used by civilians, and the eastern end was an abandoned kitchen. This kitchen in the eastern section was once used by Union inmates, but an infestation of rats and constant flooding compelled the Confederates to close it off. The abandoned area became known as "Rat Hell."
Though most of the prisoners (and guards alike) did what they could to avoid Rat Hell, a handful of Union officers schemed to break in. By removing a stove on the first floor and chipping their way into the adjoining chimney, the officers constructed a cramped but effective passage for access to the eastern basement. Once access between the two floors was established, the officers set about plans to tunnel their way out.
The floor of Rat Hell was covered in two feet of straw. This straw was a bane and a blessing for the officers. On one hand, it provided a perfect hiding place for the dirt excavated from the tunnel. Captain I. N. Johnston, who spent more time in Rat Hell than any other Union officer, commented, "I have been asked a thousand times how we contrived to hide such a quantity of earth as the digging of a tunnel of that size would dislodge. [On the floor] we made a wide and deep opening...in this the loose dirt was closely packed, and then nicely covered with straw. By such means, the Union officers were able to conceal all signs of the tunnel that might tip off civilians and wandering sentries. The straw in Rat Hell also provided a convenient hiding place for workers during the day.
One man was chosen to secrete all signs of the tunnel while the digging party scrambled up to the first floor. He would then remain buried in the straw for the remainder of the day until the next relief arrived at dusk. Johnston wrote, "...There was a large quantity [of straw] there, and but for which our undertaking must have been discovered nearly as soon as begun. As helpful as the straw might have been, it was nevertheless the main reason for the nickname, Rat Hell. Lt. Charles H. Moran, a recaptured officer from Libby, wrote, “No tongue can tell...how the poor fellow[s] passed among the squealing rats,—enduring the sickening air, the deathly chill, the horrible interminable darkness.”
Major A. G. Hamilton, a leading founder of the escape party, pointed to the dilemma of the rats: "The only difficulties experienced [were lack of proper tools] and the unpleasant feature of having to hear hundreds of rats squeal all the time, while they ran over the diggers almost without a sign of fear. Colonel Thomas E. Rose, the leader of the escape, addressed the double-edged lack of light in Rat Hell: "The profound darkness caused some...to become bewildered when they attempted to move about. I sometimes had to feel all over the cellar to gather up the men that were lost. Despite the difficulties, the dark repugnant atmosphere of Rat Hell offered the most effective cover. "On rare occasions, guards entered the large basement rooms. 'This was, however, so uninviting a place, that the Confederates made this visit as brief as nominal compliance with their orders permitted.'
Union officers meandering through the streets of Richmond late at night might appear to be a leg of the plan doomed to failure, however, the guards simply did not expect that escape from Libby prison was possible. The fact that the Libby guards were not looking for signs of escape meant that they were in a position to be more easily deceived. Union Army Lieutenant Moran described how the sentries were not interested in stopping people outside the bounds of their jurisdiction, “provided, of course, that the retreating form...were not recognized as Yankees.” The tunnel provided enough distance from the prison to stealthily subvert those jurisdictional lines and allow prisoners to slip into the dark streets unchallenged.
So effective was this buffer that 109 men escaped the prison without ever being stopped. At one point, Colonel Rose walked straight into the path of an oncoming sentinel. Unflinching, he “strode boldly past the guard unchallenged.” Even more amazing, once news of the escape way broke out among the prisoners a panicked rush resulted, creating a thunderous stampede for the tunnel. Wholly unsuspecting of the reality of the situation, one Confederate guard yelled out to a fellow sentry, “Halloa, Bill—there’s somebody’s coffeepot upset, sure!”
Despite the stampeding of prisoners, strong senior officers such as Colonel H.C. Hobart had the sense of mind to tie off the flow of escapees before dawn’s light. “The remaining prisoners replaced the bricks at the fireplace, and the guards began their morning routine, unaware that 109 escaped Union officers were making their way toward the Federal lines.” Keeping the escape secret from the Confederate guards until the last possible moment gave the evading inmates what they needed most: time. After the morning roll call came up over a hundred short, the Confederates counted frantically several more times to ensure that the Yankees weren’t pulling a trick. Such “tricks” had occurred on many occasions when men slipped in and out of the counting lines; this “repeating” was a mild prank often used to frustrate the Confederates at roll call, much to the glee of the Union prisoners.
On the morning of 10 February, the Confederates realized that this was no trick. By this time, the first prisoners had been loose for nearly twelve hours. Frenzy broke out among the Confederates: “Messengers and dispatches were soon flying in all directions, and all the horse, foot, and dragoons of Richmond were in pursuit of the fugitives before noon.” Despite the mobilization of Richmond, almost 17 hours passed before the Confederates could respond. This no doubt added greatly to the window of opportunity that helped 59 men reach Union lines. The Richmond Enquirer of 11 February, 1864 ,expressed such a sentiment: “...It is feared that [the fugitives] have gotten rather too much the start of the pursuers to admit anything like the recapture of them all.”
Just as slaves had been following the North Star to envisioned freedom, it also guided escaped Union prisoners from Libby in 1864. Most of the prisoners made reference to following the North Star, such as Captain Johnston who wrote, “I...started due north, taking the north star for my guide, changing my course only when [I] came near any of the [Rebel] camps.” Familiarity with the terrain and the guidance of the North Star played a large part in the success rate of the Libby prisoners.
Rose and Hamilton worked tirelessly together to bring about the escape. It was Rose who thought of breaking into the basement from the chimney and Hamilton who engineered the passage. Rose toiled feverishly in the tunnel and organized digging teams while Hamilton worked out the logistics and invented contraptions for removing dirt and supplying oxygen to the tunnel. The incredible success at Libby Prison was no less a direct result of the determination of these two men than any other factor. Various setbacks plagued the tunneling effort but as Lieutenant Moran recorded, “the undaunted Rose, aided by Hamilton, [always] persuaded the men to another effort, and soon the knives and toy saws were at work again with vigor.” Lieutenant Colonel F. F. Cavada, a prisoner at Libby, wrote, “To Colonel Rose is chiefly due the credit [for the escape]...Animated by an unflinching earnestness of purpose, unwearying perseverance, and no ordinary engineering abilities, he organized...working parties [which] he conducted every night [in] the cellars of the prison.” Hamilton said of his partner: “[Rose] was the acknowledged leader of the tunnel party, the acknowledged projector of the tunnel, and it was through his good sense, energy, and management...that the escape was a success.” In an ironic twist, Rose was not one of the 59 who succeeded in reaching Federal lines. Minutes from an advancing Union front at Williamsburg, he was ambushed by Confederate pickets and wrestled back to Libby Prison. Though placed in solitary confinement, the Confederates felt Colonel Rose’s presence at Libby was too dangerous. Given the chance, they gladly traded the famed escapist for a Confederate colonel on 30 April, 1864. Rose returned to his unit, the 77th Pennsylvania Volunteers, and fought through to the end of the war.