Libby Prison Escape The Libby Prison Escape was one of the most famous ( and successful ) prison break s during the American Civil War . Overnight between February 9 and February 10 , 1864 , more than 100 imprisoned Union soldiers broke out of their prisoner of war building at Libby Prison in Richmond , Virginia . 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 Prison can be found at the CivilWarSources site . Background . At the outbreak of the Civil War , Luther Libby was running a ship supply shop from the corner of a large warehouse in Richmond , Virginia . 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 . Location and layout . Libby Prison encompassed an entire city block in Richmond . To the north lay Cary Street , connecting the prison area to the rest of the city . On the south side ran the James River . The prison itself stood three stories above ground with a basement exposed on the river side . Confederate soldiers whitewashed the outer walls to make lurking prisoners instantly recognizable . 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 . " 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 . ' " Element of surprise . The tunnelers organized into three relief teams with five members each . After 17 days of digging , they succeeded in breaking through to a 50 - foot vacant lot on the eastern side of the prison , resurfacing beneath a tobacco shed inside the grounds of the nearby Kerr ' s Warehouse . When Col . Rose finally broke through to the other side , he told his men that the “ Underground Railroad to God ’ s Country was open ! ” The officers escaped the prison in groups of two and three on the night of February 9 , 1864 . Once within the tobacco shed , the men collected inside the walled warehouse yard and simply strolled out the front gate . 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 ! " Precious time . Another example of how unaware the Confederates were caught is evident in the reaction to the escape . From the " Richmond Examiner " , February 11 , 1864 : " At first it was suspicioned [ sic ] that the night sentinels had been bribed . They were placed under arrest , searched . . . for evidences of their criminality , [ and ] confined in Castle Thunder ( a civilian penitentiary near Libby Prison ) . Upon the testimony afforded by the revelation of the tunnel , the imprisoned guards were at once released and restored to duty . " Despite the stampeding of prisoners , strong senior officers such as Colonel Harrison 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 February 10 , 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 dragoon s 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 February 11 , 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 . " Prior reconnaissance . Though Union Commander George B . McClellan received little more than defeat in the Peninsular Campaign of 1862 , his men received something more . For those who would break out of Libby prison , the time spent studying maps and hoofing ground in Virginia familiarized them with the enemy terrain . Such intelligence was of weighty benefit for the prisoners forging their way back to the Federal lines two years later . From the " Richmond Enquirer " : " It is supposed that the direction taken by them all – if , indeed all have left the city – was towards the Peninsula . . . " Lieutenant Moran , who escaped late in the night , wrote , " I had served with McClellan in the Peninsula campaign of 1862 , I knew the country well from my frequent inspection of war maps , and the friendly north star gave me my bearings . " 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 . Leaders . Colonel Rose and Major Hamilton led the escape efforts . Rose , wounded at the Battle of Chickamauga , arrived at the prison on October 1 , 1863 . From the moment he stepped in the door , he was bent on escape . While exploring the darker regions of Rat Hell , he happened upon Hamilton , who was also searching for a proper tunneling point . Soon fast friends , the two worked toward the successful escape in February . Contemporarily , Libby prisoners showered Rose with admiration and credit for the escape ’ s success . Rose and Hamilton worked tirelessly together to bring about the escape . Rose thought of breaking into the basement from the chimney , while Hamilton 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 . 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 Federico Fernández 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 . " “ [ Rose ] was the acknowledged leader of the tunnel party , the acknowledged projector of the tunnel , " maintained Hamilton , " and it was through his good sense , energy , and management . . . that the escape was a success . " Despite his work in planning the escape , Rose was captured before 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 Rose ’ s presence at Libby now presented a danger . Given the chance , they gladly traded the famed escapist for a Confederate colonel on April 30 , 1864 . Rose returned to his unit , the 77th Pennsylvania Infantry , and fought through to the end of the war . Conclusion . To judge the success of the Libby Prison escape solely by the number of men who crossed Federal lines would be a mistake . Richmond was deeply affected by the break , and Libby Prison itself was thrown into chaos , much to the satisfaction and raised morale of the remaining prisoners . Lieutenant Colonel Cavada recorded some of the more humorous effects of the escape inside the prison . On one occasion , the entire camp was roused in the middle of the night for a roll call because a sentry thought he saw something down in a sewer . It turned out to be his own shadow . Even the Confederate warden , Major Thomas P . Turner , was visibly shaken . Cavada commented , " Really , when our distracted little Commandant now comes into our rooms , he keeps his knees well together , it is necessary to be very cautious , some of us might slip out between his legs ! "