The greatest prison camp escape in American history took place at Libby Prison in Richmond, Virginia, in February 1864.  On a cold winter night, 109 Union officers crawled through a suffocating, claustrophobic tunnel from a Confederate hell-hole to an empty lot near the building, and from there tried to make their way through hostile country to Union lines more than fifty miles away.  Many of them won their freedom, but many were recaptured and sent right back to prison. 

The tale of the escape is a thrilling story.  We are fortunate in that the details are well documented.  All of the escapees were officers, and therefore literate; they left behind around fifty written accounts of the escape, many of which were published in the years after the war ended.  We will begin by describing the nature of prison camp life and the conditions inside the prison, and then proceed with a narrative of the actual escape. 

In the early months of the American Civil War, neither side wanted to take on the burden of housing and caring for prisoners of war.  The usual practice was to call for periodic “exchanges”; captured soldiers would be made to sign an oath of non-belligerence, and then was released to the other side.  The system worked reasonably well, since both sides preferred to have their men fighting in the field instead of rotting in prison camps.  But as the war dragged on, and both sides became more intractable and embittered, the exchange system broke down.  Each side accused the other of putting paroled men back into circulation as field soldiers. 

Neither the Union nor the Confederacy had any experience in handling large numbers of prisoners; but the North had far more resources and provisions, and was, in general, better able to provide for its charges.  Conditions in Rebel prisons were by contrast grim.  Some of this was due to the acute shortages that the Confederacy faced in all manner of goods and supplies as a result of the Union blockade; but it was also due to the fact that caring for Yankee prisoners ranked last in the list of priorities for southern authorities.  And as the war ground on, and Confederate defeats mounted, the incentive to provide adequate accommodations for prisoners diminished even further.    

Libby Prison was an unassuming four-story brick and stone structure in Richmond.  It was originally designed in 1852 as a tobacco warehouse, but had been converted to a prison during the early years of the war.  The building was bounded on the north by Cary Street and on the south by the James River.  It was intended to hold only about five hundred men; but by 1863, it housed over 1200 men in near starvation conditions, all of the crammed together with hardly any facilities or amenities.  The guards were housed in the basement floor, which also contained a carpentry shop and the prison dungeons; above the basement was the guards’ quarters, the kitchen, and what passed as an “infirmary”; the floors above this were the prisoners’ quarters. 

The floors housing the prisoners were so filled with men that every square inch of floor space was occupied, day and night.  Lice and vermin were everywhere.  Every morning, the men engaged in what was known in prison parlance as “skirmishing”:  the methodical click-click squeezing of lice and bedbugs found in their clothes.  The Rebel commandant provided no disinfectants of any kind.  The upper floors had windows, but these barred apertures opened to the air; in winter the men froze, and in summer they roasted.  The men were not permitted to look out the windows; anyone showing his face would be shot by the guards.  Food was of the most primitive kind, basically a small piece of cornbread filled with husks and cobs, with a thin, watery gruel.  Emaciation was thus the order of the day.  Prisoners did occasionally receive what we would call “care packages” from relatives in the north, but these were usually looted by the guards or withheld from prisoners as a way to manipulate them.

The guards, of course, were just as one might expect.  No one wanted to be assigned to prison duty.  The South’s best men were in the field fighting; prison guards were thus drawn from the ranks of the mentally deficient, the very young, or the very old.  The jailer of Libby Prison was a dour and malicious man named Dick Turner, a twenty-three-year old who managed daily operations; before the war he had been a plantation overseer.  Historian Douglas Miller, the author of The Greatest Escape, the best modern history of the breakout (the third-party quotations here are taken from his account), described Turner in these terms:  “He treated Libby’s inmates the same way he’d treated slaves—with extreme brutality and mocking abuse.  Libby’s memoirists were unanimous in their hatred of the man.”

An entire book could be written on the peculiarities of Libby life.  With no sports or exercise yard permitted, the men had to find novel ways of passing the time.  One odd but therapeutic prison custom was the nightly “catechism.”  At night the POWs arranged themselves on the floor with their army blankets—there were no bunks—and would play “call and response” games for hours.  A man would call out a humorous or serious question, and anyone could shout out a response.  Amusement was derived from the cleverness of the shouted-out answer.  Sometimes the men just shouted out obscenities or made ludicrous noises.  As one prisoner later described it:

Against such hilarities, mixed with traits of vulgar rowdyism, there was no possible remedy.  A stranger passing by Libby at midnight, might have imagined himself to be near a lunatic asylum.  The place, in fact, was not on the whole, distinguished for refined manners…The braying of the ass, the cackling of the hen, the hoarse barking of the mastiff, the whining of the new born infant, all contributed to the grand nocturnal chorus, the echo of which must have penetrated high up in the streets of Richmond.

A prisoner’s first induction to life in Libby was to be searched and robbed by the guards.  Col. Louis di Cesnola, a Sardinian aristocrat who had joined the Union army and one of the first recipients of the Medal of Honor, described his entry into Libby in 1863:

A Rebel sergeant searched me from head to foot in the roughest manner possible.  He took away from me every possible trinket I had, my penknife, eyeglasses, Meerschaum pipe, matches and a bunch of small keys, and was angry because he could not find any greenbacks [dollar bills]. 

He ordered me to take off my boots for inspection; I answered him that I had a servant perform that service for me.  He insisted, but I refused until he took them off himself and searched them very minutely.  He began to abuse me, using very abusive language and denying my veracity.  I entered the gates of a Confederate prison stripped of everything.

Col. Thomas E. Rose, the mastermind of the Libby breakout, ranks as one of the greatest escape artists in military history.  He possessed all the attributes of the born conspirator:  patience, endurance, even temper, and fanatical determination.  One of his peers described him as a “brainy, cool, and intrepid man, coined for just such a daring enterprise.”  Rose served with the Seventy-Seventh Pennsylvania Infantry, and was captured at Chickamauga; he was put on a transport train to be shipped to Libby in 1863, but tried escape before he even arrived at Richmond:

On my way thither, I escaped at Weldon, North Carolina, and after wandering about for a day, I was recaptured by some rebel cavalry that came upon me accidentally.  I was suffering at the time from a broken foot, which caused me to be too slow in reaching a place of concealment.

But recapture never deterred Rose.  He took it all in stride, and upon his arrival at Libby, immediately began to survey the prison and its grounds.  From that point, escape occupied all his waking thoughts.  He arrived at Libby just as an ambitious escape scheme had been betrayed to Libby’s jailers.  Col. Abel Streight had hatched a plan to stage an uprising to take over the prison; all 1200 inmates would then release themselves into Richmond, causing general havoc and, in effect, opening up another front behind enemy lines.  But the plan came to nothing.  Rose realized that success would depend on absolute secrecy and minute planning.  He soon concluded that tunneling was the only method that had a decent chance of success.

After weeks of surveys and evaluations, Rose decided to break through one of the walls in the kitchen and tunnel into a fetid, abandoned basement the prisoners called Rat Hell.  From Rat Hell, Rose and his men would undertake construction of a tunnel through the sandy soil outside the basement.  Rat Hell had earned its name for good reason.  Frequently flooded by the James River, it was filled with rats, slime, detritus, and every imaginable sort of foulness.  That Rose and his men were able to enter this stinking hole for 17 days, work all night, and then return to the horror of their existence during the day to the upper floors, tells us much about the utter tenacity with which they pursued their goal.     

The plan was to tunnel out of Rat Hell using pen knives, pieces of wood, and a few chisels.  The tunnel would have to extend for over 50 feet from the east side of the prison, to an abandoned lot.  Into this lot the escapees would emerge, and from there make their way to Union lines.  Actually digging the tunnel was a terrifying experience.  Rose and his men had only the most rudimentary tools, but fortunately the soil had the consistency of compacted sand.  Yet they had no timber to support the sides or ceiling of the tunnel.  A cave-in would be fatal.  There was no ventilation system except a man standing at the entrance, fanning it with a hat.  It took a certain kind of man to enter the horrifyingly claustrophobic darkness, claw away the soil, and have it hauled back in a spittoon.  Some men fainted from exhaustion or lack of oxygen, and had to be hauled out by their ankles. 

But digging progressed steadily in January and February 1864.  Rose, of course, led by example and put himself in harm’s way:

We made fairly rapid progress…One night I dug six feet with my own hands.  My whole party was divided into reliefs of five men each, so that the same men went down to work every third night.

The dimensions of the tunnel were around two feet in length by eighteen inches in height.  It was so small that a man could not turn around; he had to keep moving forward or die.  If he became stuck, he would have to free himself or call out for someone to pull him out by the ankles.  These were not the only difficulties.  The advent of 1864 brought more miseries to the POW population.  Cold winds blasted through the open windows, leaving the emaciated prisoners to shiver with irrepressible chills.  The war was going badly for the south, and there were fears that rations would be cut to nothing, or that the men would be drafted as slave laborers.  A condition that World War II prisoners in the Pacific would later call “give-up-itis” infected many of the men.  An inmate named Maj. Emeric Szabad (a colorful Hungarian immigrant who had fought in European wars before emigrating to the United States) painted this picture:

An occasional prisoner gives up to grim despair; he grows melancholy, weak, and careless; finally, sickens and dies.  His remains are taken out and buried, we know not how or where—we never being allowed to assist at the funeral of any one. 

The tunnelers’ first attempt to surface in the abandoned lot was not successful.  They were ten feet short, despite all the planning and pacing out of the distance that they had done.  By some miracle, no Confederate sentry noticed it.  Rose himself plugged the hole with a dirt-encrusted rag, and resumed the task of digging.  He later broke through the surface at a place where the courtyard fence of the abandoned lot protected him from the eyes of the Confederate guards posted around Libby.  Words could barely describe the ecstasy of the prisoners.  Lt. Thomas Moran later wrote:

McDonald was overjoyed, and poor Johnston almost wept with delight as Rose handed them his victorious old chisel and some other trifle he had picked up in the outer world as a token that the Underground Railroad to God’s country was open.

The mass escape was set for February 9.  Rose and his men had to endure another day of agonizing waiting; they were tormented by the idea that some prison blabbermouth might doom them all, or that a sentinel might spot the first hole they had made and recognize it for what it was.  But nothing happened.  Libby had been touted as “escape-proof,” and as the Roman biographer Cornelius Nepos reminds us,

An overabundance of confidence is often attended by a terrible calamity.

And so it happened here.  On the night of the actual escape, some of the prisoners began a large dance to create noise to cover the movement of so many men to the basement.  Men on the roof of Libby could see the POWs emerging from the ground fifty feet away from the building and heading for freedom; the sight of it must have given them peals of joy.  Escapees were able to walk on the streets of Richmond without being challenged.  Sentries had become so used to the sight of civilian looters ransacking the prisoners’ care packages in buildings near Libby that they probably assumed the presence of so many men on the streets that night was not worth investigating. 

But now another complication emerged.  As word of the successful escape made its way around the prison, a stampede to the basement ensued.  The tunnel entrance became clogged with men trying to get out, and there was a danger that the whole escape might be revealed.  One Lt. Earle later wrote:

Only one man was allowed in the tunnel at the same time, on account, I suppose, of the bad air.  The exit of the man preceding could be easily determined by the cessation of the terrible noise made in forcing one’s body through a long, narrow shaft, which the tunnel really was.  The noise and racked produced by one man kicking and floundering against the walls of this cavern were simply indescribable, comparable to a steam engine, or cyclone, or an army reunion.

But by the time dawn broke, 109 malnourished, desperate POWs had infiltrated through Rose’s tunnel and were heading for the open country towards Union lines.  There was no turning back now.  The breakout had succeeded beyond all expectation.  But the fugitives, as well as the prisoners who remained at Libby, knew that all hell would break loose in a few hours once the jailers realized they had been played for fools.  The remaining eleven hundred inmates waited for the rising sun of February 10 with a mixture of exaltation and portentous trepidation.    

[Part II to appear next week]

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