American History Tellers - Daring Prison Escapes | Bastille of the Confederacy | 1

Episode Date: September 3, 2025

In February 1864, more than 100 Union Army officers broke out of Libby Prison, an infamous Confederate prisoner of war compound in Richmond, Virginia. It was the largest prison break of the Civil War. Libby held more than 1,000 Union officers who were crammed into the former tobacco warehouse. They faced rampant illness, meager rations, and constant abuse from sadistic guards.As conditions worsened and the death toll mounted, a small crew of prisoners resolved to escape. Working in secret, they excavated a narrow tunnel out of Libby’s rat-infested cellar in a daring attempt to dig their way to freedom.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to American History Tellers on the Wondery App or wherever you get your podcasts. Experience all episodes ad-free and be the first to binge the newest season. Unlock exclusive early access by joining Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial today by visiting wondery.com/links/american-history-tellers/ now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey, history buffs, if you can't get enough of the captivating stories we uncover on American history tellers, you'll love the exclusive experience of Wondry Plus. Dive even deeper into the past with ad-free episodes, early access to new seasons, and bonus content that brings history to life like never before. Join Wondry Plus in the Wondry app or on Apple Podcast and embark on an unparalleled journey through America's most pivotal moments. Imagine it's late at night on February 6, 1864, beneath the grounds of the Libby Prison in Richmond, Virginia.

You're a captured union officer, and you're wriggling back through a narrow tunnel, your knees sore and your shoulders wedge between pack soil and solid rock. A rat skitters across your arm as you urge yourself forward through the darkness. Finally, you reach the tunnel entrance, and two sets of hands yank you out into the open air and onto your feet. The men look at you expectantly. It's bad news, boys, we're short.

The eyes of your fellow prisoners grow wide, except for those of your leader, Colonel Rose. His eyes narrow. What do you mean short? We're short, we miscalculated. I came up and broke through the surface, but we're four or five feet short. You mean we're still in the yard? Yes, just inside the fence, and I saw a guard. I don't know if he saw me, but I sure saw him.

Well, then we keep digging. No, sir, we may be discovered. I don't know if the guard saw me, but if he did, then we need to get back upstairs to the barracks. We can't get caught down here. No, Captain, what we can't do is stop now. But if that guard saw me, if that guard saw you, then the tunnel is exposed, and we'll likely be found out whether we're here or upstairs. But if not, then we are four or five feet from freedom. But, sir, if we do nothing, that's exactly what I want you to do. Nothing. You wait here. Colonel Rose steps with determination toward the tunnel entrance and turns back to address you

and the others. Stay here, be quiet, do nothing, and just wait until I go take a look. We are too close to give up now. Rose drops onto his hands and knees and pulls himself into the tunnel. The other men exchange wary glances. You fear that when he emerges, he'll be caught by the same guard you spotted. You're fighting every instinct in your body that's telling you to run, but you trust Colonel Rose as your leader, so instead you crouch down and wait, hoping that the kernel is right, because one wrong move could put an end to any hope you have of escape. Grab a coffee and discover Vegas-level excitement with BetMGM Casino. Now introducing our hottest exclusive, friends, the one with the multi-drop.

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BetMGM operates pursuant to an operating agreement with Eye Gaming, Ontario. What if I told you that the crime of the century is happening right now? From coast to coast, people are fleeing flames, wind, and water. Nature is telling us, I can't take this anymore. These are the stories we need to be telling about our changing planet. Stories of scams, murders, and cover-ups, and the things we're doing to either protect the Earth or destroy it. This is Lawless Planet.

Follow Lawless Planet on the Wondry app or wherever you get your podcasts. From Wondery, I'm Lindsay Graham, and this is American History Tellers, Our History, Your Story. On our show, we'll take you to the events, the times and the people that shaped America and Americans, our values, our struggles, and our dreams. We'll put you in the shoes of everyday people as history was being made, and we'll show you how the events of the times affected them, their families, and affects you now. As long as prisons have existed in America, there have been inmates determined to escape. Some driven by sheer desperation, others plotting elaborate schemes of astonishing ingenuity. From the famous raft escape from Alcatraz to the biggest breakout of the Civil War, these attempts to gain freedom occupy an enduring place in the American imagination,

revealing the high stakes of life behind bars and the lengths some will go to to break free. In February 1864, a group of captured unions, officers neared completion of a tunnel that they had dug beneath the grounds of Libby Prison in Richmond, Virginia. By then, America was nearly three years into the Civil War, the bloodiest and most destructive conflict in its history. Both the Union and the Confederacy had constructed prisons to hold captured soldiers, but while conditions were harsh on both sides, Confederate prisons were especially notorious. Almost immediately after the war broke out in 1861, Confederate authorities forced Richmond merchant Luther Libby to vacate the

warehouse complex where he ran his shipping supply store and converted it into Libby Prison. It quickly gained a reputation as one of the Confederacy's most infamous prisoner-of-war compounds. And by the third winter of the war, starvation and disease had spread unchecked through Libby's cramped and frozen barracks. As the death toll mounted, a small group of union officers refused to accept their fate. In secret, they toiled for months, digging an underground tunnel out of the prison, despite knowing that they would be emerging into the heart of enemy territory. Their efforts would result in the largest prison break of the Civil War, a desperate bid for freedom in the face of overwhelming odds. This is episode one of our

four-part series Daring Prison Escapes, the Bastille of the Confederacy. On October 1, 1863, Union Army Colonel Thomas Rose arrived by train to the Confederate capital of Richmond, Virginia as a prisoner of war. Stumbling out of his, his rail car, he joined a throng of weary prisoners gathering on the station platform. Confederate soldiers barked orders and pointed bayonets, parading the prisoners out of the depot and into the streets of the war-torn city. Local residents hissed and spat at the captives as they trudged past. Colonel Rose was a 33-year-old former school principal with a thick black beard and a burly frame. Though his imposing figure commanded attention, he was a man of mild

manners and very few words. He was born and raised in Quaker country in eastern Pennsylvania, an area known for abolitionist sentiment. But from a young age, he was fascinated by military history, pouring over accounts of famous battles. And when the war broke out, he eagerly embraced the cause of the Union, leaving his wife and six-year-old son behind to enlist in the 77th Pennsylvania volunteers. Despite his reserve nature, he was a natural-born leader, and he quickly emerged as one of the most respected Union commanders fighting in Tennessee. But in September 1863, Colonel Rose was captured during the bloody battle of Chickamauga in Georgia and herded onto a train bound for Richmond. Desperate to escape, he leapt from his railcar at the Virginia border only to fall and break his left

foot. Despite his injury, he managed to flee into a forest, but Confederate cavalrymen soon tracked him down and brutally beat him before hauling him back on board the train. So as he and his fellow prisoners were marched through the streets of Richmond, Rose was hobbling in pain. Soon he and the rest of the ragged line of prisoners approached three imposing brick warehouses nestled beside a canal along the James River. Rose could see gaunt faces staring out from behind barred windows. The sign above him read L. Libyan's son, Ship Chandler's. It confirmed his worst fears. Imagine it's October 1, 1863, in Richmond, Virginia. Virginia. You're a colonel in the Union Army, and you're standing in a crooked line of fellow officers

in the yard of Libby Prison. Your broken foot aches, and you're struggling to remain standing. The guard looks at you and your crooked stature. It's my foot. It's broken. I need a doctor, please. I think it needs to be reset. The guard just smirks, though, jabbing the butt of his rifle toward your ribs. Empty your pockets. When you hesitate, he reaches into your blue officer's coat, groping around until he finds your watch. Pulling it out, he admired. the silver case. Your stomach churns. You can't take that. It's a wedding present for my wife. Well, now she's given it to me. You don't own anything, Yank. This is our prison. Our property. I'll take your coat, too. My coat, but this is a U.S. Army officer's uniform. What good is it to you?

Well, that's none of your business. End it over. You stare at him in disbelief until he delivers a sharp kick to your shin. Double over as searing pain shoots up your leg and he beckons to another guard. Would you help me with this one? The other guard walks over, and together they twist your arms back and wrench to coat off your shoulders. Then, folding it neatly over his arm, the first guard turns to meet your furious gaze. Oh, now, don't get so mad. You're going to have plenty more to worry about than a missing coat. I promise you that.

You strain to stand up straight, your breast shallow, and your heart pounding. You fix your gaze on the brick walls or the prison around you, trying to swallow your anger and block out the pain. It seems likely to you that if you stay here, you will die. And so you make a vow, you're going to escape this hell, even if it's the last thing you do. On October 1st, 1863, Colonel Thomas Rose arrived at Libby Prison, also known as the Bastille of the Confederacy, after the notorious French prison. Upon arrival, Rose and the other prisoners were lined up and then robbed of their possessions.

Then they were marched inside where they were greeted by an overwhelming stench and a chorus of inmates crying fresh fish. By the fall of 1863, the prison population had ballooned to 1,200 inmates, including roughly 20 black prisoners who had been cooks and servants of Union Army officers. The prisoners were crammed into six Spartan overcrowded rooms on the upper two floors of the three-story facility. The ground floor housed offices and a kitchen, and below that was a cellar teeming with rats. Rose was placed among hundreds of fellow inmates in an overcrowded, lice-infested room on the second floor. He was worn down from his long journey, and with her broken foot, every step caused him

pain. But his will was unbroken, and he refused to spend the rest of the war behind bars. So from the moment he arrived at Libby, his mind was focused on escape. But while he contemplated breaking out of Libby, he still had to survive the prison's hellish conditions, which reached new lows in the fall of 1863. The prisoners were forbidden from going outside, and they lacked basic necessities such as soap and silverware. They were also forced to sleep without blankets on dirty, freezing floors. Only occasionally did officials have the prison cleaned, and when they did, they ordered the black prisoners and local enslaved laborers to do the work. The stench was inescapable. Overcrowding and an open latrine created a suffocating odor,

and every surface was infested with lice, fleas, and rats. As the war dragged on, the Confederacy struggled to feed its own soldiers, let alone its prisoners. So by the time Rose arrived at Libby in October 1863, gnawing hunger hollowed the inmates from the inside out. They were given meager rations, typically stale bread and rotten meat in the morning and thin soup at night. Food shortages in Richmond often left the inmates starving for days at a time. And although overcrowding and poor sanitation created a breeding ground for disease, the prisoners received little to no medical care. Rose's broken foot went untreated, leaving him with a bad limp, and as hunger and illness spread through the ranks, the death toll mounted. There was little hope of release. Earlier in the

war, many captured soldiers had been paroled through prisoner exchanges, but by the fall of 1863, the practice had largely ceased, in part due to the Confederacy's refusal to exchange black Union soldiers. Compounding the prisoner's misery was the constant abuse they were forced to endure at the hands of Libby's officials and guards. The commandant in charge was the sadistic Major Thomas Turner, a military academy dropout, who was twice denied a commission in the Confederate Army. He delighted in tormenting prisoners through beatings and punishments, as did his deputy Dick Turner. Before the war, this heavy-set 23-year-old was a plantation overseer, and he treated the prisoners in the same brutal manner

that he treated the enslaved laborers under his watch. One inmate described Deputy Turner as vicious and sinister and the son of perdition itself. Making matters worse, Libby was severely understaffed, and its guards were untrained and incompetent. The Confederate armies needed all available manpower, so only the worst conscripts were assigned to staff prisons. The guards regularly robbed inmates of their personal possessions, including letters and packages sent to the inmates from loved ones. And no one was a bigger thief than Deputy Warden Dick Turner, who methodically stole from prisoners upon their arrival at Libby. And the guards under his command dealt out harsh and arbitrary punishments, even shooting inmates for minor infractions.

But as Rose formed his plans for escape, he knew that he would benefit from the guards' incompetence. Still, he also knew that escape carried major risks, starting with the fact that the former warehouse had few exits and constant perimeter patrols, and it was also well known that Commandant Thomas Turner had recruited informants from within the prison population. And even if Rose managed to escape Libby, the surrounding city of Richmond was teeming with Confederate soldiers and civilians ready to report or kill any fugitive they came across. Even if they could, escaping the confines of the prison and then the city would only be the beginning. Reaching Union lines met a long, dangerous journey through hostile territory.

The closest union position was 50 miles to the east in Williamsburg, Virginia, which Union forces had captured in 1862. But despite these risks, Rose devoted every waking hour to thoughts of escape. He scouted Libby for weaknesses, timing guard patrols, mapping stairways, and studying his surroundings. The guards typically steered clear of the two upstairs floors where the prisoners slept to escape the stench of unwashed bodies and to avoid catching the prisoner's illnesses. Guard shortages also left stairways unsecured, and other inmates had cut secret passageways between the prisoner barracks, which helped Rose move freely through the building after dark. Then, during heavy downpours, he stood looking out the barred windows facing the

James River to the south. And after observing how the rain sent swarms of rats scurrying out of the large sewer, he wondered if that sewer might be a means of escape. He decided to investigate the prison cellar to see if it was connected. And on one night in November 1863, Rose lift a small candle and crept downstairs. He found an unlocked door to the cellar and descended into the rat-infested darkness. But remarkably, he soon discovered he wasn't alone. Another prisoner, Major Andrew Hamilton, had gone down to the cellar with the same idea. Hamilton was a homebuilder from Kentucky, who defied the Confederate sympathies of his neighbors

by enlisting in the Union Army in the fall of 1862. The slender 28-year-old had fought in the 12th Kentucky volunteer cavalry and quickly proved himself in battle in Tennessee, earning a promotion to major. One year later, though, he was captured near Jonesboro, Tennessee. He had arrived at Libby just a week before Rose, and like Rose, Hamilton was consumed by thoughts of escape. He would later reflect on his sense of despair at Libby, describing how the days went by

like scarcely moving tears, the nights like black blots dying out of a dream of horror. Meeting in the cellar, the two men quickly gained each other's trust and agreed to work together. So throughout November and December 1863, Rose and Hamilton met in secret to discuss various escape plans. They decided that their safest option was to get into the prison's east cellar and dig a tunnel southeast toward the sewer. They believed this was their best chance of fleeing undetected because the guards generally avoided the rat-infested cellar, which was known by the nickname Rat Hell. But the next time they tried to revisit the cellar, they discovered that the doors had been bolted shut. They would need to find another way in, somewhere where the guards

weren't watching. Fortunately, guards shortages left the prison kitchen largely unsecured at night. Examining this space, Rose and Hamilton found a potential access point to the cellar, an unused fireplace. And on the night of December 19th, they began digging. a passageway behind it. Night after night, they used a small jackknife, Hamilton borrowed from a fellow inmate, to meticulously scrape out the mortar that held the fireplace's bricks in place. They worked in complete silence and almost total darkness. They were careful to restore everything before the morning roll call. Although the work was painfully slow, Rose and Hamilton knew it was their best shot at freedom. As the freezing winter wore on, food supplies dwindled.

Prison officials grew increasingly volatile, and the inmates were haunted by the constant specter of death. Escape was their only option. They were running a grueling race against time. How hard is it to kill a planet? Maybe all it takes is a little drilling, some mining, and a whole lot of carbon pumped into the atmosphere. When you see what's left, it starts to look like a crime scene.

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These are the stories we need to be telling about our changing planet. Stories of scams, murders, and cover-ups that are about us. And the things we're doing to either protect the Earth or destroy it. Follow Lawless Planet on the Wondry app or wherever you get your podcast. You can listen to new episodes of Lawless Planet early and ad-free right now by joining Wondry Plus in the Wondry app, Apple Podcasts, or Spotify. It's your man, Nick Cannon, and I'm here to bring you my new podcast, Nick Cannon at night. I've heard y'all been needing some advice in the love department.

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or subscribe on the Wondery app or wherever you get your podcast. Want to watch episodes early and ad-free? Join Wondery Plus right now. On the night of December 30, 1863, after 12 straight nights of meticulous scraping and digging, Colonel Thomas Rose and Major Andrew Hamilton completed their narrow passage between the prison kitchen and eastern cellar of Libby Prison. As they descended into the darkness below, they were greeted by a swarm of rats and the overpowering stench of sewage. But once they had access to cellar, their next problem was tunneling their way out. Rose identified a spot in the southeast corner as the closest access point to the sewer.

But it quickly became obvious that their jackknife was not going to cut it, so they began stealing tools from an abandoned carpenter shop in the prison cellar, including two chisels, a hatchet, and a hand saw. Rose also enlisted two trusted fellow officers in smuggling a coil of rope into the kitchen, which he and Hamilton used to lower themselves in and out of the cellar. The process of sneaking into the kitchen, lowering themselves into the cellar, and then silently digging was slow, stressful, and risky. Rose and Hamilton became sleep-deprived, and they feared that their fatigue might cause a fatal error.

They also knew that the longer it took to excavate the tunnel, the more likely they would be discovered. They desperately needed a faster and more efficient. way to dig. So despite concerns about secrecy, they decided to expand their crew. In early January 1864, a few weeks into their secret campaign, they recruited a group of 13 additional men. They divided themselves into three crews of five prisoners each and went to work in shifts, digging for two to three hours at a time. They also came to rely on the help of inmates who could not dig due to injuries, poor health, or old age. These silent partners assisted with collecting supplies and

reporting on the movements of guards. In this 15-man crew, Rose was the undisputed leader, keeping the men focused and motivated, while Hamilton devised creative innovations to streamline their work. Each member of the five-man crews had a specific job. The digger would fill either a knapsack or wooden spittoon with dirt. The dumper would pull the dirt-filled knapsack out of the tunnel using a makeshift pulley system and then dumped the dirt under a large straw pile that had been sitting in the cellar for years to keep the evidence of their digging hidden. The third man used a hat to fan air into the tunnel, preventing the digger from suffocating. As a secondary measure, the digger also had a rope tied around his leg, so that if he started to lose oxygen or the tunnel collapsed, the others could

pull him out. The fourth member of the crew took turns relieving the other three, and the fifth and final member served as the lookout. If any man was too weak or too ill to work, Rose covered his shift. He was by far the most effective digger. And as hoped, this additional manpower helped expedite their progress. They were also helped by the fact that the soil was soft and easy to remove, but this softness also jeopardized the integrity of the tunnel. And in mid-January, the crew suffered two major setbacks that threatened to derail their hopes of escape.

Imagine it's late at night in mid-January, 1864, in the pitch-black cellar of Libby Prison in Richmond, Virginia. You're an imprisoned union officer, and you're part of a team that has been digging a tunnel out of Libby for weeks. But earlier tonight, the tunnel collapsed, sending freezing sludge pouring into the cellar. After hours of work, you finally managed to plug up the tunnel. In your exhaustion, you press your back against the damp wall,

your boots squelching in the sewage and mud. Someone then strikes a match. As your eyes adjust to the flickering light, You see Colonel Rose crouching down beside you, inspecting the hole in the wall that used to be the tunnel entrance. Well, we'll start again tomorrow night. You stare at him in disbelieve. Start again, you can't be serious. We spent weeks on that tunnel, and for what?

It's over, Colonel. Not if we say it isn't. We'll find another way. We just spent five hours plugging up this cave in, and I'm freezing. I'm soaked in the knees and God knows what, and I can't feel my damn fingers. Son, we'll just have to find a more suitable location for our tunnel, a spot where the soil is firm enough. No, our luck has to run out sometime, and I think spending a night cleaning up frozen sewage might be a sign. It's only a matter of time before the guard's finest.

If we keep pushing this, we're going to get caught. One slip, and that's it. Look, do you want out of here or not? You want to see your wife again, your child? Well, of course I do. Then we keep digging. Failure is not an option. There are only two ways out of Libby, through a tunnel or in a coffin.

You breathe a heavy sign, looking down at your torn knuckles and the filth, coating your body. You really believe this will work? I do. Because I think you're out of your mind, Colonel. Well, so do I sometimes. You close your eyes and nod. Well, all right. Count me in for the first ship tomorrow night. Thank you, soldier. Colonel Rose turns around to inspect the walls of the cellar. You've never met a man with so much stubborn optimism. Someone's so determined to bend reality to their will, and it might just be the only reason you actually manage to break out of this hellhole. In mid-January, 1864, the tunnel beneath Libby Prison flooded, destroying weeks of hard work.

But Colonel Rose was undaunted. Major Hamilton later remembered his friend's dogged persistence, writing, Failure was never thought of. After surveying the grounds, Rose identified a second, smaller sewer, and rallied the crew to dig a new tunnel toward it. After stealing additional tools, they resumed work with renewed optimism. But they soon suffered a second setback. On January 25, 1864, the men were nearing their target when they hit a barrier of massive oak beams and solid rock. They tried to burrow below the beams, but the tunnel collapsed and again flooded with sewage, nearly drowning, rose. He managed to plug

the leak, but then discovered that the smaller sewer was too narrow for a man to escape through, A soaked and exhausted crew returned to their barracks, fearing that all hope was lost. And while the inmates mourned their second failure, Libby Prison descended into its darkest times yet. In late January, temperatures plummeted, and gusts of bone-chilling winds blew through the barred windows, making it impossible for the thinly clad prisoners to stay warm or sleep. Then prison commandant Thomas Turner imposed new restrictions on sending and receiving letters, which meant there were few comforting words from home. But worst of all, by January 1864, the prison, like most of Richmond itself, had run out of food.

Throughout the South, Union forces had blockaded ports and captured railway depots, strangling supply chains. Rations in Libby dwindled to inedible scraps. Growing numbers of prisoners died of starvation and disease, and as the death toll rose, enslaved laborers were assigned the task of carting the bodies off and dumping them in shallow graves. One morning during roll call, Commandant Turner noticed a prisoner lying on the ground, refusing his repeated orders to fall in line. He furiously kicked the inmate, but there was no response.

Suddenly, Turner understood the reason, crying out, my God, I've been kicking a dead man. But these deteriorating conditions in Libby hardened Rose and Hamilton's resolve. They agreed to dig a new third tunnel, avoiding the sewers altogether this time. They decided to try digging under the northeast corner of the cellar across a yard to the east end of the prison and out to an all-tobacco shed just beyond the prison's fence

that they hoped would provide cover as they emerged from the tunnel. To calculate the new tunnel's length, Rose enlisted the help of one of the diggers, Captain John Gallagher. Although the commandant had instituted new restrictions on mail, Gallagher convinced the guards to escort him to the tobacco shed under the pretense of retrieving a package he was expecting. The story was suspect, but the guards were nearly as desperate as the prisoners they oversaw. They agreed to Gallagher's request, eager to take a share of whatever he received. Along the way, Gallagher counted his steps and concluded the tunnel would need to be roughly 52 to 53 feet long. So with this information, in early February 1864, Rose and Hamilton began work on the third tunnel. But their now thoroughly

demoralized crew refused to help, forcing the two men to work alone. Rose pushed himself hard, often clawing at the dirt with his bare hands to dig out a passageway that was less than two feet in diameter. Hamilton stood in the cellar, keeping watch and fanning air into the tunnel. But the physical strain soon became too much of a burden for the two men to carry alone. Rose later remembered that while it seemed hopeless, he did not despair, but instead resolved to organize a new crew. His unwavering determination, coupled with the continued worsening and conditions inside the prison, eventually inspired most of the original crew to return, with one member saying, the hard fare and confinement of our prison, the monotony of which had become unendurable, and the possibility

of escape at last roused us up to exertions almost superhuman. This time, the crews worked both day and night, which helped them make faster progress. But the deeper they dug, the more dangers they faced. Diggers often collapsed from lack of air and had to be pulled out by the rope attached to their legs. And working around the clock carried other risks. In February, Libby officials tightened security, responding to a separate, small-scale escape attempt, meaning the prisoners face constant roll calls and surprise inspections. Commandant Turner ordered the inmates to stand at attention for hours at a time, and he gave the guards standing orders to shoot any inmate found standing near a window.

The guards treated this new policy like a game, competing with one another to see who could get the most kills. As a result, several prisoners died, including an inmate shot in the head after being found reading a newspaper by the light of a window. Working during the day also meant that five men would usually be missing from the increasingly frequent daytime roll calls. So Rose used a risky tactic known as repeating, having five men sneak from one room to another during a roll call

so that they would be counted twice. But it didn't always work. Eventually, one of the tunnelers, Captain Isaac Johnson, was discovered missing from a roll call, and to explain his absence, Rose's crew told the guards that Johnson, had escaped. That meant Johnston was forced to remain in the rat-infested cellar full-time. But on the morning of February 6, guards burst into the cellar, and Johnston nearly avoided discovery

by diving into the tunnel. When Rose heard about this close call, he feared that the guards were onto them. He told the other men that they needed to finish digging as soon as possible. So around midnight, that same night, one of the diggers finally broke through the surface of the tunnel, only to realize that he had emerged on the wrong side of the prison fence. He raced back to tell Rose the news declaring, we are caught, all is lost, but Rose went into the tunnel to assess. He had a moment of panic himself, when a guard appeared in the yard and curiously thrust the tip of his bayonet into the hole, grazing Rose's cheek, but the guard did not appear to sense that anything was really amiss and soon wandered off. Relieved, Rose pushed

an old shoe through the small hole from below to mark the tunnel's endpoint, then did his best to conceal the opening. The next morning, February 7th, he located the shoe from a prison window and saw that they were just five feet short of their target. Now, with the end inside, Rose was relentless. One of the other inmates remembered, from this point forward, Rose never once turned over the chisel to a relief all day long he worked with the tireless patience of a beaver. And just two days later, in the pre-dawn hours of February 9th, two of the diggers broke ground at the end of the tunnel. Rose crawled through to inspect the exit himself and emerged above ground inside the tobacco shed. After carefully widening

the tunnel exit and camouflaging it with straw, he crawled back to the cellar to share the good news. Trembling with exhaustion and anticipation, he announced, the underground railroad to God's country is open. There was no time to wait. So later that same night, Rose and his fellow inmates would flee Libby Prison and then begin the treacherous journey out of enemy territory. On February 9, 1864, Colonel Thomas Rose, Major Andrew Hamilton, and the other 13 tunnelers made the final preparation for their escape. Each man was allowed to choose one trusted companion, doubling the escape party to 30. They had already been stockpiling their meager rations, and they spent the day gathering clothing, matches, and other supplies. Rose had interrogated new prisoners about the latest troop movements, so he knew that the nearest

union lines were still in Williamsburg. That meant the inmates would face enormous danger once outside the prison walls. Richmond was full of Confederate soldiers, hostile civilians, and patrols with bloodhounds. Then, if they made it out of the city, they would still have to cross another 50 miles of enemy terrain, and the fugitives would be traveling in winter with no weapons and little food or water. So it was with great peril that at 7 o'clock, that night, 30 men gathered in the prison kitchen and made their way down the narrow passage to the cellar. Rose entrusted Colonel Harrison Hobart to pull up the rope ladder and seal the fireplace after they left. The men would then flee in pairs, in intervals spaced a few minutes

apart. They agreed to go their separate ways once they were above ground to avoid drawing attention. They chose Rose and Hamilton to go first and then said their goodbyes. Rose's broad shoulders scraped the sides of the narrow tunnel as he crawled his way through to the exit more than 50 feet away. He then hoisted himself out of the tunnel and peered around the shed entrance only to spot a guard about 20 steps away. Rose waited anxiously until the guard moved on, then signaled Hamilton to follow behind him. The two men then crept to the sidewalk and slipped through an unlocked gate. At last they had escaped the prison grounds. Then they disappeared down a dark alley heading east. Two by two, the other men made their way out and vanished into the

night. Then, after all 30 men had escaped, Colonel Hobart sealed the fireplace. But soon, word of the escape tore through the prison like wildfire, igniting both panic and hope in the hearts of its desperate ranks. Imagine it's nine o'clock at night on February 9, 1864 in the kitchen of Libby Prison in Richmond, Virginia. You're a captured union officer, and Colonel Rose has charged you with covering the tracks of his escape. You insert the fire. You insert the final brick in the fireplace, disguising the narrow passageway to the cellar below. But as you wipe the dust off your hands, you freeze at the sound of approaching footsteps. You turn, it's a fellow prisoner, Captain Abbott, flanked by three others.

His face is drawn, and there's a wicked glint in his eyes. Hey, Hobart, there's been talk upstairs. Folks are saying Rose is gone, and he took a couple dozen men with him. Sounds like a rumor to me. Yeah, well, they're saying the men escaped through this very kitchen. Well, that's a wild idea, if I ever. heard one. Then why are you in here, all by yourself? Why are you standing by that fireplace like a guard dog? You swallow hard, fighting to stay composed, but you hesitate a second too long, and

Abbott steps closer. Damn it, Colonel, tell us what you know. Fine, just keep your voice down. Rose is gone. So are another 30 men. They left in pairs through a tunnel in the cellar. There's a passageway behind the fireplace. I knew it. I knew Rose was up to something. Winston, Peterson, Get in here. I found it. You stare past Abbott as two men race into the kitchen, looking desperate and frenzied. No, no, no, no, no. Go back to the barracks. You're just going to alert the guards. But Abbott pushes past you, kneels down in front of the fireplace, and starts clawing at the bricks to loosen them.

Here it is. There's an opening. Abbott removes the bricks to reveal the narrow shoot behind them, and suddenly it's chaos. The other men surge forward, scrambling over tables and chairs to get to the passageway, even as more prisoners enter the kitchen, each with the same near delirious look. We throw up your hands, desperate to calm the frenzy. Stop! No, no. If we all try to go, they're going to catch us. We'll all be shot for it. But no one's listening. Abbott already has one leg through the hole. And as a wave of bodies presses you toward the fireplace, you give up,

and take your place in the crowd of men fighting for their chance to escape. You know the guards are coming, so all you can do now, is pray that you make it out before the shooting starts. On the night of February 9, 1864, a stampede of panicked prisoners stormed the prison kitchen, tore at the fireplace, and descended into the cellar. Dozens crammed themselves into the tunnel, rushing to escape without food, supplies,

or any plan of where they were going. All the while, the guards remained oblivious to the mass breakout. One inmate attributed their ignorance to a combination of luck, and incompetence. It wasn't until roll-call the following morning that the guards realized something was wrong. Dozens of prisoners were missing, and the remaining inmates buzzed with excitement. The guards conducted a series of increasingly chaotic headcounts. Commandant Thomas Turner was baffled. Despite a day-long search, he could not figure out how the inmates had escaped. So it fell to General John Winder, the official in charge of Richmond's prisons, to assess the situation.

Winder and Commandant Turner interrogated the guards first on the assumption that the inmates had escaped by bribing them. But then they finally discovered the tunnel, forcing a frightened enslave boy to crawl through it and locate the exit. So only after hours of bickering, dead ends, and finger-pointing, the General Winder finally sound the alarm. At last the manhunt began, a full night and half a day after Rose and his fellow tunnelers escaped. Confederate soldiers took off in pursuit of the fugitives joined by local civilians who grabbed. grabbed their guns and took to the streets, eager to join the search for the 109 men that had broken out of Libby Prison. But despite their head starred, many did not get far. During the escape, two prisoners drowned in the I.C. James River. Within 24 hours of the breakout,

eight others were recaptured, 14 more the next day. Colonel Rose, meanwhile, was making a harrowing solo journey through near frozen rivers and swamps. After parting ways with Major Hamilton, He headed east, hiding during the day and walking during the night, his still injured foot throbbing with pain. After five days, he was bloodied and breathless when he finally approached Union lines outside Williamsburg. After spotting smoke from friendly campfires ahead, he cautiously stepped into an open field. But at the sounds of footsteps behind him, he turned and saw three Confederate soldiers approaching. He managed to overpower them and flee, but they quickly recaptured him, beating him with their rifles. Scambling to his feet, Rose dared the soldiers to shoot him.

One of his captors later remembered, he was as game a man as I ever saw, as he stood there completely at our mercy and looked us fearlessly in the eye. The Confederates then dragged him away. Rose told the soldiers about his wife and child that he had not seen for nearly three years and begged them to let him go.

But the soldiers ignored his pleas and promptly returned Rose to Libby. There, avengeville Commandant Turner locked him in solitary confinement in the cellar. Rose was devastated to be recaptured after being so close to reaching freedom. Colonel Rose was one of 48 prisoners who had been caught and re-imprisoned. These escapees received starvation rations, while the rest of the prison ranks suffered under Turner's increasingly draconian rule. Now meals consisted of nothing but water and occasionally two or three small turnips.

Nevertheless, it was clear to the men that Turner was shaken by the mass escape. One inmate wrote, when our distracted little commandant now comes into our rooms, he keeps his knees well together in case we slip out between his legs. Meanwhile, outside the prison, Richmond remained on high alert as local newspapers obsessively covered the escape, spinning the Confederate manhunt as a triumph. But in truth, 59 prisoners had successfully reached union lines. Colonel Rose could take comfort in the fact that so many of his friends were free, including Major Hamilton and Colonel Hobart, the officer charged with sealing off the tunnel following the escape.

Despite his own recapture, Rose had engineered one of the most audacious and successful prison breaks in American history. And in the aftermath of this escape, in March 1864, amid rising fears of Richmond's security and dwindling resources, General Winder, ordered most of Libby's inmates moved to a new prison further south in Macon, Georgia. Over the next year, Libby would primarily be used as a temporary holding space for a smaller number of inmates. But still, Rose remained confined there. He endured two grueling months of abuse under Commandant Turner's thumb until at long last, on April 30, 1864, he was released in a Confederate prisoner exchange with the Union. After seven months of hunger, darkness, and deprivation,

Rose was finally free. The Union Army granted former prisoners of war 30 days of leave, so Rose returned home to Pennsylvania, where he was reunited with his wife and son after years apart. But his stay was brief. He was determined to see the war through, and after his horrific ordeal, he had more reason than ever to want to defeat the Confederacy. So despite suffering from scurvy and a broken foot that never fully healed, Rose rejoined the 77th Pennsylvania on the front lines. By July, he was back in command, leading forces during General William Tocompsa Sherman's famed campaign against Atlanta. His trusted escape partner, Andrew Hamilton, also served in Atlanta that summer, after having rejoined his own cavalry unit.

Then, less than a year later, on April 3, 1865, Union forces captured Richmond. Aware that the war would be over in a matter of days, Libby's guards and officials ran for their lives, leaving the remaining prisoners locked inside until Union soldiers finally arrived to free them. After the war, the tables were then turned, as federal authorities repurposed Libby Prison into a facility to hold former Confederates. And over the next three years, roughly 700 soldiers and officials were detained there, albeit under improved conditions.

One of the inmates was Richard Turner himself, the sadistic Confederate deputy commandant. The prison was finally shut down in 1868. For the rest of his life, the unassuming Thomas Rose was reluctant to speak about his achievements as the ringleader of the largest prison break of the Civil War, one that allowed 59 of his comrades in arms to reach freedom. The prison escape he engineered through the Confederate Catholic, into turmoil, rattled southern officials, and boosted the morale of the long-suffering inmates who remain. It was not only a remarkable feat of ingenuity, but a testament to the

courage and resilience of Union prisoners of war under the most brutal circumstances. From Wondery, this is episode one of our four-part series on daring prison escapes for American history tellers. In the next episode, on a foggy night in 1962, three inmates at Alcatraz, America's most secure prison attempted the impossible. Using everyday objects and extraordinary ingenuity, they launched one of the most mysterious prison breaks in history. If you like American history tellers, you can binge all episodes early and ad-free right now

by joining Wondery Plus in the Wondry app or on Apple Podcasts. Prime members can listen ad-free on Amazon Music. And before you go, tell us about yourself by filling out a short survey at Wondry.com slash, survey. American History Tellers is hosted, edited and produced by me, Lindsay Graham for airship. Audio editing by Mohamed Shazir, sound design by Molly Bach, supervising sound designer Matthew Filler, music by Thrum.

This episode is written by Ellie Stanton, edited by Dorian Marina, produced by Alita Rosansky, managing producer Desi Blaylock, senior managing producer Callum Ploos, senior producer Andy Herman, producers are Jenny Lauer Beckman, Marsha Louis, and Aaron O'Flaherty for Wondering.