Transcript

Bastille of the Confederacy | Episode 1 | Daring Prison Escapes

From American History Tellers · Episode page · Watch on YouTube

· 40 min · 7,075 words · 52 timestamped sections

This is the full, timestamped transcript of "Bastille of the Confederacy | Episode 1 | Daring Prison Escapes", an episode of American History Tellers published September 3, 2025 (40 min, about 7,075 words). It mentions 40 people, works and ideas, including Libby Prison, Major Thomas P. Turner, Confederate States Army, Union Army, Colonel Thomas Rose.

What this episode is about

The narrative delves into a tense moment during the Civil War at Libby Prison, highlighting a harrowing escape attempt by Union officers on February 6, 1864. Amidst uncertainty and looming danger, Colonel Rose leads his fellow prisoners in a desperate decision to continue digging towards freedom, despite the risk of being caught by a nearby guard.

Key takeaways

  • Prison breaks: When a literal 'yard short' leads to digging deep for freedom.
  • Colonel Rose's escape: Proof that a tight squeeze can lead to expansive opportunities.
  • In prison or life, four feet short is just another dig to liberation.
  • Libby Prison: Where civil war escapees outmaneuvered fate, one tunnel at a time.
  • Colonel Rose: From principal to principal escape artist in the crucible of war.

What is discussed, and when

  1. – 5:00: Libby Prison, Alcatraz, American History Tellers, Colonel Thomas Rose
  2. – 10:00: Libby Prison, Union Army, Colonel Thomas Rose, James River
  3. – 15:00: Dick Turner, 12th Kentucky Volunteer Cavalry, James River, Jonesboro, Tennessee
  4. – 20:00: Libby Prison, Colonel Thomas Rose, Major Andrew Hamilton
  5. – 25:00: Captain John Gallagher, Libby Prison
  6. – 30:00: Captain Isaac Johnson, Colonel Harrison Hobart, Colonel Thomas Rose, Libby Prison
  7. – 35:00: Dr. Jack Abbott, Libby Prison, General John Winder, James River
  8. – 40:00: American History Tellers, Airship, Alcatraz, Libby Prison
  9. – 40:26: Aaron Olity, Alita Rosanski, Andy Herman, Callum PL

Notable quotes from "Bastille of the Confederacy | Episode 1 | Daring Prison Escapes"

  • Imagine it's late at night on February 6th, 1864, beneath the grounds of the Libby Prison in Richmond, Virginia.
    about Libby Prison · at
  • From Wondery. I'm Lindsey Graham and this is American History Tellers. Our history, your story.
    about American History Tellers · at
  • 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…
    about Alcatraz · at
  • On October 1st, 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 rail car, he joined a throng.
    about Union Army · at
  • 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 Libyan son, ship chandlers. It confirmed his worst fears.
    about James River · at
  • 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…
    about Dick Turner · at
  • 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.
    about Major Andrew Hamilton · at
  • 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.
    about Dr. Jack Abbott · at

Who and what is mentioned in this episode?

People

  • Major Thomas P. Turner — Person · 8 mentions
  • Colonel Thomas Rose — Person · 4 mentions · first at
    On October 1st, 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 rail car, he joined a throng.
  • Dr. Jack Abbott — Person · 4 mentions · first at
  • Major Andrew Hamilton — Person · 3 mentions · first at
  • Dick Turner — Person · 2 mentions · first at
  • Captain John Gallagher — Person · 2 mentions · first at
    To calculate the new tunnel's length Rose enlisted the help of one of the diggers, Captain John Gallagher.
  • Luther Libby — Person · 1 mention · first at
    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…
  • Captain Isaac Johnson — Person · 1 mention · first at
    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.
  • Colonel Harrison Hobart — Person · 1 mention · first at
    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.
  • Winston Peterson — Person · 1 mention · first at
    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…
  • General John Winder — Person · 1 mention · first at
    So, it fell to General John Winder, the official in charge of Richmond's prisons, to assess the situation. Winder and Commandon Turner interrogated the guards first on the assumption that the.
  • Molly Bach — Person · 1 mention · first at
    Edited, and produced by me, Lindsey Graham, for airship. Audio editing by Muhammad Shazim. Sound design by Molly Bach. Supervising sound designer Matthew Filler. Music by…
  • Matthew Filler — Person · 1 mention · first at
    Graham, for airship. Audio editing by Muhammad Shazim. Sound design by Molly Bach. Supervising sound designer Matthew Filler. Music by Throne. This episode is written by Ellie…
  • Ellie Stanton — Person · 1 mention · first at
    Bach. Supervising sound designer Matthew Filler. Music by Throne. This episode is written by Ellie Stanton. Edited by Dorian Marina. Produced by Alita Rosanski. Managing…
  • Alita Rosanski — Person · 1 mention · first at
    Filler. Music by Throne. This episode is written by Ellie Stanton. Edited by Dorian Marina. Produced by Alita Rosanski. Managing producer Desi Blelock. Senior managing producer Callum PL. Senior producer Andy Herman.
  • Dorian Marina — Person · 1 mention · first at
    Filler. Music by Throne. This episode is written by Ellie Stanton. Edited by Dorian Marina. Produced by Alita Rosanski. Managing producer Desi Blelock. Senior managing producer Callum PL. Senior producer Andy Herman.
  • Desi Blelock — Person · 1 mention · first at
    Written by Ellie Stanton. Edited by Dorian Marina. Produced by Alita Rosanski. Managing producer Desi Blelock. Senior managing producer Callum PL. Senior producer Andy Herman.
  • Callum PL — Person · 1 mention · first at
    Dorian Marina. Produced by Alita Rosanski. Managing producer Desi Blelock. Senior managing producer Callum PL. Senior producer Andy Herman.
  • Andy Herman — Person · 1 mention · first at
    Rosanski. Managing producer Desi Blelock. Senior managing producer Callum PL. Senior producer Andy Herman.
  • Jenny Lowour Beckman — Person · 1 mention · first at
    Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Olity for Wondering.
  • Aaron Olity — Person · 1 mention · first at
    Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Olity for Wondering.
  • Marshall Louie — Person · 1 mention · first at
    Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Olity for Wondering.
  • General William Tecumseh Sherman — Person · 1 mention
  • Mohammad Shazi — Person · 1 mention

Books & papers

Companies & orgs

  • Confederate States Army — Company · 6 mentions
  • Union Army — Company · 5 mentions · first at
  • American History Tellers — Company · 3 mentions · first at
  • 77th Pennsylvania Volunteer Infantry — Company · 2 mentions
  • 12th Kentucky Volunteer Cavalry — Company · 1 mention · first at
    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…
  • Airship — Company · 1 mention · first at
    American History Tellers is hosted edited, and produced by me, Lindsey Graham, for airship. Audio editing by Muhammad Shazim. Sound design by Molly Bach. Supervising sound…
  • Throne — Company · 1 mention · first at
    Muhammad Shazim. Sound design by Molly Bach. Supervising sound designer Matthew Filler. Music by Throne. This episode is written by Ellie Stanton. Edited by Dorian Marina.…

Concepts & topics

Places & events

  • Libby Prison — Place · 13 mentions · first at
  • James River — Place · 3 mentions · first at
  • Alcatraz — Place · 2 mentions · first at
  • Williamsburg, Virginia — Place · 1 mention · first at
    Long, dangerous journey through hostile territory. The closest Union position was 50 mi to the east in Williamsburg Virginia, which Union forces had captured in 1862.
  • Jonesboro, Tennessee — Place · 1 mention · first at
    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…
  • Bastille — Place · 1 mention
  • Macon, Georgia — Place · 1 mention

Full transcript with timestamps

Wonder. Imagine it's late at night on February 6th, 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 packed 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 5 ft 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 that 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 5t 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, then 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 Colonel is right. Because one wrong move could put an end to any hope you have of escape.

from Wondery. I'm Lindsey 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 Union officers

neared completion of a tunnel that they had dug beneath the grounds of Libby prison in Richmond, Virginia. By then America was nearly 3 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 Libbyy'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 Bastile of the Confederacy.

On October 1st, 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 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 reserved 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 Chikamaga in Georgia and herded onto a train bound for Richmond. Desperate to escape, he leapt from his rail car 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 "Libyan son, ship chandlers." It confirmed his worst fears. Imagine it's October 1st, 1863 in Richmond 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. This is my foot. It's broken. I need a doctor, please. I 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 admires the silver case. Your stomach churns. You can't take that. It's a wedding present from 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 US Army officer's uniform. What good is it to you? Well, that's none of your business. And 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 the 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 breath shallow and your heart pounding. You fix your gaze on the brick walls of 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. 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 Bastile 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,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 liceinfested 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 parrolled 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 prisoners misery was the constant abuse they were forced to endure at the hands of Libbyy's officials and guards. The common daunting 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 Pdition 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 guard's 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 comedon 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 meant a long, dangerous journey through hostile territory. The closest Union position was 50 mi 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 prisoner 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 lit a small candle

and crept downstairs. He found an unlocked door to the cellar and descended into the ratinfested 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 blotss 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 ratinfested 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, guard shortages left the prison kitchen largely unsecured at night. Examining this space, Rose and Hamilton found a potential access point to the cellar and unused fireplace. And on the night of December 19th, they began digging a passageway behind it. Night after night they used a small jack knife 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 spectre of death. Escape was their only option, but

they were running a grueling race against time. On the night of December 30th, 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 accessed the 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 jack knife 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 handsaw. Rose also enlisted two trusted fellow officers and 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 sleepdeprived, 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 2 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 spatoon with dirt. The dumper would pull the dirt fil knapsack out of the tunnel using a makeshift pulley system and then dump 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 squatchching 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 disbelief. 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 5 hours plugging up this cave in and I'm freezing. I'm soaked to 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 guards find us. 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 sigh, looking down at your torn knuckles and the filth coating your body. You really believe this will work? I do, cuz 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 so determined to bend reality to their will. And it might just be the only reason you actually managed to break out of this hell hole. 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 25th, 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. The 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-killing winds blew through the barred windows, making it impossible for the thinly clad prisoners to stay warm or sleep. Then prison commodant Thomas Turner imposed new restrictions on sending and receiving letters which meant there were few accompanying 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, Commandon 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 commonant 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 ft 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 2 ft 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 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, Libya officials tightened security, responding to a separate small-cale escape attempt, meaning the prisoners face constant roll calls and surprise inspections. Commodon 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 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 ratinfested cellar full time. But on the morning of February 6th, 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 on to 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 a miss and soon wandered off. Relieved, Rose pushed an old shoe through the small hole from below to mark the tunnel's end point 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 5 ft 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 2 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 9th, 1864, Colonel Thomas Rose, Major Andrew Hamilton, and the other 13 tunnelers made the final preparations 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 blood hounds. Then if they made it out of the city, they would still have to cross another 50 mi 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 7:00 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 ft 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 9:00 at night on February 9th, 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 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 man 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 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 chute 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. You throw up your hands, desperate to calm the frenzy. Stop. Stop. No. No. If if 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 9th, 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. Commandon 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 Commandon 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 enslaved boy to crawl through it and locate the exit. So only after hours of bickering, dead ends, and fingerpointing did General Winder finally sound the alarm. At last the manhunt began. A full night and half a day after Rose and his fellow tunners escaped. Confederate soldiers took off in pursuit of the fugitives, joined by local civilians who 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 start, many did not get far. During the escape, two prisoners drowned in the icy 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 5 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. Scrambling 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 3 years and begged them to let him go, but the soldiers ignored his pleas and promptly returned Rose to Libby. There a vengeful Commandon 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 rank suffered under Turner's increasingly draconian rule. Now meals consisted of nothing but water and occasionally two or three small turnups. Nevertheless, it was clear to the men that Turner was shaken by the mass escape. One inmate wrote, "When our distracted little common 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 security and dwindling resources, General Winder ordered most of Libbyy's inmates moved to a new prison further south in Mon, 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 Command Don Turner's thumb until at long last on April 30th, 1864, he was released in a Confederate prisoner exchange with the Union. After 7 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 Tecumpsa 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 3rd, 1865, Union forces captured Richmond. Aware that the war would be over in a matter of days, Libbyy'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 3 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 commonant. 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 ring leader 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 threw the Confederate capital into turmoil rattled southern officials, and boosted the morale of the long-suffering inmates who remained. 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 Wonder. 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. American History Tellers is hosted edited, and produced by me, Lindsey Graham, for airship. Audio editing by Muhammad Shazim. Sound design by Molly Bach. Supervising sound designer Matthew Filler. Music by Throne. This episode is written by Ellie Stanton. Edited by Dorian Marina. Produced by Alita Rosanski. Managing producer Desi Blelock. Senior managing producer Callum PL. Senior producer Andy Herman.

Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Olity for Wondering.

Questions about this episode

What is "Bastille of the Confederacy | Episode 1 | Daring Prison Escapes" about?

The narrative delves into a tense moment during the Civil War at Libby Prison, highlighting a harrowing escape attempt by Union officers on February 6, 1864. Amidst uncertainty and looming danger, Colonel Rose leads his fellow prisoners in a desperate decision to continue digging towards freedom, despite the risk of being caught by a nearby guard.

What is mentioned in this American History Tellers episode?

40 people, works and ideas are mentioned, including Libby Prison, Major Thomas P. Turner, Confederate States Army, Union Army, Colonel Thomas Rose, Dr. Jack Abbott. Each one on this page links to its own page with every episode that mentions it.

How long is "Bastille of the Confederacy | Episode 1 | Daring Prison Escapes"?

The episode runs 40 min; the transcript is about 7,075 words in 52 timestamped sections.

More from American History Tellers

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated December 19, 2025.