Transcript

Escape from Libby Prison | Episode 5 | Daring Prison Escapes

From American History Tellers · Episode page · Watch on YouTube

· 41 min · 6,956 words · 62 timestamped sections

This is the full, timestamped transcript of "Escape from Libby Prison | Episode 5 | Daring Prison Escapes", an episode of American History Tellers published October 1, 2025 (41 min, about 6,956 words). It mentions 58 people, works and ideas, including Libby Prison, Confederacy, James River, Williamsburg, Virginia, Elizabeth Van Lew.

What is discussed, and when

  1. – 5:00: Libby Prison, American History Tellers, Confederacy, American Revolutionary War
  2. – 10:00: Confederacy, James River, Jefferson Davis, Kavada
  3. – 15:00: Confederacy, Libby Prison, James River, Jefferson Davis
  4. – 20:00: Confederacy, James River, Major Andrew G. Hamilton, Mississippi River
  5. – 25:00: Confederacy, James River, Libby Prison
  6. – 30:00: Confederacy, General Benjamin Butler, James River, Jefferson Davis
  7. – 35:00: Colonel Thomas Rose, Dick Turner, Jefferson Davis, Kavada
  8. – 40:00: Libby Prison, American History Tellers, Andre Johnson, Arizona Territory
  9. – 40:42: Aaron Oclleity, Airship, Alita Rosanski, American History Tellers

Notable quotes from "Escape from Libby Prison | Episode 5 | Daring Prison Escapes"

  • Series, during the Civil War, the Confederacy sent captured Union officers to Libby Prison in Richmond, Virginia.
    about Libby Prison · at
  • Colonel Thomas Rose who organized the escape, Major Andrew Hamilton who invented some devices to aid in the escape. Tell us some things that you learned about these men in your research and writing. Who they were, their.
    about Major Andrew Hamilton · at
  • This dating to the Revolutionary War and even before that in Europe. One of these folks was a fellow named Kavada. He was Cuban and he saw the institution of southern slavery…
    about Kavada · at
  • Ports, which prevented them from exporting, importing, trading. two Jefferson Davis and Confederate leaders were grotesqually incompetent and they ran the economy into the…
    about Jefferson Davis · at
  • You've just brought up Major Thomas P.
    about Major Thomas P. Turner · at
  • Vixsburg was important because it was the big fort that overlooked the Mississippi River. So now the Union controlled the Mississippi River. The South was in trouble and the…
    about Mississippi River · at
  • Yeah. So, remember they didn't have shovels. They didn't have construction equipment. Basically, Hamilton, Major Andrew G. Hamilton, who's kind of a maggyver person, he comes up with all these cool inventions. He steals things.
    about Major Andrew G. Hamilton · at
  • Of abolition, probably the most progressive city at the time. Her father and family were tied to the Quakers, so they were abolitionists. Her father moves to Richmond and is…
    about Quakers · at

Who and what is mentioned in this episode?

People

  • Elizabeth Van Lew — Person · 6 mentions
  • Jefferson Davis — Person · 5 mentions · first at
  • Kavada — Person · 4 mentions · first at
  • Major Andrew Hamilton — Person · 3 mentions · first at
  • Dr. Robert P. Watson — Person · 2 mentions · first at
    Today has spent a great deal of time researching who they were and how they tunnneled out. Dr. Robert P. Watson is a distinguished professor of history at Lynn University. He's…
  • Colonel Thomas Rose — Person · 2 mentions · first at
    Colonel Thomas Rose who organized the escape, Major Andrew Hamilton who invented some devices to aid in the escape. Tell us some things that you learned about these men in your research.
  • Ulysses S. Grant — Person · 2 mentions
  • Major Thomas P. Turner — Person · 1 mention · first at
  • Major Andrew G. Hamilton — Person · 1 mention · first at
  • General Benjamin Butler — Person · 1 mention · first at
    All the while, she's feeding intelligence to General Benjamin Butler, who's the top Union officer in Williamsburg. So, think of it. Every day, if a Confederate army marches out of Richmond, the Fifth Infantry, she.
  • Dick Turner — Person · 1 mention · first at
    Knew about Rose. So, I can't believe Turner didn't kill him. Turner had an assistant warden named Dick Turner. Same name, no relation, who was also a big man. It appears that Dick Turner beat Rose savagely and put him in solitary.
  • Andre Johnson — Person · 1 mention · first at
    Andrew Johnson is the next president.
  • Molly Bach — Person · 1 mention · first at
    Hosted, edited, and executive produced by me, Lindsey Graham for Airship. Sound design by Molly Bach. Music by Thum.
  • Paulie Striker — Person · 1 mention · first at
    This episode was produced by Paulie Striker and Alita Rosanski. Our senior interview producer is Peter Aruni.
  • Alita Rosanski — Person · 1 mention · first at
    This episode was produced by Paulie Striker and Alita Rosanski. Our senior interview producer is Peter Aruni.
  • Peter Aruni — Person · 1 mention · first at
    This episode was produced by Paulie Striker and Alita Rosanski. Our senior interview producer is Peter Aruni.
  • Desi Block — Person · 1 mention · first at
    Managing producer Desi Block. Senior managing producer Callum PL. Senior producer Andy Herman. Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Oclleity for.
  • Callum PL — Person · 1 mention · first at
    Managing producer Desi Block. Senior managing producer Callum PL. Senior producer Andy Herman. Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Oclleity for Wondery.
  • Andy Herman — Person · 1 mention · first at
    Managing producer Desi Block. Senior managing producer Callum PL. Senior producer Andy Herman. Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Oclleity for Wondery.
  • Aaron Oclleity — Person · 1 mention · first at
    Producer Andy Herman. Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Oclleity for Wondery.
  • Marshall Louie — Person · 1 mention · first at
    Producer Andy Herman. Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Oclleity for Wondery.
  • Jenny Lauer Beckman — Person · 1 mention

Books & papers

Companies & orgs

  • Confederacy — Company · 12 mentions · first at
    As we heard in the first episode of this series, during the Civil War, the Confederacy sent captured Union officers to Libby Prison in Richmond, Virginia.
  • American History Tellers — Company · 4 mentions · first at
    From Wondery. I'm Lindsey Graham and this is American History Tellers. Our history, your story As we heard in the first episode of this series, during the Civil War, the.
  • Lynn University — Company · 1 mention · first at
    Tunnneled out. Dr. Robert P. Watson is a distinguished professor of history at Lynn University. He's the author of Escape: The Story of the Confederacy's infamous Libby Prison and the Civil War's largest jailbreak. Our conversation is next.
  • Quakers — Company · 1 mention · first at
  • Union Army — Company · 1 mention · first at
    Knows that the Confederates must have guards hidden, spies hidden in the area in case if the Union Army marches west across this field from Williamsburg into Richmond. So Rose…
  • Chicago investors — Company · 1 mention · first at
    Fertilizer plant. it's just awful. Then it's torn down. It's torn down by a group of Chicago investors who literally transport it brick by brick every single part of the prison…
  • Virginia Holocaust Museum — Company · 1 mention · first at
    Edge of the property where Libby sat at top the bones of all these heroes is now the Virginia Holocaust Museum. I mean talk about sacred hallowed ground. What a fitting way inadvertently this honor.
  • Airship — Company · 1 mention · first at
    Tellers. American History Tellers is hosted, edited, and executive produced by me, Lindsey Graham for Airship. Sound design by Molly Bach. Music by Thum.
  • British Army — Company · 1 mention
  • Thum — Company · 1 mention

Concepts & topics

Places & events

  • Libby Prison — Place · 16 mentions · first at
  • James River — Place · 7 mentions · first at
    Formerly a warehouse complex, this prison sat along the James River in the Confederacy's capital. Around a thousand prisoners of war languished in unsanitary and overcrowded rooms. The men dreamed of escape while they.
  • Williamsburg, Virginia — Place · 7 mentions
  • Vicksburg — Place · 2 mentions
  • Eastern Pennsylvania — Place · 1 mention · first at
    Ring leader, I guess you could say. He orchestrated the prison break. He was a school teacher from Eastern Pennsylvania who became a principal. Hamilton was a homebuilder. And…
  • Mississippi River — Place · 1 mention · first at
  • Arizona Territory — Place · 1 mention · first at
    On our next episode, we go to Arizona territory in 1881, where a group of lawmen led by Wyatt Herp clashes with a band of cowboys over control of a mining town called Tombstone. Their conflict.
  • Cary Street (Richmond) — Place · 1 mention
  • Chesapeake Bay — Place · 1 mention
  • Potomac River — Place · 1 mention
  • Rio Grande — Place · 1 mention
  • Tobacco Row (Richmond) — Place · 1 mention
  • Tombstone, Arizona — Place · 1 mention

Full transcript with timestamps

from Wondery. I'm Lindsey Graham and this is American History Tellers. Our history, your story As we heard in the first episode of this series, during the Civil War, the Confederacy sent captured Union officers to Libby Prison in Richmond, Virginia. Formerly a warehouse complex, this prison sat along the James River in the Confederacy's capital. Around a thousand prisoners of war languished in unsanitary and overcrowded rooms. The men dreamed of escape while they suffered terribly from cold, hunger, lice, vermin, and the whims of a sadistic commonant and his guards. But in February 1864, Libby prison became the site of the largest escape in US history with 109 men desperately trying to make it to Union lines. My guest today has spent a great deal of time researching who they were and how they tunnneled out. Dr. Robert P. Watson is a distinguished professor of history at Lynn University. He's the author of

Escape: The Story of the Confederacy's infamous Libby Prison and the Civil War's largest jailbreak. Our conversation is next.

Dr. Robert Watson, welcome to American History Tellers. Thank you. It's a real pleasure to be here. So, you have written nearly 50 books, including three about prison escapes. I'm curious why prison escapes are interesting to you and why did you write about Libby prison in Richmond, Virginia in particular? One of my sweet spots, I guess you could say, is the history we don't know or the history that we get wrong. And to think that the country's largest prison break from a harrowing, an absolute charal house, this prison was wretched and a high death toll. To think that this isn't written about, to think that we've forgotten about it and don't know much about it, that to me was irresistible. I had to tell that story. To me, this idea of a prison and a prison break on one hand, it really gets to the essence of human nature. To think that brothers did this to brothers. These were Confederates doing this to Union

soldiers. A second thing is not only does this allow us to really get to the human condition, but aren't prison breaks just irresistible? Think of Escape from Alcatraz. Who doesn't like a prison break story? And it's even better when the prisoners are the good guys and when they manage to get out. And what makes it absolutely irresistible is when the prison announces that it is escaperoof. You add all those ingredients for each of these three books that I wrote, including the book escape on the Libby prison breakout.

Irresistible is right. This is a story of great stakes and human consequence. And in our series on daring prison escapes, we featured some of the Union soldiers held inside Libby prison. Colonel Thomas Rose who organized the escape, Major Andrew Hamilton who uh invented some devices to aid in the escape. Tell us some things that you learned about these men in your research and writing. Who they were, their personalities, what were they able to do that really sticks out to you.

Well, as is so often the case with extraordinary acts of heroism and bravery, they were ordinary men. Thomas Rose, who you correctly noted was the ring leader, I guess you could say. He orchestrated the prison break. He was a school teacher from Eastern Pennsylvania who became a principal. Hamilton was a homebuilder. And these men rise to extraordinary heights in the face of almost certain death. So I'm always inspired by the fact that so many of these wonderful heroes end up being just very common people beforehand who just rise to the challenge. Now turning to prisoners in the Civil War in general.

Now we are familiar with foreign agents or nationals fighting in the American Revolutionary War. The Hessian for instance on the side of the British or the French on the side of the Americans. What's not known so well is that foreigners fought on both sides of the American Civil War as well. And when they were captured, of course, they went to prisons, Confederate prisons, including Liby. Who were some of these men and what motivated them to fight in the American Civil War? Well, yeah. So, you're right. There's a long history of this dating to the Revolutionary War and even before that in Europe. One of these folks was a fellow named Kavada. He was Cuban and he saw the institution of southern slavery as similar to the Spanish colonialism that the people of Cuba were experiencing. So for principle he wanted to fight. He goes to Philadelphia and enlists in the war. He is an engineer. He operates these large

balloons that they would fly around in. and the person in the balloon would then get a view of the battlefield and they could then provide intelligence to their commanders. Unfortunately for him, he's shot down at Gettysburg and he's imprisoned. That ended up being a I guess an inadvertent positive thing for me because Kavada speaks multiple languages. He's very smart. He's a great observer and he survives this hellacious imprisonment at Libby and he writes about it. So his journal was a treasure trove for me and it was also inspiring to think that you know someone like him would fight for this cause. There was a couple of Hungarians that inspired me.

They were dealing with in 1848 and beyond the Russians and others were just abusing the Hungarian people. They were on the losing side of a brutal war in Europe and a lot of them were put to death. Some of them fled for their lives and came to America. When they arrive here, they see the institution of slavery as akin to the kind of atrocities they faced in Europe. So, in principle, they fought as well. So, you have all sorts of soldiers that are fighting, all sorts of officers, and this incredible mix of humanity finds its way into Libby prison during the war. So speaking about Libby prison, I mean it's hard to know the exact numbers I'm sure, but at its height, we figure that Libby held as much as a thousand Union soldiers prisoner. Our series, you know, shared some of the terrible conditions they faced, but from your research and reading the diaries and personal accounts of these soldiers.

Share with us what you know about the conditions inside Libby. Yeah, so the numbers were that high. One of the problems was there was not enough space, physically not enough space. Libby had been a warehouse. It was three warehouses that were on the James River, which is that vital river that runs from Richmond toward the PTOAC and Chesapeake. They didn't have beds. They didn't have bunks. There were no toilets or facilities. There was no nothing. It was just hard floors and open windows, which they eventually put bars on. So, the cold, the snow, the rain, the summer heat, the humidity, the bugs, everything came in. There was so little space that men were literally piled up on top of one another in order to sleep. One of the things the soldiers had to do was they would by unit they would all lie down together and spoon like a newlywed couple or something. They would all line up spooning so that that way they could

all fit. Plus they were almost naked. They were freezing and that kept them warm. Then every hour when a Confederate sentry would yell two o'clock and all is well, the commanding officer or senior officer would announce to his unit, "Okay, 3 2 1 spoon left or spoon right and they'd all roll over." That kept them moving during the night, which helped keep them alive. The men had welts on one side of their body, so by rolling over, it mitigated that. That's how crowded it was. The other thing about it was the South, the entire Confederacy, by the middle of the Civil War. So by late ' 62, 1863, they're in a starvation atmosphere. They had pretty much run out of food. They had run out of medicine. They were running out of clothing. They were running out of everything for a variety of reasons.

One, the Union wisely blockaded southern ports, which prevented them from exporting, importing, trading. two Jefferson Davis and Confederate leaders were grotesqually incompetent and they ran the economy into the toilet. So if you're in a starvation atmosphere and you cannot feed your people and you cannot feed your soldiers, why would you try to feed the prisoners? So by around December of 1863, the officers, the soldiers in Libby knew that it wasn't if, but when they would die from starvation that prompted Colonel Rose to try to find a way to escape.

What are some of the ways Union soldiers spent their time and kept their morale up in these grim conditions? So Libby was not only the central receiving place for all prisoners. They would be brought by foot, by wagon, by train to Richmond, processed. And if you were an enlisted soldier, you'd be sent out to another prison. But if you were an officer, lieutenant all the way up to general, you stayed in Libby. So because they were officers, there were a lot of impressive men, Ivy League educations, there were playwrights, there were men who were famous musicians who were mathematicians. So they decided they needed to keep their spirits up in the face of almost certain death and hopelessness. So they organized what they called the lysum, a play on the ancient Greek academy, only because the men were just bitten, harassed, and overrun by pests and lice. They called it the lice ce um u m because they they were covered in

lice. So they had classes for example some of the Hungarian officers I mentioned earlier they gave classes in European languages European history. Kavada the Cuban intellectual gave classes on Spanish. He gave classes on engineering. They even put on plays. Now, the problem for them was that the warden, a guy named Turner, who was just raw evil, if he heard them talking or appearing to have fun, he would have soldiers, guards, bust in to the warehouse and just arbitrarily beat or put officers in solitary confinement. He was known to bash men's heads in with his boot. So, what they had to do was they had to whisper their lines if they were doing plays. But it was a remarkable intellectual gathering.

Fortunately, there were a few journalists who were inside there and they kept meticulous notes with the little pieces of scrap paper and a halfbroken pencil that they managed to smuggle in. So, we have a darn near dayto-day detailed diary, if you will, of all these activities that the men did in the prison.

You've just brought up Major Thomas P. Turner, commodant of the Libby prison. Who was he and what sort of regulations should he have been following in terms of the treatment of prisoners of war?

Turner is the perfect villain in so many ways. He's physically not an impressive man or imposing man. He's a very small and weak man, but he's evil. He has a chip on his shoulder. Turner wants to be an officer and a hero, but apparently he's such a despicable person that every time he applies or tries to gain a promotion or a command, they all say no. So he's sent to Libby to be the warden. And in some ways, he's I guess the perfect warden because he is so brutal and evil that Libby eventually in his hands becomes kind of a psychological weapon of terror. In fact, the Confederacy do not try to keep the horrors of Libya secret. On the contrary, he and Confederate leaders encourage Richmond newspapers to write about it, to say that they captured this general, to say that 10 men were carried out dead the other day, to say that men are starving in hopes that it would lift southern spirits to know that they're

exacting such a horrible toll on Union officers. They were hoping that the word would get out whereby you can almost imagine, Lindsay, a group of Union soldiers sitting around a campfire the night before a battle. And you can almost imagine them looking at each other saying, "Oh my gosh, if we get captured, we're going to go to Liby." And there's only one way out of Libya, and that's horizontal. You know, if you and I could take a time machine back to 1863 1864 everybody knew about Libya. Whereas, ironically, today it's largely been forgotten. And much of the horrors were not only because the Confederacy ran out of food, not only because Libby was never a prison, it was a a warehouse, but because of Comedant Turner, just such a wretchedly evil man. I'm interested in how the Confederacy viewed Libby prison as a propaganda tool. You mentioned that the press often ran stories about the treatment of prisoners

inside Libby. And you know, let's not forget also that Libby prison was seated right there in the capital of the Confederacy in Richmond.

Yeah. So, it's location, location, location, as realators would say. Richmond is the Confederate capital. Richmond had multiple railways, multiple roads, and the James River. So, it was a transportation hub. It was about the only manufacturing center in the Confederacy. And of course, you know, Jefferson Davis is there. And the Libby prison is a stones throw away from where the president of the Confederacy was governing. And Richmond had about four newspapers. and they wrote about Libby almost on a daily basis which was a treasure trove for me. I had details on how many prisoners were brought in on a certain day, how many died on a certain day, what everybody was saying about them. So that form of propaganda, here's probably the most alarming form. The soldiers inside the prison referred to Libby as the Libby Zoo. So what Confederate authorities did was they would invite citizens or officers to

tour Libby and you would walk through the prison and they would point out just like you're going to a zoo and seeing an animal. Here's this famous general from Gettysburg and he's down to 115 pounds and he's in his own feces and he's half naked on the floor. So they would laugh, they would throw things at him. It was used to imbue southerners with the sense that gee, we must be winning the war because this dreaded Union general is stuck in Libya and he doesn't look so tough after all. So what an insult for the prisoners. One, to be humiliated on a daily basis. Two, to just face the prospect of beatings and you're going to die in the prison, but to have people walk through and lear at you like you're a zoo animal in a cage. So, uh, yeah, all that was this form of southern propaganda, if you will, to make it a psychological form of terror. Thinking about this time in the Civil War, you know, beginning of 1864, what was the

state of the Confederacy? What were things like at Libby and in Richmond? We mentioned the dire need for food, but what else was happening? It became clear by the end of 1863, early 1864, that it was not if, but when. The war was going to end for the Confederacy. They simply could not put enough men in the field. They were running out of everything. By early 1864, you have Union forces in almost every Confederate state. You have multiple Union armies advancing through Tennessee, Georgia, Virginia. By early July of 1863, Ulisses Grant had seized Vixsburg.

Vixsburg was important because it was the big fort that overlooked the Mississippi River. So now the Union controlled the Mississippi River. The South was in trouble and the soldiers in Libby understood that whenever a new officer would be brought into the prison, the first thing that happened after they were processed, often stripped, robbed, beaten, when they were put into the warehouses, all the other officers would run up and debrief them, I guess you could say. And they kept learning that the war is going on, the Union's losing, the Union's winning, this, that, and the other thing. So the the soldiers knew that even though on paper this war should be ending, it still could drag on and they were out of food, out of medicine and dying.

Therefore, the only option is to find a way to escape. So, Colonel Rose, Major Hamilton, and a small group of other men decided that enough was enough and escape was the only option. So, they began digging not one but eventually three tunnels until they could find their freedom. Remind us how they did it and how grueling this process must have been.

Yeah. So, remember they didn't have shovels. They didn't have construction equipment. Basically, Hamilton, Major Andrew G. Hamilton, who's kind of a maggyver person, he comes up with all these cool inventions. He steals things. They find part of a shovel. He steals a small knife. He steals some rope. He steals a spatoon. And they use all this to dig these tunnels. Remember, you're digging a tunnel in pitch black conditions, dozens of feet through rock and hard soil. oftentimes they run into the roots of a tree or the foundation of the building. So it's a grueling task, but the idea came from something really interesting. So Colonel Rose, who's this big bearded bear of a guy, he looks like today he'd be should be sitting on a Harley-Davidson. Rose was the officer that would lead from the front. If his line was being broken by a Confederate assault, Rose would pull his pistol and sword and charge into the sea of gray

uniforms. He also was captured at the battle of Chikamaga and he's put on a train and the train is taking him to Richmond. What Rose does is when not all the guards are watching, he jumps off the train, tries to make a run for it. He lands wrong and fractures his ankle. So Rose is in the prison with a broken ankle that's untreated and he's going to dig out and try to run to freedom. He goes to a window of the prison and he peaks out of the window because if you put your head in the window, a guard would shoot you. He peaks out of the window and he sees swarms of rats going in and out of the river. He can smell and knows that there's a sewer in the basement. So Rose has this idea if I can get down into the sewer and dig into the sewer, I could float through that raw sewage, nobody would think of that, and plop into the James River and then run.

So Rose does the digging. Hamilton hooks up a knapsack, a spatoon and rope, ties it to Rose's ankle so that when Rose fills it with dirt and rock, Hamilton can pull it out, dump it, and then pull it back in. That way, Rose doesn't have to come in and out of the tunnel every couple of minutes. Also, if Rose passes out, because he's so far underground, he's not getting enough oxygen, Hamilton can drag him out. At one point, Rose digs into the sewer and almost drowns because it floods it. They pull him out half dead. As soon as they revive Rose, what does he do? He crawls back in and starts digging again. At another point, he digs into a dead end. What are we going to do? Everybody says, "What are we going to do?" Rose says, "I'm going to start a second tunnel." So, he is indehaticable. his uh courage inspires the other men and they dig till they can finally come out hopefully on the freedom side of the wall around Libby.

Listening to you and your characterization of Rose, it seems like he's an inspiring and driven character and he eventually digs three tunnels after failing twice before. This is arduous, grueling work. I'm wondering why he continued in the face of failure like this. Was it that he is an inspiring driven person and this is the only thing he could do or was it merely an act of desperation?

I think it's both. I think you're spot on. So to make it even more grueling, what they do is they need to dig the tunnel at night while the other soldiers sleep. So as soon as the last roll call and lights out, if you will, is announced and all the soldiers bunk down. That's when Rose and Hamilton sneak down into the basement and start digging. What that means is neither of these men is sleeping. So they know that they're running themselves down physically because they're digging all night. Moreover, imagine the conditions in the basement. Thousands of rats, raw sewage, horrific conditions. They haven't eaten and now they're not sleeping. So there was something special about Rose. And Rose just managed to reach down inside himself and grab a hold of his his courage and his conscience and not let go. And he was just single-minded. And there were a couple of times when the other men said,

you know, after the first tunnel or second tunnel didn't work out, give it up. But Rose, he didn't give him a pep talk. He just grabbed a piece of a shovel and grabbed a jack knife and crawled into the tunnel and started digging again. So, you know, you wonder in those kind of conditions, we all need something to keep us going. Rose found the task of trying to escape. That's what motivated him. He stuck with it and it worked. So then finally on the night of February 9th, 1864, Colonel Rose, Major Hamilton, and ultimately 109 men in all escaped Libby prison. But that was just the beginning. Once they were outside of Libby, what was next? Yeah, it's one thing to dig out. It's another thing to manage to escape. Richmond is not only the Confederate capital, but it's the central grounds for all the Confederate weaponry, the soldiers. So it contains at any one time thousands of Confederate soldiers. The Confederacy

knows the Union would like to attack Richmond. So ringing the city. There's a perimeter of guards everywhere. So how are you going to possibly get out? So what Rose did was um he made the men that were going to escape with him, he made them walk in circles every day around the prison just to keep their legs strong, to be in shape, if you will. He also had them save food, which is hard to do. You know, if you only get one rotted biscuit a day, how do you eat half of it and save the other half? So, he's encouraging them to try to save a little water, save some food, to walk, to get enough sleep, to get ready to go when it comes. The other thing Rose does is when he's brought to Richmond on a train, one of the horrifying things of Libby was what I referred to as the gauntlet. You get out of the train and you walk down the main street in Richmond to the prison. The Confederate people, the Richmond residents would

line up on either side. And as the soldiers were marching toward their imprisonment, they would heckle boo, throw feces and garbage on them, come up and sucker punch them, hit them with a piece of wood. It was a terrifying situation. When Rose is being marched from the train station to Libby, the other men behind him thought he had lost his mind because he's kind of walking by himself in a like a zombie state, you might say. And someone comes up and hits him. Rose doesn't even flinch. If someone spits on him, he doesn't even remove the spit. What is wrong with Rose? He's memorizing every street. He's memorizing every intersection. Where are the Confederate guards? Where aren't they? which intersections have a lantern, which are dark. He's counting the number of steps. So, Rose is already planning his escape, and he devises a primitive map inside the prison that the men can use to escape. So, when you get

out of Richmond, the way to escape is along the James River. It's an easy natural landmark, and it's about, I don't know, 60 miles east to Williamsburg. They found out that Williamsburg was in Union hands. So these men need to somehow half starved rose with the broken ankle with confederates looking for you. They have to manage to get 60 miles to freedom. So it sounds like Richmond was a hostile place for any Union officer, let alone an escape prisoner. But there was at least one person in Richmond willing to help. Tell us the story of Elizabeth Vanloo.

Yeah, so I love Elizabeth Vanloo. She's one of my heroins from history. They called her Crazy Bet. She was originally from Philadelphia, which was the hot bed of abolition, probably the most progressive city at the time. Her father and family were tied to the Quakers, so they were abolitionists. Her father moves to Richmond and is probably the wealthiest resident of Richmond and dies and leaves everything to her. So, she's living on top of the hill that looks down over the river into prison. She's known as Crazy Bet because she believes in abolition and she doesn't marry. So, she's seen as this crazy older woman.

She plays it. Why? She is one of the few that has money. So, she would bake, you know, I don't know, fresh cornbread. She would cook something. She would take it down to the prison to the guards. Now, if you're a guard, you're starving, too. And imagine the smell of freshly baked goods. The guards led her into the prison. When she got into the prison, she would pass along notes to the officers like Rose saying, you know, this intersection's not guarded. Beware, there's a Confederate Union two miles outside of the city beside the James River. So, she was passing intel to the prisoners. She also let the prisoners know that if they escaped and they were too weak to run, a former slave that she purchased the freedom for this woman, she would be at a certain intersection.

You could meet her and she would guide you in the middle of the night to Elizabeth Vanloo's house and you could hide in the attic until she nursed you back to health. So, she was remarkable. All the while, she's feeding intelligence to General Benjamin Butler, who's the top Union officer in Williamsburg. So, think of it. Every day, if a Confederate army marches out of Richmond, the Fifth Infantry, she would pass intel saying the Fifth Infantry is 5,000 men. They marched northwest at 2:00 with six cannons. I mean, she was on top of the hill. She saw everything. So, she was a spy. She helped the soldiers to escape and she managed to pull it off throughout the war. Unfortunately for her, after the war, the Confederates figured out she was the spy. They basically steal everything she has. But those former Union soldiers that she helped to escape, they send her money. And later, Ulissiz Grant makes her a postmaster.

So, she has a job and an income. So, here's the crazy bet, Elizabeth Vanloo. Ultimately, 59 Union soldiers fully escaped and made it to safety. including Major Andrew Hamilton. How did they escape Richmond? Uh what were some of the ways they were able to evade capture?

Yes. So Rose had maps. Crazy Bet provided them with intel. When they went out of the tunnel, they went two by two by two. That way each man had a helper. Hamilton and Rose were the first two out. All the other prisoners voted, of course, to let those two go out because they were the ring leaders. He and Hamilton and others hid inside hollowedout logs. They hid by day, ran by night. Tragically, some do get caught to die, but thankfully many make it to freedom after all this. And when I was first reading these diaries, you know, historians are not supposed to uh let your emotions get involved. You're supposed to be dispassionate. I'm not.

I'm rooting for these guys. And I'm reading it and Rose gets captured and he gets brought back to Libby and put in solitary confinement. And I'm going, "Oh no." He makes it all the way out to the border of Williamsburg, but there's a large field outside of Williamsburg. He can smell the bacon cooking. He can hear the voices, see the campfires, but he knows that the Confederates must have guards hidden, spies hidden in the area in case if the Union Army marches west across this field from Williamsburg into Richmond. So Rose spends almost the whole day lying on his belly in the tall grass at the tree line looking for these Confederate spies. Satisfied that there are none, he goes low and fast on a broken ankle running across the field.

Several Confederate guards pop up from the tall grass and he gets into a scuffle with them. Now, if it was one or two, Rose could have beaten a you know what out of him, but there's several of them and they capture Rose and bring him back to Richmond. Thank goodness he survives incarceration to live and write this particular story.

So what did Libbyy's commandon Thomas Turner do when it was discovered that 109 prisoners were suddenly missing at morning roll call? What did this discovery set in motion?

Well, this was a panic not only for him but throughout the Confederacy. He knows that he's never going to get a promotion. He knows he's going to be held accountable. And remember, everybody in the Confederacy knew about Libby because it was used for propaganda. So, what an embarrassment. And they escape a prison that's supposed to be escape proof. And they do it right under the nose of Jefferson Davis, the president of the Confederacy, whose office is right near Libby. So, it's a full-on panic. They get guards, they get soldiers, they get units in the area, they get civilians, they get blood hounds, they get horses, they get torches. It's one of the biggest manhunts in American history until the manhunt after Lincoln is shot by John Wils Booth. And they spread out far and wide to find these prisoners. And they're going to leave no stone unturned. And consequently, that's why several of the prisoners were captured.

So the fact that so many of them, including Hamilton, managed to make it is extraordinary. There's no way they should have done it given the hundreds of men that are looking for them, given that they're running barefoot, starving and half dead. So yeah, it is a huge embarrassment for Jefferson Davis and Comedon Turner.

In another version of history writes the story the way we don't like it. Colonel Thomas Rose, our our heroic protagonist, is captured as you described. This must have been devastating for him. After Confederate troops recaptured Colonel Rose, you mentioned that he went to solitary, but when else did he face when he was brought back? Yeah, he's first thing that happens is he's beaten. He's lucky they didn't kill him. Turner had announced that he was going to kill everyone. In fact, one of the things Turner did after the escape was he ordered that slaves dig a small, I guess, pit the whole way around the perimeter of the prison and they filled it with explosives and Turner said, "If somebody tries to escape, I'm going to just blow the whole prison up." He threatened to kill everybody. I think quite frankly, it's a miracle that Turner didn't kill Rose, given that he was the one in charge of it. He's the

one who made it happen. Moreover, Rose had a reputation. He was such a beast on the battlefield that a lot of people knew about Rose. So, I can't believe Turner didn't kill him. Turner had an assistant warden named Dick Turner. Same name, no relation, who was also a big man. It appears that Dick Turner beat Rose savagely and put him in solitary. They surely, we don't know all the details, surely denied him food, healthc care, but against all odds, Rose manages to survive again. He was just he refused to die, I guess you could say.

So, Colonel Rose was finally freed from Libya in a prison exchange just before Richmond fell to Union forces. What happened to him for the rest of his life?

The problem we have is that after the war ended, Rose was asked by all the other men to write his memoir because this is such an extraordinary story and they all owed their lives to Rose. He doesn't want to write his memoir. He's too humble. They push him and push him. He eventually acquiesces and he writes a very short account where he basically says, "We escaped." I mean, he downplays his heroism. The good news was the other men that escaped were so upset that Rose didn't take more credit for this that it prompted them to write their accounts.

So, I had no shortage of firsthand diaries and memoirs, lots of them. Like Kavada, the Cuban soldier, he was stuck in the prison and he writes about Rose's poor conditions. So we do have some accounts. Rose being the, you know, patriot that he was, he stays in uniform. He spends the rest of his career in the military. He rises to the rank of general. He becomes a minor celebrity and he does write his memoir. Although, as you would love a true hero to be, he dismisses any talk that he was actually a hero.

What about Major Andrew Hamilton, Colonel Rose's right-hand man? He made it to the Union lines, right?

Yeah. Hamilton's one of the first to make it to Williamsburg. He's younger than Rose and he's not as in bad a shape as Rose, although he too is exhausted from tunneling every night, all night for days and days and days. Hamilton makes it to Williamsburg. He notifies the Union that these soldiers are escaping. So that way the Union can fan out and be on the lookout. So Hamilton becomes kind of a minor celebrity as well. He's part of the Stashing Libby break. Hamilton's from Kentucky, a border state. He goes back home after the war and it's absolutely tragic.

Hamilton and another veteran, you know, on a Saturday night they go to the local tavern. These two guys are sitting out front having a drink, reminiscing about the war. And a couple of good old boys walk up to them and we don't know the details that whether they knew it was Hamilton or they heard what he was saying or they were just drunk or just looking for trouble. These good old boys shoot and kill Hamilton. So this extraordinary man, this remarkable hero who lives through Libby, lives through the war, is shot by his own people. So that was that was heartbreaking.

So that's the ultimate fate of our heroes. Uh what about our villain Thomas Turner?

So Turner can't bear the thought of living in a country under Lincoln or the Union. Like many Confederates, he was part of this revisionism, this lost cause mythology that somehow the South was a utopian society. Slaves were like children and everybody got along. And somehow Lincoln and the Union were these oppressive monsters. So Turner along with a lot of other Confederate leaders, he runs. He makes it to Texas. He and another group of Confederate soldiers cross the Rio ground. They go to Mexico. A lot of them don't like it. Mexico.

They're never happy anywhere. Some make it to Cuba. They don't like Cuba. They go to England. They don't like England. Turner eventually goes to Canada. Doesn't like Canada. Then they come back after Lincoln's assassination in April of 1865. Andrew Johnson is the next president. He's from Tennessee. And a few years later, he offers sort of a cart blanch pardon. Any Confederate soldier can come back. All's forgiven. So Turner eventually comes back. uh he dies in anonymity. We're not 100% certain of the details, but it appears to be in Tennessee. And yeah, he never is held responsible for the horrific crimes against humanity that he perpetrated while he was the comedon. So that's our cast. What about our setting here? What happened to Libby prison itself?

So in um early April of 1865, Richmond falls as the Jefferson Davis, Roberty. Lee, as the Confederates evacuated, they burned their own city. If we can't have it, no one can have it. Lincoln wants to go to Richmond. Lincoln goes, he wants to meet with Jefferson Davis. Unfortunately, there's hardly anybody there to meet with. Lincoln tours the city. He wants to go to Libby prison. He knew all about it. He does. He goes to Libby and the crowd that gathers impromptu starts shouting, you know, we will tear it down. And Lincoln says, "No, leave it. Leave it as a memorial to the horrors of what people can do to one another. It'll be an everpresent reminder." Unfortunately, it wasn't.

Some years later, it's turned into a fertilizer plant. I mean, it's just awful. Then it's torn down. It's torn down by a group of Chicago investors who literally transport it brick by brick every single part of the prison bar by bar on the window. They transport it by train all the way to Chicago and they build a Libby prison civil war museum and for a few years it's popular then it dies out and they go bankrupt and unfortunately the owners of it announced to any tourist that was visiting just take stuff home with you. So people took bricks. They took the bars. So where is Libby prison today? There's a brick in Iowa in a barn somewhere. There's a bar that is sitting in Kansas. I mean it it it was just dispersed. So if you go to the site where Libby Prison is today, and I have many times, it's on Kerry Street, C A R Y, in Richmond, right on the waterfront, 20th and Kerry. Today it's Tobacco Row. It's Richmond's a

great city. There's all these micro breweries. It's pedestrian friendly. There's nothing there. There's a flood wall that was built by the city so that the James River and Canal don't flood the city. And the flood wall has a cut in it right where Libby sat. And people jog in and out. People walk their dogs. Every time I go there, I just for curiosity, I anybody that jogs or walks by, I say, "Excuse me, do you know what was here? Have you ever heard of Libby?" I've never found anybody. There's a little sign. It looks like a large license plate that says Libby prison.

That's it. But here's the irony. On the edge of the property where Libby sat at top the bones of all these heroes is now the Virginia Holocaust Museum. I mean talk about sacred hallowed ground. What a fitting way inadvertently this honor. I went and met with several of the people at the Holocaust Museum and I said, "Do you know what you're sitting on top of? Do you know what was here?" They had no idea. So it was picked by mistake. What an unusual but maybe appropriate irony historically.

Well, Robert Watson, thank you for reminding us about Libby and thank you so much for joining me on American History Tellers.

It's my pleasure. And Lindsay, thank you for what you do to keep history alive.

That was my conversation with Robert P. Watson, distinguished professor of history and author of Escape, the story of the Confederacy's infamous Libby prison and the Civil War's largest jailbreak. On our next episode, we go to Arizona territory in 1881, where a group of lawmen led by Wyatt Herp clashes with a band of cowboys over control of a mining town called Tombstone. Their conflict culminates in one of the most infamous events in the American West, the shootout at the OK Corral

from Wondery. This is the fifth and final episode of our series, Daring Prison Escapes for American History Tellers. American History Tellers is hosted, edited, and executive produced by me, Lindsey Graham for Airship. Sound design by Molly Bach. Music by Thum. This episode was produced by Paulie Striker and Alita Rosanski. Our senior interview producer is Peter Aruni. Managing producer Desi Block. Senior managing producer Callum PL. Senior producer Andy Herman. Executive producers are Jenny Lowour Beckman, Marshall Louie, and Aaron Oclleity for Wondery.

Questions about this episode

What is discussed in "Escape from Libby Prison | Episode 5 | Daring Prison Escapes"?

In order: 0:00 Libby Prison, American History Tellers, Confederacy, American Revolutionary War; 5:00 Confederacy, James River, Jefferson Davis, Kavada; 10:00 Confederacy, Libby Prison, James River, Jefferson Davis; 15:00 Confederacy, James River, Major Andrew G. Hamilton, Mississippi River; 20:00 Confederacy, James River, Libby Prison; 25:00 Confederacy, General Benjamin Butler, James River, Jefferson Davis; 30:00 Colonel Thomas Rose, Dick Turner, Jefferson Davis, Kavada; 35:00 Libby Prison, American History Tellers, Andre Johnson, Arizona Territory; 40:00 Aaron Oclleity, Airship, Alita Rosanski, American History Tellers.

What is mentioned in this American History Tellers episode?

58 people, works and ideas are mentioned, including Libby Prison, Confederacy, James River, Williamsburg, Virginia, Elizabeth Van Lew, Jefferson Davis. Each one on this page links to its own page with every episode that mentions it.

How long is "Escape from Libby Prison | Episode 5 | Daring Prison Escapes"?

The episode runs 41 min; the transcript is about 6,956 words in 62 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.