This is an iHeart podcast. Guaranteed human. Thank you. This is Lee Habib, and this is Our American Stories, the show where America is the star and the American people, coming to you from the city where the West begins. Fort Worth, Texas.
Much has been written about the Civil War and those involved in it. 16,000 books on Abraham Lincoln alone. making him the most written-about man besides Jesus Christ.
So it's hard to believe there's anything left to discover about our nation's bloodiest conflict. But Robert Watson, the author of Escape, and a professor at Lynn University in Florida disagrees. He's here to share the story of the largest prison break in American history. It occurred at Libby Prison in the heart of the Confederacy. Richmond, Virginia.
Take it away, Robert. A few years ago, I figured I would write a book about a prison break, but since there's so many out there, I thought, what was the biggest prison break, the largest, most successful prison break in American history? And it occurred during the Civil War. It occurred on February 9th. 1864 from a wretched, a wretched prison in Richmond, which was the Confederates capital.
And the prison was known as Libby Prison. By 1863, midway point of the Civil War, the entirety of the South. was in a starvation atmosphere. They had pretty much run out of food. They were running out of medicine, clothing, all sorts of things.
Some of the most fertile agricultural production areas in the South were being overrun by Union soldiers, which meant they couldn't rely on a fall harvest.
So, by the winter of 1864, January, February, you have a situation whereby the prisoners. In this prison libby knew. That they were going to die. It wasn't if. It was when.
They were also getting so few calories, and probably every other day they weren't even eating, but so few calories when they did eat that even if they did eat, they were going to die.
So, by February of 1864, during a particularly cold spell, the prisoners knew that it was now or never.
Some of them tunneled out, 109 of them.
Sort of like the movie The Great Escape. Only this was way before and way more successful, making it the largest prison break in American history. The name Libby comes from a sign that was hanging on the building, and the Confederacy never removed the sign. The sign said Libyan sons. When the Civil War starts in 1861, the Confederacy realizes it doesn't have enough prisons to.
To take care of Union prisoners, so it converts these three warehouses into a prison. It's just hardwood floors, open windows with bars in them.
So the men were basically warehoused into this facility. The Confederacy decided they were going to make Libby the central receiving site for all prisoners. Any Union prisoner captured during the war would be taken by foot, by wagon, or by train to Richmond. Then they had to walk down this street, which prisoners referred to as a gauntlet. They walked down the street and there they saw Libby prison and they were processed there.
If you were a private or something, you'd then be sent to some other prison, Belle Isle, Andersonville, whatever. But if you were a high-ranking officer, a colonel, or a general, you would stay at Libby. Libby Prison was sort of like the boogeyman because it had such a horrendous reputation. The Confederacy picked as the warden one of the most evil men in American history. His name was Thomas Turner.
And he was just brutal. As he would walk through the prison, he'd kick them in the head if they're lying on the ground dying, order that they be bayoneted, food rations withheld.
So he was a particularly sick guy. There's two men that were behind this great prison break, allowing 109 to escape from Libby Prison. One was Thomas E. Rose. He was a colonel from Pennsylvania, a really big guy with a big beard.
Today he would look at home playing the bass for ZZ Top, or maybe sitting on a Harley-Davidson. He was the beast on the battlefield. He was the type of officer who would pull his sword and pistol and charge into a gray line, waiting for his soldiers to follow him. He repeatedly inspired his men. The second guy is Major Andrew Hamilton.
He was from Kentucky, and Kentucky was a neutral border state. Hamilton's family would have been inclined to be pro-Confederacy, but some Confederate soldiers raided their town and were particularly brutal and ruthless. And it infuriated Hamilton.
So he joins the Union as a cavalry officer and achieves the rank of major.
So these two guys are great. Rose is the big bear of a man. Hamilton's kind of like a MacGyver. Rose, he's captured at the Battle of Chickamauga in the south. And when he takes a musket over the head that knocks him out, he finds himself on a train and he's being taken to Richmond to go to Libby.
Rose jumps off the train and tries to make a run for it. He lands awkwardly and breaks an ankle. Rose manages to elude the Confederate guards for some time before he's captured. He arrives in Richmond, where he has to walk the gauntlet.
So, all the soldiers are walking from the train station to the prison on this road. Local residents would come out and line either side of the street and throw feces or throw garbage on soldiers. They would run up and sucker punch them, get a piece of wood and whack them as if it was a baseball bat, stab them with a kitchen knife.
So, it was awful. The prisoners, the Union soldiers, are huddled up. Walking in a scauntlet, and a few of them wrote that they thought Rose, Colonel Rose, had lost his mind. Why? He's out in front, just walking as if he's a robot.
Someone whacks him in the head. Rose doesn't even move. They throw garbage on me. Don't even wipe it off. Why is he walking so robotically?
He's counting the number of steps. He's memorizing every street corner. He's memorizing the names of the street, where there are guards, where there are not, where there's hiding places, where there's a lantern at night, where there's not. When he gets into prison, he draws a map of everything.
So Rose is already focused.
Okay. And you've been listening to Robert Watson, the author of Escape, also a professor at Lynn University, telling the story of America's largest prison break. And who knew? I certainly didn't. I've read a lot.
Of Civil War history. When we come back, more of this remarkable story. Here on Our American Stories. Lee Habib here. As we approach our nation's 250th anniversary, I'd like to remind you that all the history stories you hear on this show are brought to you by the great folks at Hillsdale College.
And Hillsdale isn't just a great school for your kids or grandkids to attend, but for you as well. Go to hillsdale.edu to find out about their terrific free online courses. Their series on communism is one of the finest I've ever seen. Again, go to hillsdale.edu and sign up for their free and terrific online courses. And we return to our American stories, and with Robert Watson, the author of Escape.
The story of the Confederacy's infamous Libby Prison. and the Civil War's largest jailbreak. When we last left off, Watson was telling us about the two main men behind the prison break, Robert Rose and Andrew Hamilton. Let's return to the story. One night in prison in the winter of eighteen sixty four, Rose knows they're going to die, so he goes to the window of the prison.
There was a horrible storm that night.
Now, the roof had been leaking.
So the Confederate guards put up scaffolding to fix the roof. But a horrible lightning storm scared the Confederate guards away. They left the scaffolding.
So Rose goes to the window and is looking out thinking, if I can break these big iron bars and jump onto the scaffolding, I could climb down to escape.
Now, a normal person would never think if I could break iron bars, but Rose is like the rock. I mean, he's a big dude, strong guy. He can't break it, but while he's trying, a lightning bolt strikes right on property and it illuminates the window. And Rose gasps because there's a face right beside him in the pit's black moonless sky. That was Major Hamilton.
That's how the two of them met. They do the kind of bro nod, you know, and then they go back to their bunks to sleep. The next night Rose had been looking out the window again, And on the window, what he sees is thousands of rats coming from the James River, which is right behind the prison, into the basement, into the dungeon of the prison.
So there's a sewer that runs through the basement, the dungeon, the prison.
So Rose thinks. If I can get down into the basement, I could break into the sewer, float through raw sewage. Plop down into the James River and escape, and no one would ever think of checking the sewers.
So Rose goes, sneaks downstairs at night. There's a door with a deadbolt. Rose is so big, he busts the door open, and he's walking shoeless through a couple of inches of urine and feces with rats stepping on him, him stepping on the rats, covered in rats. He's feeling his way along the wall. In the pit's black darkness, trying to find where the sewer is.
As he's feeling his way along the wall, He hears a noise, he turns around and bumps into someone. It's Hamilton again. The two men had the exact same idea at the exact same time, two nights in a row.
So this time they shake hands and agree to team up, and they're going to skate together. The next night, they go to bust the door again, but the Confederates fix the door and put three bolts on it. But Hamilton finds a fireplace. and realizes that if he could dig down into the fireplace, They could plop down into the basement.
So he steals a knife, he scrapes away all the materials between the bricks, and there's a giant black cauldron in front of the fireplace that the Confederates use to make soup for the prisoners. Rose is so strong, he moves this giant cauldron. They dig down into the basement, which means every morning they have to come up and replace all the bricks and all the mortar and the big cauldron. But they dig and dig for several weeks. Until they're ready to escape.
Three times the digging ended in failure. They ran into a massive tree root. Another time, the sewer collapsed on Rose, and he darn near drowned in raw sewage. The guards came busting in one night when they heard something and almost catched the guys. Rose is stuck in the sewer, but finally, on February 9th, they're ready to break out.
There was a door that led to the basement. The basement was known by the prisoners by the nickname Rat Hell. It was just thousands of rats, raw sewage everywhere, and the entrance to a sewer.
So the Confederate guards never went there for one reason, filled with rats. Two, the stench, and you'd walk through raw sewage. And three, they put a door with a deadbolt. They triple deadbolted, so they figured no one would ever get in. The guards never thought.
That if somebody dug through the fireplace and plopped down, they could get into it.
So Hamilton designs a rope with knots on it. ties it off to a table. And each night they climb down through the fireplace and have to climb back up.
So pretty much for most of the few weeks that these two men are digging their tunnel, they're left alone by the guards. One night the guards do come down in there and darn near catch them. One man dives into the sewer. The other guy dives into a big pile of hay that was in the basement that they used to fill the pillows.
Now all the rats lived under the hay.
So he dives into the hay and he writes that he's ready to sneeze because of all the hay and the pollen and all the dust. And rats are running all over him, but he can't move. There's about five Confederate soldiers with lanterns, a dog. and guns. The guy says, I'm toast.
The dog makes the beeline immediately for the hay, and as he does, the rats go running out and the dog chases the rats.
So the guards basically say damn rats And then they leave because of the stench, and that's when Rose Hamilton can get back to digging. Their tunnel is probably 70 feet, but it's 50-some feet wide. But they have to dig around and up and down, depending on the rocks and the roots.
So they tunnel and dig and dig and dig. They have a little jackknife, and Hamilton steals part of a shovel. Rose is really the mastermind. He does almost all the digging, but Rose and Hamilton are the team. But here's what they realize.
The digging is slow going. There's a lot of rocks, there's roots, and they're digging with primitive equipment. They realize they need to take some men into their confidence. And they're going to come up with three teams, five men each, to do the digging. The concern is, what if you take the wrong man into your confidence and they tell on you?
They take men that they knew that they had served with. Rose takes into confidence some generals that were in the prison who knew a lot of the men and still who had stature. They helped recruit able-bodied men to do the digging. Rose told the men During the days, don't just sit there and whine and sing songs with your fellow prisoners. Walk.
He had him walking laps around the inside of the prison to get in shape. Because they were going to escape. And it was about 60 miles to Williamsburg, which the Union had secured.
So these men were going to have to follow the James River for about 60 miles, running by night, hiding by day. This was not going to be easy. They were weak, and many of them were barefooted. Rose had a broken ankle.
So he made everybody walk to get in shape. Ideally, they want to escape when there's no moon. They want a dark night. Rose had drawn a map. Everybody made everybody memorize the map on how to get out to the James River, then follow it to Williamsburg.
However, because they were starving, because the food was such, Rose then said, Look, as soon as we dig out of here, we're gone. I don't care if there's a moon or not, we've got to go. They did not have the luxury to wait for ideal conditions, a rainy night or whatever it might be. They were literally starving, they had to go. The night before they broke out, Hamilton dug far enough.
Rose goes racing through the tunnel to see where they are. He digs a little bit more at the ground and he said he could feel the cold evening air rush into his face. It was one of the guards. He almost dug into the guard's boot. Rose pulls his head down.
The guard turns and yells, rats! And he jabs his bayonet into the hole. It slices Rose's face, almost goes in his eye. Rose can't flinch. Rose can't move, can't make a sound.
The guard stabs his bayonet and calls another guard over, and they start yelling, these damn rats are digging holes, they're everywhere. The guards leave, and then Rose can run back. What he did was, when the guards left, he took a shoe off. He had borrowed a shoe from one of the soldiers, and he puts the shoe on the top of the hole. That way, the next day, he looked out the window to see where his shoe was, and he realized they were a little bit shy of the fence.
So he then says, the next night, we got to dig X number of feet further, and we're out.
So everybody was ready for the breakout of the prison. And you've been listening to one heck of a story with Robert Watson doing the storytelling. He's the author of Escape. The story of the Confederacy's infamous Libby prison. In the Civil War's largest jailbreak, And I didn't even know about this jail.
I didn't, I'd known other jails and prisons, famous ones in the Civil War, but not this one. And this prison escape, my goodness, now I know where Stephen King might have gotten the idea for Shawshank. Because if you remember, that's how the actor Timothy Robbins ended up burrowing through a pile of waste, breaking through that sewage system and crawling through it. And all of us just. Just wow.
We were just disgusted and inspired by this man's desire to be free. And boy, these guys had a desire that was even deeper because they were starving to death and they knew they'd die in that prison. When we come back. more of the story of the Civil War's largest prison break here. on our American stories.
And we return to Our American Stories and with Robert Watson, author of Escape. Sharing the final portion of our story on the largest prison break in American history at Libby Prison in the heart. of the Confederacy, Richmond, Virginia. Let's return to the story. There had long been a rumor inside Richmond that the Union had a high-placed spy in the Confederate capital.
It turned out it was a woman. Her name was Elizabeth Van Loo, nicknamed Crazy Bet. She was probably the wealthiest resident of Richmond, had a big home up on the hill, which oversaw the prison. She could also see all the Confederate troops leaving and coming into the city, so she would contact Union officers with valuable intelligence. Why was she crazy?
She never got married. She was an abolitionist and believed in women's equality.
So there's no way that the typical Southern officer would suspect a genteel yet crazy older woman to be a spy. She took food down into the prison, gave food to the prisoners, and hidden in a bowl or hollowed out in an egg, she put a little note on directions on how to get out of the city, when to escape, where the Confederate guards were, where they were not. She risked her life and helped, in a major way, a number of soldiers to escape that hellish prison. Crazy Bet had provided the intelligence and plans that allowed the soldiers to escape. She would make something to eat and tell the guards, I'm going to give you this, and you can have a couple of eggs, but as long as you let me give the rest of the soldiers, or if you don't, I'm not coming back.
So the guards are like, yeah, yeah, go ahead. And one of the eggs would be hollowed out and empty, and there'd be a note in there saying there's no guards on 6th and 14th Street. They took the James River, it's 50, 60 miles to Williamsburg, and she would say, Beware on the James, there's a Confederate army bivouacked.
So she was always giving them intel. This is amazing. Crazy bet, Elizabeth Van Loot. I'm sorry.
So after the first tunnel came up on the wrong side of the fence, they had to dig a few feet more to come up on the freedom side of the fence. and they began to break out in the middle of the night. You had to wait long enough for the guards to be asleep. You didn't want to wait too long, knowing that there would be at sunrise a roll call. And Rose had made a map.
Men escaped ranging from lieutenant to general, and they agreed based on Rose's suggestion that they go in teams of two.
So they'd always have a buddy, someone to help them. Because these men are weak.
Some can barely stand, let alone run 60 miles. Rose and Hamilton go running out. They're following the dark streets where there are no guards. They turn a street corner, and there's a group of Confederate guards. Rose, being the hero that he is, tells Hamilton to run.
Rose walks up to the guards to give himself up so that Hamilton could make it. This is the kind of guy he is.
However, Rose was covered in urine and feces, so the guards are like, ah, get out of here.
So Hamilton notifies Union soldiers in Williamsburg that they're coming, the prisoners are coming.
So Union soldiers start to fan out looking for prisoners. Rose, it takes him over a week. Remember, he's running on a broken ankle, nearly gets caught a couple times. He finally makes it to Williamsburg.
Now, there's a wide open field between the Union base and the woods. Obviously, you clear the trees and make a killing zone so the enemy can't sneak up on you.
So Rose is on the tree line, lying on the ground. He's starving. He hasn't eaten. He still has the broken ankle. He's sick.
But he says there's gotta be Confederate sentries around here keeping an eye on the Union camp.
So Rose lays on the ground for hours. He said that he could smell the bacon or whatever was cooking in the Union camp, hear the conversation, see the smoke. I mean, he was close enough to see the camp. Finally, he realizes, okay, there's no Confederate guards, so Rose gets up and runs across the field with a broken ankle. Halfway across the field, half dozen Confederate sentries stand up out of the high grass.
Rose is fighting them. He's actually beating them until one of them bats him over the head with the butt of the gun. Rose is knocked out a second time, finds himself back in Libby. He's put in solitary. And, you know, historians are not supposed to be so personally invested.
in these stories but I admit that I was so upset when Rose got caught, given that all he did. Of the hundred and nine men that escaped. Many make it to freedom. A few are recogn, some live, some die. Rose makes it through the war.
He lives through the war. He's so sick at the end of the war that they're going to discharge him. He re-ups. He stays in until the end of the war. He eventually achieves the rank of general, spends an entire career in the military.
The men he helped to escape All begged him to write a memoir. Rose didn't want to do it. The typical hero says, I'm not a hero, I was just lucky. He won't write his memoir. And finally, he agrees, but he writes a short, underwhelming version.
The good news is it prompted a lot of the men to write theirs. I found about 15 of these that even describe what they ate, the day, the names of everybody, the weather.
So it prompted his men to write the account of Rose's heroism and their escape. Sadly, when the war ends, Hamilton goes back to Kentucky. and he's sitting at a tavern. On a weekend night, sitting out front on a bench with another veteran. And you can imagine these two old guys now talking about the war and having a drink.
And a couple good old boys come by. And Hamilton had achieved a degree of fame in his hometown given this great escape. and these good old boys come by and they start screwing with Hamilton. Hamilton tells them, mind your own business and go have a drink. The one pulls out a gun and shoots and kills Hamilton.
So all that Hamilton had done Despite his escape, Two young guys who probably didn't serve shoot. and kill Hamilton. The only vestige of Libby is there's a sign there that looks like a big license plate. It says this was the site of Libby prison. And there's a cut in the flood wall where people walk through, they take their dogs on walks and jog.
So I've been there a few times, and you know, the risk of sounding ultra-nerdy, I stand there for two, three hours, and everybody that walks by says, Excuse me, do you know what the sign says? I've never met a single person that knew what was there, and most of them say, Oh, I never saw the sign before. And then I tell them. But what's fascinating is on the far end of where the prison sat, where bodies of these great heroes were buried, now there's a development. Several years ago they built the Virginia Holocaust Museum.
And it's sitting on the hallowed ground, the sacred ground of this prison.
So I've gone to meet the directors of the Holocaust Museum. I've gone in and talked to the manager, the people at the desk, the docents, and I've told them, you know what you're sitting on. Nobody knew. I'm still writing to them. My goal is to get them to put up a sign and maybe have a little exhibit that talks about maybe an inadvertent but proper way to remember these heroes through what else but such a hallowed site as the Virginia Holocaust Museum.
And out front of it, they have a cattle car, a real cattle car, and it's sitting over top of you know, the memories and bones of these Union prisoners. And a terrific job on the production, editing, and storytelling by our own Monty Montgomery. And a special thanks to Robert Watson. He's the author of Escape, the story of the Confederacy's infamous Libby Prison. and the Civil War's largest jailbreak.
He also told us a terrific story. about the prison ships in Brooklyn Harbor, the ghost ship of Brooklyn. Look that one up too. Another terrific story about our nation's history. And what a story he told here.
The characters come to life. And my goodness, crazy bet. Without her, this prison break wouldn't have been possible, and I was as angry as Watson was. That Rose was caught. But 109 escaped.
Some lived, some died. And boy, the way Hamilton ended up dying. Two idiots who probably didn't serve, but didn't like that this Kentucky boy had fought with the Union. And so they just shot him. He didn't die in battle.
He didn't die in prison. Two punks killed him for no reason at all. The story of the largest prison break in American history. Here on Our American Stories. Yeah.
This is an iHeart podcast. Guaranteed human. Mm-hmm.
