The winter of 1863. Richmond, Virginia. Libby Prison, a converted warehouse on the James River, held over a thousand Union officers. They were starving, freezing, covered in lice, and treated as numbers, not men.
The war had dragged on for three years, and prisoner exchanges had all but stopped. For these men, captivity meant the duration of the war, if they survived it. Colonel Thomas Rose, a captured Union officer, had been in the prison for months. He was a quiet, determined man, and he had a plan.
He’d noticed that the prison’s east cellar, sealed off from the upper floors, was the only way out. But getting there undetected seemed impossible. Then he met Captain Andrew G. Hamilton, a house builder from before the war.
They struck up a conversation, careful not to trust too quickly, because the Confederates sometimes planted spies among the prisoners. “I estimate the river’s about 45 feet that way,” Hamilton said, pointing. “The sewer line is probably about 10 feet down, running along Canal Street. ”
“You think we can do it?
” Rose asked. “I think we can. I built homes back before the war. I can handle this.
”
They gathered a small group of trusted men. They took a solemn pledge to reveal the plan to no one else. If word got out, the mission would be over before it began. The prisoners slept on the upper floors, but they had access to a kitchen on the lower floor, between a makeshift hospital and the room where the rebel commanders stayed.
On one side of the cellar were the quarters for captive African Americans. On the other, a sealed-off storage area. And in between, the dungeon, where guards sent prisoners to deliver a strong message. Rose and Hamilton knew the only way out was to dig a tunnel from the east cellar.
But first, they had to get into that cellar without being seen. They found their way through a fireplace. Hamilton, with nothing but a simple pocketknife, carefully removed the bricks, creating a hidden entrance. After fifteen nights of work, they made it to the basement, where they were met with thousands of rats.
“Welcome to rat hole,” one of the men muttered. The plan was to dig down, pass under the foundation, then change direction and work parallel with the wall to a large sewer that ran along Canal Street. From there, they could escape. But they had no tools for tunneling.
They had to sneak off chisels, penknives, and case knives. They used spittoons to carry out the dirt. They needed rope, about 200 feet of it. The tunneling team grew to include J.
F. Gallagher and a handful of others. They were monitored closely by the prison clerk, Erastus Ross, whose job was to keep an exact count of the prisoners. If his count was off, the whole prison would go into lockdown, and their little autonomy would be lost.
They dug. They hit water. The tunnel flooded. Their first plan was thwarted.
They tried again, passing through the outer wall to the large sewer in front. But the sewer was blocked by a solid oak grate. Too thick. Three attempts, three failures.
But Rose wasn’t about to give up. He devised an even more audacious plan. He noticed the tobacco shed on the east side of the prison, where unopened care packages were stored. The prisoners were starving, and Rose convinced Ross to let one of his men retrieve a package from the shed.
Gallagher walked the distance and counted the steps. He estimated that 52 or 53 feet of tunneling would bring them right under that shed. They started digging again. This time, they dug around the clock, in three teams of five.
The air in the tunnel was almost impossible to breathe. Four men were needed to keep the work moving. They dug blind, not knowing if they’d reached the shed until they broke through the surface. One night, during roll call, Captain Isaac Johnston was missing.
He’d chosen to stay in the cellar, hiding, rather than risk being caught. The guards marked him as escaped. Security tightened. There was no going back now.
But the prisoners had help from an unexpected source. Enslaved people and free Black workers in Richmond, who passed by the prison daily, traded information with the captives. They knew the city, the streets, the safe houses. They were risking their lives to help.
On the night of February 7th, the tunnel was thought to be long enough. The men prepared their rations, expecting to go out at 9:00. But when they broke through the surface, they found themselves just a few feet from a sentinel. The dogs started barking.
The alarm was raised. “Success? No, all is lost,” one of the men whispered. “I made a hole, a small opening on the outside of the shed.
It was within a few feet of the sentinel. ”
They quickly covered the hole with a pair of pants and some dirt. The sentinels didn’t discover it. The next night, they resumed the mining operations.
“I made it,” one of the diggers gasped, emerging from the tunnel. “We made it. But we’re going to have to wait till tomorrow. It’s too late.
We can’t get everyone out. ”
“I don’t know if I can do another night,” another man said. “I need you to close up the shop,” Rose said. “Tomorrow night.
One more. ”
Imagine the tension. Three months of work. Just one more night.
What if they got found out? The 9th of February was a long day. The men went through the motions of roll call, trying to appear calm. More than once, they feared the cup of happiness, so near their lips, would be rudely dashed away.
At 8:00, they began to leave, two at a time, ten minutes apart. Each man brought one companion. They crawled through the dark, narrow tunnel, emerging under the tobacco shed, then slipping into the cold Richmond night. “Gentlemen, it’s been a journey,” Rose said to the last group.
“But we’re not home yet. Stay in small groups when you get to the surface. Avoid the sentries. Godspeed.
”
From 8:00 at night to 3:00 in the morning, 109 men escaped. They scattered through the city, some wading through nearby wetlands to avoid rebel soldiers, others tapping into the Richmond underground, seeking known safe houses. “We were not observed, and you may be sure we did not linger,” one of the escapees later wrote. “Soon we were out of sight of that hated place.
”
It was a tangible event in the midst of the Civil War. Not Robert E. Lee, not Lincoln.
Just everyday men, tunneling out of Libby, embarrassing the Confederates, and showing that the fight would go on all the way to freedom.
