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1865 photograph of Libby Prison

The remarkable story of the Libby Prison escape

In February 1864, Colonel Thomas E. Rose inspired 109 men to escape from one of the most notorious Confederate prisons of the American Civil War.

Image: Libby Prison in 1865 | Public Domain

Great Escapes With Morgan Freeman tells the stories of the most daring prison breaks in history and the manhunts that immediately followed. The show starts Tuesday, 1st October at 10pm on Sky History.


On the night of 9th February 1864, over 100 Union soldiers pulled off one of the greatest prison breaks in history. Under the dogged direction of Colonel Thomas E. Rose, the men escaped through a tunnel and into the cool winter air.

While many of the men were later apprehended, over half of the escapees made it to safety. What’s more, the repercussions of the audacious escape meant that Libby Prison lost the fearsome reputation it had once held, eventually closing to relocate inmates to safer confines further south.


Deplorable conditions

Housed inside a converted warehouse, Libby Prison was infamous for its overcrowded quarters, squalid conditions and meagre food rations. Hundreds of men were crammed into the building’s makeshift cells.

A complete absence of beds or bedding meant they were forced to sleep on the cold, unforgiving concrete floors in spoon formation, so as to maximise space and body heat. On command, they would turn over in unison to relieve aching bones and muscles.

Of course, waking hours offered little succour. Food was scarce and unappetising, while the open nature of the barred windows meant that the prison was freezing in winter and scorching in summer. Prisoners dare not approach them, either, for fear of being shot on sight.


Rose rises to the occasion

It was into this fetid dungeon that Thomas E. Rose walked, shortly after being bested at the Battle of Chickamauga, which was the first major battle of the American Civil War fought in Georgia. Still stinging from losing his regimental colours, and appalled at the conditions at Libby, Rose resolved to escape at his earliest opportunity.

After unsuccessfully organising a prisoner revolt, as well as two failed attempts to simply slip past the guards, Rose struck upon the plan of tunnelling his way out. Joining forces with the like-minded Major Andrew G. Hamilton, Rose created an opening behind the kitchen stove which led to the basement below.

This area, known amongst both prisoners and guards as ‘Rat Hell’, was covered in straw and infested by vermin. But despite the obvious discomfort and disgust, it provided the perfect cover for the escape attempt, since the guards themselves avoided the room like the plague.

It was Rose’s determination and encouragement which saw the project through to completion. Despite several close shaves and catastrophic setbacks – which saw the vast majority of the conspirators give it up as hopeless – Rose was able to persuade them to keep chipping away, one spittoon of soil at a time


An illustrious escape

After 17 devastatingly difficult days of digging (much of which was carried out exclusively at night), Rose and Hamilton directed their tunnel to the surface. Coming up in the tobacco shed of the warehouse lot across the street from the prison, the inmates simply walked out of the door and melted away into the city, before heading north to meet up with Union forces.

Once word got out that an escape was underway, there was something of a stampede among the prisoners to access the tunnel. Despite the ruckus that this caused, the guards were so confident in the security of the jail that they did not investigate.

Just as the Titanic became one of the deadliest shipwrecks of all time despite being dubbed unsinkable, Libby was the site of one of the biggest prison breaks of all time despite being deemed inescapable. In total, 109 inmates fled the prison walls that night.

Libby’s legacy

Of those 109 escapees, 59 made it to the safety of Union lines. Two perished while trying to swim across the James River and the other 48 – including Colonel Rose – were captured and incarcerated in Libby Prison once more.

However, it wouldn’t last. Rose’s presence alone was enough to cause concern amongst the guards, given how instrumental a role he’d played in the escape last time. Less than two months later, he was exchanged for a captured Confederate colonel. At the close of the war, the prison became a detention centre for many who had once ruled its roost, including its notorious warden Major Thomas P. Turner.

Years later, the prison was dismantled and then rebuilt, brick by brick, in Chicago, Illinois as a tourist attraction. Despite initial success, it had a lifespan of less than a decade and all that remains of the prison today is a plaque commemorating one of the greatest and most daring escapes of all time.