American History Tellers: "Daring Prison Escapes | Bastille of the Confederacy | 1"

Host: Lindsey Graham
Date: September 3, 2025
Podcast by Wondery

Overview

This episode launches a four-part series on daring prison escapes in American history, focusing on the largest prison break of the Civil War from Libby Prison—a notorious Confederate POW camp in Richmond, Virginia. Host Lindsey Graham recounts, with immersive storytelling, the brutal conditions faced by Union officers, the leadership and ingenuity of Colonel Thomas Rose, and the harrowing tunnel escape of 109 prisoners. The episode uses vivid narrative, historical context, and dramatized scenes to bring this dramatic story to life.

Key Discussion Points & Insights

1. Introduction to Prison Escapes in American History

• Theme: The enduring fascination with prison escapes, from the famous Alcatraz break to Civil War escapes, highlighting the desperation and ingenuity required to attempt such feats.
• Relevance: These stories illuminate the human spirit’s fight against captivity and the conditions that push people to risk everything for freedom.
• Quote (05:18):

  "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." — Lindsey Graham

2. Setting the Scene: Libby Prison, Richmond, 1863–1864

• Libby Prison’s Notoriety:
  • Converted from Luther Libby’s shipping warehouse, Libby was infamous for severe overcrowding, starvation, disease, and abuse.
  • Prisoners faced brutal neglect: “By the third winter of the war, starvation and disease had spread unchecked through Libby’s cramped and frozen barracks.” (06:16)
• Arrival of Colonel Thomas Rose:
  • Rose’s capture at Chickamauga, his failed escape attempt, and rough treatment upon arrival at Libby signal the episode’s central figure and mood.
  • Dramatization of Rose losing his only keepsake:

    “You can't take that. It's a wedding present for my wife.”
    “Well, now she's given it to me. You don't own anything, Yank. This is our prison, our property.” (10:38)

• Prison Life:
  • Overcrowding: up to 1,200 prisoners, grim hygiene, minimal food, and rampant violence/abuse from guards.
  • Rigid, sadistic commandant (Major Thomas Turner) and deputy (Dick Turner “the son of perdition itself”).

3. Concocting the Escape Plan

• Formation of the Core Team:
  • Rose, despite injury, remains resolute in escape plans.
  • Meets Major Andrew Hamilton, similarly determined.

    “[The days went by] like scarcely moving tears, the nights like black blots dying out of a dream of horror.” —Major Hamilton, recalling Libby (15:57)

• Initial Tunnel Attempts:
  • Began in December 1863 behind a fireplace; progress painstakingly slow with only a jackknife, then repurposing stolen tools.
  • Expansion of the team to 15 men, innovative use of straw piles and pulleys to conceal dirt, elaborate shift work.

4. Major Setbacks and Perseverance

• Two Tunnel Collapses:
  • Tunnels collapsed and flooded with sewage, nearly drowning Rose, but his stubborn optimism keeps the group going.
    Quote (24:45):

    “There are only two ways out of Libby. Through a tunnel or in a coffin.” — Dramatized Colonel Rose

• Life in Prison Worsens:
  • Intensified hunger, cold, increased guard violence, communication with home restricted.
    • Roll call punishments become lethal: “...guards treated this new policy like a game, competing with one another to see who could get the most kills.”
• Final Tunnel Plan:
  • Abandoning the sewers, Rose chooses a direct 52–53 ft tunnel to a tobacco shed outside the fence (with clever recon by Captain Gallagher).
  • The crew is demoralized but Rose inspires a renewed effort—work continues around the clock despite risk.

5. The Escape Night: February 9, 1864

• Execution:
  • Rose, Hamilton, and 28 others (plus chosen companions) escape in pairs, using the tunnel.

    “The Underground Railroad to God's country is open.” — Rose, at the completion of the tunnel (34:03)

  • Another 70+ prisoners follow in a chaotic rush, many without planning or supplies.
• Aftermath:
  • Guards only discover the breakout the next morning after chaotic roll calls.
  • Confederate authorities react with confusion and suspicion, ultimately discovering the tunnel—using an enslaved boy to traverse it.
  • Manhunt launched much too late.

6. The Fate of the Escapees and Libby Prison

• Recapture and Aftermath:
  • Rose is recaptured after an arduous five-day journey, nearly making Union lines, and is brutally beaten and returned to Libby (48 returned, 59 make it to Union lines).

    “He was as game a man as I ever saw...and looked us fearlessly in the eye.” — Confederate soldier on Rose (53:41)

• Impact:
  • Turner becomes increasingly harsh; conditions worsen further.
  • The escape rattles Confederate officials. The story is a morale booster for Union prisoners and an embarrassment for Confederate authorities.
  • Libby Prison is eventually phased out after the escape, and the building is later used to house Confederate prisoners post-war.
• Colonel Rose’s Legacy:
  • Despite personal suffering, Rose’s leadership enabled 59 successful escapes, making it the largest prison break of the Civil War.
  • Ultimately released in a prisoner exchange, Rose returns to family and later the front lines—continuing to fight for the Union.
  • The episode closes with Rose’s reluctance in later life to boast of his achievement, his legacy one of “courage and resilience under the most brutal circumstances.”

Notable Quotes & Memorable Moments

On conditions at Libby Prison:

• "The stench was inescapable. Overcrowding and an open latrine created a suffocating odor, and every surface was infested with lice, fleas and rats." — Lindsey Graham (13:00)

On the escape effort and hope:

• “Failure was never thought of.” — Major Hamilton, on Rose’s leadership (27:02)

On Rose’s character:

• “You've never met a man with so much stubborn optimism. Someone so determined to bend reality to their will.” — Dramatized narrator (26:30)

On the mass breakout:

• “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.” — Lindsey Graham (58:35)

Important Segment Timestamps

• Introduction and Dramatization: 00:00–03:59
• Libby Prison background and Rose’s arrival: 06:16–15:12
• Conditions inside Libby & planning the escape: 13:00–18:30
• Initial failed tunnels and renewed attempt: 18:52–31:37
• Final successful tunnel: 34:03–37:59
• Night of the escape: 40:00–44:56
• Confederate discovery, aftermath, and Rose’s recapture: 46:30–55:00
• Legacy, impact, and Rose’s later years: 57:45–End

Tone & Language

The episode employs vivid, immersive storytelling, alternating between lush historical narration and dramatized scenes from the perspectives of both prisoners and guards. Lindsey Graham’s sober yet empathetic narration underscores the drama with gravity, hope, and respect for the individuals involved.

Conclusion

Episode 1 of this series on prison escapes powerfully recounts the adversity and resilience found in Libby Prison’s legendary escape. Through meticulous attention to historical detail, deeply personal dramatizations, and sharp commentary, listeners gain a compelling window into one of the Civil War’s greatest tales of ingenuity and endurance—paving the way for further episodes exploring America’s most daring breakouts.

Next Episode Preview:
The series continues with the mysterious 1962 Alcatraz escape, promising more stories of audacity and determination against impossible odds.