American History Tellers – Daring Prison Escapes | Escape from Libby Prison | S5E5

Date: October 1, 2025
Host: Lindsay Graham
Guest: Dr. Robert P. Watson, Distinguished Professor of History, Lynn University

Overview: Episode Theme and Purpose

This episode concludes the series "Daring Prison Escapes" by exploring the infamous Libby Prison escape of February 1864: the largest prison breakout in U.S. history. Lindsay Graham interviews Dr. Robert P. Watson, a historian who has extensively researched Libby Prison and authored a book on its harrowing conditions and the remarkable jailbreak. The episode delves deeply into the lives of the prison’s key leaders, the profound suffering endured by Union officers, the mechanics of the escape, and how Libby became both a propaganda tool and a symbol of Civil War brutality. It also reflects on the fates of the main characters post-war and what became of the site itself.

Key Discussion Points and Insights

Why Libby Prison and Prison Escapes Matter

• [03:38] Dr. Watson shares a passion for “the history we don’t know or get wrong” and explains why Libby’s breakout—a story “irresistible” for its drama and humanity—has been overlooked.
  • "This idea of a prison and a prison break, on one hand, it really gets to the essence of human nature… And it's even better when the prisoners are the good guys and when they manage to get out." (Watson, 04:14)
• The notion of an "escape-proof" prison makes the story even more compelling.

The Men Behind the Escape: Leadership and Ordinary Heroism

• [05:12] Colonel Thomas Rose, the main organizer, was a schoolteacher and principal; Major Andrew Hamilton, the critical engineer, was a home builder. They exemplified how “ordinary men” can rise to “extraordinary heights.”
  • "So many of these wonderful heroes end up being just very common people beforehand who just rise to the challenge." (Watson, 05:36)
• Their backgrounds underscore the Civil War’s transformation of civilians into unlikely heroes.

Foreigners in the Civil War and at Libby

• [06:15] Many non-Americans fought for principle—such as Frederico Cavada, a Cuban who saw parallels between slavery and colonial oppression, and several Hungarian exiles who recognized slavery’s resemblance to European autocracies.
  • Cavada’s diaries, kept through his ordeal (having been captive after Gettysburg), became a key historical source.

Appalling Conditions Inside Libby Prison

• [08:28] Prisoners endured severe overcrowding, lack of facilities, starvation, cold, and lice infestations.
  • "They didn't have beds. They didn't have bunks. There were no toilets or facilities. There was no nothing… You'd be piled on top of one another in order to sleep… spooning so that … they could all fit." (Watson, 08:40)
  • "…by December 1863, the officers, the soldiers in Libby knew that it wasn't if, but when they would die from starvation…" (Watson, 10:24)
• The Union blockade and southern economic collapse intensified the deprivation.

Maintaining Morale and Intellectual Life in Despair

• [11:02] Despite everything, educated officers created “the License”—a lice-infested Lyceum—offering classes in European languages, history, engineering, music, and even staging plays (in whispers, out of fear of Commandant Turner).
  • "They organized what they called the Lyceum … they called it the License because they were covered in lice." (Watson, 11:17)

Commandant Turner: The Villain of Libby

• [13:20] Turner's cruelty became both a psychological weapon and a tool of Confederate propaganda; Richmond newspapers documented suffering to boost Southern morale and intimidate Union troops.
  • "…Libby eventually in his hands becomes kind of a psychological weapon of terror…" (Watson, 13:50)
• Public "zoo" tours of the prison further dehumanized prisoners.

The Confederacy’s Desperation and Use of Libby as a Symbol

• [15:23] Libby’s prominent location in Richmond and its daily coverage in newspapers made it a central part of Confederate psychological warfare, fostering dread among Union soldiers.
  • "They would invite citizens or officers to tour Libby… 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…" (Watson, 16:07)

Digging for Freedom: Mechanics of the Escape

• [20:44] With no tools, Rose and Hamilton invented makeshift implements to tunnel under the prison, enduring filth, vermin, and near-drowning as they repeatedly failed before finally succeeding.
  • "You're digging a tunnel in pitch black conditions, dozens of feet through rock and hard soil…" (Watson, 20:57)
  • "…[Rose] crawls back in and starts digging again." (Watson, 22:38)
• Rose’s background as a battlefield leader and his earlier escape attempts primed him to seize on hazards such as the sewer system for their plan.

Escape Night and the Perilous Journey to Union Lines

• [25:15] On the night of February 9, 1864, 109 men escaped through the tunnel. Rose had meticulously prepared: prisoners strengthened their legs, saved scraps of food, and learned reconnaissance from his observations.
  • "He was memorizing every street … which intersections have a lantern, which are dark… He devises a primitive map inside the prison that the men can use to escape." (Watson, 25:50)
• Most escapees hid by day and ran by night, avoiding Confederate patrols.

Elizabeth Van Lew (“Crazy Bet”): The Unsung Heroine

• [28:15] A wealthy abolitionist and secret Union spy in Richmond, Van Lew provided intelligence to prisoners, helped escapees hide, and relayed crucial information to Union commanders.
  • "She plays it [the ‘Crazy Bet’ persona]... When she got into the prison, she would pass along notes to the officers…" (Watson, 28:46)
  • She suffered retribution after the war, but former escapees and President Grant later supported her.

The Aftermath: Hunt, Punishment, and Fate of the Protagonists

• [32:39] Commandant Turner ordered a massive manhunt; although some escapees were recaptured and two died, 59 made it to safety, including Hamilton.
• Rose was recaptured, beaten, and put into solitary, but survived and rejoined the Union through a prisoner exchange.
• After the war, he remained humble, refusing to write of his own exploits; his fellow escapees’ memoirs keep the story alive.
• Hamilton made it to safety but was tragically killed after the war in Kentucky (39:02).
• Turner fled, lived in exile, returned after amnesty, and died unpunished and obscure.
  • "He never is held responsible for the horrific crimes against humanity…" (Watson, 41:19)

Libby Prison’s Ultimate Fate

• [41:35] Lincoln visited Libby Prison after Richmond fell, wanting to preserve it as a warning, but it eventually became a fertilizer plant, then a museum in Chicago, and its material was finally scattered.
  • The site is now home to the Virginia Holocaust Museum—with few aware of the former prison’s history.
  • "There's a little sign… that says Libby Prison. That's it… On the edge of the property… is now the Virginia Holocaust Museum… I mean, talk about sacred hallowed ground…" (Watson, 43:21)

Notable Quotes & Memorable Moments

• On the Human Appeal of Prison Escapes:
  "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."
  — Dr. Robert P. Watson [04:22]

• On Conditions in Libby:
  "There was so little space that men were literally piled up on top of one another in order to sleep… 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…"
  — Dr. Robert P. Watson [09:06]

• On Elizabeth Van Lew’s Subversion:
  "When she got into the prison, she would pass along notes to the officers, like Rose, saying, you know, this intersection’s not guarded… 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… you could hide in the attic until she nursed you back to health…"
  — Dr. Robert P. Watson [28:41]

• Turner’s Threat:
  "Turner 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."
  — Dr. Robert P. Watson [36:57]

• On Libby’s Lost Memory:
  "Every time I go there… 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… on the edge of the property where Libby sat… is now the Virginia Holocaust Museum… What an unusual but maybe appropriate irony historically."
  — Dr. Robert P. Watson [43:00]

Timestamps for Important Segments

| Segment/Topic | Timestamp | |----------------------------------|---------------| | Guest intro: Dr. Watson | 03:11 | | Why Libby matters | 03:38–04:47 | | Rose and Hamilton’s backgrounds | 05:12–05:46 | | Foreigners in Libby | 06:15–08:09 | | Libby’s conditions | 08:09–10:56 | | Morale, “the License” | 11:02–13:09 | | Commandant Turner’s cruelty | 13:09–15:08 | | Propaganda & the “Libby Zoo” | 15:08–17:11 | | The Confederacy’s desperation | 17:11–18:50 | | Mechanics of escape (tunnels) | 20:27–23:58 | | Night of escape & aftermath | 25:15–28:03 | | Elizabeth Van Lew’s aid | 28:15–30:37 | | How escapees evaded capture | 30:37–32:39 | | Turner’s panic/manhunt | 32:39–34:07 | | Rose’s return & punishment | 36:11–37:36 | | Fates of Rose, Hamilton, Turner | 37:36–41:30 | | Libby Prison’s fate | 41:30–44:24 |

Conclusion

This episode provides an immersive and moving account of the Libby Prison escape, capturing not only the drama and suffering but also the ingenuity, courage, and perseverance of those involved. Through Dr. Watson’s research and storytelling, the episode revives a largely forgotten chapter of Civil War history, connecting listeners to the human stories behind one of the greatest jailbreaks in American history.

Next Episode Preview:
The series moves on to the Arizona territory of 1881 with the notorious shootout at the OK Corral.

[For American History Tellers, hosted by Lindsay Graham.]