Podcast Summary: "Who Did What Now" – Ep. 180: Robert Smalls Vs the Confederacy

Host: Katie Charlwood
Release Date: February 4, 2026
Theme:
This episode celebrates Black History Month by shining a light on the extraordinary life of Robert Smalls—born enslaved, self-liberator, Civil War hero, entrepreneur, and U.S. Congressman—and the audacious night he stole a Confederate ship to seize freedom for himself and his family. Host Katie Charlwood brings her signature humor, sharp historical insight, and candid asides to recount Smalls’ journey from bondage to national prominence.

Episode Overview

Katie introduces Robert Smalls’ story in the context of Black History Month, pushing back against critics who challenge her discussing Black history as a white woman—a concern she addresses with frank humor. The episode’s driving theme is the daring and impact of Smalls' life, and its resonance with America's ongoing struggles with race, agency, and historical remembrance.

Key Discussion Points & Insights

1. Context: Black History Month, Slavery, and Education

• Katie opens with tongue-in-cheek commentary about blowback for covering Black history as a white host:
  "I am whiter than Taylor Swift’s dancing… I’m so white I glow in the dark, okay? I am a very white person.” (03:15)
• She stresses the importance of context in studying history, rejecting arguments that discussions of the transatlantic slave trade should be balanced by mentioning every other slave trade in world history (04:20).

2. Robert Smalls’ Early Life in Slavery

• Born April 5, 1839, Beaufort, South Carolina—to Lydia Polite, an enslaved “house servant.” Father likely Henry McKee, her owner (08:00).
• Katie explores the cruel hierarchy of house slaves vs. field slaves and colorist classifications like "mulatto, quadroon, octoroon," and their impact under the “one drop rule” (11:30).
• Lydia, fearing Robert’s relative comfort, arranged for him to labor in the fields and witness whippings, to teach him the grim realities of slavery (15:00).
• Katie contextualizes how children transitioned quickly to adult work, with no adolescence—by 12 (20:00).

3. Early Work in Charleston & Family Life

• At age 12, sent to Charleston to learn a trade; worked as a busboy, lamplighter, and "knocker-upper" (alarm clock) for miniscule wages, most taken by his enslaver (21:45).
• Katie describes young Robert’s growing skill as a wheelman/pilot, his knowledge of Charleston Harbor, and social dexterity.
• Smalls falls for Hannah Jones (hotel maid, 31 to his 17), and they marry with owners’ permission—legal only for property purposes (26:00).
• Katie discusses the cruel logic of chattel slavery: “because chattel slavery… every generation after you is also enslaved”—and the dynamic of enslaved men buying their loved ones’ freedom (28:00).
• Robert attempts to buy Hannah and daughter Elizabeth’s freedom for $800 (equivalent to $31,621 today), but cannot save enough before the Civil War (28:50).

4. Civil War & The Plot for Freedom

• Abraham Lincoln’s election in November 1860 triggers secession; South Carolina first to leave Union (31:00).
• Clarifies: Civil War is about “the right of slave ownership, okay, that’s the rights.” (33:45)
• Smalls is wheelman on the CSS Planter—a transport ship for Confederate troops and arms, manned mostly by enslaved men (35:00).
• Union blockade of Charleston squeezes the Southern economy; Robert Smalls’ mother escapes to freedom, but he remains enslaved (41:30).
• Katie introduces the pivotal moment: a failed barge “defection” by enslaved men sows seed of hope, making escape seem possible (43:00).
• Fellow crew jokes about stealing the Planter; Smalls treats it seriously, and a small, trusted circle develops a daring escape plan—knowing failure means death (44:30).

5. The Daring Escape (May 13, 1862)

• Night of May 12th, white officers leave Smalls and crew unsupervised, as was custom (48:45).
• At 3:30am, with captain’s hat and jacket, Smalls pilots the Planter, collecting his wife, children, and other families en route (49:30).
  • Notable moment: “If their plan fails, they’re just going to blow up the boat with them on it”—freedom or death (50:30).
• They pass five Confederate checkpoints using learnt flag signals and timing (52:00).
• Nearing Union lines, they raise a white bedsheet as a flag of surrender.
  • Robert shouts: “Good morning, sir. I’ve brought you some of the old United States guns, sir, that were for Fort Sumter, sir.” (54:00)
• The Planter and crew are celebrated in the North; the Confederacy is humiliated by the audacity and strategic loss, the white officers jailed for negligence (55:30).

6. The Aftermath: Heroism & Advocacy

• Smalls receives $1,500 (crew $450 each; less than deserved), but more importantly, critical freedom and national celebrity (58:30).
• Smalls helps Union by piloting and removing Confederate mines; he earns much more than the average black soldier ($40/mo vs. $13/mo) (59:45).
• He becomes a strong abolitionist voice, persuading Lincoln to enlist black soldiers—“up to 5,000 black men” join the Union thanks to his advocacy (01:02:45).
• Battle bravery: When a cowardly white captain flees during a Confederate attack, Smalls takes command, saves ship and crew, and is promoted to captain (making $150/mo) (01:04:00).
• Personal tragedy as his infant son dies of smallpox; Katie issues a fiery pro-vaccine rant (01:06:00: “Vaccinate your f*cking kids, okay?”).

7. Postwar Triumph & Political Life

• Buys his former master’s home in Beaufort; allows McKee’s destitute family to live there, funds his likely half-brother’s education and daughter’s needs (01:09:30).
  • “He is an incredibly decent man; I am an incredibly petty person. Robert Smalls is not.” (01:13:00)
• Becomes businessman, landowner, newspaper founder, advocate for education, and political leader—the “King of Beaufort County” (01:16:00).
• Elected to state and federal office: State House, Senate, and five terms in U.S. House (1870s–1880s), one of the first black Congressmen (01:17:30).
• Explains party realignment in the U.S.—how Republicans were the anti-slavery party then, Democrats opposed black rights (01:16:30).
• Faces white violence (red shirts, Ku Klux Klan), false bribery charges, and relentless attempts at disenfranchisement/gerrymandering (01:19:00).
• Landmark Supreme Court case over property ownership sets precedent for black homeowners in the South (01:22:00).
• Despite set-backs and institutional racism, Smalls regains his seat multiple times; dedicates his life to education, civil rights, and public service (01:24:00).

8. Legacy and Later Years

• Both wives (Hannah and Annie) predecease him, but he continues advocating for education and public work for his children and community (01:26:00).
• Appointed customs collector at Beaufort port by multiple presidents, serving until 1912 (01:28:30).
• Smalls dies in 1915, “marginalized again by the same country he had saved, served, and reshaped”—but never gives up on his dignity or activism (01:30:00).
  • “Robert Smalls was one hell of a dude in, like, he’s one of the few men in the world that I think that having the audacity is just like super good for him. Like 10 out of 10.” (01:33:00)

Notable Quotes & Memorable Moments

• On whiteness and teaching Black history:
  "I am whiter than a mayonnaise sandwich on Wonder Bread… so white I glow in the dark." (03:18)
• On the escape plan:
  “If we get caught, we're going down… They decided that if they get caught, if their plan fails, they're just going to blow up the boat with them on it because that is a better option than what they will face on the other side.” (50:24)
• Upon reaching Union Lines:
  Smalls: “Good morning, sir. I've brought you some of the old United States guns, sir, that were for Fort Sumter, sir.” (54:10)
• On Civil War causation:
  “There’s always going to be someone who’s like, oh, no. The Civil War was fought over states rights. Which rights, dear fellow? … It was about slavery.” (33:50)
• On pettiness vs. kindness:
  “Robert Smalls is probably more decent than a lot of people in the world… I am an incredibly petty person. Robert Smalls is not.” (01:13:00)
• On vaccines:
  “Vaccinate your fucking kids, okay? … You’re saying that you would rather have a dead child than an autistic child, which that’s fucked up, right?” (01:07:00)
• On Smalls’ legacy:
  “He lived long enough to see Reconstruction rise, fall, and be betrayed. He lived long enough to be marginalized again by the same country he had saved, served, and reshaped. But he never stopped insisting on his own dignity.” (01:33:15)

Key Timestamps

• Intro & Black History Month Rant: 01:20 – 04:50
• Robert Smalls’ Early Life & Parentage: 08:00 – 14:00
• Charleston Work & Family: 21:30 – 28:00
• Buying Freedom Attempt: 28:30 – 30:00
• Civil War & CSS Planter Role: 31:00 – 40:00
• Formulating Escape: 43:00 – 46:00
• Execution of the Escape: 48:40 – 55:00
• Freedom & Fame: 55:30 – 58:00
• Influence, Advocacy, and Captaincy: 59:30 – 01:07:00
• Buying Former Owner’s House: 01:11:00 – 01:13:00
• Business & Political Career: 01:16:00 – 01:25:00
• Facing Racist Backlash in Politics: 01:19:00 – 01:23:00
• Later Life, Appointments, and Death: 01:28:30 – 01:33:15
• Closing Thoughts & Recommendations: 01:33:15 – End

Overall Tone & Style

Katie’s narration is witty, irreverent, and deeply empathetic—mixing scholarly insights, pop culture references, personal asides, and explicit language to confront both the horrors and heroism of history head-on. Her storytelling embodies both anger at injustice and admiration for Smalls’ relentless dignity and audacity.

Final Reflections

The story of Robert Smalls is, by Katie’s measure, better than any superhero or royal drama—a true historical epic of cunning, bravery, and progress. Smalls’ life is presented as a powerful counter-narrative to both lost cause mythology and the myth that Black Americans were mere passive subjects of their fate. His audacity changed the course of a war, empowered others, and set the groundwork for future fights for justice.

Katie’s Recommendations (01:35:00)

• Book: “Invisible Man” by Ralph Ellison
• Podcast: “Black Girl Nerds”
• TV: “Lovecraft Country”

For listeners, this episode serves as a vibrant, thorough, and moving introduction to Robert Smalls—an essential figure for anyone seeking to understand American history, Black agency, the Civil War, and the long arc of justice.