BEHIND THE BASTARDS Episode Summary:
Part One: Thomas Thistlewood: Slave Plantation Owner and Diarist
Release Date: November 11, 2025
Host: Robert Evans
Guest: TT Lee

Overview

This episode explores the life and legacy of Thomas Thistlewood, an Englishman who became a notorious slave plantation overseer and owner in Jamaica during the 18th century. Thistlewood is infamous not merely for the brutality of his acts—which were common among his peers—but for his obsessive, detailed diaries. These diaries provide historians with a chilling, first-hand account of the daily mechanics and horrors of Caribbean slavery, including sexual violence, torture, and the normalization of cruelty and dehumanization. Through the episode, Robert Evans and TT Lee dissect Thistlewood's background, motivations, and broader context, connecting his personal narrative to structural forces of British colonialism and the enduring fascination with so-called "bad guys" in history.

Key Discussion Points & Insights

1. Why Study Thistlewood? (04:12–08:18)

• Historical Documentation: Thistlewood’s diary is a rare, unflinching record from a perpetrator’s view, akin to Nazi internal documents ("like some of those internal notes that the Nazis took" – Robert Evans, 05:37).
• His Ordinariness: He’s important not for being exceptionally monstrous, but because he was typical—a “normal” man of his time whose extensive diaries reveal the everyday, systematic violence of slavery.
  • "He's a pretty normal guy who owned people, who was unusually detailed in his normal note taking." (Robert Evans, 05:53)

2. Thistlewood’s English Roots & Early Life (12:03–18:04)

• Family & Upbringing: Second son of a moderately successful English farmer, excluded from inheritance; "the perfect foot soldier of the British Empire" due to his transactional view of relationships and need to hustle.
  • "This is gonna kind of turn him into the perfect foot soldier of the British Empire." (Robert Evans, 15:55)
• Early Hardship: Childhood shaped by paying relatives or guardians for board, emphasizing a lifelong transactional mindset.
  • "That's a very transactional way to think of your childhood." (TT Lee, 15:45)

3. Early Adulthood: Sex, Money, and the Search for Status (21:35–31:32)

• First Job – East India Company: Sought fortune as a ship’s purser; his diaries begin as ledger-like records of personal transactions.
• Attitude Towards Sex & Women: Obsessively catalogued sexual encounters, often in Latin and code, including notations about cost and "alphabetical" counting of women (25:33–26:01).
  • "He's just, like, alphabetically listing [women]." (Robert Evans, 25:33)
  • "There's a lot of debate as to, like, why did he write about sex this way?" (Robert Evans, 25:59)
• Exposure to Disease & Quack Remedies: Chronic venereal disease, interest in abortifacients, and 18th-century quack medicine—reflecting a "scientific" curiosity intertwined with vice (29:06–31:09).
  • "That's what he's taking for VD. It's like arsenic? Yeah. And, like, probably mercury and shit..." (Robert Evans, 30:51)

4. Colonization as Social Climbing (32:07–36:59)

• Attraction to Jamaica: Marketed as a “poor man’s country,” promising equality (for white men) and opportunity—mainly due to a high death rate, low supply of labor, and necessity for white overseers.
  • "There's this level of egalitarianism for white men in Jamaica, right?" (Robert Evans, 42:17)
• Brutality of Plantation Life: White newcomers faced staggering fatality rates from disease and climate, but if survived, could quickly rise socioeconomically.

5. Enslaving for Profit – The Jamaican System (45:17–52:00)

• Racial Demographics & Social Structure: White population vastly outnumbered by black slaves (~18,000 whites to 170,000 enslaved), driving white solidarity and “egalitarian” pretenses for survival.
  • "That's the reason for this quote unquote egalitarianism." (Robert Evans, 47:41)
• Upward Mobility Through Violence: Thistlewood worked as a bookkeeper/overseer, began buying and renting out enslaved people before acquiring land himself—all as a means of passive income and social ascent.
• Normalization of Atrocity: His actions and attitudes—while horrifying—were entirely ordinary among his class and context.

6. The Diaries: Sexual Violence and Scientific Pretense (57:37–67:13)

• Sexual Assault Against Enslaved Women: First rape recorded five months after Thistlewood’s Jamaican arrival, detailed through Latinized wordplay and codes (57:37–60:15).
• Documentation as Rationalization: He frames and codifies sexual violence as scientific “research”—influenced by the legacy of Linnaeus and classical education.
  • "He is a naturalist...Those are kind of the early scientists in this period of time...And so part of what he's doing is walling off these sexual experiences and documenting them as if he's doing scientific research." (Robert Evans, 61:29)
• Breeding as Investment: Kept notes to track the parentage of enslaved people he raped, as children of enslaved women were property and increased his wealth.
  • "Part of what he's doing here is keeping notes as to who he's sleeping with so that he can document the parentage of different people that he's going to own and sell." (Robert Evans, 62:06)
• Classical Myth as Self-Justification: Compared his actions to mythical narratives—e.g., Rome’s legendary origins through rape and conquest—framing his brutality as part of a “civilizing mission.”

7. Relational Dynamics and Survival (73:31–77:27)

• “Relationships” with Enslaved Women: Explains the complexity of power, coercion, and survival for victims, like Ginny and Fiba, who sometimes tried to leverage sexual violence or “relationships” for protection or improved circumstances.
  • "If I get in this guy's good graces and pretend that I like him, the next time he tries to beat one of my friends, I can convince him to stop." (Robert Evans, 76:10)
• No True Consent: Stresses repeatedly that such “relationships” were never truly consensual.

8. Thistlewood As a ‘Typical’ Slaveowner (78:57–81:32)

• Banality of Evil: Thistlewood’s behavior was not seen as unusual or particularly cruel among slaveowners—he stood out only for the detail of his record keeping.
  • "There's no evidence Thomas Thistlewood was particularly bad for a slave owner or an overseer in Jamaica in this period of time...They were all like this. He just kept a diary." (Robert Evans, 78:54)
• Historical Importance: His diaries strip away romanticized or sanitized views of slavery; abolitionists later used such “normal” accounts to shock publics outside slave societies.

Notable Quotes & Memorable Moments

• On the Disturbing Fascination with Infamy:

  “There’s a reason the History Channel has produced hundreds of documentaries about Hitler but only a few about Dwight D. Eisenhower. Bad guys (and gals) are eternally fascinating.” (Intro/Description)

• On Domestic Evil:

  “He’s a pretty normal guy who owned people, who was unusually detailed in his normal note taking. Right. That’s why we know about this.” (Robert Evans, 05:53)

• On White Solidarity in Jamaica:

  “There’s this level of egalitarianism for white men in Jamaica, right?...That’s the reason for this quote unquote egalitarianism is the wealthy plantation owners know that they need to keep these poor white guys on their side.” (Robert Evans, 47:41)

• On the Usefulness and Horror of the Diaries:

  “You'll find whole books by people that are just, like, exerting the stuff from his diary about the weather, because that's important for climactic science...and then there's this larger branch of scholarship that's about his crimes against humanity.” (Robert Evans, 08:02)

• On Scientific Pretense and Sexual Violence:

  “He’s walling off these sexual experiences and documenting them as if he’s doing scientific research...keeping notes so that he can document the parentage of different people that he’s going to own and sell. Right. And he sees this scientifically in the same way as people who are, like, breeding livestock.” (Robert Evans, 62:06)

• On Myth and Colonial Justification:

  “He sees this as part of this very scientific and high minded colonial project. England is colonizing and civilizing the wilderness and making it better. And these sex crimes I’m committing are a part of the scientific effort to improve...by inserting my DNA into these populations. That’s how he’s thinking about this, right?” (Robert Evans, 66:45)

• Host Commentary on Justifications:

  “This is not how they lived with themselves, but how they felt good about themselves for doing this.” (Robert Evans, 70:22)

Timestamps for Key Segments

• 00:05–01:30 — Banter, show intro, transition to topic
• 04:12–08:18 — Why Thistlewood’s diaries matter/his historical context
• 12:03–18:04 — Early life and the influence of transactional relationships
• 22:44–26:01 — Diary structure, sex notation, and coded language
• 29:06–31:09 — Quack medicine and “scientific” mindset
• 32:07–41:37 — Voyage to Jamaica; white mortality; “poor man’s country”
• 45:17–52:00 — Plantation economy in Jamaica; Thistlewood’s social ascent
• 57:37–67:13 — First rape recorded in Jamaica; scientific and mythological framing
• 73:31–77:27 — Relationships with enslaved women, Ginny and Fiba
• 78:57–81:32 — Thistlewood as everyman, not an “exceptional” bastard

Tone & Atmosphere

Robert Evans maintains his incisive, sardonic tone, occasionally bantering with TT Lee about the bleakness of the subject ("Wouldn’t we all like to age less?" 02:26; "There's not much to be light hearted. Yeah." 81:54), but the episode does not shy away from the horror and detail of Thistlewood’s world. Both express horror, curiosity, and at times gallows humor, but are consistently respectful and careful in handling deeply disturbing material.

Conclusion

Part One establishes the historical, psychological, and structural scaffolding of Thistlewood’s story, revealing how ordinary men come to rationalize and record extraordinary evil. It resists easy distance from the past—emphasizing how the banality of atrocity and intellectualized justifications underpin both historical and modern systems of oppression. The episode prepares listeners for ongoing, more detailed explorations of Thistlewood’s crimes and the world that enabled him in future parts.

“...within the community of assholes, he’s a normal asshole. I think it’s the way I would come down on him.” (Robert Evans, 81:32)

For more on the mechanics of slavery, white supremacy, and the documented normalization of brutality, stay tuned for Part Two.