Behind the Bastards

Part One: Thomas Thistlewood: Slave Plantation Owner and Diarist

November 11, 2025

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  • The detailed diary of Thomas Thistlewood, a Jamaican slave plantation owner, is a crucial but bleak historical source because his unusual level of note-taking documented the day-to-day brutality of the chattel slave trade. 
  • Thomas Thistlewood's early life as a second son who had to pay for his own upbringing fostered a highly transactional view of relationships, which fueled his later career as a colonial agent and slave owner. 
  • Thistlewood documented his sexual assaults on enslaved people, such as the woman named Sylvia, using Latin shorthand and classical references, suggesting an attempt to frame these crimes as scientific observation or to conceal them from uneducated readers. 
  • Thomas Thistlewood documented his sexual crimes against enslaved people with a scientific detachment, viewing the resulting offspring as property in a manner akin to breeding livestock, linking his actions to his admiration for Carl Linnaeus. 
  • Thistlewood framed his horrific acts, including rape, within a self-aggrandizing, mythological colonial project, drawing parallels to Roman foundation myths to see himself as a noble civilizer rather than merely a criminal. 
  • The details recorded in Thomas Thistlewood's diary, while horrifying to modern listeners, were considered normal chronicling of daily life by his contemporaries in the slave-owning community, highlighting how abolitionists used such accounts to shock outsiders. 
  • The discussion revealed the bleak choices available to enslaved individuals like Ginny, who attempted to leverage a relationship with Thistlewood to gain control and protect others, ultimately leading to her failed assassination attempt against him. 

Segments

Introduction and Guest Welcome
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(00:00:05)
  • Key Takeaway: Robert Evans introduces the episode of Behind the Bastards focusing on Thomas Thistlewood, a slave owner and monster whose crimes are documented in his diary.
  • Summary: Robert Evans welcomes his friend Titi Lee to the podcast, which focuses on detailing the worst people in history. The episode is announced as the first part of a series about Thomas Thistlewood. The opening banter includes humorous speculation about reality TV shows for dictators.
The Value of Thistlewood’s Diary
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(00:04:57)
  • Key Takeaway: Thistlewood’s extensive diary provides historians with rare, day-to-day documentation of the brutality of the Atlantic chattel slave trade from the perspective of a plantation owner.
  • Summary: The diary is considered a vital source because it offers internal notes from someone actively participating in the system, unlike many other accounts which come from escaped individuals. Thistlewood’s entries detail horrific crimes alongside mundane observations like the weather. Scholars study his diaries for both climatic science and his crimes against humanity.
Thistlewood’s Early Life and Inheritance
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(00:11:49)
  • Key Takeaway: As a second-born son in 18th-century England, Thomas Thistlewood inherited little, fostering a transactional view of relationships as he had to pay for his own education and apprenticeship.
  • Summary: Thomas Thistlewood was born in 1721; his father died when he was six, leaving the estate to the firstborn son, John. Thistlewood received a small inheritance (about $40,000-$50,000 in modern terms) which he spent covering his upkeep while being educated. This necessity to constantly pay for care shaped him into a mercenary figure, fueling his later pursuit of fortune.
Early Adulthood and Near-Trouble
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(00:17:55)
  • Key Takeaway: Thistlewood’s near-imprisonment for fathering a child out of wedlock motivated him to leave England and seek fortune abroad.
  • Summary: At age 18, Thistlewood began working as a livestock dealer, but an unplanned pregnancy with a local girl led her parents to refuse marriage, putting him at risk of prison or fines. After the pregnancy ended, he decided to escape his hometown by signing on with the East India Company in 1746.
Voyage and London Debauchery
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(00:20:35)
  • Key Takeaway: After a two-year voyage as a ship’s purser, Thistlewood returned to London in 1748 nearly broke, having spent his wages and side-hustle profits on gambling and prostitutes.
  • Summary: His job involved managing ship finances and engaging in personal trading, but he squandered his earnings upon returning. He began keeping a diary, often prefacing entries about sex with ‘XXX’ and writing them in Latin, possibly as a form of coded concealment or intellectualization.
Interest in Abortifacients and STDs
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(00:27:29)
  • Key Takeaway: Thistlewood’s diary entries reveal a casual interest in recipes for abortifacients and treatments for venereal diseases, including arsenic-laced pills, reflecting the dangerous medical practices of the era.
  • Summary: In 1749, he recorded a recipe for an abortifacient involving bitter apples steeped in beer. He also documented remedies for STDs, such as taking purging pills until discharge matched semen consistency. One potential treatment he used involved ‘Ward’s Pill and Drop,’ which contained arsenic and other poisons.
Migration to Jamaica and Early Success
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(00:38:34)
  • Key Takeaway: Thistlewood migrated to Jamaica in 1750, drawn by its reputation as the ‘best poor man’s country’ where any white man could gain respect and opportunity, despite high mortality rates for newcomers.
  • Summary: Jamaica was the British Empire’s wealthiest colony, producing vast amounts of sugar, but it was deadly for new arrivals due to disease, a process called ‘seasoning.’ Thistlewood survived this initial period because he was a diligent note-taker and did not drink heavily, unlike many others. His survival made him valuable, allowing him to quickly secure raises as an overseer.
Financial Ascent via Slave Rental
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(00:48:41)
  • Key Takeaway: Thistlewood rapidly accrued wealth by leveraging his value as a competent, surviving overseer to purchase enslaved people and rent their labor back to his employers for passive income.
  • Summary: The enslaved population vastly outnumbered the white population (170,000 to 18,000 white people upon his arrival), necessitating the employment of white overseers. By buying enslaved individuals and renting them out, Thistlewood established an income stream that allowed him to eventually purchase his own plantation.
Documenting Sexual Exploitation
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(00:52:03)
  • Key Takeaway: Thistlewood first documented sexual assault against an enslaved woman named Sylvia in December 1750, framing the act within his diary using Latin references to classical mythology and science.
  • Summary: He recorded the assault on Sylvia, an Igbo woman, using Latin shorthand that referenced the Roman word for forest, suggesting he viewed the act as a scientific documentation or an act of power, similar to breeding livestock. Scholars theorize this coding was a mechanism to conceal the unacceptable nature of his crimes from general readers while aligning them with his scientific interests.
Scientific Documentation of Crimes
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(00:57:01)
  • Key Takeaway: Thistlewood documented sexual crimes to track parentage for financial gain, treating enslaved people like livestock for breeding.
  • Summary: Thomas Thistlewood connected his work to Carl Linnaeus’s taxonomy system, using his diary to scientifically document the parentage of enslaved people whose births increased his property holdings. He viewed the sexual exploitation of enslaved individuals as having a financial motivation, similar to breeding livestock. This documentation allowed him to track ownership of children born from these assaults.
Classical Justifications for Violence
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(00:59:43)
  • Key Takeaway: Thistlewood’s initial rape of Sylvia may have been symbolically linked to Roman foundation myths involving sexual violence and conquest, reflecting his self-perception as a civilizer.
  • Summary: An article suggests Thistlewood’s rape of Sylvia carried symbolic weight related to Roman foundation myths, where sexual violence initiated the story of conquest. Thistlewood saw his actions as part of a high-minded colonial project to civilize the wilderness by inserting his DNA into the population. This reliance on classical mythology provided a noble justification for his cruel acts, aligning him with a perceived ‘civilizing mission’.
Thistlewood’s Self-Perception
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(01:02:37)
  • Key Takeaway: Thistlewood used his classical education and scientific pursuits to elevate his self-image beyond that of a mere wealthy criminal into a participant in a noble global endeavor.
  • Summary: For Thistlewood, who did not grow up extremely wealthy, framing himself as a man of science was a way to fit into aristocratic society. He needed lofty intellectual justifications for his vicious acts because he desired to see himself as part of a mythological, global endeavor to civilize the world, rather than just a criminal seeking wealth. This mirrors how modern white supremacists use classical literature to frame base impulses as heroic.
Rape as Civilization
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(01:05:04)
  • Key Takeaway: Thistlewood literally viewed his sexual assaults as an act of ‘raping civilization’ into enslaved people, often noting their lack of consent in his documentation.
  • Summary: Thistlewood compartmentalized his sex crimes, viewing rape as a method of imposing civilization, and he documented instances where the enslaved women did not appear receptive. He never wrote about equivalent consensual relationships, only paying for sex in London or committing assaults in Jamaica. His diary entries about these assaults were treated with the same detached documentation as notes on the weather.
Overseer Job and Flora Incident
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(01:06:48)
  • Key Takeaway: Upon becoming overseer of the Egypt plantation, Thistlewood immediately committed another sex crime against Flora, paying her four bits, a small fraction of a Spanish real.
  • Summary: In January 1753, Thistlewood became overseer of the Egypt plantation, earning 60 pounds sterling annually. He immediately replicated his Sylvia wordplay by assaulting an enslaved woman named Flora, paying her four bits, which was equivalent to about $5 to $10 today. This payment may have been an attempt to frame the assault as transactional sex work rather than a pure sex crime.
Ginny’s Attempted Control
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(01:09:39)
  • Key Takeaway: Enslaved woman Ginny attempted to gain influence by entering a relationship with Thistlewood, hoping to intervene when he punished others, which ultimately led to her bringing a knife to bed.
  • Summary: Thistlewood began a year-long relationship with Ginny, whom he claimed consented, but she increasingly intervened when he assigned punishments. Ginny’s strategy was to use her position to protect friends, but when Thistlewood grew annoyed, she brought a knife to bed, ending the relationship after he discovered it. She was punished, likely whipped, for the attempted murder.
Fibba Relationship and Normalcy
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(01:12:03)
  • Key Takeaway: Thistlewood began a lifelong, grotesque parody of marriage with the enslaved cook Fibba immediately after his relationship with Ginny ended.
  • Summary: Following the end of the situation with Ginny, Thistlewood started a relationship with Fibba, the previous overseer’s mistress and his cook, which lasted the rest of his life. Crucially, there is no evidence Thomas Thistlewood was exceptionally violent or worse than his peers; he simply kept a detailed diary of behaviors considered normal for a slave owner in Jamaica at that time.
Plugs and Conclusion
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(01:16:07)
  • Key Takeaway: Titi Lee plugged her friend Zach Broussard’s parody Christmas book, ‘Scary Stories to Make You Scared of Christmas,’ before concluding Part One.
  • Summary: Titi Lee expressed feeling sad for humanity due to the bleak content discussed in the episode. She plugged the book ‘Scary Stories to Make You Scared of Christmas’ by Zach Broussard, available online and on Amazon. The hosts confirmed they would return for the second, equally depressing part of the series.