Ambivalent Offenders: Re-Examining History’s Most Questionable Figures

To celebrate the 250th anniversary of the Declaration of Independence, this month on Patreon, we did our own official power ranking of the American Revolutionary War Founding Fathers (and Mothers! Don't worry, Abby Adams, we did not forget the ladies!). We are sharing a clip of us discussing George Washington's contributions, but if you want to hear more, please follow the links to get access to the entire episode where we also discuss Thomas Jefferson, John Adams, Ben Franklin, and Alexander Hamilton (sadly, we do not sing this entire section). 

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If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!

Erin and I (Jamie) return to the story of Carolyn Bessette-Kennedy in this special episode. This time we focus on the final hours leading up to the 1999 plane crash that killed John F. Kennedy Jr., Carolyn, and her sister Lauren.

Drawing directly from the official NTSB accident report and other primary sources, Erin breaks down the chain of events—weather conditions, pilot experience, aircraft details, and widespread misconceptions—to offer a clear, factual “anatomy” of what happened that night. 

Along the way, we address persistent myths, discuss how public perception of the Kennedys has shifted, and reflect on the cultural moment in which the tragedy occurred. Our hope is a respectful and hopefully illuminating look at a story often clouded by rumor.

Tell us your thoughts! Do you agree with our take? Share your take!

Support the show

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• Buy Me a Coffee (one time support)
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If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!

NOTE: The entirety of this episode will be published in a week to our main feed. But to access it early, just join our Patreon at ANY tier! Link is in the show notes or if you search "Patreon Ambivalent Offenders."

Erin and I (Jamie) return to the story of Carolyn Bessette-Kennedy in this special episode. This time we focus on the final hours leading up to the 1999 plane crash that killed John F. Kennedy Jr., Carolyn, and her sister Lauren.

Drawing directly from the official NTSB accident report and other primary sources, Erin breaks down the chain of events—weather conditions, pilot experience, aircraft details, and widespread misconceptions—to offer a clear, factual “anatomy” of what happened that night. 

Along the way, we address persistent myths, discuss how public perception of the Kennedys has shifted, and reflect on the cultural moment in which the tragedy occurred. Our hope is a respectful and hopefully illuminating look at a story often clouded by rumor.

Tell us your thoughts! Do you agree with our take? Share your take!

Support the show

• Instagram
• Patreon
• Buy Me a Coffee (one time support)
• TikTok
• Show website 

If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!

We return to Ambivalent Offenders in 2026 with a fresh look at Carolyn Bessette-Kennedy—now back in the cultural spotlight thanks to FX and Hulu’s Love Story: John F Kennedy Jr. and Carolyn Bessette. In this special 20 minute segment from our full Patreon episode, we revisit our original two‑part deep dive, unpack how the new series reshapes Carolyn’s legacy, and explore why she remains such an enigmatic figure decades after her death.

From the mystique surrounding her public image to the long‑standing narratives shaped by JFK Jr.’s inner circle, we dig into what the show gets right, what it smooths over, and why Carolyn’s real story is far more complex than the “ice queen” trope she’s often saddled with. If you want to listen to the entire 1.5 hour episode and our follow-up series on the episodes of Love Story itself, click here or search for "Ambivalent Offenders" on Patreon!

Tell us your thoughts! Do you agree with our take? Share your take!

Support the show

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If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!

In this first episode of the series, we are diving deep into the often messy and violent early life of William the Conqueror. From his tumultuous childhood in 11th-century Normandy to gaining his infamous title of conqueror, we explore the turbulent road that saw a young bastard son of a duke become one of history's most controversial figures. It is a wild ride of political maneuvering, violent power plays, and, there at the heart of it, a man to be both feared and loathed. 

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Support the show

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If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!

In Part 2 of Harold Godwinson’s story, Erin and Matt chart Harold's rise to power after the death of his father, his (very) brief kingship, and the bitter betrayal of his brother, which ultimately led to the showdown with Duke William of Normandy at the Battle of Hastings in 1066. A battle in which a nation would be changed forever. Cameos include multiple Ediths (how many wives named Edith can ONE man have?) and a mention of Scooby Doo. 

Tell us your thoughts! Do you agree with our take? Share your take!

Support the show

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If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!

Erin and Matt dive into the wildly dramatic life of Harold Godwinson, the last true Anglo-Saxon King of England. In Part 1, we rewind to the Anglo-Saxon world to follow the rise of Harold’s ambitious, king-making father, Godwin, the chaos of Viking invasions, and the messy family dynamics that shaped England’s fate. Follow along as we chart Harold’s road to the throne, which was paved by exile, wives, and plenty of political backstabbing, all leading to a cataclysmic end at the Battle of Hastings. 

Tell us your thoughts! Do you agree with our take? Share your take!

Support the show

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If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!

Join Jamie, Erin, and Matt as they dive into the extraordinary life of Toussaint Louverture—born into slavery, educated under the eyes of plantation masters, and soon the driving force behind the Caribbean’s most pivotal uprising. In this episode, we set the scene beyond Saint-Domingue’s brutal sugar-and-coffee world: we map the global stage of rival European powers, revolutions, and shifting alliances that shaped his path. Discover how a man described as short and unassuming rises to become a visionary leader whose name and legacy sparked abolitionist movements worldwide. We’ll explore the social hierarchies of the colony, the complexities of freedom and ownership, and the delicate balance between mercy and power that defined his approach to revolt and governance. It’s a story of resilience, strategy, and moral ambiguity—a reminder that history is rarely black-and-white, even when the man at the center is called the Black Spartacus.

Tell us your thoughts! Do you agree with our take? Share your take!

Support the show

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If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!

Join hosts Erin, Jamie, and Matt as we unpack the life of the heretic pharaoh who upended centuries of religious practices for a sun disc with hands. Along with his famous wife, Nefertiti, Akhenaten built an entire city from scratch for his new religion, and dragged the whole country along for the ride, whether they liked it or not. Spoiler: they did not. Was he a visionary ahead of his time or just an ancient megalomaniac tyrant with a (literal) god complex? We get into all of it: the high cost of religious reform, the disappearing wives, the unnervingly long skulls. 

Tell us your thoughts! Do you agree with our take? Share your take!

Support the show

• Instagram
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• Buy Me a Coffee (one time support)
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If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!

Yoko Ono has long been cast in the shadow of John Lennon—or worse, blamed for breaking up The Beatles. But the truth is far more powerful. In this episode, we dive into Yoko’s groundbreaking solo art career, her fearless activism, and the decades of backlash she endured as a woman, an outsider, and a visionary. From participatory art and peace towers to the biscuit incident and Get Back reappraisals, we unravel the myths and celebrate the legacy of a cultural icon who turned pain into purpose and never stopped creating.

Tell us your thoughts! Do you agree with our take? Share your take!

Support the show

• Instagram
• Patreon
• Buy Me a Coffee (one time support)
• TikTok
• Show website 

If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!