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

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

Just like history isn’t all black and white, neither are the people who lived it. So who are the ones living in the grey? Welcome to Ambivalent Offenders— where we dig into the lives of people who’ve been called a lot of things: villains, scoundrels, monsters, misfits, or just plain morally messy. But were they really as bad as history says… or have they gotten an unfair rap? In each episode, we unpack the stories, facts, and cultural myths surrounding some of the most questionable (and sometimes misunderstood) figures from the past — all in a tone that’s more friend-at-brunch (according to one listener review) than lecture hall. No dusty textbooks, no moral grandstanding. Just conversational storytelling, questionable behavior, and a little historical tea. Ultimately, we’re here to do what humans do best: judge the hell out of some pretty interesting people.

Episodes

October 22, 2025 107 mins

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 ...

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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 backst...

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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. Discove...

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August 4, 2025 111 mins

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 w...

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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 celebr...

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History is rarely black and white—and neither are the people who shape it. *Ambivalent Offenders* explores the lives of controversial historical figures who “live in the grey.” Hosted by twin sisters Jamie and Erin, along with frequent guest co-host Matt, the show blends rich historical research with approachable, conversational storytelling. No lectures—just layered context and a healthy dose of curiosity and fun.

Tell us your thou...

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July 1, 2025 119 mins

In Part 3 of our series, we wrap up the glamorous, chaotic life of George Villiers, Duke of Buckingham, a man who somehow managed to fail upwards until the very, bitter end. From his attempts at diplomacy (Cardinal Richelieu has now entered the chat) to his ill-fated military campaigns, George had a knack for turning everything that he touched into a spectacular mess. Discover how his bromance with (Baby) Charles I led to political...

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Was Yoko Ono really the reason the Beatles broke up… or is there a lot more to the story? (Spoiler: there is.)

In this emotional and eye-opening episode of Ambivalent Offenders, we explore the real Yoko Ono — far beyond the tired headlines and fan theories. From her childhood in wartime Japan to her bold entry into the avant-garde New York art world, Yoko was already a creative force before she ever met John Lennon.

We trace:

  • Her ...
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June 24, 2025 103 mins

We continue the story of the ultimate Favorite, history’s greatest boy toy—George Villiers, Duke of Buckingham. Stick around for the disguises (fake mustaches!), Cardinal Richelieu popping up like a movie villain, and a dirty joke that had be censored (don’t worry, we kept some of it). There’s even a dash of true crime, because is it even a podcast without that?


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This is episode one of "Just Throw Away the Key, the Hidden World of Prisons Behind Our True Crime Fascination," the podcast where we talk about what happens after the true crime story ends because there's so much left about what comes next, things that impact you and I in ways we sometimes are blind to one thing being...

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This is the trailer for my (Jamie typing here) podcast, "Just Throw Away the Key: The Hidden World of Prisons Behind Our True Crime Fascination."

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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 c...

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We are tackling the action-packed and brief life of George Villiers, the Duke of Buckingham, who became the powerful favorite and lover of King James I of England. He’s also the George in the new show “Mary & George.” In Part 1, we cover George's early life, how he found himself dangled in front of a king (thanks to his mother and the Queen), and all the complexities of being a favorite. Spoiler alert: it's a lot more...

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May 15, 2025 111 mins

We conclude our series on Mary Todd Lincoln, covering her life post-assassination, her insanity trial, the betrayal of her eldest son, and how she spent her final years. Expect a rant (or two!) about Robert Lincoln, everybody’s least favorite Lincoln child. 

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May 6, 2025 102 mins

We continue Mary Todd Lincoln’s story as she enters the White House, diving into her controversial tenure as First Lady, her exploration of spiritualism, and the assassination that turned her world—and the nation—upside down. Will Erin make it through the pod without crying? Spoiler: absolutely not. But at least we got to roast a (dead) senator and his muttonchops before the overwhelming sadness.

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April 24, 2025 161 mins

Mary Todd Lincoln has the distinction of being one of the least popular First Ladies of the United States, even as her husband tops the lists of greatest Presidents. Their marriage has been the topic of entire books and careers. Mary has been called crazy, a spendthrift, certainly not the intellectual equal of her husband. Listen to part 1 of our series on Mary Todd Lincoln to hear about her early life in Lexington Kentucky, the co...

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We are marking the 160th anniversary of Abraham Lincoln’s assassination on April 14, 1865. As we prepare to release our upcoming series on Mary Todd Lincoln, we are going to go forward in her story and talk about the assassination and its aftermath. Explore with us the details of the plot, the events of the day, and what Lincoln's body has gone through after his death (spoiler alert: it is a lot--more than you would expect a b...

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Grab your ice skates—we are going back to the ‘90s to talk all about Tonya Harding! Harding survived her bad childhood to become a rising (and controversial) star in the figure skating world...until the scandal broke that put her in the pantheon of “Bad Women" and ruined whatever was left of her reputation. 

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March 24, 2025 92 mins

The original oligarchs of America are on trial this week. Grab your monocle and best suit as we head back to the Gilded Age to meet Andrew Carnegie and his gang of fellow robber barons…and spend not an insignificant time discussing HBO’s “The Gilded Age.” 

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March 10, 2025 111 mins

We have arrived at the end of Mark Antony's story...and his life. Join Erin and guest co-host, Matt, as we discuss his relationship with Cleopatra, the final showdown with Octavian, and how it went so horribly, inescapably wrong. 

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If you have a judgement on any o...

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March 3, 2025 98 mins

Join Erin and guest co-host, Matt, as we continue on in the life of Mark Antony, as he navigates life as Julius Caesar's faithful deputy, the horrific aftermath of the Ides of March, and feuding with a teen. 

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If you have a judgement on any of the figures that we ...

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