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

July 5, 2025 1 min

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.

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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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Available now wherever you listen to podcasts! Please subscribe to follow for future episodes! 


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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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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Mark Antony--Shakespearean hero, Roman bad boy, lieutenant to Julius Caesar, and a man whose death often overshadows his life. With guest co-host, Matt, we begin our series with discussions of the very egalitarian Roman Senate (just kidding!), the Roman Republic, Antony's debauched early life (man loved a short tunic), and his time at Caesar's side.  

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February 12, 2025 40 mins

We conclude our first Dueling Villains series with the judgement on John Brown and Aaron Burr. Matt fills in for Jamie and helps us break down the flaws and the greatness of two of history's most enigmatic (and frustrating!) figures. Brown or Burr, who is the greater villain in our history?

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NOTE: We always have a 7 day free trial for our Patreon memberships so this could be the perfect time to check that out!

Hello listeners! We've been dealing with illness, job changes, issues with our editing program, and the usual chaos of life that has pushed us behind schedule. We just wrapped a full episode for our Patrons on Patreon to make up for January's mini-episodes there and thought we'd give you a little p...

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January 8, 2025 92 mins

Follow the rest of Aaron Burr's story, as he vies for the presidency in the Election of 1800, enters that infamous duel with longtime rival/future musical star Alexander Hamilton, and finds himself dabbling in some *light* treason. Emperor Aaron I has a nice ring to it, does it not?

Sources: The Great American Rascal: the Turbulent Life of Aaron Burr by Noel Gerson

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December 18, 2024 78 mins

We are covering Aaron Burr (SIR!) as the second half of our "Dueling Villains" series. In this episode, we cover Burr's early life, the American Revolution and his role in it, as well as his political life up until the election of 1800. There's babies attending college, cougars, and absolutely insane attempts at staying neutral in between! We also pitch Timothee Chalamet the role of a lifetime. 

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