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
59 episodes
Anatomy of a Crash: Full Episode
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 ...
PREVIEW OF EARLY ACCESS: "Anatomy of a Crash"
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."...
PATREON PREVIEW: Carolyn Bessette & A Look at FX's "Love Story: John F Kennedy Jr. and Carolyn Bessette"
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 ...
William the Conqueror: Part 1
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 turb...
Harold Godwinson: Part 2
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 Norman...
Harold Godwinson, the Last Anglo-Saxon King of England
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 Vi...
Toussaint Louverture, the Black Spartacus: Part 1
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 episo...
Akhenaten, the Heretic Pharaoh of Egypt
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...
Yoko Ono, "the So-Called Woman Who Broke Up the Beatles": Part 2
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 decad...
Trailer for “Ambivalent Offenders”
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...
George Villiers: Part 3
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...
Yoko Ono, "the So-Called Woman Who Broke Up the Beatles": Part 1
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 —...
George Villiers: Part 2
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 c...
NEW PODCAST TRAILER (HOSTED BY JAMIE)! "Just Throw Away the Key: The Hidden World of Prisons Behind Our True Crime Fascination"
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."
George Villiers, Favourite to King James I: Part 1
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 Ge...
Mary Todd Lincoln: Part 3
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 L...
Mary Todd Lincoln: Part 2
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 ...
Mary Todd Lincoln: Part 1
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 c...
President Lincoln's Assassination and Aftermath
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 after...
Tonya Harding, Figure Skating’s Most Controversial Star
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 pantheo...
Andrew Carnegie and the Robber Barons
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 G...
Mark Antony: Part 3
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.
Mark Antony: Part 2
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.
Mark Antony, Roman politician & lover of Cleopatra: Part 1
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!), ...