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.
Ambivalent Offenders: Re-Examining History’s Most Questionable Figures
PREVIEW OF EARLY ACCESS: "Anatomy of a Crash"
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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!
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 ambivalent.offenders.podcast@gmail.com!
Welcome back to Ambivalent Offenders. This is Jamie. And this is Aaron. And we are continuing our free examination or a follow-up with our original Carolyn Bissette Kennedy series. Many of you might have listened and just talked about that. That was our third episode. So we apologize for some of the crosstalk and we were using Zoom back then.
SPEAKER_00It was in our early days. It was a rougher version of the podcast. We've at least upgraded our technology at this point. Yeah. Even though this is still, again, this is a sidekick. This isn't our main source by any means. No, we're we're not wrecking in the millions from podcasting. No. Go figure.
SPEAKER_01But many people have been interested to learn more about Carolyn Bissett Kennedy, especially because she is such a Enigma. So I know many of you found our podcast through that. Or we also did the start of a love story talk that was finished on Patreon. I do want to acknowledge first we have some new Patreon members. So some of our paid members who are new, Courtney, Katie, Sophie. Thank you so much for supporting the pod. Thanks, guys. It really helps. Again, we just do this for fun because we love history and we love to tell stories and it connects us as if you didn't know, we're twins, so it helps connect us. And then we also have some new free members. We have William, Jennifer, and Heidi. Thank you as well. Hey guys. So for those who are not familiar with our Patreon, go to our Patreon link. It's in our show notes. Or you can just go to Patreon and search Ambivalent Offenders. We have a free level, which we do offer some little extras, some mini episodes, sometimes polls that we'll even allow for free members. Or we have two member tiers. We have a$3 a month and then a$5 a month, and you get with that bonus content. For example, we know we're doing more love story bonus content on our Patreon.
SPEAKER_00We're going to wrap up the series since the show just wrapped up. So you're going to get at least one more love story episode. And you will get as we go and move into our Kennedy series, which is next.
SPEAKER_01Preview preview. I'm going to be doing Rose Kennedy. So JFK, not JFK Jr., but JFK's mother. And Aaron's going to be doing Joseph Sr.
SPEAKER_00The man, the myth, the legend.
SPEAKER_01And it's kind of perfect timing because Netflix just released a still of Michael Fassbender as Joe Sr. Because they're doing their own American version of royalty. So like the crown.
SPEAKER_00We talked about flattering casting. Michael Fastbender is Joe Sr. That's right up there for some very flattering casting.
SPEAKER_01Those ones we're going to be doing on the main pod, but then on the Patreon pod, I will be doing Ted Kennedy and we'll see. There's so many Kennedys that have so many interesting stories. We know not everybody's interested in the Kennedys. So our series most likely will just be those two to start Rose and Joe Sr. And then if you're interested, you can always reach out to us at ambivalent.offenders.podcast at gmail.com or the best source to find us is our Instagram. If you search Ambivalent Offenders podcasts that will come up or ambivalent offenders pod. Aaron does amazing previews for our episodes. That's a great way to see what's coming up, especially if you're somebody who's interested to know what's coming up. We're trying to get back into about every two weeks recording our lives. Sometimes just take those turns, as we said, not our full-time job, but our goal is to do every two weeks. And you can always get a preview of when that next episode's coming with Aaron on Instagram with a preview. Also, I noted on Instagram, but I realized that our listeners don't always know we have an Instagram page. So it was a bad thing to do. Was I noted a giveaway for Once Upon a Time, which was the Carolyn Bissett Kennedy biography that love story is based on, technically based on that was that's the core text. So we're doing a giveaway of that, except I announced it on our Instagram and not on our podcast, which I was like, we don't have there's not always a crossover. So I'm changing the date. If you were on our Instagram and you're like, I haven't heard anything, let's because we're gonna change the date. So it's now gonna be open till April 10th. For those who are paid members on Patreon, you get three already three entries into our giveaway. Our free members on Patreon get an extra. So you get two entries. And then everybody else, if you give us a review, we can obviously see your name. So if you give a review, then you will get in with one entry. If you rate us, we can't see who rates us, but you can just email us or put under our giveaway, which we'll put on Instagram, you can say reviewed, Mungle Trust You will play the honor system. We're Midwest girls. We will play the honor system. That will give you an entry. So you can do multiple things. You could rate and review, and that would give you two entries. And you could also join the Patreon, however you want to do it. If you do the paid version, you also do get a week trial. So if you're like, oh, they want to see what they already have out there, we have already some bonus episodes and things like that. You get access to all of that past stuff.
SPEAKER_00You can always try it out and go from there. Hopefully, you'd do a trial and like what you see and want to sign up. But at the very least, try to do the giveaway because the book is good. And if you've been enjoying what we've been talking about here or been enjoying Love Story, I think you'll enjoy reading that book to learn more about Carolyn's life and story. So today, Aaron, what what are we focusing on? If you've clicked into the episode, you'll know it's called An Anatomy of a Crash. So we are going to be talking about obviously the plane crash that killed John F. Kennedy Jr., Carolyn Bassett, Kennedy, and her sister Lauren Bassett. We're going to get into the details. I know in the original series, I skimmed over. I didn't want to get too bogged down into the crash because there's so much that you can talk about. A lot of this information is out there. There is a report out there that you can read. Yep, it's public record. It is. Just a note that we're gonna try to keep this as factual as possible, as we're not gonna try to speculate about what was going on in the cabin during the flight. This is not the show. We're not here to speculate or talk about what they would have been feeling like. This is just facts that we know. And it was a small plane, so there's no black box, you know, for some of those bigger plane crashes. There's a black box. You usually can hear what was going on. Yeah, there's not here. So we don't know, and I think any speculation is unhelpful. So yeah, that's what we're gonna do.
SPEAKER_01We will compare though to what we do know with versus what the show shows based on other factors, but not the black box. If you finished the show, you know, obviously, as part of the finale, the crash happens in real life. That was kind of one of those moments that I do really remember, even though at that time it's not like we were huge history buffs. We were 11. We have a brother who played hockey. We were at a hockey tournament. It would have been that Saturday after when they started the search. I remember them. It was still a search at that point.
SPEAKER_00Yeah, there's the search and rescue, people not knowing what happened. There's a potential thought that maybe they had landed somewhere else or something else. So obviously, until the plane was discovered, we didn't know exactly what had happened. It is one of those moments, and I know people of our parents' generation who were alive during the John F. Kennedy assassination, it's a bookend. There's these two bookends. It was in July 99. You're a couple years out from 911. 911, which is also a big moment where people say the 90s truly died.
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