Henry VIII and Anne Boleyn are the Ross and Rachel of history

Summary

Podcast Summary: "Henry VIII and Anne Boleyn are the Ross and Rachael of History"

Podcast: This is History: History’s Greatest Fails
Hosts: Dan Jones & Elizabeth Day
Date: April 14, 2026

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Episode Overview

This episode of "History’s Greatest Fails" explores the theme of failed historical romances—those love stories that ended in disaster but also had profound historical consequences. Dan and Elizabeth use the cases of Henry VIII and Anne Boleyn, Antony and Cleopatra, and Edward VIII and Wallis Simpson to investigate how private passions collide with public duty and reshape the course of history.

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Key Discussion Points & Insights

1. Why Study Failed Romances in History?

• Failed romances are not just personal tragedies, but often shape the fate of nations.
• Dan sets out to discuss three famous examples:
  • Henry VIII & Anne Boleyn
  • Antony & Cleopatra
  • Edward VIII & Wallis Simpson
    (03:13–03:50)

2. Henry VIII & Anne Boleyn: The Tudor Catastrophe

Setting the Scene

• Henry VIII was married to Catherine of Aragon for most of his reign, presenting a "glorious Renaissance couple" early on.
  (04:02–04:49)
• Over time, Henry grew desperate for a male heir and enchanted by Anne Boleyn.

The Failure

• Henry’s desire for Anne, coupled with Catherine’s inability to produce a male heir, led to the annulment of his first marriage and a catastrophic break with the Catholic Church.
• Elizabeth: "Henry has staked an enormous amount on [Anne's] ability to do that… She has to play this incredibly careful and precise game at court." (07:53–09:16)

The Consequences

• Massive religious, cultural, and political upheaval: The English Reformation, dissolution of monasteries, and major shifts in monarchy’s relation to the church.
• Anne Boleyn failed to provide a male heir and became a scapegoat, ultimately executed (beheaded).

Humanizing the Players

• Dan discusses Henry as a "psychologically fragile" Renaissance man—torn between humanist and Machiavellian philosophies, powerful but deeply insecure.
  (10:05–11:24)
• Elizabeth highlights Anne Boleyn’s personal strength, especially in her execution:
  • "In her final words, she actually speaks highly of Henry VIII… she wants to protect her daughter Elizabeth, who at that point is only three. And I just think that says so much about the strength of that woman." (13:02–13:42)
• Dan connects Anne’s modern "secular saint" status with contemporary views on patriarchal abuse and martyrdom:
  • "She is the character for that culture because she is a character so out of her time, also ahead of her time… she's a character absolutely of the moment." (13:42–15:21)

3. Antony & Cleopatra: Love or Politics?

Historical Background

• Antony meets Cleopatra in 41 BC; she was allied with Caesar and had a child with him before Antony.
  (17:22–18:23)
• The political implications are inseparable from the romance.

Where Love and Power Intertwine

• Their relationship forced Antony to choose between loyalty to Rome and his alliance with Cleopatra.
• Dan: "The romance is part of the presentation of the political alliance… [For ancient people], most of our mores, most of our beliefs...would think were fucking insane, basically." (19:24–20:09)
• Elizabeth questions whether their romance or their political strategy was central.

Memorable Moment: The Double Suicide

• Cleopatra stages her own death to manipulate Antony’s emotions (21:29–22:43).
• Antony botches his own suicide, is carried to Cleopatra, and dies in her arms—an event compared to Romeo and Juliet (25:03–25:36).

The Real Failure

• Their love didn't fail for lack of devotion, but due to political and military defeat by Augustus.
  • Elizabeth: "It's not a failure of devotion, it's a failure of viability." (26:47–27:06)

4. Edward VIII & Wallis Simpson: Abdication for Love?

Context and Stakes

• Edward VIII falls for divorced American Wallis Simpson; British law and Church forbid the marriage for a reigning king.
  (28:58–29:53)
• Their relationship triggers a constitutional crisis in 1936.
• Both are later revealed to have Nazi sympathies, raising the historical stakes further.

Personal vs. Public Failure

• Dan: "The question I think with Edward is did he really abdicate for love or did he abdicate because he didn’t want to eat shit from anyone?" (30:43–32:00)

Institutional Consequences

• The crisis clarifies the limits of royal power in Britain:
  • Elizabeth: "It's the sort of Henry VIII complex, isn't it?...[but] unlike Henry VIII, he didn’t get it." (32:00–32:10)
• The monarchy is revealed to be subservient to institutions and public will.

The Psychology of Edward

• Elizabeth offers a Freudian analysis: Edward’s fraught childhood made him desperate for unconditional love (33:21–34:20).
• Dan agrees that despite politics, personal quirks and emotional needs often shape history:
  • "Those emotional vulnerabilities...are the incidental movers of history." (34:20–35:10)

5. The "Mysticism of the Other" and Misogyny

• The trope of the "exotic," bewitching woman (Anne Boleyn, Cleopatra, Wallis Simpson) recurs through history and cultural portrayals.
• Dan: "Gosh, there's a lot of misogyny about, isn't there?" (28:33–28:37)

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Notable Quotes & Memorable Moments

• Dan Jones, on Henry VIII breaking with Rome:
  "Get rid of her any which way I can and marry Anne Boleyn and somehow concoct this political legal case for getting out of the marriage…create both a tragic love story and the greatest upheaval in English religious history, cultural history, political history of the whole period." (06:44–07:35)

• Elizabeth Day, on Anne Boleyn’s final moments:
  "On her final day, she was said to have this strength and dignity in her final moments...she actually speaks highly of Henry VIII. The reason…is potentially because she wants to protect her daughter Elizabeth…" (13:02–13:42)

• Dan Jones, on historical empathy:
  "You’ve got to remember we live in the weirdest time of all time, and that most people in the whole of human history would have had more in common with each other than with us...most of our beliefs...would think were fucking insane, basically." (19:55–20:09)

• Elizabeth Day, on Antony and Cleopatra's suicide:
  "It's not a failure of devotion, it's a failure of viability." (27:06)

• Dan Jones, cynically on Edward VIII's abdication:
  "Did he really abdicate for love or did he abdicate because he didn't want to eat shit from anyone?" (30:43–32:00)

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Timestamps for Important Segments

• 03:13 — Framing the episode: Why failed romances matter
• 04:02 — Setting up Henry VIII and Catherine of Aragon
• 07:53 — Anne Boleyn's struggle and miscarriages
• 13:02 — Anne Boleyn's execution and legacy
• 17:22 — Antony & Cleopatra’s historical setup
• 21:29 — Cleopatra's feigned death, Antony’s suicide
• 28:58 — Edward VIII’s abdication crisis
• 32:00 — Political consequences of the abdication
• 33:21 — Edward’s childhood and psychological analysis
• 34:20 — Final reflections on personality shaping history

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Conclusion

Episode Tone and Wrap-Up

Witty, irreverent, and poignant, the hosts blend historical narrative with personal anecdotes to illuminate how big historical failures often hinge on intimate human flaws. The episode closes by teasing the next topic, "history's forgotten women," with both hosts reflecting on the limits of love, the power of failure, and the unpredictability of private passions in shaping public destiny.

Final Note

Elizabeth: "But I agree with you, Dan, that that's probably enough about heartbreak and beheadings." (35:24–35:39)
Dan: "That is enough about heartbreak and beheadings. Elizabeth, what failure have you got for me next week?" (35:39–35:45)

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Perfect for listeners who relish the intersection of history, personality, and power, this episode shows that when love fails on a grand stage, the consequences echo through ages.

Transcript

[Elizabeth Day]

Dan, are you a heartbreaker? I can't take that question seriously.

[Dan Jones]

Well, thank you. Well, you could try and like, think that I might be. I. I don't know. I'm more of a heartbroken. We're going to be talking about failed romances, right? So I was thinking about worse dates. Now, for me, it's a long time ago, but I remember going on holiday with a girlfriend. Kind of tail end of the of the relationship. Maybe going on holiday isn't the thing that's gonna fix it. We went to a Greek island and about halfway through the week on the Greek island, my girlfriend said, oh, there's this party in Athens. Loads of fun people are gonna be going. And I was like, yeah, that sounds cool. She went, I'm gonna go to the party in Athens. Right. Wow. You can stay here. So for the second half of the holiday, I was just on my own in a. Let's call it what it is, a three star hotel in a Greek island.

[Elizabeth Day]

Did you fly back together?

[Dan Jones]

I think we did.

[Elizabeth Day]

Did you stay together after that?

[Dan Jones (advertisement voice)]

Yeah, for a while.

[Dan Jones]

Like, the one consolation we can take from this is that in the olden days in history, there were worse outcomes to failed romances than just being on your own in a hotel on a Greek island. Reading Julian Barnes

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[Elizabeth Day]

It's not a battle. So glad the Saja boys could take breakfast and give our meal the rest of the day.

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[Elizabeth Day]

No, it's our honor.

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[Elizabeth Day]

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[Elizabeth Day]

Hello. This is History's Greatest Fails with me, Elizabeth Day, author and podcaster.

[Dan Jones (advertisement voice)]

And I'm Dan Jones, fellow author and podcaster. Now, we're old friends and fellow history

[Dan Jones]

graduates, and in this podcast we're going

[Dan Jones (advertisement voice)]

to dig into failures of historical proportions

[Elizabeth Day]

to understand why failures make history.

[Dan Jones]

Now, let's get stuck in. One of the things I want to talk about is in this episode today is failed romances in history. And there are some very famous ones. Famous not only because of the sort of the personal stories of love gone wrong, but also because these stories of love gone wrong have such huge, profound, resonant historical consequences. And so some of them that I thought we could maybe chew over Together, as it were, were Henry VIII and Anne Boleyn, Anthony and Cleopatra, and maybe one from more recent history, Edward VIII and Wallis Simpson. You want to do that?

[Elizabeth Day]

Great. Great selection.

[Dan Jones]

Any preference where we start?

[Elizabeth Day]

Yes, I'd like to start with Henry VIII and Anne Boleyn.

[Dan Jones]

I was hoping you'd say that.

[Elizabeth Day]

I feel a historical affinity with Anne Boleyn, which I'm sure many women do. It's partly because, you know, I love a name comparison. So my middle name. One of them.

[Dan Jones]

Jesus. No, this can't be. We can't just be choosing historical anecdotes that have some relevance to the name Elizabeth Day.

[Elizabeth Day]

Or can we, Dan?

[Dan Jones]

Elizabeth Ann Day, I presume.

[Elizabeth Day]

Elizabeth Ann Melanie Day. So that's gonna be trickier when we get to Melanie.

[Dan Jones]

But not a lot of Tudor Melanies.

[Elizabeth Day]

No. Anne. I'm Anne with an e. And so was Anne Boleyn, and so was Anne of Green Gables. And Anne, obviously, had a daughter, the great Elizabeth I. Okay. And she's got six fingers on one hand.

[Dan Jones]

Well, did she?

[Elizabeth Day]

Well, we're gonna get into that. Why are you going to stop me there? I don't have to.

[Dan Jones]

Firstly, to count your fingers. Secondly, to say. I mean, spellings are not regularised in the 16th century.

[Elizabeth Day]

Again, it was such a buzzkill.

[Dan Jones]

Thank you very much.

[Elizabeth Day]

But tell us about Henry viii, because I know that you're desperate to. So he was married to Catherine of Aragon, and she was quite a popular queen, wasn't she?

[Dan Jones]

Yes. I think what's often overlooked with Henry VIII is, is that for most of his reign, he was married to one person. It's Catherine of Aragon. I mean, they get married very early on, I think 1509, and they're married through to 1533. And, well, he's. I mean, he's dead a decade and a half after that. So most of his reign, he was married, if not always happily, then contentedly to Catherine of Aragon. And certainly at the beginning of the reign, yeah, they presented us this sort of glorious Renaissance. Again, this speaks a little bit to the way that we think about Henry VIII and we think about historical characters in terms of fixed caricature images. I mean, when I say Henry viii, what are you thinking of?

[Elizabeth Day]

Instant, like, snapshot, that famous portrait, the Holbein portrait, of him with the globe in the background and him in Hampton Court. And. Yes, with his hands on his hips and wearing that little skirt that he liked, that little tennis skirt.

[Dan Jones]

But it's the big, fat Henry viii.

[Elizabeth Day]

Yes, it's big, it's powerful. And I find what's interesting about him is that even though he behaved abominably to his wives, he still has this reputation as a sort of sexy lothario.

[Dan Jones]

Don't sexy Lotharios often behave abominably towards women?

[Elizabeth Day]

Yes, but they don't always behead them or split from the Catholic Church and ransack monasteries as a result.

[Dan Jones]

And that's why I think this is so interesting, because. And I think there's a bigger point about the Tudors here. What we see here is in some ways a relatable story, only blown up to grotesque and monstrous proportions in every way. Everyone has a story of love gone wrong, right? Especially if it's gone wrong for reasons they don't understand in the moment and can only reflect on afterwards, and especially when it's ended in terrible pain and heartbreak. Back to the narrative. Henry VIII marries Catherine of Aragon when they're very young. It is crucially to the. The other end of the story. Catherine had previously been married to his elder brother, Arthur. There was a question about whether this marriage had been consummated because they were both teenagers when they were married. Arthur died, Henry married his brother's widow. At the time, this was all sort of dealt with. All the paperwork seemed to have been done. A daughter is born, the future Mary I. Everything seems sort of fine until in the middle of the 1520s, and certainly by 1527, Henry has started to have doubts about whether this is the woman he should be married to. Partly because he's found other women he thinks he might quite like to get married to, and one in particular with Anne Boleyn, but also because he's convinced himself that. That their failure, or as he would say it, her failure to have any more children is a sign that God is displeased with him, them for contracting this marriage, which must be in some way illegal, and the dual consequences of that. Get rid of her any which way I can and marry Anne Boleyn and somehow concoct this political legal case for getting out of the marriage, create both a tragic love story and the greatest upheaval in English religious history, cultural history, political history of the whole period.

[Elizabeth Day]

Because he's not just concocting a case to get away from Catherine of Aragon and with Anne Boleyn, he's also concocting the case to get away from God as he's known him, the entire perception of organized religion up until that point and the various legal and religious and moral and political loopholes he finds in order to effect the Reformation. So he and Anne Boleyn get together. They marry in January 1533. Their daughter Elizabeth was born in September15. It won't surprise you to learn that I'm a big fan. Was born in September 1533. But one of the great sadnesses of Anne Boleyn's story is that she went through probably at least two miscarriages, and one of them must have been so horrendous to experience. She miscarried at 15 weeks on the day of Catherine of Aragon's funeral. And the amount of grief she must have felt on a human level, combined with the level of anxiety she must have been living with daily because she's not producing this male heir, which is. Henry has staked an enormous amount on her ability to do that, and she knows what happened to Catherine of Aragon. So she has to play this incredibly careful and precise game at court. And it must have been so unbelievably challenging. And it doesn't end well, does it, Dan?

[Dan Jones]

No, it doesn't end well in the slightest because mixed up in all of this is not only, as I say, the romance, but also the. The politics, the court politics, and then the politics of conscience. And Henry, early in his reign was as staunch a defender of the Catholic Church as you could imagine. And so the. By the end of the decade, to be completely flipping that position and saying, actually, you know what, yeah, never mind the Pope, we're going to get rid of him. We're going to have royal supremacy in England. And that whole. That whole marriage, which I've, you know, I' so much of my life, that was never the case anyway. There is so much sort of psychologically loaded here on a person in Henry who is deeply, psychologically fragile.

[Elizabeth Day]

That's so interesting. So do you think that he's looking for an escape hatch through romance, the idea that love will make sense of it and can complete him and will give him the psychological safety that he needs?

[Dan Jones]

I think so, but I think that I would come to that conclusion which feels like a Freudian analysis through probably a different set of analytical tools, which is to see Henry as a prince of the Renaissance, born in the late 15th century and educated. Really. There are sort of two poles to his education. David Starkey's written brilliantly about this. And there's this whole new way of seeing Henry VIII's reign, which is, you know, you have these two intellectual. Henry's a brilliantly educated young Renaissance prince, and you have, on the one hand, Erasmian humanism, and on the other hand, sort of Italian machiavellianism. At play in his mind, but at the beginning of his reign, I mean, you're looking at the type of guy that is denounced routinely on the Internet every day today. Right. It's all male ego, which, which presents as power but is really kind of damaged and fragile.

[Elizabeth Day]

Well, it's also making me think of Boris Johnson. I wonder why, I wonder why. But I think therefore what's so interesting about this particular failure is that it's so multi layered. Obviously you have the failure of the relationship in dramatic fashion. You have the failure of Anne Boleyn to escape her tragic fate, but you also have the. Of Henry viii. I feel like what I get from him is a desire to break free of the shackles of institutions. And yet he discovers that he's not big enough to do that with the monarchy itself. The fact that Anne Boleyn hasn't produced an heir ultimately signs her death sentence. So their love was incredibly strong, but not quite strong enough. Ultimately, between power and love, Henry's desire for power and his self identification with power is what won out. Would you agree with that?

[Dan Jones]

I think I'd agree with that. And I think it's the case that what do they say about killers, once he killed once, they'll kill again.

[Elizabeth Day]

I mean he, he sees that he can do it.

[Dan Jones]

And that's absolutely the magnitude of the first decision and the, I mean the, the enormous difficulty, the legal case that has to be gone through to get to the, the annulment in the first place and then the tearing up of the entire fabric of the English church and the dissolution of the monasteries and everything that sweeps in with Cromwell and with Anne Boleyn. And then when that doesn't work out, that's when it just becomes a sort of rolling habit of another one, another one, another one, another one.

[Elizabeth Day]

On her final day, she was said to have this strength and dignity in her final moments where she knelt down and she had to keep kneeling with her head held high, knowing what was to come, knowing that this swordsman was about to slice through her neck. And in her final words, she actually speaks highly of Henry viii. And the reason she does this is potentially because she wants to protect her daughter Elizabeth, who at that point is only three. And I just think that says so much about the strength of that woman.

[Dan Jones]

I agree. One of the things we were talking about when we discussed Richard III last week was that characters have their moment now. I don't think her stock has ever been higher. I don't think she's ever been more of a Sort of secular saint, if you like, than in the sort of post MeToo era. She is the character for that culture because she is a character so out of her time, also ahead of her time, so dignified and brave in many of her moments, particularly her last moments, as you say, faced with such a grotesque caricature of everything that is, like, hideous and wrong with a matrimonial patriarchy that seems. I mean, Henry VIII as Harvey Weinstein doesn't take a lot of sort of, you know, imagining. Even if the characters themselves are not the same. Henry VIII was, I think, in many ways, more enlightened. However, she's a character absolutely of the moment. And I think that one of the things that we're attracted to in looking at history today are these tragic victims, hero victims. You know, the idea of the victim as hero, the hero as victim, the overcoming the. The tremendous odds, the dying for a cause or the sort of noble martyrdom are things that we're absolutely attached to in storytelling today. And Anne Boleyn, however she presented to her own times, is now a sort of a poster girl for what we love to do.

[Dan Jones (advertisement voice)]

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[Dan Jones]

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[Dan Jones (advertisement voice)]

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[Dan Jones]

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[Elizabeth Day]

Let's seamlessly segue into our second doomed couple, Anthony and Cleopatra. This is quite a confusing time of history. I find it quite confusing. I'm not great at maths, so the whole like, BC chronology, where it's a countdown rather than a count up, essentially. They first met in 41 BC in modern day Turkey, and Cleopatra was the last ruler of the Ptolemaic family.

[Dan Jones]

Ptolemaic?

[Elizabeth Day]

Yeah, in Egypt. Who? They ruled Egypt after Alexander the Great and she'd been with Julius Caesar and allied with him and even had a child with him. And when Antony and Cleopatra met, there was an instant bonding, so it seems. Yeah, so it seems. Although we don't know whether that was political or personal. Certainly culture and Elizabeth Taylor films would have you believe that it was personal.

[Dan Jones]

Right.

[Elizabeth Day]

Tell us more, Dan.

[Dan Jones]

Cleopatra's it's just a sort of perfect story because Cleopatra, first of all has had a child with Julius Caesar, whose death is the catalyst for the second triumvirate in which the two main players are Mark Anthony and Octavian, the future Emperor Augustus. From Caesar, she takes up with Mark Antony. That relationship forces Anthony to choose between whether he's loyal to the Roman Republic, as it's soon not to be, or whether he's loyal to Cleopatra, who is easily presented as the love of his life, but could also be the sort of key to his political success in the east of the Roman Empire. So here we have the sort of perfect, kind of seamless blending together of politics and romance. But your question, as usual, is incredibly perceptive and drills down to the very heart of the issue, which is to what degree is this politics and to what degree is this romance? And the answer to that, I think, is that might not be a distinction that was possible to make. The romance is part of the presentation of the political alliance. And because we live in such a weird time in the early 21st century, and I say this to particularly to young people, people who are starting to study history, you've got to remember that we live in the weirdest time of all time, and that Most people in the whole of human history would have had more in common with each other than they would with us. So most of our mores, most of our beliefs.

[Elizabeth Day]

That's a massive statement. Okay.

[Dan Jones]

It's massively true. Thank you. Most of the things that we think almost everybody who lived in all societies before us would think were fucking insane, basically. I think we are so weird and so ill equipped really to empathize with most other human times. That's my starting point for historical analysis. That may be an extreme expression of it, but I think that's where you ought to start. One ought to start.

[Elizabeth Day]

Let's assume that they are both brilliant strategists and they're both trying to consolidate power. And it just so happens that they enjoy their time together and have three children and Mark Antony acknowledges them. But then I think the element that might slightly prod at that belief is their suicides. Now, this is such a strange and esoteric and moving story where Cleopatra, as a kind of power play, correct me if I get this wrong, pretends that she is taking her own life and she retreats to her mausoleum, which is also a sort of temple for security reasons. And she allows word to spread of her death because she wants to see how Mark Antony responds.

[Dan Jones]

I mean, that's the great dream, isn't it? What would they actually say?

[Elizabeth Day]

It's sort of the refuge of the perpetually needy, those with an insecure attachment style who bloody love it now, but let's have a little segue into a failed romance of mine. I am incredibly susceptible. I was incredibly susceptible to people saying nice things to me and essentially being love bombed, I guess, in the early days of any fling because historically I was also insecure and needy and I just needed to hear nice things to shore up the whole of my self esteem and hole without a W. And I remember getting into what I didn't realize was a relationship with a man who acted in increasingly unhinged ways. And he was very keen from the very start. And I thought, well, isn't that nice that he's so keen? And here's someone who's sort of consistently saying that I'm great. And I remember it came to a head the third time I ever met him. He came round to my flat and buzzed on the intercom and I answered and he said, oh, could you come down and help me? Help me with something. So I went downstairs. And as I was going downstairs, I do remember thinking, what if he's an axe murderer? Because I actually don't know him.

[Dan Jones]

That well, even though, is he asking for help with his axe, he's asking

[Elizabeth Day]

for help with a bulky parcel that he removes from the passenger seat of his car. And I question it mildly as we're walking upstairs. I'm like, what's this? Then he said, oh, it's a camp bed. I was like, oh. He was like, yeah, your mattress is really uncomfortable and it's so bad for my lower back pain. So I've brought my own futon. And what happens, Dan? And you know, apologies if any listeners or viewers are of a delicate nature, but we are intimate on my mattress, which is totally fine. And after we have done the act, he sort of unrolls his futon, then rolls onto the futon like a sort of faithful hound lying at the feet of his Tudor retainer. And I remember going to sleep thinking, this is totally fine, you know, how great to be with someone who just knows his own body, who is self aware enough to acknowledge that he has lumber issues and he's taken action. And then in the middle of the night, I woke up, sat bolt upright, and I just thought, this man cannot be my boyfriend and I need to break it off. And I did the next day. And he said, well, as long as you don't come back to me in six months having changed your mind, because by then your ovaries would have dried up and I won't be interested. And I thought, well, I'm so glad that the camp bed happened because it was an unignorable red flag.

[Dan Jones]

Somehow I find that more horrific than Henry VIII having Anne Boleyn behave with a sword. I know it's not, and I think it's just the shock of the new. But that is atrocious.

[Elizabeth Day]

And also because at the time I was in my late 30s, I'd gone through a divorce. It was. Dating was a hellscape, and I know it still is. But at the time, I was so grateful for meager crumbs from someone's table that I was genuinely thinking of having a full blown relationship with this individual. So it was a good wake up call and in a way, so was Cleopatra's fake suit.

[Dan Jones]

I wondered how we were going to get back to Cleopatra. I wondered maybe if you sat bolt upright in the middle of the night while your man was on this sofa bed, whether you thought, if I retreat to my mausoleum now, the guy will think and then I'll find out what he really thinks. But he was going to tell you that anyway. As it turned out.

[Elizabeth Day]

As it turned out.

[Dan Jones]

Wow.

[Elizabeth Day]

So Cleopatra stages her Death. And Mark Antony takes it badly. He tries to kill himself essentially, but does a very bad job and doesn't do it. But he's sort of, he's bleeding from various self inflicted wounds and he insists on being transported to Cleopatra's mausoleum and being winched inside on his camp bed. On his camp bed. Futon. And he dies in Cleopatra's arms.

[Dan Jones]

Yeah. This is so Romeo and Juliet coded, isn't it?

[Elizabeth Day]

It is

[Dan Jones]

pretended to commit suicide and then maybe you have, maybe you haven't woken up. She's dead. Oh God. You know, this is, this is something we're familiar with from drama. Suicide, noble suicide, dying each other arms. I mean this is. These are the sort of tropes of romance, I guess is what I'm saying. Attenuated in our minds through the, the. What is the word I'm looking for? I can't remember. Through their use as portrayals. Portrayals. I wanted a cleverer word than that, but never mind.

[Elizabeth Day]

Oh my God. Sometimes you need to humble your and use the straightforward word because otherwise you just come across as a. Okay, so I'll give you that gift for free. Continue their portrayals.

[Dan Jones]

I will continue my moron monologue. Diffusion was the word I was looking for. Okay, thank you. Their diffusion through drama. I can't remember the beginning of the sentence, but nice alliteration. Yes, I'll take it a compliment. Anything. Oh, please hand them down. The. My point is that this, these are all dramatic tropes. But what we see quite commonly in many societies at high political level is that when you fucked up, you were supposed to kill yourself. And that's a noble way to go.

[Elizabeth Day]

So Antony and Cleopatra as a failed romance is an interesting one because we're not even sure that it ticks the boxes of our modern day conception of romance. But what I would say is that it's not a failure of devotion, it's a failure of viability.

[Dan Jones]

And it's a military failure, ultimately. Military and political failure. That this, this political, military alliance that was sort of contracted between two people who could have a romantic or sexual or you know, marital type relationship failed because they're defeated by one of the greatest politicians who ever lived, Octavian, you know, Augustus. What are the consequences of that failure?

[Dan Jones (advertisement voice)]

Well, I mean, one of them is

[Dan Jones]

the final destruction of the Roman Republic and its rise into the empire under Augustus. And I suppose opinions between rational people can differ as to whether we think the end of the Roman Republic and the rise of a sort of autocratic empire is a good thing or a Bad thing. That's a question that's probably sharpened by discourse in world politics today.

[Elizabeth Day]

Yes. There's another thread that I'd like to sew between these two stories, which is. And actually three stories. Cause the one we're coming onto is a great example of this. This idea of the mysticism of the other, of the exotic woman who sort of casts her female spell over this benighted man. So Henry VIII literally accused Anne Boleyn of casting a spell over him. And again, the way that Cleopatra has been portrayed through the ages is of this very sort of beautiful, magnetic character who could pull on that to get men to do what she wanted.

[Dan Jones]

My main observation is there's. Gosh, there's a lot of misogyny about, isn't there?

[Elizabeth Day]

There is, isn't there? Dan, well done. I'm slowly educating you.

[Dan Jones]

Yeah, well, I found out a lot in the last two episodes. But there's one more, and I think, to your point, about the sort of the bewitching, exotic outsider that sort of brings us on to the final, doomed, failed romance with historical consequences, which is Edward VIII and Wallis Simpson.

[Elizabeth Day]

So Edward and Wallis. So we're in 1936. Edward VIII, as he is then accedes to the throne. He's the son of George V and Mary of Teck, but he is also in love with an American divorcee called Wallis Simpson. And the issue here is that he's head of the Church of England. So the Church of England does not allow at this stage, marriage to divorcees. Although times have changed and it's a really. For Britain and its slightly disintegrating empire. So the Commonwealth still has an enormous amount of power, but it's also a time where it's the birth of radio, so there's more instant communication that people are getting. People are starting to question old institutions and that sets the scene for what happens next.

[Dan Jones]

Not the two most sympathetic characters.

[Elizabeth Day]

Yes, exactly. Because that brings me onto my second point, which is that they became Nazi sympathisers. Now, if this is a big if, but if Edward had become King, what would that have meant in terms of World War II and what side we were on and could we all be living now under a Nazi state? So there, again, stakes are quite high. The stakes are high and that's not a failure. So in a way, like the failure of institution, if you look at an abdication crisis like that doesn't betray the fact that their relationship on a personal level was probably successful. And thank goodness that the Nazis were defeated.

[Dan Jones]

Well, I think there's an argument to say that this is actually a success story all round. Okay, not to sound like the cynical non romantic here, but the question I think with Edward is did he really abdicate for love or did he abdicate because he didn't want to eat shit from anyone? And I think that's a key distinction to make. Yes, the matter at hand was him wanting what he wanted, which in this case was Mrs. Simpson. But deep down the issue was does the King have any right to do what the fuck he wants when there are clear protocols, norms and rules here that say he can't do this? And Edward wanted to do what he wanted to do. And this was a test effectively of the British constitution, which as we know is, if not unwritten, then is written in diffuse places and not codified, thankfully, because it becomes, he makes it more flexible over time. The view I always have of Edward is that actually this was a test of what kind of king he wanted to be. And it could have been some other issue, but actually here was a very clear sort of defining issue which is I want this person. Well, he can't have them.

[Elizabeth Day]

It's the sort of Henry VIII complex, isn't it? It's like, well, I want this and I'm King or I'm going to be king so I can get it. But actually, unlike Henry viii, he didn't get it.

[Dan Jones]

Yes, and I suppose that they are both tests of the political process and the constitution in some ways. I mean, Henry viii, even given the bloodshed and the upheaval of what Henry VIII does, he does jump through a certain set of legal hoops. In the case of Edward and Wallace, again we see these institutions and these norms tested and Edward finds that actually he's unable to go, well, I want to marry her. So we change all the rules. I mean, times have moved on now. But that process sort of starts with Henry viii, which is if I want to do this, it still has to be a sort of parliamentary process and their institutions and norms. It's a crisis test of the British constitution which has changed somewhat by it, which is at least is clarified by it, which sets out the limits to what a king, what a monarch as head of state can possibly do when their will runs up against the opposition of Parliament of Britain. And then, I mean, let's not forget the rest of the Empire Commonwealth saying, well, we're not going to go along with this either.

[Elizabeth Day]

You know, you mentioned I was a bit Freudian earlier and I am, and I make no apology for it.

[Dan Jones]

It's Not a criticism. Not a criticism at all.

[Elizabeth Day]

He also experienced a childhood typical for that social context and that age. But I remember hearing the story about how as a young child, he was farmed out to nannies. And there was one particular nanny who was rather brutal with him and used to sort of pinch him and hit him to make him cry at the moment that he was wheeled in front of his parents at the end of the day. So his parents, Edward VII and Mary of Teck. And whenever they saw Edward crying, they'd think, oh, he's not very well behaved. We don't want anything to do with him. And so he felt this sort of isolation and alienation, I think, and a lack of love from a very early age. And it kind of makes sense to me that therefore love becomes so important. He wants to stake everything on it and he wants someone who is also going to love him in a maternal way.

[Dan Jones]

Yes, that is interesting. And I suppose that over the course of this conversation in particular, I've found myself to be incredibly cynical and unromantic and trying to delineate the romantic and the political. So I'll just wheel back on that slightly to agree with you, which is to say that. That for all that we can analyze all of these cases in terms of politics and constitution and norms and institutions, that actually, the one thing we've always got to do in history is remember that the quirks of the individual, their loves, their private passions, their peccadilloes, their weirdnesses, their fetishes, their just blind spots, can often be the moving forces in history. And those emotional vulnerabilities that lead them to make certain choices, act in certain ways, often are the incidental movers of history.

[Elizabeth Day]

Beautifully put. The other.

[Dan Jones]

Thank you. I'll use some long words, then, but you like those?

[Elizabeth Day]

I love those. Yeah, they. I feel they pass muster.

[Dan Jones]

We should stop talking about this.

[Elizabeth Day]

We should. But it's been great.

[Dan Jones]

Yes, I've enjoyed it as well.

[Elizabeth Day]

It's been. I mean, we've discussed tragedy and failure and heartbreak, but it's been so interesting. And let's just remember that without Wallis Simp, we wouldn't have had Queen Elizabeth ii. But I agree with you, Dan, that that's probably enough about heartbreak and beheadings.

[Dan Jones]

That is enough about heartbreak and beheadings. Elizabeth, what failure have you got for me? Next week.

[Elizabeth Day]

Next week we are going to be talking all about history's forgotten women. We're going to find out how their failures weren't always an active choice.

[Dan Jones]

Well, that is almost all for us this episode. But Elizabeth, where else can we find out about more failures?

[Elizabeth Day]

Well, I'm so glad you asked, Dan. You can listen to my podcast how to Fail, where I've had people like Pamela Anderson, Jon Bon Jovi, and Kate Winslet talk about how they survive failure in the present. And what about you, Dan?

[Dan Jones (advertisement voice)]

Well, if you're one of my this Is History royal favorites, listen to this week's bonus episode. To hear me and producer Al discuss your favorite historical failures, [e-mail] thisishistory or you can listen to this is History.

[Dan Jones]

A Dynasty to Die for.

[Dan Jones (advertisement voice)]

I've had Edward the First, Edward ii, Edward iii.

[Dan Jones]

Just some famous history guys.

[Elizabeth Day]

And if you've got a question about anything we've discussed on greatest fails so far, Dan's royal favourites can DM him on Patreon or email [e-mail] now friends, let's make history.

[Dan Jones]

Let's fail again next time.

[Ryan Reynolds]

Ryan Reynolds here from Mint Mobile. I don't know if you knew this, but anyone can get the same premium wireless for 15amonth plan that I've been enjoying. It's not just for celebrities. So do like I did and have one of your assistant's assistants switch you to Mint Mobile today. I'm told it's super easy to [e-mail]

[Elizabeth Day]

Switch upfront payment of $45 for 3 month plan equivalent to $15 per month Required intro rate first 3 months only, then full price plan options available, taxes and fees, extra fee, full [e-mail] do you think she' one that got away?

[Dan Jones]

She got away all right. Her head got away.

[Elizabeth Day]

I got away from her body

[Dan Jones]

all right.