Adrienne Dillard on Anne Boleyn: Brave or Just Lucky?

Adrienne Dillard on Anne Boleyn offers a fresh, unfiltered look at one of Tudor England’s most iconic and controversial figures. In this exclusive conversation, historical fiction author and Tudorcon favorite Adrienne Dillard joins us to unpack Anne Boleyn’s charisma, agency, and lasting impact on English history. From public backlash and court intrigue to the truth behind her family’s ambition and her role in the Reformation, Adrienne sheds light on both the myth and the reality. If you’ve ever wondered whether Anne was truly powerful or just caught in the current of change, this deep dive is for you.

Transcript of Was Anne Boleyn Brave or Just Lucky? A No-Holds-Barred Chat with Adrienne Dillard

Heather: I have a bit of a treat for you today. One of the perks of being a member or patron of this podcast is regular author chats. This is a chat we had with my dear friend Adrienne Dillard, who is a historical fiction author, longtime Tudorcon speaker, and all-around just brilliant human being. We talked about all things related to Anne Boleyn. This was in May, the month when Anne was executed.

Adrienne is the author of, among other books, The Raven’s Widow and Cor Rotto. She’s currently deep-diving into George Boleyn’s writings on the Knowles sisters, so this is definitely going to be good.

This conversation went everywhere—from Anne’s charisma and courage to the mob of angry Tudor women who chased her down the Strand, to whether Anne really changed history or just surfed the waves already forming around her.

Also, fair warning: this conversation contains confessions of fever dreams, mild soapbox moments, and some very honest takes on feminism, Henry VIII, and the Anne Boleyn fangirl industrial complex. So grab your tea or your wine and settle in for a juicy, slightly rebellious chat with the one and only Adrienne Dillard.

Heather: Adrienne Dillard, you have written books, you have spoken at Tudorcon. I always say this story about you, but I’m going to say it again. I just always remember you because your book on Jane Boleyn—I read it when I was really sick, and I was on the couch reading it, and then I had this horrible fever. I kept waking up through the night thinking that I was Jane Boleyn and George, and that I was being killed, and that I was with Katherine Howard, and it was just this fever dream all night.

I didn’t know what was going on. I was half awake and not awake, reading and dreaming at the same time. So I always associate you with that really sick time I had—but in a good way, because it was kind of trippy and kind of enjoyable, but also weird.

Adrienne: I love that I inspire nightmares. I think that’s a great life goal for a woman to have—to inspire nightmares.

Heather: I agree. Total professional goals— inspiring nightmares. Yeah. So talk to me a little bit. This has been a year-long shindig of a court, of a study group, whatever we want to call it, that people are in. And we’ve been looking at the top moments in Tudor history. This past month, we’ve been focused on the Great Matter. Because we have been looking at the Great Matter itself, the rise of Anne, then the Act of Supremacy, and now this last week was the Dissolution. So we have been digging deep into this stuff.

But I would like to speak to you specifically about Anne and how she basically upended England and English history, and how England is different because of her and her family and where she came from. There are a lot of myths about Anne and her family, and I want to break some of that down. So my first question to you is: what made Anne so special?

Adrienne: I think some people just have that thing, right? And nowadays, we tend to see them as celebrities, and a lot of that comes from charisma. I think one of the things we can say about Anne is that she had a lot of charisma—whether you were on her good side, her bad side, or even if you did not like her.

I think Eustace Chapuys is a perfect example. He did not like Anne. He did not support her in any way, but he was still really impressed by her—impressed by her composure, impressed by the way she carried herself. One of the quotes I love the most is where he calls her braver than a lion.

That quote, in itself, sums Anne up perfectly. Whether you agree or disagree with the choices she made, whatever she was doing took great courage—for good or for bad. She was a really powerful woman. She was very influential, and she had the ear of the king. I do not buy into the idea that she was playing hard to get, but I am also not totally attached to the idea that she was just a helpless victim in all of this either.

We see time and again that she had agency and power. My own personal belief is that when Anne was turning Henry VIII down in the beginning, I think she was being sincere. Because look at what had happened to her sister. I think she was saying to the king, “I deserve a true marriage.”

And I think it was not until it became clear to her that Henry was going to do whatever it took to end his marriage to Katherine of Aragon and marry her. At that point, Anne was like, okay, then we are going to buy into this, and my family is going to buy into this. Because really, you could not marry higher than the king—the king was as high as it got.

And I think in Anne’s head it was like, okay, well, if we can get the Pope to sign off, and then when that did not happen, they were like, okay, well if we can get this new idea moving, this new path… Because really, the new religious changes dovetailed really well with making Anne queen.

You can see them as two separate issues, right? Because reform was already starting to happen in the church. So, I mean, the divorce—the Great Matter itself—and the Reformation are actually two separate issues, because the Reformation had already begun.

And it just so happened that this new marriage with Anne fit into that. The pieces fit together so well and dovetailed so neatly that they kind of get conflated. Because really, you had to have the Reformation in order to have the marriage. You almost could not have one without the other. So then they end up going together.

But I think that Anne came in and she was just… she was really well-educated, she was very smart, she was very opinionated. She had learned how to behave at court, and I think that is what made her really attractive.

Heather: And so you talked a little bit about the idea that she had agency. There is that myth that her father was almost like pimping her and her sister out. Tell me what you think about that.

Adrienne: I mean, no, I do not believe that at all. In fact, actually, I believe there is commentary—I do not know if it is actually in Thomas Boleyn’s own words—but there is commentary that Thomas did not actually want this match between Anne and the king.

He thought she was going to end up a mistress and then be discarded like Mary Boleyn was. So it really was not until it became a sure thing that Anne was going to become queen that they really put their efforts behind it.

I do not know. I mean, I feel like the jury is kind of out as far as how Mary became a mistress to the king. And of course, we cannot even date it for sure. We do not even know how long it lasted. Literally all we have to go on—and it is not even an actual confirmation—is kind of like, he says never with the mother. Right?

And then we have the dispensation. The dispensation says “perhaps,” if he had perhaps had a relationship within however many degrees. There is never any actual confirmation. I think there is enough circumstantial evidence that we could say yes, it did happen.

But I tend to think that Mary was clearly very different from Anne, and I think maybe it was something she got swept up in. At that time, Henry was young and attractive, and he was having relations with other women—there are all sorts of stories about him with different young ladies at court. So I think that is probably what happened. And then she got married to William Carey because it was like, okay, we are done with that, and we are going to set you on your path.

Heather: So talk to me about the response to Anne becoming queen and to their marriage. And maybe talk to me a little bit about—let’s back up—their timeline and how they eventually got married. So we are looking at 1532 as the trip to Calais, where they start having relations, right? And there was a secret—talk to me about the timeline then for that next year, leading up to the birth of Elizabeth. Let’s just say from September to September.

Adrienne: Yeah, so they were over in Calais, and that was kind of like their great triumph, right? Because François really greeted Anne as the queen. There was a whole lot of pomp and circumstance, and it was just seen as very blessed. And then these storms came and they were not able to leave. So of course everybody is kind of hunkered down.

Anne and Henry are really excited. They have just managed to accomplish what they did not think was going to happen. They got Francis’ buy-in, and so I am sure if they were already having some level of intimacy, they just kind of got to the point where they were like, it is happening. You know? Right. We do not have to wait. And they were excited. I think January is just too late. I mean, I think that would make Elizabeth too premature for me. Obviously, it is only a difference of a couple of months.

When they come back—they are back in England in January—they get married in secret. There are only a few witnesses, and we know George is one of them. We also know that there was a woman, one of Anne’s ladies, who was part of it as well. But yes, it was very, very secret.

To use an example, I was pregnant, and my son was born literally just a couple of days before Elizabeth’s birthday. And I fell pregnant with him in early December. So for me, I feel like January is just too late. Maybe, but Logan, my son was born right on time—he was right on his due date. That sticks in my mind a lot, and I think about that. That is what makes me think January was just too late.

Heather: Hannah was originally—she was early—but her original due date was the 21st of August. So like two or three weeks early. Two and a half. And that was Thanksgiving weekend. Funny how we know this stuff. So that was the end of November.

Adrienne: Right, right. Well, we were tracking, and so that is how I know. Right? And so, like, I know. And I think about that, and then I think about how it just very much fits. It does fit a narrative that they were there, she got pregnant, and by January she would have known. Or she would have at least been very late.

And then they needed to get married. Because if you think about it, it was still kind of a rush. Yes, they had accomplished a lot, and it was pretty sure that they were going to be able to get married and everything, but you would think that after as hard as they fought and as much time as they waited, they would have done it differently. And they did not.

So that is just my opinion. We do not have a smoking gun, but in my opinion, you know, there is a little jubilation when she finds out she is pregnant and all of the astrologers are saying, “Oh, it is going to be a boy.”

Heather: Yeah. And how did the crowds react? Because there are those stories of when she was being crowned, her processions had people laughing and saying “Ha ha,” and even, I think it is in The Tudors, one of the shows, they showed a mob attacking her before she was queen because they were so supportive of Katherine. Talk to me about how people viewed her.

Adrienne: That did happen. There was a mob. They had actually gone—and I know this specifically because I wrote this scene in The Raven’s Widow, and I remember just being shocked when I read the actual account of this.

One thing that is really interesting is that it is very clear Anne had the full support of the Boleyns. This ties back into that question you asked earlier. One of the things that really stands out to me is that they had homes very near to London so that Anne could be in London. They could attend the trial of Katherine, they could attend Parliament, and all of these things.

So, when this mob happened, Anne was staying at her father’s house on the Strand. He had a house on the Strand, and the Crown was actually paying for an apartment for Jane Boleyn and George so that they could live there and be near to court while Anne was at court.

So Jane and George were a huge presence in that early part and were really supportive of her. It is often said that Jane was not, but there are so many little details that I do not know if people have missed or if maybe they are not realizing that Jane was also part of that.

I found a lot of things that were attached to George, but Jane was also listed in there in some way. One of them is that Henry paid for an apartment for them to live in, which is really interesting.

Heather: Yeah, it is. So there were kind of mixed feelings within the populace at large about her.

Adrienne: Yes, exactly. So she was at this house on the Strand, and these women just showed up because they were all there, kind of planning out her household. A bunch of just regular civilians showed up and they were yelling at her, calling her a whore, calling her names, throwing stuff at her. They ran down to the river, got on a riverboat, and got away just in time.

But these things were happening, quite often, because the people were in support of Katherine. They were seeing how she was being treated in court and by Henry and his advisors. They could not act out against Henry, but they could act out against Anne.

Heather: Yeah, for sure. And it makes sense why they would be upset. Katherine was treated terribly, and so often in history people want to pit these women against each other. And I mean, in the end they were kind of against each other, but it is really Henry who is the monster here. You know, let us not forget.

Adrienne: Right? Yeah. And I mean, as much influence as Anne did have, ultimately there was not a thing that she could do. Even if she were to say, “You know what, no, no, no, never mind. This is too much. I don’t… you know, we’ve gone too far. I don’t want to…” there is no way that Anne could have said that to the king at any time.

Heather: Yeah, yeah. What are you gonna do? Yeah, it’s really sad. It’s really sad for all these women, getting mixed up with him. Bad move. I mean, not that they could have made a choice.

So tell me about then how like… so that was regular women and regular people where there was this kind of divide and people still supported Katherine. What about the nobility? Were the nobility quick to jump on supporting Anne and supporting the Boleyns, or… I mean, I’m thinking no, because there was still this conservative faction. Talk to me about that.

Adrienne: It was really kind of divided. Both Katherine and Anne had their supporters, and I think they were probably pretty equally split down the middle. You tended to see most of the newer nobles were for more of the Boleyn faction, and then you had the older, traditional conservative nobles who were for Katherine.

But at the same time, you had Norfolk, who was one of the oldest nobles at court, and he was related to Anne. Yes, he did support Anne for a time, but then when she drew some boundaries with him, he did not like that and thought, “Who are you to tell me?”

And so he defected to the other side. You could not assume who supported which side, because it really just depended, sometimes, on which way the wind was blowing and who had the king’s ear at that time.

Even, you know, we are discovering some stories that you have John Gage, who was the Constable of the Tower. He was actually the Constable of the Tower after Anne’s death, because Master Kingston was before him. But John Gage was actually trying to resign in protest of Anne and complained about her because he was conservative and he did not support the new Reformation changes.

But then, as we found out—like, I don’t know, five or six years ago—Dr. Kate McCaffrey from Hever discovered that John Gage and his wife had kept Anne Boleyn’s Book of Hours. That was the last place you would think it would be, but it was there.

And so I think that we have to remember that we are looking at official paperwork, right? And even today, sometimes the things we put in official paperwork are not necessarily the way we really feel.

So I think we can make our best guesses as to who was on whose side and why, but the reality is we are never actually going to know who the real movers were behind Anne’s downfall. We all think it was Thomas Cromwell, and certainly he had a big hand in it, but how much more of a hand did Henry have in it, or these other people who worked for Cromwell? I mean, it’s all very shadowy.

Heather: Truly, and it’s hard to know from 500 years away and looking at incomplete records and all of that. Nobody knows, and everybody is guessing, and you can put together some good guesses, some educated guesses, but yeah, it’s still a guess.

So you had said—the Reformation—I want to go back to this point you mentioned, that the Reformation was already happening beforehand. So I’m wondering, just playing some alternative history, if Katherine had had a son and there was no need to go outside, how do you think history might have gone without Anne?

Would England have hosted the Spanish Inquisition, the northern part? Or do you think, since Henry was the Defender of the Faith and all that, that the power of the Reformation would have taken over eventually anyway? What are your thoughts on that?

Adrienne: That is such a good question. And as a baptized and confirmed Lutheran, someone is saying that the Reformation would have happened anyway. I think…

Heather: I think Jonathan is also a baptized and confirmed Lutheran, so that’s fun. You’ve been like, the power of the Bible in the vernacular, and getting rid of the Popish stuff, and having a direct relationship with God and all of that was different. Overpower it.

Adrienne: Yeah, I think ultimately that would have won out. I mean, really, we give Anne and Henry so much credit for the Reformation, but really, they never changed. They were practicing Catholics, right? They only did away with the things that did not benefit them. I mean, Henry was crawling to the cross like two years before he died—well after he had broken from Rome.

And so, you know, really, the people surrounding Henry—I would say actually Thomas Cromwell did more for the Reformation than Henry did. I think what it was, is Henry had a problem. There were people around him that said, “Look what can go.” Right? But they were already deeply embedded. I mean, as we know, like Thomas Cranmer, he was deeply embedded in that already. You know, and it was the Boleyns who said, “Well actually, yeah, we are our friend.”

Heather: So that makes me wonder, like, if Henry hadn’t had that problem, would there have been a use for Thomas Cromwell? Would there—I mean, Thomas Wolsey wouldn’t have fallen, right? Because he wouldn’t have had to—so all of that. Would there have been a use for Cranmer? Would there be—who knows? It’s interesting to think about. So yeah.

Adrienne: I mean, I think—yeah, I think it ultimately would have happened, but I think that the players might have been a little bit different.

Heather: Gotcha. I like to think of that too, because I am an Episcopalian, so you know, it’s a little bit the same. Go Protestant. Yes. Team Bible in English. So, all right, I guess I just want to ask you about what she accomplished as queen and then, I guess, just her downfall. We can talk a little bit about that and how it changed England—and the idea that a queen could be killed—and what that did to England, if anything. And then we can wrap up with that. So tell me a little bit about her reign as queen.

Adrienne: Yeah, I mean, for being a queen consort, she actually had quite a lot of influence on Henry, particularly in the early days, before she was actually queen. You know, because really, she was not a queen, but she was in that role for longer than she actually was queen in the role.

So for me, I have a hard time separating the two, because in many ways, she was already wielding that power. And I think that she brought in a lot—like you said, with the Reformation and stuff like that. She brought in a lot of the literature and the players. I mean, she and George were bringing in literature from Protestants on the continent. And we know this because some of it still exists and is in the British Library, because it was confiscated from them.

They kind of had a tendency to know the right people. They knew the right people. And I want to say that they were very good at sizing up how people—like, how a person could help them best.

And I don’t say that in a selfish way—not like help them selfishly—but what they could get the best from a person. I think Anne was good at putting people, kind of influencing them into these roles of where they should be in the court. I think that she and her dad and her brother had a huge hand in that.

And she also—I think she sort of could—I’m trying to figure out how to phrase it, because Anne wasn’t a feminist. And I think there’s really a draw to want to call her that, but she wasn’t. But she did elevate women in many ways that she could. You know, she really was known for taking care of her women.

And I’m not talking about the nobles who attended on her. I’m talking about her gentlewomen, her maids who worked with her on a daily basis. She could be very, very generous to them. She helped with education, helped fund education, and she did a lot of things that were in the realm of what we would consider feminism today. But she was also a huge part of the patriarchy in that role too.

Heather: I have such an issue when people put those modern—well, we’ve talked about this before, haven’t we?—talked about these modern terminologies on people who wouldn’t have understood them. It’s not—I don’t know. It’s kind of like if, in 500 years, there’s some movement of some type, something we can’t even imagine right now because we haven’t thought about it.

And in 500 years they go back and say, “Oh, well Adrienne, she was clearly”—like “Read Adrienne’s book. She was clearly a WSA bus fusha,” or something. I don’t know.

Adrienne: Right.

Heather: Yeah. And it’s just kind of like—it bugs me to put that on people because I don’t think it’s fair to assign that.

Adrienne: Right. And it’s a completely different thing. A feminist today is not the same as what a feminist back then would have been. In fact, there was not really any possible way for someone to truly be a feminist in that world.

Heather: Yeah, and it changes. Feminism today is different than feminism in the 1930s, and different again from feminism during the suffragette era. It’s all different, right? I don’t know. So just to go back and say Anne was a feminist—

Adrienne: Yeah, I don’t like that either. We also have to consider the fact that these labels—even if she was a feminist—do not make her perfect. It does not mean that she maintained this perfect ideal. That’s one of the things about Anne—she truly is a gray character.

She did some really dumb things. Not because she was dumb—she was incredibly intelligent and clever—but she was human, right? And sometimes we do things that are illogical or rash or impulsive or whatever.

We always want to make her the saint or the sinner, but really it’s somewhere in the middle. Because yes, she did do a lot for women, but at the same time, she wasn’t doing anything that was outside the realm of what she should have been doing as queen.

Heather: Katherine of Aragon did a lot for women too, being like a warrior queen who wanted to go lead a battle in the Battle of Flodden and all of that. That was a really big step for women too. So again, pitting people against each other—anyway, I will now skip my soapbox.

Adrienne: Okay. I’m almost hesitant to say it because I’m nervous about the Anne Boleyn warriors coming for me, and this is going to be a controversial take. I think the reality is that Katherine had more accomplishments—things she did on her own, right?

But the accomplishments that we attribute to Anne are, one, often colored by one, our more modern thinking, and two, tied to the fact that we give her credit for a significant part of the Reformation that was actually being done by other people. And that’s not to say I don’t think Anne accomplished things, because I do. But they weren’t really outside the prescribed notions of what a queen should be doing.

So if we were to just look at it and ask, “Who was more accomplished, Katherine or Anne?” Well, it’s really easy to say Katherine, right? Because of Flodden, because she was pregnant, because she did all of those things.

Anne doesn’t really have that. But that does not mean that she didn’t accomplish things. Because she did. She elevated voices, she brought in more knowledge. She had invisible hands in things, but she wasn’t doing them alone. It was a groundswell that she was a big part of.

Heather: I’m excited to see if there are any Anne Boleyn warriors who get mad at this. I’m here for it. Actually, no, I won’t. I don’t read comments.

Adrienne: Me, I love Anne. It’s so funny because I came into this starting out with Anne, right? She was my entry into the world of the Tudors. And my perception of her has changed a lot as my research horizons have expanded. And I started to look outside of the Anne sphere. Because there is a lot more to Tudor history than just Anne.

Heather: There is, yeah. And we’ve just spent a lot of time talking about her because she is still important, obviously. But there is a lot more than just Anne. There were other people doing other things. Mind blown.

Anyway, you’ve been so generous. I want you to tell people where they can find you, all of the cool things that you’re up to, all of the amazing stuff, how they can buy your books, all of that kind of stuff.

Adrienne: Well, I recently, well not recently, a couple of months ago, deactivated Facebook because I just needed to be done. So I’m not really on Facebook anymore, but I am on Instagram. I have a TikTok, and mostly what I post are just funny videos of my cat.

But I’ve started to try to branch out, and I’m learning that medium a lot more. Let’s see. Oh, and I also have a website. You can find me at Adrienne-dillard.com, because Adrienne-dillard.com was already taken. Let’s see. You can find my books on Amazon. You can find them all on barnesandnoble.com. You can buy them from the Apple Store, wherever you get your books.

I’m working on a couple of different things right now. I’m continuing to research George Boleyn and his book, so I will be going back to the British Library next year to do some more research on his book The Torments of Marriage. I’m working on that.

I’m also working on a contemporary novel, and it’s called Project Archer. It’s sort of an autobiography, but it’s part true and part false. So there’s going to be a lot of my experiences in there, but it’s going to be a fictional story. Yeah, so that’s kind of interesting and new. I’ve almost got two chapters written, so I’m working on that.

And then, of course, I’m still researching my book on the Knollys sisters. I’m writing about Elizabeth and Lettice Knollys, and it’ll be called The Sisters Knollys. It’ll kind of center on Lettice and her relationship with Elizabeth, the Queen, and also Elizabeth Knollys’ relationship with the Queen, because they had very different relationships with her.

So it’ll be kind of fun because you’ll get to see a young Queen Elizabeth through the eyes of two of her closest relatives who had very different perspectives of her. And then there’s that kind of classic sister tussle.

Heather: Guys, I just love you so much. I need more Adrienne Dillard in my life. That’s just all I can say. You’re just such a joy. You’re just such a bright light of, like, I don’t know. You just are this light of joy, and I just love it. Thank you.