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Book Club Q&A: Roseanne Montillo


Interview and Book Club Review by Law&Crime’s Stefanie Doucette

Roseanne Montillo is the author of Deliberate Cruelty: Truman Capote, the Millionaire’s Wife and the Murder of the Century. Her book chronicles the murder of wealthy banking heir Billy Woodward at the hands of his wife, Ann, in 1955. Before Montillo, the case also fascinated Truman Capote, who made an ill-fated attempt to write about it in his New York society exposé, Answered Prayers. Montillo writes an exciting blend of midcentury New York City history and the true crime story at the center of it all.

Stefanie Doucette (SD): As a New Yorker, I was so shocked that I had never heard about this case before. It sounds like it was such a big case at the time, but doesn’t really get talked about that much anymore. How did it make its way onto your radar?

Roseanne Montillo (RM): Well, I’m a fan of Truman Capote, as I think a lot of people are. And he’s most famous for his other book In Cold Blood. So I think when people think of him, they think of him as, you know, the big writer who got his nonfiction start through that. But really he became famous for his other book, Answered Prayers. And I think a lot of people don’t really know that he was sort of a fan of these cases. So, when I read in some biographies and articles that he was also somewhat involved — not as deeply as he was in the In Cold Blood case, but at least sort of involved — in the Woodward case, I had the same reaction you did. I didn’t really know as much as maybe I should have. So, I became really interested, as well.

It seemed like it was something right up his alley, because it happened in New York. It was really kind of glittery and I wouldn’t say fun, but, you know, it was kind of something in his milieu. It was something in his backyard. It was something that he was really involved in because it was about upper class people. It was really something that took the country by storm. And it was a couple that was wealthy. Billy Woodward came from a very well known family. And here you have this woman who came, I wouldn’t say from nothing, but she was a woman who came from, well, a poor background. And suddenly you have this contrast. And characters who were involved in a murder. And a writer who wants to write or at least use your case to make a point in a story. So, I became fascinated with the piece and sort of the parallel lives between Truman Capote and Ann Woodward. I mean, they were similar in many respects.

SD: I really liked in the book when you drew those comparisons. What are some of the main similarities between Ann and Truman that struck you?

RM: Oh, well, they both came from, I don’t like to use the word poor, but they came from very humble backgrounds. Their mothers were sort of the kind of people who worked very, very hard, but they wanted a better life for themselves. At the risk of sounding harsh, they put their children on the back burner a little bit to try and make a living for themselves. Which is not unusual, a lot of people do that. But they weren’t the best mothers that they could have been, especially Truman Capote’s. Both Ann and Truman worked really, really, really hard to make a name for themselves in New York society. So they could have been friends. I found that both of them could have been very good friends and potentially could have used each other. They could have shared stories about their beginnings and how they made it in New York, and how they came upon having this newfound place. Instead, they seemed to be very hostile towards each other. Especially, I don’t want to say mistreatment, but they really didn’t like one another at all. And there was something that sort of, I don’t know, made them enemies. And it wasn’t just the idea that Ann was very spiteful towards Truman and what she said when they met. But there had to be something more as to why they didn’t like one another. I found it very curious that although their backgrounds were similar, they couldn’t understand one another.

SD: It was so interesting because you’d think she would be a perfect candidate to have been one of his famous “swans,” and yet they just absolutely hated each other…

RM: They did. He used to say that she was a fake and she couldn’t be part of his group, but the other women were not much better. You know, they were also self-made “swans.” They had backgrounds. Maybe they had married for money and not necessarily for love. My personal belief is that they had skeletons in their closets just as Ann did. So, if you were to dig even deeper than I did, they deserve a book of their own, each and every one of them.

SD: From a writer’s standpoint, what do you think of Answered Prayers? Do you think it deserved to be such a big flop, or do you think there was some potential in it to be the big, influential novel Capote dreamt of it becoming?

RM: You know, he had big plans for Answered Prayers. He had huge plans. I don’t know if you read the book that Random House eventually put out and the short stories. I mean, they were just selected pieces of what he had already published and the whole book was never really found. Truman Capote had huge, huge plans for that book. I’m not really sure that he managed to complete the whole book. It seemed like his plan was to reach something like eight or nine hundred pages and eventually went down to six and eventually went down to three hundred. He was already very tired.

I hate to say it, but I think In Cold Blood drained him a little bit. I’m not sure if he was drained because the experience was such a difficult one and the subject was so difficult — or because he became so successful and that just allowed him to have everything that he desired. And I think he took advantage of that. He became part of the in-crowd. He was partying a lot. He was drinking a lot. He was doing a lot of drugs. And I think he took advantage of that. I think his creative juices kind of went a little bit by the wayside. Which is shameful.

I mean, In Cold Blood was sort of his downfall. It was the height of his career and also, I think, the end of his career in a roundabout way. Answered Prayers, he wanted it to bookend his career. And I’m not sure that there really was ever a complete manuscript. I think if there was, someone was bound to find more pages. Unless someone has it stashed somewhere. But his friends, his lovers, his editor, Joe Fox, looked everywhere and in his house, in his apartment.

SD: Oh, wow, I didn’t realize that there was this huge hunt for the manuscript…

RM: He had a house in Long Island where he kept a lot of his material. Nothing was found there. Nothing related to Answered Prayers. Nothing was found in his apartment. He said he stashed it in a mailbox in a bus depot, but I don’t know.

SD: Deliberate Cruelty is a really unique true crime book. It blends the main story of the murder so well with all this literary history. What do you think it is about true crime that’s such a fit with these other two topics — literature and history?

RM: I think true crime now has, I don’t know, taken over literature. People are fascinated by true crime. I’m not sure what it is or what it says about us, which is a little bit disturbing, I have to be quite honest with you. But, I think there is a difference between like, oh boy, crime and this sort of a blend between literary crime. I think sometimes true crime has a way of blending into literature, and it has sort of in this book. I tried to do that. And kind of give it a little bit of a less, I don’t want to say bloody feel, but yeah. I’m not as attracted to those kinds of books that show really true violence.

SD: I think my favorite parts of the book were all the historical sections, about Old New York and the Cafe Society scene. Our office is actually just a few blocks away from where the El Morocco club was, so I really wanted to run down there and check out the remnants of it while reading. Is this a time in history that you’re particularly interested in?

RM: I do. I love history, as you probably noticed in the book. So, anything that’s related to history and, you know, literature, the blending of it. And I love New York. So of course, anything that takes me there, it’s just fun for me to do that.

SD: I haven’t had the pleasure of reading your other books, but I know that you’ve written a lot about other kinds of female characters and influential women in history. How does this story, and Anne Woodward in particular, fit in line with those other works? Or is she just a totally different type of subject for you?

RM: Well, Ann is the kind of woman, I think, that you can either feel very sorry for or the kind of woman that you probably would hate. I think she’s the kind of woman that, even though she did what she did, I think before you judge her, you have to know her to make a decision. And I think a lot of people have come up to me and said, “Why would you want to write about a woman who killed her husband?” Well, I think before you jump to that conclusion, I think for me, it’s always interesting to find out what prompted her to do that.

I’m not the type of person who just makes up her mind right away and says, well, she’s guilty or innocent. I want to know what led her to do that. So, I want to know where she came from. I want to know what kind of person she was when she was younger. What her dreams were that she desired. And, you know, whether or not she was abused or whether or not it was in self-defense or whether she even did it on purpose or it was just, you know, it might have been an accident. And then you make up your mind.

What I think about Ann could be completely different than what you think about her. And I write about women because in many books, they just write about men. And I think a lot of the women I write about have never been written about before. I wrote about a girl who was an Olympic champion and nobody even knew about her. And if you look at all the books about the Olympics, she’s not even mentioned. She won two Olympic gold medals when she was younger. And I have a new book coming out for middle readers and all of them are about female doctors and nurses. These women have never been mentioned before. It’s difficult for women to have a voice. Whether they were what we call good women or whether they were just a little different, you know? It’s difficult for women to have a voice.

SD: One thing that really stuck out to me about your book is how well researched it was and how you really seem to know these main players inside and out. Their voices did come across as very vivid. But in the acknowledgments, you mention that there were some pretty big research obstacles during the pandemic. What was your research process like and how did you go about even getting all of this information?

RM: It was difficult, I have to say. This was one of those books that was slightly different from the others because I sold a proposal in the late fall of 2019 and then the pandemic hit. So, I usually tend to go places and visit archives and libraries and I just need to be where these things happened. But as soon as the proposals were sold, it just so happened that the system shut down. But, you know, librarians never stopped working. I used to work in libraries myself many years ago. So, I find that librarians are very dedicated to their jobs. So, I was able to get in touch with many of them through emails and Instagram and LinkedIn. So, a lot of my work happened remotely. But luckily I got what I needed and I was able to get all these packages and boxes of materials into my home. It was a little different, but luckily I got everything I needed sent to me and emailed to me and eventually when everything opened up, I was able to go where I needed to go.

SD: And you mentioned a lot in the book how Capote had such a strict and methodical approach to writing. Do you relate to that at all, or do you just have a completely different style?

RM: Oh, no, I’m pretty disciplined. I have to tell you, I get up incredibly early in the morning. I don’t sleep very much, so I’m up even before dawn. I drink a lot of pots of coffee. And I write every day. It’s not just a passion, I mean it’s also a job. I read every day and I write every day. A lot of people complain about writer’s block. I have to tell you, I try to unblock myself as much as possible. I always have more than one project going on at the same time. So if this one’s stalled, I have five more that I can go to. They take so long to finish that you have to have more than one thing going on. You have to be passionate about what you do. And you know, the research takes so long. You have to be methodical and disciplined and you have to treat it not just as a passion, but very much like a job.

SD: So last question just for fun. What are you reading right now?

RM: What am I reading right now? I’m reading a book about Italian truffle hunting.

SD: Oh, that sounds so interesting. I don’t know anything about Italian truffle hunting.

RM: I don’t either. My sister found an article about competing truffle hunters in Italy who are fighting over a piece of land. I thought, Oh, wow. You know, and I don’t know why, it’s not like there is a book there that I’m writing about. But I thought it sounded fun.Once in a while you need something outside your expertise. And it’s a good book.

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