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Kate Winkler Dawson
I'm Kate Winkler Dawson. I'm a journalist who spent the last 25 years writing about true crime.
Paul Holes
And I'm Paul Holes, a retired cold case investigator who's worked some of America's most complicated cases and solved them.
Kate Winkler Dawson
Each week, I present Paul with one of history's most compelling true crimes.
Paul Holes
And I weigh in.
Narrator/Analyst
Using modern forensic techniques to bring new
Paul Holes
insights to old mysteries.
Kate Winkler Dawson
Together, using our individual expertise, we're examining historical true crime cases through a 21st century lens.
Paul Holes
Some are solved and some are cold. Very cold.
Kate Winkler Dawson
This is buried bones.
Paul Holes
Hey, Kate. How are you?
Kate Winkler Dawson
I'm well, Paul. How about you? Have you been thinking about the case?
Paul Holes
Of course I have.
Kate Winkler Dawson
Poor Billy Woodward. I know, I know. So this case has been for us about is this an accident or is this murder? And I feel like we have kind of contradictory evidence, but I'm not quite sure. Where do you think we stand? Now, I know you've been thinking about it this week.
Paul Holes
Yeah. We don't have all the information yet to make that determination. And these cases can be difficult because sometimes, you know, the evidence could support either theory. And that's, that's where I'm interested to see where this goes as the case unfolds. Because right now I think there's some inconsistencies in Ann's initial statement. However, there's some aspects where, you know, it appears that how she said, you know, the shooting went down, killing Billy, you know, could be possible based on what she said. So I, I'm wanting answers. You know, this is, you know, what I used to do during aspects of my job is to try to look at physical evidence to answer accidental or homicide. You know, it's funny. Use the term murder. I never use the term murder.
Kate Winkler Dawson
I've been using the term murder for four years with you, Paul.
Paul Holes
No, well, I, you know, because I Just as I am in the true crime space. My role was, you know, working homicides. You know, I'm waiting for the pathologist to rule was, is it homicide or accidental or natural, et cetera. We have homicide investigators, we don't have murder investigators. Murder, at least in California, is a legal term. It isn't murder until a DA charges murder. It's a homicide up to that point. That's my perspective. It's my little mini rant, if you will. But you can use murder. I'll accept it.
Kate Winkler Dawson
That's good, because I'm probably not going to stop using murder. But that is a good explanation. Let me do a very quick summary of this case. So it's 1955. We have a very, very wealthy couple, the Wood, Billy and Anne. They leave their estate. They have two kids, two boys. One is 8 and one is 11. I don't think I mentioned that the last time. The boys are asleep in the family room when Anne and Billy leave. They go to a really ritzy party with the former king and his wife. They come back and everybody in the neighborhood is scared, essentially in this area of Long Island. Everyone in this area of Long island is very wary of intruders. There's robberies. And then Billy has been afraid that there's a squatter that's been in their garage. And so there's a lot of mischief around. They check the house, nothing seems amiss. They go to sleep in separate bedrooms, which isn't unusual. And then Ann says that she hears something, she thinks on the roof. Then she says there are shadows bouncing off the walls in her bedroom. She grabs her shotgun, which is in a chair next to her. That also doesn't seem unusual. She's a hunter. And especially if everybody's freaked out Billy had a couple of gun, that wouldn't be unusual. But what is unusual is she picks up the gun, she goes into the hallway, she sees a dark, shadowy figure near her husband's bedroom door. She shoots twice and Billy is dead with no clothes on. Halfway in his bedroom, halfway out in the hallway. Lot of pooling blood. One pellet from this shotgun, apparently, according to the medical examiner, kills him, goes into the brain. And then there are, I think, three more pellets in his skull, but his face has been hit really hard with pellets in his head. And then I think I remember correctly that the spray was about a 2 foot long spray right against the back wall of his bedroom. From these two shots?
Paul Holes
Yeah.
Kate Winkler Dawson
Number one, does that sound all right? And number two, what was contradictory from what you remember that she says versus what maybe the evidence could be telling us now.
Paul Holes
Yeah, no, I think you're spot on. The one thing that is a big piece of evidence that needs to be addressed is her initial statement is that there is a shotgun blast through the door mechanism into Billy's room. At least in the photograph that you showed me, I am not seeing any damage to the inside of that door. And from a shotgun blast from a 12 gauge shotgun, even with birdshot, it's going to do some significant damage that I would expect to see even on the inside of the door. So that's one of the, the, you know, pieces of the puzzle that I'm hoping to get some clarification on, whether it be through, you know, more details on the physical evidence or through the investigation itself. The two foot spread pattern on the back wall, you know, is not going to be accurate to the distance the shooter was from Billy because those pellets flew a longer distance after the initial impact with Billy. So these just happened to be pellets that missed him. Just because the way pellets spread as they go downra and so it's more of the spread on Billy himself and the injuries, the impact with the shotgun wads, you know, that's what's kind of more indicative that we're dealing with, you know, an intermediate range shot. And again, this is, you know, just educated guessing, but somewhere, you know, 5 to 15ft away, it's not, this is not a close range shot. If it had been and Billy's face was impacted, you know, on the right side, half of his face would be gone. You know, shotguns are devastating weapons at close range.
Kate Winkler Dawson
Okay, so you know, I had given you details that he had a torn ear and his cheek was ripped up, but still, that still doesn't say close range, right? Because a 12 gauge shotgun, as you said, would have just destroyed his face
Paul Holes
at a close range. Yes, for sure. You know, and then basically a contact shot from a shotgun causes the head to explode. So it's a devastating weapon.
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Paul Holes
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Yeah, okay. You know, I start thinking about this International Women's Day and you know, of course it brings up my mom and my wife and I've not been the easiest son or husband over time and so I can be a source of a lot of stress. And for them to have shown the strength dealing with me, I most certainly probably have driven both to therapy, come to think of it. So that's where I think, you know, a service like Better Help is something that is invaluable. It's so convenient.
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Kate Winkler Dawson
so let's talk about what becomes of big interest to the people in the media because now this is out, you know, you and I really have been talking about, I would say a timeframe from 1am when they get home until 11 or 12pm the next day when the medical examiner comes out with his findings. I don't think we've even gotten past that. So now we need to talk about the churn that happens of gossip. Things that will affect this investigation, but also sort of more facts that come out that could inform us of what may or may not have happened. Because I know, you know, we could talk about inconsistencies or consistencies. She fired far away, but still, she certainly could have fired on purpose and killed him. Or someone else could have fired on purpose and killed him. And at the same time, why would that have happened? And will there be suspicion that turns on her? So let me talk about really the relationship because that's what people home in on here. So Ann is questioned by police, but only after she goes to the hospital and is sedated and sort of sequestered on her own for a couple of days under orders of her doctor because she's so hysterical or she doesn't want to talk to police. So New York society is whispering about this. They did not have the greatest marriage, Billy Woodward and his wife. So people, and I think friends and family had thought they were heading for a divorce at this point anyway. Which I know I said, you know, people can sleep in separate bedrooms. And that was not abnormal in the 1950s. But this might have been because they didn't want to sleep in the same bedroom. But they did go to parties together. But that could have been keeping up appearances, right?
Paul Holes
Absolutely.
Kate Winkler Dawson
Okay, so let me just tell you about these people, because that is part of this narrative here. So totally mismatched couple. It sounds like Billie came from, you know, this banking family. Millions and millions of dollars. Ann came from a very humble family from Pittsburgh, Kansas. She came to New York in the 1930s looking for work, and she found it as a model. She was a radio actress, and eventually she became a showgirl at this swanky place called Fifi's Monte Carlo Nightclub in Manhattan. You know, this is a showgirl, entertainer, performer, lots of wealthy men there. And Ann actually first met Billy through his father, William Sr. The banker. And William Sr. Met Ann at that nightclub. So he's the one that spots her first. There had been speculations all over the place. One speculation will be that Ann and William Sr. Were involved either beforehand or during the marriage. The other speculation has been that William Sr. Sat Billy down and said, there is a very attractive, nice woman at this club that I've met. I would like you to get involved with her because people are spreading rumors that you're gay, and we can't have that.
Paul Holes
Okay.
Kate Winkler Dawson
There's a lot happening. You want to tell. I know. You have a look on your face like there's a lot already. I haven't even gotten halfway through it.
Paul Holes
Well, just, you know, Senior possibly having a relationship with Ann and ends up with Junior. Senior maybe continuing a relationship with Anne even though she's married to his son. There's sort of an ew factor that's like a. You know, that's an unusual arrangement. And then, of course, in 1955, you know, if there's rumors of Billy being gay, that's going to be something that could hurt Senior's reputation, the family's reputation, you know, so I could see where there could be family pressure, you know, for Ann and Junior, Billy Junior, to, you know, get married. But then under that dynamic where there isn't the sexual attraction, was Senior still dating Ann, even though she has this facade of a marriage to Billy? You know, so it's kind of a. Both of those initial things you said are in some ways, you know, unusual lovers triangles. And we know that those can go sideways.
Kate Winkler Dawson
Yeah. And I think, you know, of course, this is part of the gossip, and this would be denied by William Sr. And I don't know if how much of the gossip was that it was happening during the marriage. Definitely gossip that they had an affair. He said, I'd like you to get involved with my son, who, you know, William Woodward was very, very handsome in all of the photos I've seen. So this would not have been a stretch for Anne. I will say let's throw another complicated person into the mix. William Sr. Billy's mother, her name was Elsie Ogden Kreider. She cannot stand Ann. So Elsie comes from a very well to do family also. She was a descendant of John Adams and the niece of the president of the Union Pacific Railroad. Lots of money. And then she marries William Woodward and she has Billy with him. And so she has big, big dreams of Billy marrying into maybe the Royal Family or having just a different type of wife. A former showgirl who could have potentially had an affair with Elsie's husband was not the dream. So Elsie was incredibly hard on Ann. But Ann and Billy got married in 1943, and then they had the kids shortly after that. So, you know, the. In 44 and 47. In 1947, Billy filed for divorce and. And Ann said, hell no, and she refused to give him a divorce. And so that's when they both started having public affairs. And they were fighting in public one time, Ann shouted at Billy, why don't you just bring a man in our bed? That's what you want.
Paul Holes
Well, the toxicity in this relationship is not new. I mean, this is going back to before they were married. You know, the family pressures. You know, dad possibly was having sex with Ann prior to her marrying Billy. And then now Elsie is not liking the fact that Billy's going to marry Ann. You know, it's kind of maybe on the side, not relevant to the case, but I kind of question Senior and Elsie's relationship. And you know what that was like, you know, but obviously it's. There's a lot of family pressure contention at the very beginning. And then now you have Billy, you know, wanting to file for divorce really early on in. In the relationship, you know, and it's. And Anne is not Wanting that, which is interesting to me. It's okay. Why not? Especially if she's now starting to, you know, think, well, he might actually rather be with, with another man than, than with her, you know, is she looking out for her kids? You know, maybe, you know, it's, it's also, is there a length of marriage
Narrator/Analyst
that's needed for it to be considered
Paul Holes
a long term marriage?
Narrator/Analyst
So she fully qualifies for all the
Paul Holes
assets she possibly could have access to
Narrator/Analyst
from this very wealthy family that may
Paul Holes
be part of it.
Narrator/Analyst
You know, maybe he's pulling the trigger so fast where she gets aced out
Paul Holes
on, you know, a lot of financial
Narrator/Analyst
gains because it would be characterized as a short term marriage. You know, so post Billy's desire to divorce or filing for divorce. Now they're fighting all the time. Now there's all this domestic abuse. Neither one of them wants to be in this relationship, but they stay together until 1955. And now it's like, well, okay, so what happened? You know, Ann at least has admitted to shooting Billy and killing him, but what was the reason for her doing that if it wasn't accidental?
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Kate Winkler Dawson
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Kate Winkler Dawson
I think deceit is a big part of this relationship. You know, for the record, Billy's dad dies two years before he dies. So this just leaves the mom who is constantly sort of on top of this relationship and disapproving of it and being really difficult on Ann. So he has affairs. Ann very publicly denounces them and is very upset about it. Their fights play out in public and sometimes they come to blows. There's physical violence between them. And as recently as the night Billy was shot at that party with the former king of England, they argued about his airplane purchase, that helio courier craft thing of his, and that she thought it was strange that he went to
Sponsor Voice
her hometown to buy the plane.
Kate Winkler Dawson
She thinks he is trying to dig up dirt, which is what his friends confirm. And then, you know, you have to think, well, what's the dirt that she's covering up? And there were a couple of things that she lied about to Billy. One was that, you know, she said that she was an orphan. She wasn't. Her father was actually alive and he was a streetcar operator who had abandoned her and her mother when she was 8 years old. So she lied about that and she was concerned, it sounds like, that he was gonna find out by going back to Kansas, you know, that she had made up some stuff. Now, I mean, is that worse than both of them having an affair and she's screaming at him in public, why don't you just go bring a man into our bed? That's what you want. In some ways, I was thinking a self defense claim might be better for her because, you know, their acrimony was so explosive and especially if they were physical with each other.
Narrator/Analyst
Sure.
Kate Winkler Dawson
Would it be surprising, especially in 1955, for a woman to say, my husband finally did it, he exploded. And you know, I luckily was able to protect myself, assuming that, that things did not go the way she said they went.
Paul Holes
I mean, if she had decided to kill him, that probably with the, you know, relationship history, that possibly would have been a better way to go. She's painting it under the guise of the recent burglaries that had happened. The break ins in the neighborhood, you know, the squatter in their garage. That's why she pulled the trigger on the shadowy figure. You know, she. She was upset that he bought the helio airplane. I mean, he's going all the way out to her home city to dig up dirt. There must have been some rumors that were significant enough for him to go, I gotta go check this out.
Kate Winkler Dawson
You Know, and I was reading through her background when she came to New York in 1937. She had done things to reinvent herself. She tweaked her name a little bit. She got a nose job, but I didn't. There was nothing. That was a huge red flag. But you're right, if she is, it could have been just the mere idea that he was looking, that that's the level he would go to in a divorce. That scared her. Because then what would stop him from making up stuff or hiring somebody to make up stuff about her? You know, it could have just been even that fear, maybe not something she actually had done in Kansas.
Paul Holes
No, potentially. I just, you know, I. I kind of lean towards. She had something she was really concerned about, and it may be something we have no clue about today, you know, and it was never discovered by Billy or never discovered by, you know, the people he talked to or the people she knew.
Narrator/Analyst
But that.
Paul Holes
That timing seems significant. Okay, so, you know, this is where, you know, the relationship, Billy's actions, Anne's
Narrator/Analyst
actions, I really, you know, this is
Paul Holes
all seeming to be what I call churn. There is a lot of churn, you
Narrator/Analyst
know, where now you have this contentious marriage, and it just happens that Anne was the first one to act. This could easily have gone the other way.
Paul Holes
Right.
Narrator/Analyst
And I just think Ann is either protecting her reputation and.
Paul Holes
Or protecting what she potentially could gain
Narrator/Analyst
from a divorce from such a wealthy husband.
Kate Winkler Dawson
Yeah, absolutely. And. And I question whether it's Billy pushing to get custody of the two boys or if it's Elsie, his mother, pushing.
Narrator/Analyst
Sure.
Kate Winkler Dawson
I don't want to think ill of men in the 1950s, but it surprised me a little bit to read that this is somebody who was, you know, he was pursuing this. There's no mention of. Because she's going to take all my money. It's more of I do not want her to take my boys from me. And I could be totally wrong, but I do think Elsie had a lot involved with this, you know, with these two boys that she cared about, too, and her husband was gone.
Paul Holes
I think that's. That's a very good observation, and I. I would not undersell the death of Senior. Senior dies two years before Billy is killed. Senior most certainly has a will. You know, Elsie is the one that's probably going to be the primary beneficiary. But what else was distributed from Senior down to Junior, you know, where now Junior's assets are even that much more appealing to Ann.
Kate Winkler Dawson
Okay, well, listen to this, because this story gets really weird. I felt like we took a couple of left turns, but this is a left turn. And then around the corner. So they find a witness. The witness is a burglar.
Paul Holes
He breaks. He breaks into the Woodward house and he's sneaking around. All of a sudden hears a shotgun go off and he's like. Like what?
Kate Winkler Dawson
I mean, so let me tell you. Let me tell you what happens.
Paul Holes
Oh, good God.
Kate Winkler Dawson
Right. All these rumors are going around that Anne is this Ann is that she is still considered an outsider, even though she had been married to this man for 12 years and had two kids with him. So all of a sudden, New York society's turning on her and saying this must have been done on purpose. Especially with all of the rumors going around between him being gay and her, you know, having dirt dug up on her. What's going to happen next? And then, of course, everybody, we read about the fights that they had. Gosh, it's like it's so hard for
Sponsor Voice
me to get past the fact that
Kate Winkler Dawson
they were having these awful, vicious fights in public, Paul. And number one, they were still invited places. But number two, they still went places together. And that goes back to the manicured lawns. For me, it is a hundred percent appearances. They are both beautiful people. They have two gorgeous sons. And this facade, I guess even when it breaks down, you know, when they both get too drunk at the Vanderbilts, then you know, this is still important to them. It's amazing. Miserable.
Paul Holes
I would say it's important to them, as, you know, during the time that they're a couple, but it's important to them in their future because they're envisioning themselves being divorced and separate. And so they need to have allies.
Narrator/Analyst
Right?
Paul Holes
For both of them, they need to maintain relationships. So they are still in that, you know, that type of social circle.
Kate Winkler Dawson
Okay, here comes the prowler. So our witness is a prowler. He's 22, he's from Germany. His name is Paul Worths. He said, I've been burglarizing mansions in the neighborhood, including this property, the Woodward property. He said that a few days before the murder, he had broken into the six car garage. Remember, the property manager said the window was broken out of the garage. So he is also a squatter, Burglar and a squatter. But on the night of the shooting, he says he was over a half a mile from the estate. And that night he had broken into a local country club and taken food from a refrigerator. But he changes the story. He said after he hit that country club and took food out of the refrigerator. He went back to Sunken Orchard, the Woodward home. And then he says he broke into the pool house where he had been before he ate four frozen hot dog rolls. And that same night, when all the lights in the house went dark, which you have to presume is between 1am and 2am, Paul says he climbed this tree. And he enters the house through an open window, which enters onto the second floor hallway. Now, Billy and Ants, I told you before, was on the first floor. Right. He hears shotgun blasts. He freaks out. He runs back out and jumps through the window, climbs towards the roof, and he jumps off and he runs away. And investigators say to Paul, okay, burglar, squatter, why don't you reenact this? And so he goes and explains everything. He says, you know, this is the way I did it. And when they look outside of Anne's bedroom, there is a broken tree branch. And so they're saying, this is, as you like to say, churn. Maybe there is some churn there. Now you can react. But also there's that last photo in your packet that actually gives you a sketch of what Paul Worth says happened that night where he heard the shotgun blast. Now, he's not saying Ann did it. He's not, you know, he's not saying anything happened. It is placing him, by his own admission, at the scene.
Paul Holes
Well, this is definitely a different view of the house than the other part. So this is showing what appears to be a primary entrance into the house. And I don't know if this is the rear of the house or considered the front of the house, because it appears that there are, you know, there's a cobblestone drive where the police car and another vehicle are parked. And then you can see that this house is. Even though it's only showing part of this house, it's a significant house. This is a rambling large house. I'm surprised that Billy's bedroom window and Ann's bedroom window are right there, ground level, right by this main entrance.
Kate Winkler Dawson
Yep. Now, one note Paul, I want to make is that Paul has said, our burglar witness, that he has come to this house before because he liked to peep at Ann. And I think that the reason that this has become a big deal is because Ann had said, I heard somebody on the roof. I freaked out. I took a gun and I shot at the person who I thought had been on the roof. Now we've got a guy who says he's been on the roof. He was sitting there peeping at her. And they're Looking to see if they can find this physical evidence. Just wanted to explain.
Paul Holes
Yeah, well, you know, and I think that that's significant in terms of corroborating the reason Ann got up, you know, and now you have. You have Paul Worth saying, well, yeah, I was there, you know, so, you know, what a coincidence. But, you know, stranger things have happened in my experience, so this is not anything that I would even come close to dismissing. You know, one of the things about Paul Worth that stood out to me, you know, and we kind of talked about this when we first started talking about this case, is he is that burglar that is just prowling in this community. And, you know, he's running, he's needing food, and, you know, so this is a real deal. And these types of neighborhoods, you know, he's not going into, you know, houses where there's a lack of valuables. He's going to score every single time he breaks into any of these houses just because of the wealthy nature of this location. But the fact that he went into the Woodward house that night, knowing the family was home, he sees them turn off the lights.
Narrator/Analyst
This is what is an evolution of
Paul Holes
your typical evolution of your, like, your Fetishberg type of individual, you know, and you. When you mentioned that, you know, he admitted to peeping on Ann, I wasn't surprised at all. I was like, yeah, you know, burglars
Narrator/Analyst
that are financially motivated don't want to go into structures when people are there. They try to avoid that at all costs because their interest is the property, and they don't want to be confronted
Paul Holes
by, you know, the owners or the family.
Narrator/Analyst
And that's why you often see residential burglaries occurring during the day, because that's
Paul Holes
when people are at work and school.
Narrator/Analyst
And then you see commercial burglaries happen at night because all the employees are home, you know, asleep, you know, so that's. That's where. When. When he's at night and he's going in to the Woodward house, it's like, oh, okay, this. This guy's more than just a financially motivated burglar. And I'm not surprised at all. He was peeping. Now, of course, that. That elevates him as a potential suspect.
Kate Winkler Dawson
She's admitted to it.
Paul Holes
That's just it. You know, if. If she had not admitted, then I would think, yeah, the investigation probably would have really drilled down on Paul Worth, you know, and him just putting himself inside this residence at the time the shotgun goes off. I mean, that's. That. That is a significant statement. But I, you know, with, with Ann admitting shooting Billy, you know, I truly think Paul worth with what I know. I mean, he's, he's an ear witness. He doesn't see the shooting. You know, he just hears a shotgun go off. And I'm sure, you know, he, he probably got the hell out of that house as fast as possible, thinking that maybe that shotgun was aimed at him.
Kate Winkler Dawson
Now, let me tell you the rumors which would not shock me. So remember I told you that Paul the burglar had changed his story. When they initially interviewed him, he said he was a half mile away robbing a country club. Then two days later he changes his story and says, yeah, I did that. I ate the hot dog buns or whatever the hot dog rules. And then I came and decided this would be a good time to peep at Ann. And the fact that he changed his story made people raise their eyebrows. And it's because of this, Elsie Woodward was so concerned about her family's reputation that the thought is that Elsie really sat down and thought about it and said, what would be worse for my daughter in law who potentially murdered my son to walk away and maybe I get the boys or for her to be convicted and there be a massive murder scandal in our family. So the thought was that she paid off Paul the burglar to say that he was on the roof instead of his original story. Now, he had peeped before for sure, but I don't know what we know about these people. What do you think makes the most sense?
Paul Holes
Yeah, that's, you know, what I'm trying to do is I'm trying to determine how that changes the course of the investigation. Let's say you're falsely inserting this burglar into the residence at the time of the shooting. He most certainly is going to be eyeballed very, very closely. If the idea is, is that he is the shooter, then it's also going to be he's going to have to offer up specific details that match up with how the shooting went down. Yeah, you know, and so that's, that's how the investigators are going to have to sit him down. If he's cooperative and he's providing details, they just have to be able to drill down and see is he factual about how the shooting went down or not.
Kate Winkler Dawson
It sounded that they were trying to retrofit him into this whole scenario, like they knew he was the Oyster Bay prowler. He had said when police interrogated him, yes, I've been on their property before. And whether or Not Ann was lying about it. She said she heard, you know, steps on the rooftop and that's what triggered her to pick up the gun. And so it seems a little complicated to then have Elsie send somebody to find this guy who is probably in jail, pay him off and say, well, you've said you've been there in the past. Why don't you just say you were? I don't know, it just didn't. Doesn't make a lot of sense. But Elsie is very concerned about a scandal.
Paul Holes
I know that it is a big stretch to think that Elsie would be able to identify Paul Worth as the person that's been prowling in this area, especially if he has not been arrested for a similar crime in that area, or law enforcement is unaware that he's doing that. That the, the fact that Paul Worth initially says he was like six blocks away, right?
Kate Winkler Dawson
Yeah, he said he was a half a mile away. But they do, they do suspect and they, and they do get out of him that he was the Oyster Bay Cove prowler. So they track him down and start asking, who have you been prowling? And then the Woodwards were one of them. And so that's how they start to make that connection.
Paul Holes
Okay.
Narrator/Analyst
You know, but his initial statement, this
Paul Holes
is a guy doing, you know, he's doing property crimes.
Narrator/Analyst
If he recognized that he was in
Paul Holes
the homicide house at the time the
Narrator/Analyst
homicide occurred, he's not going to freely admit that.
Paul Holes
Right.
Narrator/Analyst
And, and so he's, he's, you know, basically telling investigators, oh, no, I wasn't there.
Kate Winkler Dawson
Okay.
Narrator/Analyst
Because, because I think, you know, this is just, just, you know, your typical self preservation lie. And so not, I'm not dismissing outright the fact that Elsie could have potentially worked through intermediaries in order to, you know, influence him to at least complicate the investigation. But I just, I just don't see where, you know, if the investigators are doing their job, you know, it probably would become very clear pretty quickly that he wasn't just in the house, but he was the actual shooter. It just, it doesn't negate Ann's admission, the use of Ann's shotgun, you know, everything else from the victimology. So that's, I think where I, right now I'm, I'm sitting on pretty firmly on the, the side that he was a witness.
Kate Winkler Dawson
Yeah.
Narrator/Analyst
And it was just a coincidental thing. He was in the house at the time the shotgun went out.
Kate Winkler Dawson
But does it add to her credibility? Because she, she does hear his footsteps. She freaks out, she picks up the Gun. Does this now sound more like an accident rather than a spiteful wife who's scared her husband is gonna just rip apart her life?
Paul Holes
I think it does.
Kate Winkler Dawson
Okay.
Paul Holes
It does not determine the difference between accident and homicide. However, let's say Ann intentionally shoots Billy. But now she's making it as an accident and she's lying about it. People weave true things into their lies. And she may have heard something up on the roof. And so as she's telling what, you know, this lie about what happened, she's building that in because she knows she did hear something. But it's also can be argued the other way. She heard something, she got up. She thought there was a prowler inside the house and shot him. It's just, again, the discrepancies in her initial statements, I do have concerns with.
Kate Winkler Dawson
Yeah. And I think, you know, so this goes to a grand jury, there's a lot of testimony and the contention of some of the witnesses. Many of the witnesses were they heard Paul on the roof. Ann grabs a gun, and Billy jumps up from bed, even though he doesn't have his weapons with him, totally naked. And this is where all of this happens. I mean, I don't think you're gonna be surprised at all to know they did not indict her. It was unanimous. And, you know, they were all pretty convinced that this was, you know, an accident and just a terrible coincidence that they were having an absolutely awful, toxic relationship while this was happening. So I don't know if you wanna wrap up the crime part of this, because the aftermath is about as interesting as the prelude to all of this.
Paul Holes
You know, the lack of the indictment is not surprising in this case. You know, and I've worked cases with, you know, that were husband reports wife committed suicide, or girlfriend reports suicide. And there's evidence to suggest, no, that's not looking like a suicide. And yet there is not enough to be able to determine either for sure or to convince a prosecutor to file charges. Because the prosecutor is looking downstream. Can I convince 12 people in the jury?
Narrator/Analyst
Right.
Kate Winkler Dawson
Right.
Paul Holes
It's just not strong enough of a case. You know, I think the circumstantial evidence with Ann, the victimology, the marital history, you know, there's a lot of things that point to possibly, you know, this argument at the party, she was done, you know, and. And there's a financial component to that. It's unclear. But when, what. And how she would get the assets for the Woodward estate would be significant. And so there's a lot of motive for her to Possibly take Billy out to preserve that down the road. It's also possible that what Ann said, she heard something on the roof. She comes out, she sees a shadowy figure, thinks it's a stranger inside the house, shoots and kills a stranger, then recognizes that it's Billy. And that some of the initial statements that are inconsistent with the crime scene itself may just be a result of the dynamics, the psychological and emotional trauma that she most certainly would have experienced under that type of scenario. And so it really is a. A tough case to come down with a definitive answer. And so I would say I kind of lean towards Ann purposefully killing Billy, but I can't conclude that, not with the state of the evidence and the circumstantial stuff. It's just. It is a complicated case on that front.
Kate Winkler Dawson
It is. And the aftermath is complicated too. So Anne is not indicted. She is shunned by New York society. And Elsie makes a statement. She says, and we know how Elsie feels about Ann. She says, I know Ann loved Billy very much. And the shooting could be nothing but an accident. And then Ann and the boys move in with Elsie. And then Elsie sends the boys almost immediately to a boarding school in Switzerland. And this is all to protect the Woodward name. I mean, these people, you know, but
Paul Holes
that's also part of the dynamic of this, you know, these powerful elitist types of individuals, is that there's. There's a different perspective, you know, in term on how they approach their decision making because of their status, preserving their status, their reputation, their allies, their, you know, their wealth, health. That, you know, probably most people that are in our society, they don't think about it and they don't worry about that kind of thing. You know, I've. I've been involved in some cases with some significantly wealthy individuals, but the circumstances
Narrator/Analyst
weren't such like this to where there's any concern about reputation.
Paul Holes
You know, they weren't at the level
Narrator/Analyst
of the Woodwards, for sure.
Kate Winkler Dawson
Well, let me tell you what happens. There's a lot that happens, and I'll try to shorthand it. So the boys go to Switzerland, and eventually Anne goes to Switzerland, too, to be around them. In Switzerland, she has a fateful encounter with a man named Truman Capote, who I know, you know, In Cold Blood, which I think a lot of people, you know, associate with sort of the first modern true crime book. I think that's true. I thought his writing is amazing. In Cold Blood. But a lot of this is not accurate. And the victim's families hated the way that he portrayed the Clutters in the book. So Truman Capote could be nasty. And what he did was he was looking for another true crime story around 1959. And cold blood had been, of course, a massive hit. And. And Billy Woodward's death, which involved, you know, high society, sex, gossip, all the stuff that Capote would have loved appeared perfect for him. So after he met her, he started referring to Ann Woodward as Mrs. Bang Bang, which caught on. And he named a character, clearly based a character in a book that he had written as a follow up. And it was a tremendous amount of public shaming for her, especially with Capote, because he was so in with all the high society gossips. And so this became, you know, a really, really big deal. It just decimated her character. And Capote really used her for better or for worse, whatever we think of whatever Anne did or what that relationship was like, he really used her as a way to elevate himself, but also just, I mean, wrestling her character. She was described as a murderess, the jazzy little carrot top killer. And the high society ladies said that she was brought up in some country slum. They called her inescapable white trash and a slut. And then, you know, among Capote's friends, they were talking about Billy, mocked as an anal oriented, Episcopalian, weird insult, but okay. And, you know, there was an excerpt from this book that Anne was based on that was so offensive that it ended up turning on Capote. So it kind of ruined that project for him. And it just becomes this unraveling of this family that goes on for several generations. In 1975, everybody's still alive after enduring years of gossip, a lot of it really spurred on by Capote. Ann takes her own life by taking cyanide. Elsie is still alive, and she says, well, that's that. She shot my son and Truman Capote murdered her. And so now I suppose we don't have to worry about that anymore. Elsie boy is something else. And then I would say in adulthood, things were very rough. Both of Anne's sons take their own lives, too. Wow. This is part of sensational true crime. And the reason that I appreciate this story so much is that to me, it is one of those stories. It's like the epitome of the disgustingness of what true crime can be, where you're taking someone's life, like what Capote did with Ann Woodward and turning it into this character and this narrative of when she's a real person and it just destroyed her is what it sounds like. I am not a fan of Truman Capote, in case anybody doesn't know. I just. I just. I did not like what he stood for. And so this is. This is the antithesis of what you and I try to do on this show, really is.
Paul Holes
Yeah. You know, I've. I've never read In Cold Blood.
Kate Winkler Dawson
The writing. I love the writing. I think the writing's great. It's just that he made up a lot of stuff.
Sponsor Voice
Stuff.
Kate Winkler Dawson
And the Clutter family said he was awful. The way he treated Mrs. Clutter. Yeah. And they really. And they, you know, I mean, they come. There was just a documentary out about it. They have come out and said this was not good. And I think Capote had a lot of regrets, too. But, I mean, he is definitely held up as one of the icons of true crime. And I'm not refuting that. I'm just saying look at your icons sometimes.
Sponsor Voice
Sure.
Paul Holes
Well, in many ways, it sounds like he. He was in, you know, lockstep barrel with the media at the time. How salacious the media was covering these types of cases, you know, and, you know, the salaciousness sells. Right? So, yeah, you know, especially hearing that there's not a lot of factual stuff or there's, you know, basically fiction in Capote's book. I mean, that just turns me off. I don't want to read something like that. You know, I go after, you know, content that is going to be informative about the case and not misleading.
Kate Winkler Dawson
That's why when I teach my true crime class at ut, that the very beginning, I've told you this before, the very beginning, I say, my goal is for you, by the end of this class to at least recognize what good content in this genre is. It doesn't mean you're going to listen to it or read it or pay any attention to it after this class. But I'm going to make you listen to it right now, and you're going to be able to recognize it later on. And, you know, I'm not perfect. You're not perfect. Everybody, everybody I know who is a high quality journalist or somebody who produces this content says things where people are like, wait, what? And the intent, though, with everything that we do, I think is always to be good to the victim, to be good to the survivors and the families, and to just educate people on things. And so this is that case when you have, you know, encounter somebody that has that name recognition where I just kind of go, God, that was gross. He's gross. That was gross. And I've read a lot of accounts of that. And so, you know, I'm not here to slam Truman Capote, but I am here to say that sometimes, you know, people who are in history and you just think are, you know, incredible, and we're so thankful for parts of it. Yes. But there were problems, and there always will be problems with true crime reporting, I think.
Paul Holes
Yeah. You know, and kind of getting back to the Woodward case, you know, I'd be curious, you know, if they actually documented Billy's body adequately. And good autopsy and everything else, you know, good photos of the crime scene. I mean, you know, I'd be wondering if I could spot something that could, you know, either kind of tip the scales, if you will, if Ann accidentally shot him or if it was intentional.
Kate Winkler Dawson
Yeah, it'd be interesting to know, I think, you know, I come back to Ann, of course, the boys who are totally innocent in this, the two sons who didn't hear a thing, by the way. I mean, every time people say, how could somebody not have heard anything? These are two boys with. I mean, they didn't hear a shotgun blast and two of them.
Paul Holes
Sure.
Kate Winkler Dawson
And the ruckus. And so really, though, if you look at Ann, there's some things wrong with their marriage, obviously, but we really don't know if anything. If she had done anything, whether she was a gold digger or any of that, you know, any of those things. That the way that her life turned because of a couple of people she was involved with, to me is just so sad, for sure.
Paul Holes
Well, Kate, this was an interesting case. Thank you.
Kate Winkler Dawson
I know you're ready to go. Usually you want to keep talking. You're like, I've got to stop talking about this flipping case. I know. Well, you know, there are cases that stick with you. And, you know, I think. I know most of our cases stick with you, but I'll have something fresh for you for sure.
Paul Holes
All right. As always, looking forward to it. Bye.
Kate Winkler Dawson
This has been and exactly right production.
Paul Holes
For our sources and show notes, go
Narrator/Analyst
to exactlyrightmedia.com buriedbones sources.
Kate Winkler Dawson
Our senior producer is Alexis Amorosi.
Paul Holes
Research by Alison Trouble and Kate Winkler Dawson.
Kate Winkler Dawson
Our mixing engineer is Ben Tolliday.
Narrator/Analyst
Our theme song is by Tom Breifogel.
Kate Winkler Dawson
Our artwork is by Vanessa Lilac.
Paul Holes
Executive produced by Karen Kilgariff, Georgia Hardstark and Danielle Kramer.
Kate Winkler Dawson
You can follow Big Buried Bones on Instagram and Facebook at buriedbonespod.
Narrator/Analyst
Kate's most recent book, all that is
Paul Holes
A Gilded Age Story of Murder and the Race to Decode the Criminal Mind, is available now.
Kate Winkler Dawson
And Paul's bestselling Memoir My Life Solving America's Cold Cases is also available now.
Paul Holes
Listen to Buried bones on the iHeartRadio app, Apple Podcasts or wherever you get your podcast.
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Podcast: Buried Bones
Hosts: Kate Winkler Dawson & Paul Holes
Date: March 18, 2026
Episode Focus: Continuing the examination of the 1955 shooting death of Billy Woodward, discussing evidence, family drama, the impact on society, and the enduring legacy of the case.
In the second half of their deep dive into the infamous Woodward shooting, journalist Kate Winkler Dawson and forensic investigator Paul Holes unravel the tangled web of social intrigue, marital strife, and forensic ambiguity surrounding the case. The episode transitions from the night of the shooting through the media frenzy, the complicated relationships inside the Woodward family, the surprising "prowler" witness, and the long-reaching consequences—including the devastating aftermath often overlooked in true crime storytelling.
(Starts ~04:26)
Summary of the Incident:
Discrepancies and Forensic Puzzles:
"Her initial statement is that there is a shotgun blast through the door... I'm not seeing any damage to the inside of that door." (08:20, Paul Holes)
Definitions Matter:
"It's not murder until a DA charges murder. It's a homicide up to that point." (05:39, Paul Holes)
(Starts ~15:22)
Marriage Under Scrutiny:
Society’s Whisper Network:
"Why don't you just bring a man in our bed? That's what you want." (21:18, Ann to Billy, recounted by Kate)
Possible Motives & Pressure Points:
(Starts ~33:08)
A New Twist:
Worth’s Changing Story:
Forensic Relevance:
"People weave true things into their lies. ... It can be argued the other way." (46:57–47:41, Paul Holes)
(Starts ~47:41)
No Indictment:
Societal Judgment & Ann’s Downfall:
(Starts ~52:03)
Public Shaming:
Multi-Generational Tragedy:
"She shot my son and Truman Capote murdered her. ... Now I suppose we don't have to worry about that anymore." (54:24, Elsie)
Critical Reflection on True Crime:
"To me, it is one of those stories... the epitome of the disgustingness of what true crime can be." (55:45, Kate)
"I'm not here to slam Truman Capote, but I am here to say that sometimes... people you think are incredible... there were problems." (57:05, Kate)
On language:
"Murder, at least in California, is a legal term. ... We have homicide investigators, we don't have murder investigators." (05:39, Paul Holes)
On physical evidence:
"From a shotgun blast from a 12-gauge shotgun, even with birdshot, it's going to do some significant damage." (08:20, Paul Holes)
On the toxic marriage:
"This is going back to before they were married... family pressures... Senior possibly was having sex with Ann prior to her marrying Billy. ... There's a lot of family pressure." (21:32, Paul Holes)
On the role of the ‘prowler’:
"He has come to this house before because he liked to peep at Ann." (37:48, Kate)
"Burglars that are financially motivated don't want to go into structures when people are there... It's more than just property for him." (39:59, Paul Holes)
On Capote’s influence:
"He started referring to Ann Woodward as Mrs. Bang Bang... She was described as a murderess, the jazzy little carrot top killer." (53:01, Kate)
"She shot my son and Truman Capote murdered her." (54:44, Elsie, recounted by Kate)
This episode deftly explores the intersection of forensic ambiguity, toxic social dynamics of wealth and reputation, and the lasting devastation wrought by both violence and the sensationalism that followed. While forensic uncertainties left the case open to multiple interpretations, the aftermath—propelled by society’s cruelty and the opportunism of Truman Capote—became as tragic and instructive as the crime itself.
Paul’s final verdict:
Leans toward the possibility of intentional killing, but recognizes the evidence is far too equivocal for a definitive conclusion.
Kate’s closing reflection:
A warning against the dark side of true crime narratives and a call for humility, accuracy, and compassion in storytelling.