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You are now listening to True Murder, The most shocking killers in true crime history and the authors that have written about them, Gasey, Bundy, Dahmer, The Nightstalker DTK. Every week, another fascinating author talking about the most shocking and infamous killers in true crime history. True Murder with your host, journalist and author Dan Zupanski, Good Eating. Three young women abducted and brutally murdered. For years, their killer remained a
mystery as the cases turned. Then a crime Stoppers call led to his arrest. Charming and handsome serial killer Oscar Ray Bolan married a member of his legal defense team, and he toyed with the criminal courts for decades while on death row. This is the first book about Bolan and his victims. Book they were featuring this evening is Death Row Romeo, The True Story of Oscar Ray Bolan, with my special guest, journalist and author JT.
Hunter. Welcome back to the program, and thank you very much for geting this interview. JT. Hunter.
Hey, Dan, glad to be here, Thanks for having me back.
Thank you very much. Another wild tale that I had not heard of, and I'm sure the audience is not so familiar with. So here we go with death Row Romeo. Let's get right into this. I want to ask you the typical question why you got involved with this? This is an incredible story, and I think that's enough I
think to know. Let's start with as you do. You set the scene in January twenty fifth, nineteen eighty six, Churches Fried Chicken and Tampa area, and Natalie Blanche Hally, twenty six years old, and you say she's a daughter of Charles Holly, a lawyer, judge and state legislator from Penelas County. Tell us a little bit about Natalie Blanche Holly and where she's working and what she's doing, and tell us the encounter then about with officer or Deputy Sheriff Ron Valente that same evening.
Okay, well, well, Natalie Holly is a young young lady twenty six years old at the time, and as you said, she was working at Church's Fried Chicken restaurant. She was a knight manager there on the evening of January twenty six, nineteen eighty six, and shorked pretty late. She worked into the wee hours of the morning working that late shift.
Particular night, she worked a shift as normal, cleaned the place up, locked it up, secured it and everything, and left sometime early in the morning, around one thirty or so, and she walked out in the parking lot, got in her car along with the co employee, helped her close the restaurant down and lock it up, and you know, they went there their separate ways, and the co employee watched, you know, as Natalie drove out of the parking lot
and drove down the street. And later on that evening, the deputy that you mentioned with the Hillsborough County Sheriff's office, his name was Ron Valenti was he was a pretty pretty young deputy sheriff, hadn't been on the force for too long, just a couple of years.
He was also working in.
The league shift. And around around two o'clock that morning, so roughly about a half an hour after Natalie had closed up and left the restaurant, Valente Officer Valente was on his way to a service call in Tampa there and he came to an intersection at Lake Magdalen Road and Smitr Road, which was the intersection there turned right at a stop sign and saw two cars parked over
on the side of the road. One of the cars had its urgency hazard lights blinking, the one the one in front, and then the other car was parked ray behind it. So, you know, obviously this being a little unusual to have two cars sitting there with one of them with its emergency lights blinking. The deputy pulled up there.
To check it out and see what was going on.
And he pulled up to the first car there, the one with the ergency lights, looked inside, you know, put his spotlight in there inside, and nobody was in there. So he car forward a little bit more to the to the second one that was behind it there, and found a man and a young man and a young woman inside that one in the front seats. The man was sitting in the driver's seats and the young woman was sitting right next to him in the passenger seat.
And Pty Flint, you know, came up there, and you know, as you might imagine, he kind of went up and said, you know, hey, what's going on you guys?
Okay? Everything all right? Do you have an accident? You need help.
Sort of thing, And you know, the man behind the wheel said, you know, we're fine. I just I just ran out of gas and she was helping.
She was going to take me to.
The to the station to get some more gas, basically what he told the deputy. And you know, at the time, the deputy thought it was a little strange the response that he was given, because if the if the man had ran out of gas, it was kind of weird, kind of weird that he was in the driver's seat, they're going to drive her car to get gas instead of her driving him to get gas. So it just
didn't quite mesh with what he said. But so the deputy asked to asked the woman directly, you know, is everything okay?
You know, and and she she looked.
Over at him, and that the band next to her kind of looked at her for a second. Then she looked over at the deputy and said, yeah, you know, everything's okay, officer. And so, you know, Valente was satisfied everything seemed to be what it was supposed to because the woman didn't indicate any sort of distress or didn't
seem nervous or anything like that. So he was her answer basically satisfied him, and so he said, okay, you know, he says, have a good night and all that sort of thing, and drove on to on his way to respond to the original call he had gotten, leaving both of.
Them sitting there in the dark.
And it turns out, you know, later that the woman was Natalie Holly in the car there.
You also talked that the officer was suspicious enough or did his job enough, that he ran the two vehicle tags in the first car on Black nineteen eighty four, as you ride, a Grand Prix was registered to Oscar Ray and Cheryl Boling, and neither vehicle was stole and sold. There was no red flags, and as you say, he resumed his patrol. Right now, you talk about an attorney named Gerald Sage. He's out on his usual Saturday morning
jog and he found a woman. Tell us what he finds, and tell her what he what he finds, and then later what the crime scene texts find.
Okay, so yeah, it's Gerald Stage. You know. Later that morning it was about two am when when the deputy came on Natalie Holly and the car belonging to the
Bowlin's Oscary and Cheryl Bowlin. So seven thirty five and a half hours later, this Cheryl Sage is out going for a jog and comes across, as you said, this, this this body lying in the wheat there, just a little bit off the road and an overgrown orange groove, and you know, he obviously graces back and calls the calls the sheriff's office, and you know, they come out and respond to the scene there and they find this this woman, this woman's body there. She had been she
had she had met a brutal end. It was pretty pair right. She had been stabbed numerous times. You know, they later came to determine she was stabbed about ten times. And her eyes are still open in death, so you know, as if as if, you know, still experiencing the violence
of it, the shock of it. And there was an apron wrapped around her with Church's chicken written on it, and you know, they were able to determine that the body was Natalie Holly, and they ended up finding her car about four miles away from where the body was, which wasn't very far away from the church's restaurant where she worked either. And uh, you know, you know kind of calculating, well, you know, if she was going straight home after leaving work, which way she would she had gone.
They determined that where the where the car was located was consistent with the direct pride back to her house. And you know, later on they.
Came to some.
Uh you know, the theory as to how what had happened, how she had been stopped, and they figured that, uh that Bolan may have bumped her get her to pull over on the road there and then you know, obviously uh put her under his control. You know, he had a he had a gun with him at the time he pulled her over. And even at the time that officer of Valente, Deputy Valente came by there and spoke to them that he was Bulan was pressing a gun to Natalie's waste the whole time.
So that's that's how Natalie ended up.
Becoming a victim of Bolan.
You talk about there was some evidence. There was an athletic shoeprint identified as men's track brand tennis shoes. There was some fiber carpet fiber, and so there was impressions and there was some forensic evidence at that time. But you say, as well, despite the barbarity of the barbarity of the crime, Tampa Bay Residents' attention was for another horrific event. Tell us a little bit about that before we talk about November fifth, nineteen eighty six.
Well, in the day that they found Natalie's body, it was the same day that the Space shuttle, the Challenger Space Shuttle exploded. As you know, most people that heard that where they were viewing at the time, they heard huge news event. So you know, perhaps not surprisingly that kind of took center.
Stage and kind of took a little bit away from the.
News or coverage of Natalie's murder.
Next, talk about November fifth, nineteen eighty six and his next victim. Stephanie Collins, seventeen years old, born in Kansas, a senior at high school. Tell us a little bit about what she was doing, where she was working, and how she goes missing.
Okay, so Stephanie Collins, this is later later on the same year. As you said, she's a high school student. She's a senior, seventeen year old senior at Chamberlain High School there in Tampa. You know, she was was by all accounts a very well liked young lady there at the school and was active in the school choir and whatnot.
And you know, it being getting close to Christmas. She was wanting to earn a little extra money so she could buy some nice gifts for her for her family and friends, and so on this particular day on November fifth, she stopped by the police that she worked part time, which was an Ecker drug store there and in the Tampa in the Tampa suburb there, Carol Wood is the name of it, off of Dale Mabrey Road.
So she stopped by there.
You know, she pulled into the shopping center parking lot and got out, went into eckerd and talked to the the manager in there to see if she could get some extra work. And you know, he actually offered to let her work that night because he needed somebody, but she had a a choir concert coming up that she needed to prepare for. There was choir practice that same night, so she wasn't able to take him up on the offer to work that night.
So she you know, thanked him and.
Walked out of the drug store to go back to her car, and that was the last time that anybody saw her alive. Around four fifteen in the evening around November fifth.
You write about her parents tearful televised plea for her safe return but you write. December fifth, nineteen eighty six, one month after Stephanie's disappearance, a man named Donald Gibson spots a group of vultures. Tell us what he first sees and what he discovers to his whoror.
Okay, So yeah, this guy, he was he was driving to work in the morning there on December fifth, and he spotted this this flow the birds, you know, these large birds gathered up by the road is you know sometimes you see you know, it's road killed that sort of thing.
So he saw that, you know, at first he thought.
That they might be turkeys or something, but but he got closer, he saw they were actually Italy vultures. And you know, in Florida we have these, uh these turkey vultures, so that that's what they ended up being. And so he was a little curious about it, just wanted to
kind of see what it was. So he so he he pulled up there and got out of his car and walked off to the side of the road there and dirt road a little bit there and then and he he saw what was attracting the birds, and it was a pair of pair of human feet and uh ahead, human head that was, you know, the getting the attention
of the birds. They're they're obviously feasting on it. So he found this badly Decomo's body there, you know, off the road there a little bit and it was wrapped up in some cloth and obviously notified the police quickly, and they responded out there and you know, investigated and found uh, found this badly uh decomposed, you know, feltonized body out there with a wrapped up in a hospital tal it turned out it said hospital property on it, and they, you know, they later were able to identify
the remains as those of Stephanie Collins.
So she had been missing.
Just about a month exactly when her when her body was found. And you know, similar to Natalie Holly, she Stephanie Collins had been stabbed, but she'd also had skull injuries. Her skull had basically been crushed, uh in part of it.
You're right.
On the same day, the Pascal County Sheriff's Office received word of another gruesome discovery. Moving crew discovered the body of twenty six year old Terry Lynn Matthews. Tell us what they found and what was her condition? Tell us a little bit about her, all right.
So, yeah, So Terry Lynn Matthews twenty six, same age as Natalie Hawley, and uh you know, and this this is the same day that they found Stuffannie Collins's body. Strangely enough, but they found they found Terry's body in a witted area in a rural part of Pascoe County. Her body was fully closed. It was ramped in, wrapped up in a in a sheet that was that was wet, which was odd because there had not there hadn't been any rain recently or anything, so it was strange that
the sheets she was wrapped wrapped in were wet. But like like Collins and Holly, Terry Lynn Matthews had also been been stabbed repeatedly. She'd been stabbed in the neck and chest and then similar to Stephanie Collins, she also had head injuries launch trauma, head injuries and uh, you know, Matthews had been She had worked at at a bank in Tampa predecessor of being in America. Essentially she worked.
She worked a night shift typically too, and worked the night of December fourth, so just you know, the night before she'd worked and after work it stopped by her boyfriend's house and was last seen, you know by him leaving about, you know, early in the morning, about two fifteen in the morning or so in the morning of
December fifth, which was the morning her body was found. Atally, when she didn't call him later just to say that she got home safely, her boyfriend got a little worried, as you might imagine, and so he decided to go out looking for and drove from you know, drove the route from from his place to where her house was, where she lived with her parents in a little town
called Reserve Town in Florida. So on his way there, he passed by the post office in Landa Lakes and spotted you know, her car sitting there in the parking lot of the post office and pulled up to it to take a look, and found a bunch of envelopes mail that was addressed to her her parents kind of littered around on the ground there right outside the car there, and you know, obviously she was nowhere to be found.
You say too, that they found a pink and turquoise ear rings, pair of pink and turquoise e rings, and her front her person in the front seat. Now you talk about Oscar Ray Bolan born in January nineteen sixty two, his father, Oscar Ray Bowlan Senior and Mary Brock tell us about his life and what you found him growing up in the environment in Portland, Indiana.
Yeah, so Bolan, you know, he he was described by his mom as being a little bit different than her other kids. He was she described as being very quiet and odd acting is what she called called it. But he wasn't in trouble much growing up with uh as far as you know, formal problems with authority or or law enforcement. He didn't seem to have any real real problems as far as that went, but he did.
He did have some.
Injuries when he was growing up. When he was younger, he fell off a roof of a house and hit his head and you know, as you might imagine, he hit it so hard that it wasn't good. He got a lost consciousness, had a concussion, and apparently had had quite a few concussions growing up as a kid. And when he was a little bit older he was hospitalized for having a vitamin vitamin deficiency vitamin K deficiency.
Was described as a loner.
By some and did eventually as he got more into his teenage years, did eventually end up having some adverse encounters with law enforcements, you know, started having some some thefts, things like this, and by the time he was fifteen, he spent some time in juvenile attention, was let out on probation. Shortly after that, ended up leaving home, going out on his own and started working, you know, just
various various jobs, construction jobs, things like that. His his his family members owned a carnival and he started working with them and some of the puble dose and things like that. So that's how he survived there after he after he moved out.
Around that time, you say, or soon after he meets his future wife. But at that time Cheryl Haffner, and again you say, he talks about the continued petty theft or convicted of theft, nothing any more serious than that. Even say he receies a ten year of prison sentence, but then it was suspended one year probation. But in the eighties, Bollen plans to move to the Sunshine State, to Florida with Hafner, and he relocates to Pascal County.
Tell us what he does there and how he survives again in this area before we talk about nineteen eighty two and a major incident with Halfner.
Well, he had relatives there in Florida, and you know, I think part of the reason why he decided to relocate back down to Florida was he was starting to have too many, so many bad marks against him, so to speak, up there and where he was, so he kind of wanted to get away from all that. So he had relatives there in Florida, and you know, they helped him get various jobs when he moved down there.
He worked all kinds of all kinds of jobs, you know, carpenter, welder, security guard, truck driver, lived all different areas in the in the Tampa Bay area. And you know that that kind of eventually ended up with with what you mentioned there about this incident in eighty two with his girlfriend there.
He they had some sort of argument and he ended up forcing her into his car and basically basically held her hostage for for several hours in his car just kind of drive and around the stuff in the area
there in the Tampa Bay area. He ended up getting arrested for it for false imprisonment, but the charges ended up being dropped subsequently because his girlfriend, Cheryl Hafner, refused to cooperate in the prosecution of it, so he didn't end up having to face any sort of repercussion for that incident.
You talk about. Soon after, his brother Arthur was killed in a hit and run, and this seemed to affect him. But in February eleventh, nineteen eighty three, Hafner and Bolin were married in Brooksville, Florida, and you say later just a few months later a grand theft again tell us what happens in the eighties between the couple and what their life could be characterized by.
Well, they had a they had a volatile relationship, and they had some they had some tough times. In December of eighty five, right before the new year there, Cheryl gave birth to their their son, their first child, oh, Christopher Bowling, And you know, it was following a difficult pregnancy. The pregancy was it difficult for her. She was a diabetic and had a lot of medical issues going on
with that. So, uh, he was he was born, which you know, obviously for most people would normally be a joyous occasion, but in this particular instance, it didn't work out that way. That the child, Christopher had been born prematurely. He didn't have his lungs weren't fully developed. Uh, you know, he ended up living not even days after being born. So this obviously impacted Cheryl quite a bit. But it
also it also really hit hit Bowling hard. He took it really hard, and Cheryl went into a depression and and and Bowling and it wasn't doing too much better. So it definitely was something that that impacted him deeply. You know. He later he later talked about it, mentioned that he thought it was it was it was as hard on him as as it was on her. And you know, it wasn't long after that that and Natalie Holly ended up being killed. You know, it was just it was less than a month after that.
You talk about within months, like you say that he was looking at the fast food restaurant, and we get back to Church's Chicken and Natalie Hawley. As you do in this, you talk about other arrests and the difficulty,
the difficult pregnancy. Tell us about as you take us through the three murders, the investigation for police, what have they done in terms of linkage, and what have they done in terms of gathering forensic evidence and what are some of the conclusions that they do have and they have made and tell us a little bit about the task force that is.
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Okay, Well, you know, there were some similarities between the three murders well as far as the victims went, as far as how they were, how they how they were last seeing, how they were abducted, and then also as far as a forensic evidence at the scene, there were some some common elements that that later later came up as far as fiber evidence that was recovered at the scene. You know, the the police in Tampa were obviously they
were working the case as hard as they could. They were they were trying to they were trying to establish all these similarities and trying to come up with suspects. And they you know, they they asked for assistance from the FBI for a profile, criminal personality profile of the killer. So the FBI prepared that for them, so they had that information, but there wasn't a lot of positive movement in the case as far as getting closer to finding
out who did it. So, you know, two a few years later after the after the last body discovery that that of Terry Lane Matthews, you know, several years after that and in the summer of nineteen ninety, the Hillsborough County Sheriff decided to call together the task force as you mentioned, to be made up of personnel from his office, Hillsborough County Sheriff's Office there, but also from Pasco County Shriff's office, Tampa Police Department, and also personnel from the
FBI as well. And this task force was going to be devoted to trying to solve these three murders, the Hally, Collins and Matthews murders. And the sheriff, you know, appointed a captain there to oversee this. His name was Gary Terry, was a veteran there of the Sheriff's office, have been there a couple of decades, a lot of experience, so
he was appointed to head the task force there. He had actually successfully overseen a similar task force that had been put together just a few years before to work on a serial killer case there in the Tampa area another another serial killer case, the Bobby Joe Long case. So Terry had experienced had experienced with that, so he was he was decided he would he would head up this task force as well on this case to try to solve these three murders.
And you talk about.
Okay, go ahead. Sorry, Well, I'm just gonna say. You know, they kept working the case, and not long after actually this task force was formed, they got a real lucky break. They had a call come in on a crime stoppers hotline in Indiana and Fort Wayne, Indiana, July twelfth, actually, and the caller provided some detailed facts about the three murders, the Hallway, Collins, and Matthews murders that had occurred there
in Tampa Bay. And the information provided, you know, identified Oscar Ray Bowen as the other person who had been involved in those murders.
You talk about the killer of being the caller, pardon me, that was Daniel Coby. Who was Daniel Coby? And how does he get to be privy to this information?
Well, by this time Cheryl.
Happener, Oscar Ray's girlfriend then wife. By this time she and Oscar Ray had separated and had divorced, and Cheryl had remarried and she was now Cheryl Kobe. So she had married Daniel Kobe.
And.
You know, at some point had kind of spilled her guts so to speak to her husband, her new husband, and she told Daniel about some things that she had experienced or scene with when she was still married to Bolin, and Kobe ended up calling the crime stoppers you know, after after that, some time after that, and gave them the information, and you know, basically said that she told the crime stoppers there that that one had had been involved in the murder of the chicken woman, even going
so far as to describe the encounter with the deputy alongside the road their deputy.
So wow.
You also talk about that the associates of Bolan at that time had provided an alibi for him, so there was no further investigation that correct.
Yeah, you know they had, they had they had run the uh, the information on the car back then, and you know, Bolan's name had had had been there and the police records and whatnot, and they had they had looked at him.
Early on in the case.
But like you said, there was a there was an alibi for him, so they kind of marked him off and kept looking. Wow.
You talk about within twenty four hour whereas Captain Terry sent Detective King and Corporal Lee Baker to Union City, Indiana to interview in person Cheryl Boby, and she met them at Portland, Indiana Police Department. Tell us what she told them in that interview at in Portland Police Department.
Well, the detectives went up there to Indiana and they interviewed her, and you know, at first she was pretty reluctant to talk to them, but eventually eventually did and she told them she gave him a lot of information to leak Bowen to the three killings. She also pointed them to Boland's brother Philip as having been involved, not directly in the murders, but having been involved after the
fact and disposing the bodies things like that. So so that that opened up a whole other area of inquiry for the for the detectives there, But she gave them enough evidence to allow them to move forward with you know, formal charges against Poland and being an indictment and uh, you know, going forward with the rest and prosecuting.
You talk also that Daniel Kobe had other motivation other than altruism or public safety when he went public with this information or later when he went public with this information as and and identified himself as an anonymous caller. Tell us a little bit about this little motivation for Daniel Kobe to do this.
Well, well, he called you know, probably out of spite, you know, he and and Sheryl had braided and worked together anymore. And you know, he was obviously not in a good mood about that. I'm not happy with that situation.
So he decided he probably wanted to get back at her a little bit, and so figured by conveying this information that she had given him, you know, under trust confidentially, that he could get back her a little bit, you know, either by getting back at her former husband to hurt her that way, or you know, having her involved in it directly as well.
You talk about that there were ten days of interviews and they secured valuable evidence. What type of evidence that they get in those ten days regarding that they could use later.
Well, it turned out that Cheryl had accompanied Bolin Oscar Ray Bowlin h to when he went to get rid of a bunch of the evidence in the murders. Cheryl had had gone along with him back to Natalie Holly's car. Remember this was the car that the deputy Valente had
found them in. So so Cheryl accompanied Oscarray back to that car and you know, watched him as he wiped the car down and you know got a you know, a big branch tree branch that was on the ground and used it to wipe away the tire tracks from from his vehicle that had been left there at the scene.
And also.
You know, getting rid of of other items that might link him to to that murderer. And then also with respect to your disposal of the other bodies of Stephanie Collins and Terry Lynne Matthews. So they got evidence on all these things. Between Cheryl and Philip Bowen.
You talk about too, that the police don't stop there. They ask her to be if she'd be wired, and then three days of visits in prison. You don't talk about any kind of guidance. We'll say on what kind of questions to get to elicit this kind of evidence. But it is incredible some of the information that she gets from him at this visit. And you say, despite that he's guarded. So tell us a little bit about this initiative by police and what they get from this. As a result, Bolan.
Had been It turned out that Oscar Ray had been arrested for another crime and was serving time in Ohio. For this crime, he was sentenced convicted of a rape and a sentenced to prison in Ohio, So he was serving time in Ohio by the time this Prime Stoppers call came in, by the time the Florida investigators got all this information linking Oscar Ray to these three murders.
So once they got that, once they talked to Cheryl, Yeah, they said, you know what, we want you to try to get some more direct information from Oscar Ray himself.
So they set it up so that she.
Would go visit him, you know, during the visitation.
Hours or whatnot at the prison there in Ohio.
So she had that several times, trying to get him to incriminate himself. And you know, while he would, he would he would discuss a lot of things kind of around the peripheral area I guess of the crimes. He never really you know, came out and directly incriminated himself. He didn't didn't give information that uh that would make it, you know, a slam dunk kind of kind of case,
so to speak. He did say a lot of incriminating things, a lot of things that that really showed that he had knowledge of these crimes, and you know, certainly certainly seemed to be involved with him, which you know, there's a there's a lot of quotation of it in the book, like the conversations between between Cheryl and Oscar Ray there in the prison. The things he's saying, even though he's
you know, he's purpose, he's being guarded. You know, he obviously doesn't he's worried that someone might be listening or something like that. So so he's very guarded. But there is a lot, a lot of things he says that do really rate some flags.
So there's no actual confession. You talk about this. Uh, they call him Pop's Baker after this and after they realize they're not going to get any information, he comes up from the back tell us about this confrontation, very very interesting and fascinating.
Well, and you know, by the time they'd had several days of Gerald trying to get this this confession directly from the Oscar but by the time that they figured, you know, they're not going to get anything more than they have.
Baker he's you know, one of the.
Detectives from from Tampa there. He was listening in a room nearby there.
And so he comes out and.
You know, kind of confronts Oscar Ray about it, pressing him, trying to get him to to talk about it, and uh, Oscar Ray says, you know, I you know, I'd like to find you know, I'll talk to you about it, but but I think I need an attorney.
And it was just kind of the magic.
Words, so to speak, the mentioning of the attorney, and Gary Terry, the head of the task force there, had had experience with that before. Back again, and this isn't the Bobby Joe Long case. There's a similar sort of circumstance where they're trying to get information from Bobby Joe and he mentioned, you know, maybe needing an attorney, and they kind of kept pressing him for information even after he said that.
And you know, it.
Turned out later on that that has a lot of problems with the prosecution of Bobby Joe at trial and stuff. So so Terry had learned from that for sure, and so once he heard this this mention from Oscar about an attorney, he came out and you know, tilled pop speaker, you know that we got to stop here, We got to stop this interview. You can't you can't go forward
with it. So, you know, whatever inclination that Oscary may have had to talk to that time, you know, it went away because you know, he ended up subsequently speaking to an attorney and clammed up after that.
You talk about there's a press conference August first, nineteen ninety Sheriff Walter Heinrich, and what's the statement that he makes and about and also the statement he makes about other suspected murders.
Well, yeah, the sheriff has this, holds this press conference, and a couple of weeks later, so you know, an now we're beginning of August nineteen ninety, hold this press conference. You know, this had been these three murders had been in the news a lot, so there was a lot of media attention going on with those. So he called express conference to announce that they have this suspect in the murder of these women, and.
You know, also said that the bold one.
Is suspected in some other murders in Hillsboro County as well, you know, possibly five other murders in Hillsborough County there and then a couple other ones out of state.
So he so he makes that announcement and.
You know, credits obviously the investigators and their efforts and everything, but also the crime Stoppers tip that came through. Obviously, that really was the break that they needed, that really cracked up with a case there for him, and you know, also mentioned that based on all the evidence and everything that they gathered, that it seemed like that there's a serial killer. Not Uscary was a serial killer.
They're talking about the electric chair and also this guy's busy, and you talk about Hillsboro County Sheriff that he's fight find a homemade handcuff key when he searches self, so he's a higher risk. And then you talk about November nineteen ninety he has a girlfriend. Again, it's just crazy. It's his first cousin, Charlotte Kennedy tell us a little bit about some of the things that he's doing behind bars.
Well, plans you know, he comes up with obviously this attempt to.
He's this.
Key that he fashioned, you know, to be able to get out of the handcuffs or whatnot. But he's also making plans with people he knows, you know, including his girlfriend.
And one of the things that that they kind of that the police kind of stumbled on and monitoring him was that he was gonna have this plan where he would have have her, have Kennedy, his girlfriend, and another convict, the three of them would have this came up with this plan where they would kidnap family members of several of the key people involved in his prosecution, namely being the sheriff there, Walter Heinrich, family members of him, also his son who's a judge in the area there, and
then Gary Terry from the sheriff's office, and then Pops Baker as well. It's kidnapped members of their family. And then.
You know, they.
Let Oscar Ray out of prison, let him go or bad things are going to happen. So they planned to abduct him, take him out of state, and then they were going to kill him if Bolan wasn't released.
They also find during this tape conversation that Boland referred to a conversation with Douglas Tedrow, Kennedy's brother about the strangulation murder of a Dallas woman, Deborah Diane Stone tell us why they thought that she might be linked to this and what do they do as a result of what does Terry do? Is captain Terry do as a result of finding out this information that seems to link him to Deborah Stone in Texas?
Well? Yeah, so there was mention during the during the conversations there about Kennedy's brother who was with Bolan apparently during a murder that had happened in March of eighty seven, which was shortly after the the time period there where Bolan had been in Tampa and and Holly and Collins and and Matthews in December of eighty sixth there had been had been killed and uh, you know after that Bowlan had made his way out of the state there
and apparently had been involved in this murder in March in the Dallas area there. And you know then later on that same year had had ended up raping another woman and getting arrested for that, which is how he ended up in prison in Ohio there. So so Bolan was still still out there active after even after he left Florida. And you know, obviously you would have you would have kept going if he hadn't then in prison there in Ohio for that rape as well.
You talk about that. Bolan asks at some point, and he makes it clear that he's afraid of this electric chair, but he asked to see Captain Terry, and there was some bond between him and Captain Terry in terms of that at least he would agreed to talk to Captain Terry. Tell us about this call and what do they get if anything as a result.
Well, yeah, So, so Terry had built up some rapport with Bolan, wanting to wanting to to use that to to you know, be able to get more information to prosecute him with basically, but he had he had built up this rapport by kind of helping Bowlin out with jail complaints about conditions and things like that.
And uh, you know, so Bolan kind of had.
Sort of a trust for him, I guess for Terry. And one day he sent a request asking him talk to Terry and he wanted to talk to him about two murders that had occurred back in eighty five in the Tampa area, to to two girls whose bodies had been found in floating in the Hillsborough River there. But before Terry could get over there, an attorney from the Public Defender's office ended up speaking to Bolan, and you know, by the time he got out of that meeting, didn't
want to talk to Terry anymore. So again, you know, talk to the attorney and ended up claiming up before he could before the police could talk to him.
You take us to March nineteen ninety one, and Bolan is in court in Pascal County, Florida for the Terry Lynn Matthews murder, first degree murder. You say, somebody makes the comments no remorse, charming, manipulative, you talk about that, but you also talk about an incredible again, incredible scene in this book. I say, it's very cinematic. Rosemary Callous gets a call from her husband, Bob, so tell us
about a little bit about the first degree murder. And then just a couple of weeks later, after Bolan sent this thing for kidnapping and Rosemary Callous and the call from her husband Bob.
Okay, so, yeah, So in March of eighty one, they're bowling, you know, makes an appearance there in court in in Pascoe County and in connection with the Terry Lynd Matthews
case and please not guilty to that. And not not long after that, a couple of weeks after that, Bob Callus ends up following up his wife at her at her work there at a car dealership and in the Bay area there, and she picks up the phone and notices, you know right away that that her husband Bob there sounds depressed, and you know, he tells her, you know, honey, I love you, but I can't take it anymore. Us.
I shouldn't have had that boy working for us. And just almost immediately after that, Rosemary here's a loud bang of a gun being fired, and it was her husband, Bob, killing himself. And you know, the boy that he referred to that they shouldn't have had working for them was Oscar Ray Bowling. They had hired him back in November of eighty six to work for their record service there in the Tampa area, and you know, he kind of played on them and told him he needed money badly
and all this sort of thing. And when a call came in about a disabled vehicle, they let him go out and respond to it alone, even though you know, typically that's not what they did with with new hires.
And whatnot, but they let him go out on this job alone.
And it ended up being h end of the beginning of December, December fourth of eighty six, and Bowlin took out their record truck.
And basically kind of.
Just disappeared for for hours. They kind of the kind of raised them on the radio or anything, and didn't hear from him again until really until the next morning he showed back up. You know, it was really disheveled, dirty looking and that stuff, and you know, it's kind of upset and whatnot. And later on that day they were sitting there in the office and the news report
came on about the Matthews and Stephanie Collins murders. And it was strange because oscar Ay got really excited when when that coverage news coverage came on and kind of ran back and got some of the other guys and wanted them to look at it.
And I was really excited about him.
It was like, you know, aren't those aren't those girls really pretty? And all this sort of thing. And you know, later on, obviously they understood why, because you know, he had he had just murdered him recently and turned out, you know, he used the wrecord in uh in Stephanie Collins's sorry in interry, then matthews murder or before bringing it back that next morning. So that's why Bob Corlis had been so distraught about it, because you know, if he if he hadn't hired him, he wouldn't have had
the record truck to use. And you know, Flas felt somehow responsible for the murder. You know, maybe maybe he couldn't have pulled it off without the the truck or something. So he really, uh, he really took that hard and really it really weighed on him, and you know he ended with his his suicide.
You take us to June twenty second, nineteen ninety one, say Bolan was unresponsive, rushed to hospital suspected poisoning. In his cell was a cardboard box three letters in his cell. Six page letter to Captain Terry. Tell us what the gist of what he wrote to Captain Terry and what did he think he was doing in this letter?
Yeah, so in the cell there they found the letter and the letter was addressed to Terry, and it basically told Terry that, you know, if you want details of the murders of the Collins, Matthews and Holly murders, you can get those from from Cheryl, my ex wife Cheryl. That's essentially what the letter said. And you know he also basically apologized than a letter to Terry as well for or for going out this way, you know, meaning
that that he was intending to commit suicide. And it turned out that Bullen had been you know, saving up his medications for a while in the in the jail there, and you know, tried to overdose to kill himself. You know, they were able to save.
Him by by pumping out his stomach and whatnot.
You talk about the opening of the trial with the Guardian angels marching outside demanding for asking for his death, and you say the prosecution star witnesses, Cheryl Kobe uh tell us what she said at trial on the stand about that night.
Well, Kobe testified about the Holly case, about accompanying Oscar Ray one night to go get coffee at Burger King or something. And you know this this was this was real located across the street from the church's restaurant that Holly worked out, and Bullan just kind of pulled up in the parking lot there facing the church's restaurant. I'm just kind of watching it.
For a while, for a couple of hours.
They're kind of staking it out, so to speak. You know, this was shortly before Holli was abducted. And so we also testified about Bulan returning home early in the morning. We're in bloody tennis shoes. He had a woman's purse with him and he told to hold her. Told the chryl that he had abducted this woman from the church's for a chicken restaurant that he had scoped out earlier that night and told her that, you know, he ended up having the killer in Bolin made her.
Go with them, go with uh with him.
As he got rid of the body. As we talked about a little bit earlier on mm hmm, and she you know, she probably rided details about that and and details about getting rid of you know, the other evidence like the purse and clothing and things like that that might link him to the crime.
You also talk about the next day she was called by investigators as a very eerie scene as well. What what did she say to investigators? What did they say in this close call.
Well, they wanted to know about the you know, the license weight number bet it come up, and she told them that, you know it was it was her plate, but that the car had been at the house all that throughout that whole night and that you know, it was there so it couldn't have been out at another location.
And they asked her why she lied and what was her response.
Garray was sitting there with her, so you know she couldn't.
She was scared.
Yeah, now you say July eleventh, nineteen ninety one, also Frank Bolin testified as well, but really her testimony was the key testimony. What was the verdict? What was a sentence?
One was guilty first sery murder and received death penalty. Sentence of death penalty by a majority vote of the of the jury. So he was sentenced to death.
And that you then talk about October October ninety one, Stephanie Collins again, Cheryl Koby providing information. Uh what does she say about Stephanie Collins and her participation in that crime?
Well as it was again is similar to the the other circumstance that uh, you know, Bowen tells her that and there's a body in the in the trailer there and that he needs her help getting rid of it, and uh, basically threatens her if she's she's just not gonna help them, that you know, something that's gonna help it happen to her as well, essentially saying something like, you know, you can end up just like that person
in the trailer in the trailer over there. And it turns out that, you know, after he had abducted Stephanie Collins from that Eckert shopping plaza, that he had brought her back to the trailer there and killed her there in the trailer. And and Cheryl Kobe described what she saw on the trailer. She said there was blood on the curtains and carpets and on the walls. She saw a big butcher knife on the kitchen counter that was wet.
And she testified about riding the bowling down to uh location there and watching him throw Collins his body into a ditch, so go ahead. Shortly after that, she testified that a story came on TV about the Collins murder, about the discovery of the body. And but one it said, that's her, that's that's the girl that was in the trailer, that's her.
You talk about the two witnesses that testified that on the afternoon she went missing, they saw in a white van with an unknown male. This is unsettling too. What did they see? And again it doesn't talk about what they did, But what did they what did they witness? What did they witness?
Well, they saw Stephanie in a white band with someone they didn't recognize, and she seemed to be distressed about something. She was, you know, waving her arms excitedly and stuff, and certainly didn't seem like she wanted to be there, and you know, it turned out that somebody testified trial that Bolan had a friend who owned a white van and that you know, this friend had moaned him that band in the past, so there was you know, potential link there with with the bands Bolan.
You talk about another eerie scene in this as well, when investigators retrieved Collins' purse. Inside was a piece of paper with a handwritten note. What was on that note.
Had had had a three digit number and three letters and then the name Ray. And there was some testimony that Oscar Ray went by the.
Name Ray, his friends and family called him that, and.
The numbers and the letters were matched the like this plate number of his truck. So that was certainly a strange, ultimately unexplainable item of evidence that was found. Yeah, it never really did determine how that came to be there.
Or why you say that he was pronounced guilty and sentenced to death for the murder of Stephanie Collins. Then you talk about Bolan Philip Bowl and testifying at the nineteen ninety two Pascal County trial for the murder of Terry Matthews. Now this is an incredible testimony as well at nineteen years of age, he's at trial, but at thirteen Bolan was trusted to watch him while his parents were away. Tell us what he experienced at thirteen years old with his uncle.
So Oscar Ray showed up there at the house one night, banged on the door there and had Philip come out. And now when Philip came outside there, he heard a strange sound, kind of this moaning sort of sound. He said, it sounded like like his dog had been run over or something. And then he saw something flying over there on the ground where the where the noise is coming from, and was something and a wrapped up in a in
a in a sheet, a big white sheet. And he watched Oscar Ray go over to the the figure in the sheet there and to do several things to it, one of which was running water from a hose over the top of it, essentially trying to trying to drown uh, you know Terry Matthews is Terry Lynn Matthews that was was wrapped in the sheets, essentially trying to drown her by running water down onto the face there. And that
didn't seem to be working. Bowlan grabbed a club basically that he had and Philip saw him raise it over his head like he was going to strike Terrylin there and Philip looked away. But he heard these thumping sounds, which was the thumping sound of the club striking Matthews in the head. And he heard that a few times and then the noise stopped.
You talk about that as well as his testimony. They were provided in court a letter that Bowlan had sent to Philip November nineteenth ninety one. Tell us what he wrote to Philip and what he asked for in that letter.
Ross Gray, He was essentially trying to get Philip to stay out.
Of out of Florida, not to come back there, not not to not to testify at his trial. So he was, you know, appealing to him to as a you know, as as his brother, as his half brother, appealing to him to you just to stay out of the out of the state. He obviously knew that he had some incriminating evidence against them.
Now with this sentencing that it looks like he has DNA testing. You talk about as well that when they did the more complex testing and match Bolin guilty for Terry Matthews murder. At the sentencing, what did they try to or mitigate or what did they try to use as a tactic to mitigate the sentencing and avoid the death penalty. What do they try to put forth?
Well, there was the you know, as frequently as they do in these kind of cases, there was a testimony from psychologists about Oolan's mental state and whether you know, he could have the capacity, the mental capacity to you know, to actually know that he's committing these crimes and guilty
of premeditated murder and all these sorts of things. So there was testimony from psychologists about that about you know, whether or not he actually knew what he was doing, or whether he was mentally ill and these sorts of things, or whether he had brain damage that would have.
Paused him to be acting this way, committing these.
Kind of crimes, and whether that should be used in mitigating his responsibilities.
You talk about too, that the Hillsbury County detectives suspected Bolan for other murders in the Tampa area, and you mentioned a Lisa Eisman and Kim Viccario, Connie Jones, and a Sharon Hopper, And they also went into investigating him as a suspect because he worked in trucking, long haul trucking, from eighty five to eighty seven, suspected his involvement in
murders in at least nineteen states. Tell us what police do in terms of that pursuit of further or other murders that they could put on him.
Well, I mean there, you know, they had this information from other sources about his involvement in these other murders, you know, some of it which was Bolan bragging to other inmates and things about Brian c he had committed. So you know, they they they followed up as best they could, but you know, hard definite evidence that could
convict him of the of the killings. You know, ultimately it ended up being the three and Natalie Holly, the Stephanie Collins and material and Matthews with with a three that they really had the hard evidence on. You know, there was this other case in Texas where they had a lot of witness testimony in that case as well, but.
The Texas UH.
Texas courts decided not to not to prosecute Bowling for that one. They decided especially that you know, they knew that he had the three cases pending in Florida, and you know that they would let him be be prosecuted there in Florida for those.
You talk about Now we skipped this, but this is the beginning of the book, and you talk about October fifth, nineteen ninety six before we talk about the the bacle that he puts state of Florida and the entire country. But talk about October fifth, nineteen ninety six and Rosalie Martinez.
Yeah, so Rosalwly Martinez was certainly an interesting character in the story. In Rosalie had was married to a prominent lawyer in the Tampa community there somewhere who traced his family traced back to the early days of Ebore City there in the cigar industry, a well established family, you know, well off, and she ended up marrying into that family. So Rosalie was actually very well off. And she she
worked in the court system there. She had a court reporting system for reporting company that she ran, and she ended up segueing into working with the Public Defender's office in Tampa, and as part of that, she ended up working on Oscarray Bowen's case, in his representation and in his trials and his appeals and retrials and whatnot. So she met Oscary Bowen in I guess it was in ninety five, nineteen ninety five, and she was immediately struck
by him, became fascinated with him. I was attracted to him, kind of fell under his his charm.
Uh.
He Oscar Ray could be pretty charming when he wanted to be, you know, like like he was not in common with serial colors, they can have a very charming side that they can put on when they want to. So she kind of fell under his spell and came to the got to the point where she essentially was in love with him and decided she wanted to be with him instead of with her husband and her family.
So she left behind her her her well to do lifestyle and her you know, life of privilege basically that she was living, and left behind her husband and left behind her daughters and decided she was going to marry Oscar Ray Bowland.
Even though he was.
Convicted for these multiple murders you talk about.
Just an year earlier, in ninety four, the Florida Supreme Court overturned his first degree murder conviction for the Natalie Holly case because of spousal privilege. Just explain that a little bit, because this is very important to this case moving forward.
Yeah, So the spousal privilege in Florida just essentially says that one spouse can't be retired to testify against the other spouse in court, in criminal court, you know, if it will somehow caused them to be exposed to criminal prosecution.
And so since in Oscar raised trials, since they had used testimony from Chryl you know, linking him to these crimes, the testimony about for helping him get rid of the bye, or helping going with him when he got rid of evidence at Natalie Holly's car, and all this sort of thing. All that kind of testimony the higher court rules should not have been admitted because of the it's because of the privilege there.
So they have the ordered for a retrial, and based on that same spousal privilege, they have a problem with the other trials as well. So that's he's being successful in court at least getting those things re examined. You then talk about January fifteenth, ninety seven, Rosalie Bolan appearing on Montel Williams to discuss her relationship. Tell us about this event and who else also appeared, and just tell us a little bit about it. Again, a very un eerie scene.
Yeah, well this is this is in the midst of you know, this this ongoing appeals and seeking retrials and everything that was going on with bones cases and you know which which by the way, just.
Went on and on and on, and you know ended up being.
Decades worth of these things. You really just you really played the system really effectively and getting these these retrials granted, you know, multiple retrials and in each of these cases, and then you know, having the appeals after that and getting other retrials. It really dragged it on for a
long time. But but yeah, back in so in January ninety seven, as you said, so Rosalie appears on them Montel william Show and you know extensively to kind of promote his case and kind of defend him and whatnot. So so she's on there, Bowland himself is on there
via video from from prison there Florida State Prison. Also on the show, they had the house sister of Terry Lynne Matthews and she was not in a good mood obviously and not happy what Rosalie was doing and trying to do and bringing coverage and attention to Oscar raise
appeals and whatnot. So she was, you know, pretty confrontational with with Rosalie on the show about how you know, and really, you know, I wanted to know how she could, how could how Rosalie could do what she did, meaning how could she leave her husband and daughters for this this killer? And Rosie you know, defended her what she did. He said, I love him, meaning Oscar Ray, and that she's willing to do whatever it takes to prove his innocence.
You also mentioned Montel Williams again, this is fascinating. He says, two, Rosalie, you better hope he doesn't get out of jail. You better pray that your four daughters aren't walking down the street when he's looking for somebody to rape. I thought that was amazing.
I think he he was the voice of a lot of people's reaction to to what happened. I mean, the the Rosalie marriage decision to marry Oscar Ay.
I mean, it was it was a it was a big deal when it happened.
I mean, he got a lot of coverage, a lot of media coverage, you know, not just in Florida, but nationally, uh even even internationally, and and uh, you know, she ended up appearing on twenty twenty. The wedding ceremony itself was conducted via telephone and on TV on twenty on the show twenty twenty and twenty twenty even did a
follow up of the story, you know, years later. So it was a it was a big deal, this wedding, and you know a lot of people really were I think I think why it was is people were just so you know, probably a combination of of outrage and fascination and you know, just wanting to know, well, how could somebody do something like this? How could somebody give up all all of these things, give up this life and this loving family and everything for the serial killer on death row.
Yeah, you also talk about ten murder trials and all ten you say, spending almost thirty years, but you say he's finally sentenced to death February twenty and thirteen, and he's in Stark, Florida. Tell us a little bit, as you do, this is rare that you take us right into that death chamber, and who of the family and who of the law enforcement, if any are there, take us into that chamber death chamber?
All right? So yeah, so you know, as you said this, this this seemingly never ending legal process. You know, thirty years, three decades really of appeals and retrials for this guy.
I mean, you can imagine the.
A cost to this state of Florida.
Yeah, for all of this.
I mean it's it's got to be astronomical for three decades worth of that stuff going on. But so yeah, so they finally do get to the point where he's exhausted all of his appeals and his death ward is signed by the Governor of Florida, and so he does have his execution date and January seventh, twenty sixteen, so last year is his date, and you know, he tries for one last appeal there to the US Supreme Court, and his execution is supposed to come at six o'clock PM that day.
But that that comes and goes.
You know, he's he's been all prepped and there's you know, been been made ready for this sentence of death to be carried out. But the six o'clock time comes and goes as the Supreme Court appeals going on, of Supreme Court considers whether.
Or not to.
Stay his execution or not, and you know, hours later about ten o'clock finally comes back down the appeal has been denied, so that's that's his last last shot at getting out of it. And the sentence has passed there in the in Florida State Prison by thethal injection and no oscars us west words and no services reply, and the sentence is carried out. And there are you know, there are members of the sentants, the couple of the the mothers of of the three women that have been killed.
Her there. You know, they've they've been dragged through the courts this whole time, obviously have gotten much older themselves in the process. But but Kathleen Reeves is there. She's the mother of Terry Lynn Matthews and she's there to witness it, as well as the mother of one of the other victims. There a Whitmer there as well, so they're there. Natalie Islam by this time had had passed away, so she wasn't able to attend, but the others who were there to witness it.
You also talked about Cheryl Kobe couldn't couldn't didn't make the third trial because she had diabetes complications and she died from soon after. And you say, with this electric chair or pardon me, with the lethal injection he joined Danny Rowland's, Danny Rowling, Aleen Warno's and Ted Bundy in being executed in Florida. Just as we think the story ends, there's also the Supreme Court. A week after Bolin's execution,
the US Supreme Court rules Florida's deathfinitely unconstitutional. And this decision gave the right to more than two hundred inmates to seek resentencing. And after reading about this thirty years of retrials and appeals, what a mess. Anyway, you talked about Gary Terry retiring in two thousand and nine as well, and just tell us what as you write Gary Terry's sort of conclusions after all this, his thoughts and ruminations on this case.
Well, when I you know, I spoke to Gary mister Terry about it. He you know, he even now he's still affected by by the cases. He still still feels, you know, very much connected to them. You know, as you might imagine he cases for a long time like that, they tend to become a part of these people that are working on them, these investigators, and so Terry definitely.
Still felt impacted by it.
And he uh uh that Oscar Ray was brother killings as well, that he wasn't prosecuted for He really firmly believed that that Oscar Ray had had a lot of other victims, and he obviously was thankful that the sentence
was finally carried out. You know, he's still he talked to he talked to me about still seeing and his head still seeing the crime scenes, you know, finding the body, seeing the bodies out there and you know what Oscar Ay had done to them, and Oscar Ray's you know, reaction afterward, and how nonchalant he was about the killings and things, and you know, so it really impacted Terry,
really hit him an emotional level. So he was he was definitely excited, happy, glad to see that the justice had been served and the the sentence was finally carried out. And you know, he credited the crime Stoppers tip coming in, and you know, he pointed to that and said, you know, that's really a great example of the value of the Crime Stoppers program, is that you know, this case here, which if but for that that call, that crime Stoppers tip might never have been solved.
Certainly, I want to thank thank you very much JT. Hunter for coming on and talking about death Row Romeo. The true story of Oscar Ray Bolan has been fascinating for those that might want to take a look at You have a Facebook page or some contact for you. Tell us a little bit about that.
Yeah, I'm on Facebook, sleinner JT. Hunter, and you know, the book, as well as my other books, are all on Amazon. You just plug in the title Death Row Romeo or JT. Hunter. They'll pop up there, or the publisher's website RJ. Perker Publishing is also on the internet as well.
I want to thank you again JT. Hunter. It's always a pleasure having you come on talking about your incredible books, Death Row Romeo. Thank you very much, have a great evening and hope to talk to you again soon. Thank you, thank Take care, take care, good night.