Jimmy “Jamie” Riddle (9 of Diamonds, North Carolina)

Our card this week is Jimmy, Jamie Riddle, the Nine of Diamonds from North Carolina. In the fall of 1991, just as the season was starting to change, a couple fishing at sunrise at a small lake in Fayetteville, North Carolina noticed something floating near the surface of the water. At first, they thought it was a blow-up doll, but upon closer inspection, the couple saw hair on the legs and realized this wasn't a doll. It was a human being, a person who would be identified as 24-year-old Jimmy Riddle. Jimmy was also known to some of their friends as Jamie, but how much their identity played into their death isn't clear. What police have to go on are potential witness statements, items left at the crime scene, and maybe, just maybe, DNA. Nearly 35 years after Riddle's killing, there is a new detective on the case, a detective determined to unearth answers once and for all. I'm Ashley Flowers, and this is The Deck. On the evening of September 26, 1991, Max Riddle was sitting at home in Fayetteville when the phone rang. It was someone that he knew, saying that he should watch the news that night because his younger sibling might be on TV. Now the tone of the call must not have been ominous because Max sat back on the couch and held his baby, thinking that his brother, who he knew as Jimmy, was going to be highlighted in some way. Now through our reporting, we learned that Riddle also went by Jamie on occasion, though their family didn't know that, so throughout this episode, they will refer to their brother as Jimmy. And because of that, you'll hear us refer to them as Riddle. According to reports, a couple of friends say that Riddle used Jimmy and Jamie interchangeably, often more feminine clothing, but no one knew exactly how they identified. To their family, it didn't matter. I don't think it was ever talked about because we wouldn't raise to be like that to people and stuff. We were raised to be nice and being kind to everybody, and it doesn't matter what they are or what they do. Riddle was loved within the family for being charming and charismatic. Someone who, and I know this is going to sound cheesy, but it's true. Someone who could light up a room. So when Max sat down on the couch with his new baby in his arms, he was excited to see what was going to come on TV, because in his mind, it could only be something good. I didn't know if he was on the TV show or what, but when the news came on, it said they found a body, and when they did, they were trying to find out who it was, identify the body. The body, they spoke about, had been found earlier that day, floating face down in college lake. They didn't show pictures, didn't even give many identifiers, but instantly Max's world shifted. That call he'd gotten earlier that day took on a different tone, and when the news anchor made a call to the public asking anyone who might be able to identify the victim to come forward, Max knew that he was going to have to be that person. Now, Max never found out how that friend knew what happened first, and now that he's passed away, we can't ask that friend. But at the time, Max, who is a military veteran, instinctively snapped into action. He gently handed his baby to his wife, grabbed his keys, and drove straight to Cape Fear Valley Medical Center. It was the only place that he knew to go. I went to the desk, and I asked, I said, hey, I was told that my brother was found dead, and that he was here, that somebody needed to identify him. So they ended up getting somebody, and they took me back there, and they pulled the sheet up over his head, and that's what I knew it was him. In that dark moment, Max quickly became the family's point person. He was a role that made sense to everyone who knew him. The Riddle family are members of the Lumby tribe, the largest Native American tribe east of the Mississippi River, and Max had long carried a deep sense of responsibility to his family. He was the first to graduate from high school, and when his mother, who was only able to attend school through the fifth grade, wanted to learn to read and write, it was Max who patiently taught her. He was the one that people leaned on, the one who stepped up. So when the person he'd known, all of his life as his brother Jimmy was killed, that same instinct to protect his family pulled Max to become the nerve center of this tragedy. Max got on the phone, calling his mother in Florida, and all three of his siblings to share the horrible news. And for all of the calls he made, Max told our reporter Annie Roddrick Jones that there was one call that he was expecting to get that just never came. I don't recall nobody ever reaching out to me from the police department or nowhere. Never reaching out to you. No ma'am, I don't recall none of that. Not the first year? No. I still don't even know who the detective was back then. It wasn't even just the first year. Max can't remember ever speaking to a detective, neither can his sister Anne. Me and my girlfriend, we were roommates at the time. We sat on the 12 o'clock news. It was called the boot dog. We knew that's where people went and parties, so we were wondering, geez, who is it? Is it one of our friends, you know, because that's where the teenagers hung out and stuff. When we were in school, they didn't say any names. They just said a man was found dead in the lake at college lakes. And what did you think when you were watching that? We were just wondering who it was, you know, never in the middle of the years. Did I think it was my brother? And then how did you find out it was your brother? That caught and told me that it was Jimmy that they found. And then after that Anne, did police come to your house to talk to you? No. We've never spoken to the police, they've never talked to me. And did you wonder when they were going to call you? Yeah. Always, it was like, surely they'll be talking to us. Yeah, that's our little brother, but the call never came. Why do you think that is? Personally, I think it's because he was a little gay Indian boy, but they didn't care. You're just another gay guy who cares. For their family, it seemed like no one did. Anne says she last saw her sibling about a month before the murder when they'd come to do her hair and makeup for a date. She says that's who Riddle was, helpful, attentive, someone who liked making the people around them feel good, which is what made the next time she laid eyes on her younger sibling of five years so shocking. It was the day of the funeral, right before the service. You could see it on his face, where we went to see him. They tried to cover it up, but you couldn't cover up all the bruises on his face. They beat him, whoever it was, beat him, and nobody deserves that. I don't care who they are, they don't deserve that. The beating isn't what killed Riddle. Their official cause of death is listed in the autopsy report as drowning, complicated by ligature strangulation. But the family was in the dark about that when they laid their loved one to rest in Harper's Fairy Baptist Church Cemetery alongside the rest of their family. For decades, the grave had no headstone. Me for many years, it was an expense that the family couldn't afford. But in 2021, Max was finally able to buy one, giving his siblings and the family a place where they could come to grieve and lay flowers. But Riddle's mother never got to see that headstone. She died in 2020, nearly 30 years after her child was murdered. You know, every mom has a favorite. They won't come and tell you, but we knew it. They had just a special relationship, and we knew it, but we didn't care. We all had a relationship with our mom, but it broke her, you know, especially if she died, not knowing who killed her baby. For almost 30 years, she knew even less than that. The whole family had been left completely in the dark about the police investigation, and they didn't have the strength to push. I think we have this unrealistic expectation of families sometimes. We want them to fight to demand answers and investigate themselves and fill in investigative gaps where a department falls short, but that's not their job. They shouldn't have to, and sometimes just surviving is the hardest thing to do. Anne and Max had young families of their own that they needed to be there for. You don't get to stop showing up to work when something like this happens in your family. They don't defer the water bill or your mortgage. The way they survived was by moving forward. One step at a time, one day at a time. Hoping that one day the phone was gonna ring and they would finally get that long-awaited call from police. Well that phone did ring over three decades later but it wasn't police on the other end. It was us calling. And the timing, it was serendipitous because not only were we able to help bring together police and family for the first time in over 30 years, it came right at a time when a new detective had been assigned the case and he was able to share some major breakthroughs. When the deck team reached out to Max Riddle in December 2025, he was happy to talk with us, but he was pretty up front that he knew next to nothing about the actual investigation, which we took as a challenge. Even if we couldn't solve the case, just getting answers for the Riddle family would be a huge step forward. So our team reached out to the Fayetteville Police Department and we were connected with Detective Joseph Bergamine. And there was something I can only describe as fate about the timing of this call because Detective Bergamine had just recently, like a couple of months before we called, picked up a few of the department's cold cases and this was one of them. When Annie sat down with him, a stack of handwritten notes was spread across his desk. His attempt at consolidating the information that had accumulated over many years via work by multiple detectives. Detective Bergamine walked our team through how the investigation began and how, more than 30 years later, they're still trying to piece together what happened back in 1991 when Riddle was found in the lake. So officers and detectives were called to the scene. They didn't notice that there were tire tracks in the sand and they actually took a tire cast from those tracks. They also found several items of evidence that they documented. When Riddle was pulled from the shallow water, the only thing they had on were white nylons pulled below the waist, black, knee-high boots, and a single, dangly earring hanging from one ear. But more of their stuff was found on the ground, not too far away from the water's edge. They observed some blood in a dirt area approximately 50 feet away from the water. Around that same area, there's a disturbance in the sand. From that disturbance in the sand, they then see drag marks which appear to be like someone's feet dragging towards the water. Some items of evidence that they collected was a pink wallet or purse and earring that matches the one that Jimmy had on. They also collected a beer carton as well as two beer cans with that, a condom wrapper, a condom that was used in a military style belt buckle. I know a crime junkie's mind instantly goes to the used condom or beer cans thinking about DNA. But the belt buckle was actually a really interesting find because that told them something. The belt buckle was described in the file as being a military style belt buckle on which led me to believe that it probably did belong to a male. This was important because they did find what they believed was Riddle's clothing at the scene. A skirt, shirt, and jean jacket. That belt buckle was the outlier and likely belonged to the killer. Who might have been military, which would make a lot of sense, but would also open them up to a large suspect pool. You see, just to the west of Fayetteville, North Carolina is home to Fort Bragg, one of the largest military bases in the world. Now it probably isn't going to come as a surprise to anyone. When I say that in 1991, this case wasn't given much attention. I mean the family themselves told you that police never even bothered contacting them. And our reporter confirmed there were zero records that the family was ever contacted about Riddle's murder. Anne's assumption that they wrote her sibling off early on feels accurate. And the little police presence resulted in even less media coverage. After that initial broadcast came out about an unidentified body floating in the lake, the only other thing that circulated publicly was that a quote, cross-dressing male prostitute had been murdered. Now it seems like police had somehow found and spoken to people who knew Riddle and confirmed they did sex work. That's how they got to the quote, prostitute portion of what they released to the press. But authorities failed to include the other things that they learned from those same people like the fact that Riddle used both Jamie and Jimmy along with both he and she pronouns among a small group of friends. In the early 1990s, trans and non-binary identities weren't as well understood in mainstream culture except as jokes or stunts on daytime talk shows. People who didn't identify strictly with the sex they were assigned at birth often didn't have the language to describe their experience. So while police would never get information from the public who may have known our victim only as Jamie, it wasn't complete radio silence from the community. There were there were several tips that came in. Detectives did follow up on a lot of those tips. They continued to come in even months after the case and they didn't make contact with several people. Three people in particular really helped police fill out a timeline of Riddle's last known movements. Terry Hunt, Victor Bowling and James Oxandine. They were all out on Bragg Boulevard in the early morning hours of September 26th and Bragg Boulevard was this main drag that cut through the center of town. People frequenting that area and picking up sex workers was a common thing. So even though a lot of cars pass through if you were out there on a regular basis you learn to pay attention to who's coming through and who's getting into what cars and everyone clocked that Riddle was with two white guys in a red pickup truck. So on the early morning hours at approximately 12 30 or 1 a.m. Victor Bowling and James Oxandine see the two white males in the red GMC pickup truck in the area Bragg Boulevard. At approximately 2 a.m. they see the same red truck with the two white males with Jimmy inside the truck. They provided a pretty detailed description of the truck that there was a Fort Bragg or military sticker on the rear window and possibly three gray stripes and it was a later model GMC pickup truck. Detectives also got information from them that one of the white males stated to the other white male let's go Shay. At least two of the witnesses actually encountered these two men later that same day. Terry Hunt was at his trailer located at 18 Shaw Road in the Thomas Mobile Home Parks by 2.45 or 3 o'clock that morning and that's when Riddle, Shay and this other truck guy showed up wanting to use Terry's place for a sexual encounter. One of Terry's friends who was there told police that Riddle was charging the men $20 each but Terry wouldn't agree to let them use his trailer. He said no and so some arguing between Riddle and Terry ensued and then Riddle supposedly walks off on foot alone back in the direction of Bragg Boulevard. The occupants of the trailer then advised that the two white males get into a red GMC truck and they drive away to the same direction as where Jimmy was last seen walking. Now that walk to Bragg Boulevard would have been a quick 15 minutes but no one reported seeing Riddle again instead a few hours later and seven miles away Riddle is found face-down in college lake. Police don't know how Riddle made it to college lake or who was there with them but evidence suggests that the GMC truck may have made it there at some point. So they took cast of the tires at the boat ramp as well as tire tracks at 18-chall road. They sent those both to the seat loud to be compared. According to Detective Bergamine the lab report they got back red quote. The tire track impressions represented are of similar type of tread design and could have been made by the same brand of tire. However the question impressions are of insufficient quality and detail to determine if the question impressions were made by the same tire. End quote. So kind of a long jargony way to say maybe it was maybe it wasn't. But whether or not it was the same tire impressions at both the trailer location and the lake. Detectives knew that finding the two mystery men was their best bet at moving this case forward. So they have a composite created of both of them and they made that public. The guy named Shay appeared to be in his early 20s. He was 62 about 165 pounds with a muscular build and he was clean-shaven. He had sandy blonde short-cropped hair with a distinct hairline. If you're not watching this it's a little hard to describe but it's like he has a deep widow's pee but it's deeper on his right side so it looks almost slanted. Now the other guy he's also a white guy in his 20s. He was shorter about 5'7 and maybe 150 pounds with short and what honestly looks kind of like wavy or curly dark brown hair. Now he had a mustache and glasses with what I can only describe as like a late 80s style frames. The black and white pencil drawing makes this guy come across a little older than his 20s. So if you're not watching right now think like your high school biology teacher. Now Shay looks distinctly military but guy number two's mustache was throwing me a little bit. I mean I assumed military men had to be clean shaven. Well, shame on me. Assume nothing. I looked up the army's grooming standards. AR 670-1 which were in effect in the late 20th century and it says that "faces must be clean shaven, must stashes must be neatly trimmed and not extend over at the top lip line or beyond the corners of the mouth." Dead Ringer for guy number two's stash. Though interestingly his hair does seem scruffier and longer than the two-inch maximum listed in the same grooming standards guide. But between the belt buckle found at the lake, the Fort Bragg military sticker seen on the truck and the physical descriptions of these two. Everything was pointing early investigators toward one place to look for their suspect. Fort Bragg. And it feels like that shouldn't be that hard, right? Point me in the direction of Shay who has access to a red GMC truck. But for some reason nothing comes of this. And I mean not nothing, nothing. They brought a few people in, gave polygraphs, but it began to feel like a merry-go-round. Red truck, guy named Shay, red truck. But whatever they were getting it wasn't enough for an arrest. Or even enough to name anyone as a real suspect in the case. But they had to have been on the right track because there was chatter going around the base. Specifically one military member overheard some guys talking about beating up a trans person. And then this got back to police. You know this conversation that they had was lining up with the assault on Jimmy and his death because they didn't know of any other incidents that occurred in the past few months. One of the main individuals was brought in for questioning and he ultimately did not take a polygraph. He initially was going to but then he did not take a polygraph and he was interviewed but he denied any involvement and was never, nothing ever pinned out from that as well. Detective did learn that this person owned a red truck and interestingly went on to sell it to an auto place there in Fayetteville. Suspicious, right? Well police did their legwork. First off this guy was not named Shay and he didn't match the description of either man in the suspect's sketches. They still tracked down the truck and it turns out it wasn't even the right kind. They're looking for a GMC but this guy had sold a Chevy. Detective Bergamine told us that beyond that overheard conversation there just wasn't any additional evidence to support that this guy was one of their suspects. As time wore on the information coming in dwindled and without fresh injections of information the police focused their attention on other cases and it's not like the media was banging down their door asking for updates. But still, Riddle wasn't altogether forgotten. In the early 2000s a new detective came along and used some new technology to develop the cases first real breakthrough. Detective Bergamine told our reporter that in 2006 Lieutenant Jeff Locklear was working the department's cold cases and the Riddle case was prime for new DNA testing. They had loads of evidence including that belt buckle that they theorized might be their killers. So they sent that off for testing first but that was a bust. Next they tried the beer cans beer carton and that one single earring that had been lying on the ground that matched the one in Riddle's ear. There wasn't unknown male profile found on the earring and then there was a male profile on one of the beer cans that there was a codeus hit for in 2006. A detective Bergamine's request we won't be naming this individual because they're actively reviewing him as a strong possible suspect. So I'm going to call him Mark and Mark in my opinion bears a striking resemblance to the dark haired suspect sketch. He's a little taller than described and in the one picture I've seen of him from a few years before the murder he wasn't wearing glasses but the mustache the hair it fits and though Mark wasn't in the military he was raised in a military family. By the time of this codeus hit Mark was already in prison. After brushing up on police reports Bergamine told us that Mark first went away in 1991 for assault on a female carrying a concealed weapon driving with a revoked license and assault on a law enforcement officer. But he was out by January of 1998 because that is when Mark picked up a teacher sexually assaulted her tied her naked to a tree and left her there believing she would die. He went to prison for that crime in 1999 and began serving his sentence which was a minimum of 28 years maximum 34. Now Mark was known to be controlling and abusive toward women so finding our victim badly beaten would not be an unlikely MO for him which seems significant considering how riddle bore signs of severe violence when they were found. Except for reasons detective Bergamine didn't know this is where the investigation seemed to stop. I don't know if the Fayetteville PD just had the mentality of like "whoop good enough" as in this guy's already in jail off the streets would be for decades to come at that point. Good enough. Maybe Locklear intended to circle back around to it because maybe one of the other cold cases was popping off or something present day came up. I mean in Fayetteville new crime pops up regularly that needs investigative attention. I don't know I cannot explain to you why this white hot lead was dropped but it was just left on the floor waiting for someone anyone to come pick it back up and that someone would be detective Bergamine. By the time he entered the picture Mark was still in prison for the 1998 offense against that teacher but he still had never been spoken to about riddles murder and Bergamine picked up on something really interesting. So Mark first went to prison for a 1991 offense right? Well he was convicted on September 24th 1991 but for some reason he didn't begin serving his sentence until September 27th 1991 as in one day after riddles murder. So what was he doing on his last day of freedom? Since no one had ever spoken to Mark to find out detective Bergamine knew that was going to be his first stop. And on February 23rd, 2026 he took a trip out to the correctional institution where Mark was incarcerated for a face-to-face. Where was he on September 26th 1991? Well, Mark said probably getting ready to go to prison. Mark says the reason that he wasn't incarcerated right away is because the court provided him some time to get his affairs in order before reporting to serve his sentence. And so that's what he told Bergamine he was doing during that time, paying bills, getting his belongings intact. But was he really doing that from midnight to 3am? Seems odd to me. When confronted with the fact that his DNA was found at the scene, Mark couldn't explain it. He denied ever having been near the crime scene. He denied knowing riddle. Denied knowing anybody named Shay. Now detective Bergamine said that Mark never owned a red truck. But he is still actively looking to see if he's ever known someone who did. And there are other leads that Bergamine is pursuing related to Mark as well. Which is something that he not only told our reporter Annie, but he also got to tell Max and Anne. After our interview with Max and Anne, our reporter had them follow along in Max's truck to the Fayetteville police station. It would be the first time that they had ever met anyone who worked on their siblings case. And on March 10th, 2026, they finally got the meeting that they had waited nearly 35 years for, right at the entrance to the Fayetteville Police Department. "How you doing, sir?" "I am a great, sir. How you doing?" "Good. It's at the Bergen Mines." "Great, back for it." "It's at the Bergen Mines. Nice to finally meet y'all." "Hey, you two, sir. I'm really thrilled that, you know, somebody's looking into this. Hopefully, something comes out of this so we can find what happened to my brother." Detective Bergen Mines, along with Max and Anne, stepped aside from our camera crew to have a private conversation. And as Max held on tightly to his sister's shoulders, Bergen Mines finally told them the story that I just told you, most of which they were hearing for the very first time. And he answered the question that we all have after hearing this story. "So what was happening between 2006 and 2026?" "I don't know. I don't have an answer for you there." Detective Bergen Mines, though, has a plan about what he's going to do next. "We've already contacted several individuals in the caseball and that includes witnesses, involved parties. Anyone that we can identify that's still alive, we're going to try to make contact with and touch base and get a statement from them. While doing so, we're also going to send those items to a private lab for DNA testing. Again, much more advanced now than it was back then and even in the early 2000s. So those are some of the next steps we're going to be taking." Specifically, they want to get a better profile on the unknown male DNA found on the earring, which to be clear was not a match to Riddle's DNA. He's also going to send off the one thing that, "I'm sure my real astute crime junkies thought about right away." And that's the used condom. In addition to that, they're going to send the clothing that was found at the scene. The ones that they believe belonged to Riddle. Those have never been sent off, and Detective Bergen Mines says that based on the way the clothing was found in the bushes, he firmly believes that the suspect would have had to have handled those at some point. So it feels like we are this close to another breakthrough. When our reporter asked Detective Bergen Mines if he felt like this case was solvable, he seemed very hopeful. "I believe with some DNA, with the DNA technology in place and the items we still have, I believe that this is definitely, even though it's been such a long time that we can solve this case." And the pressure is on, because solving this case could have huge implications, not just for the Riddle family, but for the citizens of Fayetteville in present day. Because according to Detective Bergen Mines, Mark is projected to be released from prison on April 7th, 2028. For the first time in a long time, Max and Anne have some real hope. Hope for a solve. Hope for a day when they'll see justice. Until then, Anne holds tightly to the memories that she has, like the way that her sibling would play their favorite band, Vanity Six, and Dance Around the House. Or the rocking chair Riddle gave her daughter, carefully hand-drawn with her face. She still has it to this day. For Anne, it's impossible not to wonder who her sibling would be now, what their life might have looked like. "I would hope she would live in his true self, and be in heaven, be in whoever he truly was. And I think we would have a loving person in his life that cared about him as much as we did." Max continues to be the family's north star. He has four daughters and ten grandchildren, and tells them every day that he loves them. He has multiple alarms set on his phone throughout the week to call his siblings and his cousins, making sure that they're all right. For a family that has spent decades waiting, waiting for answers for justice for closure, that question still lingers. Who took their siblings' life? And how much longer will it take to finally find out? If you know anything about the murder of Jimmy or Jamie Riddle in Fayetteville, North Carolina, please call the Fayetteville Police Department at 910-433-1529. You can also call the Fayetteville Cumberland County Crime Stoppers with tips at 910-483-8477. Anonymous tips for an open and unsolved case through the Fayetteville Cumberland County Crime Stoppers could receive up to a $5,000 reward for information leading to the arrest. The Deck is an audio chuck production with theme music by Ryan Lewis. To learn more about the Deck and our advocacy work, visit thedeckpodcast.com. I think Chuck would approve.