New York Cold Case 1999 — They Went Hunting Together Only One Made It Back!

The coffee in Raymond Callaway’s thermos was still warm when the shot came. It was the first Saturday of November 1999 and at 6:14 in the morning, the sky above the Catskill Ridge they called Miller’s Bluff was the color of pewter, flat, cold, not yet promising anything. Two men had climbed it in the dark the way they had done every November for 20 years.

 Their boots breaking through the frost-crisp leaves in the half-silence of a world not yet awake. They had eaten sandwiches before dawn at the truck, shared the thermos. They had split off at the limestone outcrop the way they always did. Dale going right toward the hemlock line, Ray going left toward the creek bend where the deer trails crossed.

 What happened in the next 40 minutes would consume the next 22 years of Margaret Callaway’s life. At 6:53 a.m., a 911 call came into the Delaware County Sheriff’s dispatch from a payphone at Beasley’s General Store on Route 28, 6 miles from the ridge. The voice on the line was Dale Prescott. He said his hunting partner had been shot.

He said it was an accident. He said he thought Ray was dead before he could get to him. He was right about that last part. But the rest of it, the part about what happened on that ridge, would take 22 years to unravel. To understand how, you first have to understand who Raymond Callaway was. And why the one person who never stopped asking questions was not a detective.

She was the woman who washed his hunting vest every October and hung it by the back door so it would be ready when he needed it. Raymond Arthur Callaway was 44 years old in the autumn of 1999, A union pipefitter who had worked the same Binghamton job site for 16 years and whose hands, according to his youngest daughter Dina, felt like tree bark, rough and permanent and completely safe.

 He had grown up in Chenango County in a house where the heat came from a wood stove and hunting wasn’t recreation, but something closer to religion. A ritual that connected men to their fathers and their fathers’ fathers through the specific cold of the Catskills in November. Through the smell of gun oil and wet wool and the silence that falls over the mountains before first light.

He had learned to hunt from his father Gerald who died of a heart attack in the winter of 1987. When Gerald died, Ray inherited two things. A debt that took four years to pay and a blaze orange hunting vest worn at the elbows with Gerald’s name written in ballpoint pen on the inside collar. Ray wore it every deer season without exception.

His wife Margaret told him it was due for retirement. He told her it still had good years left. Ray and Margaret had been married since 1981. They had three children. Thomas, who was 19 and working construction. Kevin, who was 16 and already 6’2. And Dina, who was 11. And who on that particular Saturday morning was asleep in her bedroom with a Spice Girls poster on the ceiling and a baseball mitt on the floor beside her bed.

Ray coached her Little League team. He had been coaching it since she was six. He always said that no matter what season it was, he would not miss a game. And in five years of coaching, he never had. He had known Dale Prescott since 1979 when they worked summer construction together before Ray went into the pipe trade and Dale went back to school for his teaching certificate.

 They had been hunting together every November since 1982. Always the same week. Always the same stretch of Delaware County ridgeline that Dale’s uncle had hunted before them. They had a system, split at the limestone outcrop. Work the ridge for 3 hours. Meet back at the truck by 9:30 for coffee and whatever they’d done. In 20 years, it had been the same.

The truck, the thermos, the dark climb, the split. On the night of Friday, November 5th, 1999, Ray told Margaret he would be back Sunday. He kissed Dina on the forehead. She was reading. He told her he’d see her at batting practice Monday. She didn’t look up from her book. He smiled at that. He got in the truck with Dale Prescott just after 10:00 p.m.

and drove north into the dark. That was the last time Margaret saw him alive. That was the last time anyone who loved him saw him whole. They made camp at the trailhead on November 6th. The night was cold enough that their breath hung in the air outside the truck and the temperature had dropped to 28° by the time they started up the ridge in the early dark of November 7th.

Leaves were down. The ground was loud underfoot. At 6:10 a.m., they reached the limestone outcrop. At 6:14, they split. Ray went left toward the creek bend. Dale went right toward the hemlocks, which is exactly where he told investigators he was when the shot went off. At two hunters from Margaretville, brothers named Carl and Dennis Webb, heard a single rifle shot from the direction of Miller’s Bluff.

They noted the time because they were still working their way up the trailhead and the sound made them stop. One shot. Then, silence. At 6:53 Dale Prescott called 911 from the payphone at Beasley’s General Store. He had driven 6 miles down the mountain. He told dispatch that his partner had been shot in what appeared to be an accidental discharge.

He gave Ray’s name and a location, the eastern face of Miller’s Bluff below the creek bend. He said he’d found Ray on his back on the slope. He said he’d checked for a pulse. He said he was already gone. Dispatch asked him to return to the scene and wait for officers. He said he would. Delaware County deputies arrived at the trailhead at 7:41 a.m.

They climbed the ridge and found Raymond Callaway exactly where Dale had said. On his back on the slope below the creek bend, one round fired. The wound consistent with a rifle shot from a distance of less than 100 ft. Dale was standing near the body when they arrived. He was calm. He answered every question carefully.

He said he had heard a sound, not quite a shot, more like a crack, from Ray’s direction about 40 minutes after they split. He said he moved toward the sound, but it took time because of the terrain. He said when he found Ray, he knew immediately there was nothing he could do. He said he came down the mountain to call for help because he didn’t have a cell phone with him.

That detail, the cell phone, went into the report. The Delaware County Coroner ruled the death an accidental gunshot wound. The official notation, consistent with victim handling his own firearm on uneven terrain. The case was classified. The file went into a cabinet. Margaret Callaway was notified before noon.

She was told it was an accident. She never believed that. The investigating officer on the case was Deputy Frank Serrell, 11 years on the job. Thorough by the standards of a rural department handling its first hunting fatality in 8 years. He photographed the scene. He collected Ray’s weapon. He collected shell casings.

He interviewed Dale Prescott for 90 minutes at the scene and for another 2 hours at the department that afternoon. Dale’s account was consistent across both sessions. He grieved visibly. He spoke of Ray as his oldest friend. He declined a lawyer. He said he wanted to help however he could. Deputy Serrell noted one thing that he logged in his supplemental report but did not pursue.

When responding deputies had arrived at the trailhead, Dale’s truck keys were still in the ignition. The engine was cold. But Dale had told dispatch he had driven down from the ridge. A 6-mile drive on a mountain road in November should not have cooled a truck engine in under an hour. Serrell wrote it down. Then the Coroner’s ruling came in and the case was closed.

Margaret Callaway called the Delaware County Sheriff’s Office 11 times in the 18 months following Ray’s death. She spoke with Serrell, with his supervisor, with a victim’s advocate, and finally with the office of the Delaware County District Attorney. She said the same thing each time. Her husband was one of the most careful men with a firearm she had ever seen.

She said he had been handling rifles since he was 12 years old and had never once in all those years had an accidental discharge. She said Dale Prescott had a life insurance policy on Raymond. A policy she had not known about. Taken out 2 years earlier and payable to Dale in the amount of $150,000. She said she wanted someone to explain that to her.

The department’s position did not change. The ruling stood. Accidental discharge. The primary suspect considered in those early months was a third man. A hunter named Gary Pell who had a prior dispute with Ray over a property line near their trailhead parking area. Gary Pell had been seen on Route 28 the morning of November 7th.

He was interviewed twice. He had an alibi. He was at a diner in Walton from 6:00 a.m. onward, confirmed by the waitress and four other patrons. He was eliminated. Without another credible suspect and with the coroner’s ruling in place, there was no investigative path forward. The case did not technically remain open.

It was classified. Done. Margaret took out a second mortgage to hire a private attorney. He sent letters. He requested the case file. He got it. He read it carefully. He told Margaret that the file, as assembled, did not support a homicide investigation. He told her the insurance policy question was troubling but not prosecutable without physical evidence of intent.

He told her he was sorry. She paid him for 4 months. Then she couldn’t afford to anymore. She kept the case file in a box under the bed. She kept Ray’s orange hunting vest on the hook by the back door. She kept coaching. By 2005, 6 years had passed. Thomas Callaway was 25 and had a daughter of his own. Kevin was working in Albany.

Dina was in her first year of college studying criminal justice at SUNY Binghamton, a choice, she would say later, that no one in her family found surprising. The house on Laurel Street was quieter than it had been. Margaret still worked at the elementary school where she had worked since the children were small, answering phones, keeping order, organizing things that needed organizing.

She was the kind of person who made lists and kept them. The Beasleys General Store on Route 28 had closed in 2002. The payphone in its parking lot had been removed. The building became a storage unit rental operation. Dale Prescott was still teaching shop at Vestal Senior High School. He had remarried in 2001, a woman named Carol from Owego.

And he attended the same church where he had always been a deacon. He coached the school’s woodworking team to a regional title in 2003. He was, by every observable measure, a respected member of the community. The detective who had assigned herself to the Callaway case, not formally, not with departmental authorization, but privately and methodically, was Carla Meehan, who had joined the Broome County Sheriff’s Office in 2001, and who had heard about the case from a colleague who had heard about it from Margaret.

Carla had grown up in Cortland County. Her own father had died in a hunting incident in 1988. A case that was ruled accidental and that Carla had never fully accepted. She had become a detective because of that case. She had not forgotten what it looked like when an official ruling shut a door before anyone had looked behind it.

She requested the Delaware County case file through an inter-agency records process in 2004. She read it twice. She made her own notes. She flagged the cold truck engine. She flagged the insurance policy. She flagged the timeline, the 40 minutes between the split and the shot, the 6 miles to the payphone, the single [clears throat] call.

She kept her notes in a folder she labeled simply Calloway, R. The reward poster that Margaret had printed and laminated and placed in the window of the VFW hall on Front Street had faded by 2008 to almost nothing. The ink has gone pale. Ray’s face is barely visible behind the plastic. But nobody took it down. Then, in March of 2021, something happened that no one outside of a forensic data center had anticipated.

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Your support is the reason we’re still here. Now, back to Ray Calloway. And back to the thing that finally changed everything. In the winter of 2020, as part of a federal initiative to digitize rural law enforcement case records, the Delaware County Sheriff’s Office uploaded several hundred pre-2005 case files to a shared state database, including the Callaway file.

Among the documents digitized were the supplemental reports, including Deputy Serrell’s notation about the cold truck engine. Carla Meehan, by 2021, a senior detective in the Broome County Major Crimes Unit, was reviewing cold case flags from the database as part of a routine audit when the Callaway file came up.

She had not looked at it in 3 years. She pulled it again. This time she had something she hadn’t had in 2004. Access to historical cell tower records. In the years since Ray’s death, telecommunications regulations had changed, and carriers were required to archive signal data for a minimum of 7 years. But the relevant data for 1999 was long gone, destroyed in routine purges in the early 2000s.

What Carla had instead was something different. She had a name. In March of 2021, a man named Leonard Dowd submitted a tip to the Broome County Sheriff’s tip line. Leonard Dowd was 63 years old and had spent 30 years as a licensed hunting guide in Delaware County. In the tip, submitted anonymously at first, and then confirmed in person 2 weeks later, he told investigators that in November of 1999, he had been on Miller’s Bluff, on the western face, above the hemlock line, during the morning of November 7th, he said he had seen Dale Prescott on the

ridge at approximately 6:40 a.m. Not at the hemlock line, where Dale had told police he was stationed. Not moving toward Ray’s position in response to a shot. He had seen Dale Prescott moving away from the creek bend, away from where Ray was found, with his rifle at his side. He had said nothing in 1999 because Dale Prescott’s uncle had been his client for 15 years, and he had not wanted to get involved.

He said he had thought about it almost every day since. He said he was 63 now, and he did not want to carry it anymore. Carla Meehan was in her office at 7:15 on a Tuesday morning in March when Leonard Dowd’s signed statement landed on her desk. She read it without putting it down. She read it again. She picked up the phone and called the Delaware County DA’s office.

By noon, a prosecutor had been assigned. In the months that followed, investigators reconstructed what they believed had happened on the ridge that November morning in 1999. The reconstruction was built from Leonard Dowd’s testimony, from a reanalysis of the original evidence, and from one additional finding that the original investigation had not been equipped to evaluate.

The pattern of gunshot residue on the sleeve of Dale Prescott’s jacket, preserved in evidence storage for 22 years, was inconsistent with a shooter standing at the distance Dale had claimed. The residue pattern placed the shooter closer, much closer, within 20 to 30 ft. Dale Prescott had not been at the hemlocks when the shot was fired.

He had not been moving toward Ray in response to a distant sound. He had been within range. Close enough that the question of accident collapsed entirely. Dale Prescott retired from Vestal Senior High School in 2017 with a plaque and a ceremony and a framed photograph of every woodworking team he had ever coached.

He was 65 by the time detectives showed up at his house on Maple Drive in Vestal on a Thursday afternoon in October 2021. His wife, Carol, was at the grocery store. Dale was in his garage. Investigators later described him as quiet when they arrived. He looked at the warrant. He said nothing for a long moment.

Then he said he’d like to call his lawyer. The arrest warrant cited second-degree murder. The probable cause affidavit outlined the timeline, the residue analysis, and the testimony of Leonard Dowd. It noted that in 1997, two years before Ray Callaway’s death, Dale Prescott had taken out a life insurance policy on Raymond Callaway through a plan offered by a fraternal organization to which both men belonged with Dale listed as the sole beneficiary.

He had collected on that policy in January 2000. The amount was $147,000. He had never mentioned it to investigators. The community of Vestal in Chenango Valley found out the following morning. Former students of Dale Prescott called the local news. The congregation of his church issued a statement. The woman at the dry cleaners where Dale had brought his suits every spring told a reporter she felt physically ill.

Three of his fellow deacons resigned their positions. The phrase that kept appearing in coverage of the arrest, from neighbors, from former colleagues, from people who had known him for decades, was some version of the same thing. I would never have believed it. He had stood at podiums. He had prayed publicly.

He had stood at Ray Callaway’s memorial service in the church and told people that losing Ray was like losing a part of himself. In March of 2022, in a courtroom in Delhi, New York, Dale Prescott entered a plea of guilty to second-degree murder. His attorney cited his age, his lack of prior record, and the passage of time.

The judge sentenced him to 18 to life. Before sentencing, a victim impact statement was read into the record. It was written by Dina Callaway Reyes, who was 33 years old by then, and had been working for the past 4 years as a criminal justice investigator in Broome County, in the same building, though not the same office, as Carla Meehan.

She had not known, when she took the job, that Carla had been quietly carrying her father’s file for 17 years. She found out later. She went to Carla’s office and sat down and didn’t say anything for a while. Neither did Carla. In her statement, Dina described her father. She said he had hands like tree bark and a laugh that went all the way to the ceiling.

And a theory that the best thing you could do for a child was show up, reliably, no matter what. She said he had never missed one of her games. She said she still had the mitt from that season. Still had the batting gloves he bought her. She said she did not forgive Dale Prescott and did not intend to. She said she hoped in the years he had remaining that he found a way to sit with what he had done.

She said her father deserved better than the 22 years he didn’t get, but she was glad finally that someone had said his name out loud in a courtroom. She said it felt like he got to come home. Raymond Callaway was 44 years old on the morning he climbed that ridge for the last time. He wore a faded orange vest with his father’s name written in the collar.

He had a thermos of coffee. He had a daughter at home with a baseball mitt on her floor and a game coming on Monday. He had a life that was entirely, completely his, built slowly, brick by brick, the way union men build things. He had a best friend. He deserved to come back down the mountain. 22 years is a long time for a family to carry what Margaret Callaway carried.

 It is a long time for a daughter to walk into a career in criminal justice and not know, consciously, exactly why. It is a long time for a retired hunting guide named Leonard Dowd to wake up at 3:00 in the morning and see a man walking away from a creek bend with a rifle at his side. Eventually, what is carried long enough becomes too heavy for one person to hold.

 The orange vest is still on the hook by the back door in Binghamton. Margaret hasn’t taken it down. I want to ask you three things before we close. First, does a sentence of 18 to life feel like justice for what Dale Prescott did? Or is there a number that could possibly be enough? Second, what does it mean that the investigation came together not from forensic science, but from a 63-year-old man who finally decided he’d carried something long enough? And third, how many other cases from the 1990s and early 2000s are sitting in evidence lockers and digitized databases waiting

for someone to put together pieces that were never connected the first time? Leave your answers below. This channel exists because people who stay until the end, who believe that truth is worth the time it takes. Justice found Raymond Callaway after 22 years. Stories like his are why we’re still here. If you believe it, too, subscribe so you don’t miss the next case.

And if you want more cold cases from the Northeast, the playlist is in the description below. Thank you for watching.