MISSISSIPPI 1964 Cold Case Solved After 43 Years — Justice Served After Decades

Forty-three years ago, a 19-year-old schoolteacher’s aide from Yalobusha County, Mississippi, disappeared one Sunday afternoon in July, leaving behind a single yellow dress shoe in the middle of County 9 Road and a small cloth-bound notebook, the kind girls keep in their apron pockets, lying open on the summer grass.

  The authorities at the time concluded that he had left on his own.  There is no evidence of a crime and no worthwhile investigation.  The case was closed before the end of summer and the city of Coffeeville moved on. His family never did.  Then, in the summer of 2005, a cold case analyst in Jackson opened a cardboard box that had been in a state archive for four decades and found a single piece of evidence that had never been processed: a buried work boot with something inside that the original investigators hadn’t thought to analyze, because in

1964, in Yalobusha County, Mississippi, nobody was looking for a reason to analyze it.  What that boot contained would take two more years and a database that didn’t exist until the internet age to decipher.  But when the answer finally came, it pointed to a man who had been living 30 miles away for the better part of four decades coaching children’s baseball, attending Sunday mass, and sitting with his neighbors at the Coffeeville Diner as if he had nothing in the world to answer for.

His name was Harland Dupree.  He was 82 years old when they put the handcuffs on him. But to understand what justice ultimately meant in this case, we must first understand what was lost.  And to understand what was lost, we have to go back to that July afternoon.  We have to go back to Coffeeville.

  We have to go back to Ruby Jean Callaway.  The summer of 1964 arrived in Yalobusha County as it always did.  Slow and heavy.  The kind of heat that settled in the cotton fields at 8:00 in the morning and didn’t go away until well into the night. Coffeeville was a town of fewer than 900 inhabitants.  Most of them had known each other since before they could remember.

  The roads that ran through the center of the town were paved.  But most of the county roads to the farms were not. The mill could be heard with the west wind.  That pungent pine smell that would stick to your clothes if you stayed outside too long.  At nightfall, the cicadas began and did not stop until dawn.

  Ruby Jean Callaway had grown up 4 miles from the city, in a white wooden house on what the Callaways called their plot, 16 acres of pasture and orchard that Ruby’s father, James, had worked since before Ruby was born.  She was the eldest of five siblings and, since she was 12 years old, she had understood that being the eldest in the family meant something.

It meant that you were showing the way.  At 19, Ruby was already proving it.  She had been working for 2 years as a teacher’s aide at Coffeeville Elementary School , helping younger students with reading and arithmetic in a county school system that was overcrowded and under-resourced.  The children adored her.

  He had the habit, which his students would talk about for the rest of their lives, of carrying a small cloth-covered notebook in his apron pocket.  Whenever I found a word that I thought children would find beautiful or surprising, I wrote it down.  Not the definition, just the word.  He believed that if a child heard a word at the right time, with the right voice, he would want to know what it meant.

  I wanted to give them that moment.  That summer, Ruby was preparing for something she had been working towards for 2 years.  She had been accepted into a teacher certification program at a Jackson college, the first person in the Callaway family to obtain a formal credential after high school.  Her mother, Loretta, had been sewing Ruby a new skirt for the trip.

  Her father had been saving money to help with the fees.  Her four younger brothers thought that their older sister would go to a place where words like hers wouldn’t reach, and they weren’t entirely wrong.  He was supposed to go to Jackson in 4 weeks.  That Sunday afternoon, Ruby stayed late in the church hall to help set up the chairs for the next choir rehearsal .

  He told his mother that he would be home before dark.  She was carrying her church hymnal and wearing her yellow Sunday dress.  The one with a white collar and small pearl buttons on the front.  Her younger sister, Darlene, who was 9 years old, saw her walking down the street from the front porch and waved goodbye .  Ruby returned the greeting without turning around.

  Like older sisters do when they know they’re being watched.  That was the last time any of them saw her in her entirety.  What happened in the next two hours would remain unanswered for 43 years.  At 9:00 that night, Ruby had not returned home.  His father drove the pickup truck down County Road 9 with a flashlight.

  He found the yellow dress shoe at the side of the road, near the crossroads where the gravel turned into grass.  A few meters further on , he found the notebook open face down among the undergrowth, as if it had fallen from a moving hand.  He found nothing else. James Callaway returned to the town and found the county deputy’s office .

  He told them what he had found.  He told them that his daughter had disappeared.  The deputy who answered the call that night, a 26- year-old named Leonard Ware, drove to County Road 9 in less than an hour.  He stopped at that intersection with a flashlight and saw what James had seen.  The shoe, the notebook, a flat area in the grass that could have meant something or nothing.  He wrote everything down.  He asked questions.

He told James Callaway that he would start in the morning.  What happened that morning was the beginning of a long institutional failure that the Callaway family would spend the next four decades fighting against.  The sheriff of Yalobusha County in 1964 was a man named Earl Birdsong.

  And Earl Birdsong was not a man who believed that a missing black girl on a county highway required the sustained attention of his department.  A week after Ruby’s disappearance, he had come to the conclusion, without evidence or investigation, that she had left of her own free will.    He had probably headed to Jackson earlier.

  He probably had his reasons.  The file, just as it was, was stored in a cabinet and never touched again.  Leonard Ware objected.  He was young enough to think that objecting would get him anywhere.  That wasn’t the case.  They told him the matter was settled and that he should mind his own business.  They never found the Ruby church hymnal.

  The notebook was returned to the family.  In the following weeks, Ware quietly asked questions in his free time.  Questions about who had been on County Road 9 that afternoon.  Who had seen Ruby after she left the auditorium?  Who could have crossed paths with her on that stretch of road?  One name came up more than once.

  The name was Harland Dupree.  Dupree was the foreman of the county sawmill, a man in his forties, broad- shouldered and well-regarded in the white community.  He was known to do business near the Calloway property.  Something related to a property deed that James Calloway had contested.  He had been seen at least twice watching Ruby in the cemetery.

  A witness, a woman who lived on County Road 9, told Ware that she believed she saw Dupree’s truck parked on the side of the road that Sunday afternoon near the intersection, around the time Ruby would have driven by.  Ware took Dupree to court. Dupree denied everything with the naturalness of a man who had trusted all his life that no one would believe him.

  The sheriff told Ware to let him go .  Ware wrote his notes.  He kept them in the file.  The file went into the closet.  And that was the last official action taken in the Ruby Jean Callaway case in four decades.  His body was never recovered.  Time has a way of burying things, not just evidence, but people.

  Not just cases, but also pain.  By 1969, five years after Ruby’s disappearance, James Callaway’s hair had turned white.  He continued driving the same route on County Road 9 on Sunday afternoons.  I didn’t know what I was looking for.  He kept driving anyway .  In the mid-1970s , the elementary school where Ruby had worked had a new wing, new teachers, and children who had never heard her name.

  The notebook, the one with her words written in it, was in a box in Loretta Callaway’s bedroom closet.  Loretta would sometimes take it out and turn the pages.  She never stopped believing that her daughter had not left.  Nobody who knew Ruby believed it.  But belief, in a county like Yalobusha in 1964, was not the same as evidence.

  And evidence was not the same as justice.  Leonard Ware retired from law enforcement in 1998. He had spent 34 years as a sheriff’s deputy and then as a detective in two Mississippi counties. And in all that time, he had never been able to do anything about the one case that had stuck in his mind .  He had kept his notes. I had kept a photocopy of the original file.

  He had boxes full of them at his house, then in his garage, and later, when he moved to an assisted living facility in Hattiesburg in 2003, in a storage unit paid for by his son, because Ware didn’t dare throw them away.  In Coffeeville, the old reward poster that James Callaway had hung in the restaurant window had faded almost to the point of disappearing, but nobody took it down.

  The restaurant changed owners twice.  The sign remained. Darlene Callaway, Ruby’s little sister, the 9-year-old girl on the porch who had waved, had grown up, had children and grandchildren.  She kept the notebook.  Sometimes he would take it out, as his mother used to do, turn the pages and read the words that Ruby had written in her careful handwriting.

Words that Ruby had chosen for children she would never finish teaching.  Then, in the summer of 2005, a state cold case analyst named Sandra Hollis walked into a Mississippi Bureau of Investigation warehouse and began going through a box of unprocessed evidence from the 1960s. Before we talk about what she discovered, if you’ve been watching this channel and believe stories like Ruby’s deserve to be told, please take a moment to like and subscribe to this video.

  It takes weeks of research to reconstruct the real lives behind these cases, and your support is what makes that work possible.  Leave a comment telling us what part of the world you are watching from. Now, let’s go back to Ruby.  Sandra Hollis had been in the cold case unit for 3 years when she pulled out the Callaway box.

  I had reviewed hundreds of files.  I had learned to read the particular silence in which ancient evidence speaks.  What was there and what was conspicuous by its absence.  What was in the Callaway box wasn’t much .  Some photographs of the crossroads, Wears’ original notes , a brief summary from the sheriff’s office, just two pages long, concluding that no crime had occurred.

  And at the bottom of the box, in a brown paper bag for evidence that had never been officially registered, a single work boot, size 11, men’s, made of dark leather, the kind worn by factory workers.    He barely saw her.  The bag was not labeled.  They had put her in the box without a chain of custody record.  Whoever put it there did so silently and then said nothing.

  And then Sandra could only guess that she had moved, or that she had been moved, or that she had given up.  He didn’t give up .  He sent the boot to the state crime lab in Jackson.  The forensic laboratory found what 41 years of storage had preserved.  A small amount of dried biological material was found in the inner lining of the boot, near the toe, in a fold of the leather where the original processors had not looked or thought to look.

  It was enough to extract a DNA profile.  But the profile didn’t match anything in the state database.  Nothing in CODIS .  The trail went cold again.  This time not for years, but for two more.  Two years while the profile was in a queue.  In the fall of 2007, the profile was sent to a forensic genealogy service.

  This is one of the same processes used by public ancestry databases , the ones ordinary people use to trace their family trees, locate distant relatives, and work their way toward a possible source.  The process involves comparing partial DNA matches among thousands of family histories, creating a genetic map that narrows down to a single unknown contributor.

  It came down to one family, one county, one man.  Sandra Hollis drove to Hattiesburg with the case file under her arm.  She found Leonard Ware, 80, on the glassed-in terrace of his residence, contemplating the afternoon light that streamed through the windows.  He showed her the name.  He looked at him for a long time.

  He left the paper on the table.  He said, in a very low voice, that he had known it for 43 years.  Harlan Dupree was 82 years old in 2007. He had lived those 43 years as a respected man.  He coached Little League baseball in Coffeeville until he was over 60. He attended the First Baptist Church on Sunday mornings.

  She knew the names of her neighbors’ grandchildren.  He was the kind of man a community trusted without hesitation.  The kind of man whose presence in a room makes people feel that things are in order.  He was a deacon.  He was very well loved. He was invited to everything.  He had been present in the Callaway case from the beginning, in the background, where a confident man knows he should remain.

  He was questioned once, 43 years ago, by a young assistant who was later ordered to stop asking any more questions.  She had left that room and returned to her life without a single mark.  The evidence surrounding him was silent and unequivocal. The boot’s DNA matched that of Harland Dupree with a statistical certainty of 1 in 430 billion.

  According to forensic analysts , the boot was consistent with footwear worn by textile workers in the early 1960s. The soil embedded in the sole matched the composition of the soil adjacent to Callaway’s property, land to which Dupree had access through a logging contract that extended until the summer of 1964. A second search of the property, conducted by the Bureau in November 2007, recovered partial remains at a location consistent with a cover-up.

    He was arrested on a Thursday morning in December 2007 at his home on the outskirts of Granada.  The officers who arrived found him in his kitchen drinking his morning coffee.  He didn’t run.    He did n’t seem surprised.  He glanced at the order and then brushed it aside, as old people sometimes do when something they’ve been waiting for finally arrives.

  The Coffeeville community didn’t know what to do with what they were feeling.  There was shock, the kind of genuinely nauseating shock you feel when a person you’ve bumped into at the grocery store for decades turns out to be something completely different from what they seemed.  There was anger.  Some people commented that they always knew something was wrong with him, while others said they couldn’t believe it.

  And both groups were telling the truth about what they felt , although only one of them was right about what had been true all along.  Harlan Dupree pleaded guilty in September 2008. He was convicted of first-degree murder and received a sentence of life imprisonment without the possibility of parole. He died in the state penitentiary in 2014. He never gave any explanation.

    He never addressed the Callaway family directly.  He took what he thought gave him the right to do what he did and kept it.  Darlene Callaway was 53 years old when the verdict was delivered.    She was sitting in the courtroom in Jackson surrounded by her children and grandchildren.

  Her parents, James and Loretta, had died before the case was reopened.  Her father died in 1991, her mother in 1999. Neither of them lived to this day.  After the verdict, a journalist asked Darlene what she wanted people to know about her sister.  She remained silent for a moment.  Then he said, “Ruby was going to be a teacher.

”  He said it simply, as one says something that is true but incomplete.  At the time of her disappearance, Ruby Jean Callaway had four weeks left before her scheduled departure date to Jackson.  Four weeks before becoming the first in her family to obtain a formal teaching credential.  Nothing can be recovered of what he would have done with it, who he would have taught, what words he would have written in the notebooks he would have carried with him for the next 40 years of his life.

It belongs to the category of things that are simply gone.  But some things did change because of what happened to him. The year after Dupree’s conviction, the Mississippi Bureau of Investigation’s Cold Case Unit expanded its unprocessed evidence review program to include all pending cases from the 1950s through the 1970s.

Seven more convictions resulted in the following decade .  Sandra Hollis, the analyst who found the boot in the box, would later say in an interview that she thinks of Ruby Jean Callaway every time she opens a new bag of evidence.  He wants to know what it contains.  He believes that’s what Ruby would have wanted too.

Leonard Ware, who was 82 years old when the verdict was delivered, was brought into the courtroom in a wheelchair.  He had kept his notes for 43 years in the storage room that his son paid for.  When the sentence was announced , she clasped her hands in her lap and bowed her head.  He said nothing to the press.  It wasn’t necessary.

What does it mean when justice is four decades late? Does it arrive in any meaningful sense when those who most deserve it are already dead? Is it enough that the truth, however slow it may be, is still able to surface? And what do we owe to the Ruby Jean Callaways of history?  Those whose cases were closed before they were opened by systems that were never designed to search for them.

  Take some time to answer those questions in the comments.  They deserve the conversation. Justice found Ruby Jean Callaway after 43 years. Stories like yours are the reason this channel exists, because the truth matters, even when it takes longer than a lifetime to arrive.  If you agree , subscribe so you don’t miss the next case.

  More unsolved cases await you in the description.  Thank you for being here.