Just IN: Florida EXECUTES Oscar Ray Bolin – Serial Killer of 3 Women | His Last Meal + Final Words

After spending more than 24 years on death row at Florida State Prison, Oscar Ray Bolin was executed by lethal injection on January 7th, 2016. The state sentenced him to die for the murder of Terry Lynn Matthews, a 26-year-old bank worker who was abducted from a post office parking lot in 1986 with her engine still running and her keys still in the car.

He also received death sentences for the murders of Stephanie Collins, 17 years old, and Natalie Blanche Holley, 25 years old. All three killed the same year. All three stabbed to death. All three cases unsolved for nearly 4 years. He maintained his innocence to the end. He was tried and convicted 10 times by 10 separate juries, and he said, “Not one of those verdicts was right.

” The night before his execution, he sat in front of a camera and said, “My conscience is clear.” On the following evening, the state of Florida put a needle in his arm. In this video, we will talk about his crimes,  the cold case that almost stayed cold forever, the woman who left her family to marry him on death row, and everything that happened in between.

To know why  the state had to kill the condemned, we have to go back. Portland, Indiana. 1962. Oscar Ray Bolin Jr. was born on January 22nd into a family that did not stay in one place long enough to build anything. His people were laborers and carnival workers, the kind of family that moves with the seasons, following the work wherever it appeared across Florida, Indiana, Kentucky, and Ohio.

There was no permanence, no roots, no single town that  could call itself home. What there was instead was a was a father who used his hands for the wrong things, >>  >> and a mother who, by at least one account, who walked her son to the school bus on a leash. The household was described by those who knew it as physically and mentally abusive toward all the children.

Oscar grew up in the margins, learning early that the world was something you move through quickly and  trust did not at all. By the time he was 15, he had his first arrest in Ohio, >>  >> theft. It would not be the last. In the early 1980s, Bolin moved to Florida.  He had a girlfriend named Cheryl Hefner, and he had picked up work as a carnival laborer and a long-haul truck driver, the kind of employment that keeps a man on the road, moving between cities, visible to no one in particular,

accountable to nothing except  the next destination. He was young, he was transient, and he was already showing the people closest to him exactly what he was capable of. In 1982,  a Cheryl Hefner went to authorities. She told them that Bolin  had kidnapped her, that he had taken her and driven her around the Tampa Bay area for hours without her consent.

 He was arrested for false imprisonment. The charge was dropped. The following year, 1983, the two of them were married in Hillsborough County, Florida. Cheryl Hefner became Cheryl Bolin, and the incident, the abduction, the hours spent driving became something that did not officially exist anymore, but it had happened, and the man who did it was still out there.

Tampa, Florida. 1986. The city is warm the way Florida cities are warm in January, the kind of heat that makes midnight feel like noon, and that softens the edges of everything into something almost comfortable. Natalie Blanche Holley was 25 years old. Uh she was the night manager at a Church’s Fried Chicken restaurant in Tampa, a woman who had worked her way into a position of responsibility at a job that demanded reliability and presence.

  She locked up the restaurant with a colleague on the night of January 25th, 1986 at approximately 1:30 in the morning. She said whatever she said to her coworker, she walked to her car. The night was quiet and warm >>  >> and completely ordinary. A jogger found her body a few hours later in an overgrown orange grove.

Oscar Ray Bolin had stabbed her 10 times, 10 times in the chest and the throat. She was left in the dark between the trees where she had not been before, surrounded by the smell of citrus and the Florida heat, and no one would know for almost 4 years who had done it or why. Natalie Holley’s murder went into the file.

 That the investigation produced nothing that led to an arrest. The case did not close, >>  >> it sat. The city moved forward the way cities do. Nine months passed. Stephanie Collins was 17 years old. She was a student at Chamberlain High School in Tampa, the kind of teenager who balanced school and a part-time job, and who was building the ordinary architecture of a young life without knowing she was doing it.

On November 5th, 1986, Stephanie finished her shift at a drugstore and walked out into the Tampa evening. She was 17 years old, and she had just worked her shift, and she was heading home. >> [clears throat] >> She never arrived. For a month, nobody knew where she was. Her family searched, her community searched.

The leads went nowhere, and the weeks accumulated, and Stephanie Collins remained missing in the specific, terrible way that missing people haunt everyone around them, somewhere between present  and gone, between hope and the thing nobody wants to say out loud. On December 5th, 1986, her body was found off the side of Morris Bridge Road wrapped in sheets and towels.

She had been stabbed to death. Her skull had been crushed. The same day they found Stephanie Collins, a 26-year-old woman named Terry Lynn Matthews did not come home from work. Terry Matthews had a life that was assembling itself piece by piece the way lives do when a person is working toward something.

 She worked nights at a bank in Tampa. She worked nights specifically so she could spend her days taking scuba diving lessons, on to a new obsession she had developed and was pursuing with a particular enthusiasm of someone who has discovered something that makes them feel alive.  She had a serious boyfriend. She had just bought a mobile home and was in the process of fixing it up so she could move out of her parents’ house in Silverhill, where her mother, Kathleen Reeves, and her father ran a Greyhound transportation business. She was 26

years old, and she was in the process of becoming the person she was going to be. On the morning of December 5th, 1986, Terry Matthews left the bank after her shift. She stopped at a post office in Pasco County, just north of Tampa. She parked her car. She went inside. When she did not return home, her mother, Kathleen, assumed she was with her boyfriend.

>>  >> It was an easy assumption to make, on the kind a parent makes when nothing has ever gone wrong before. When her boyfriend called the house asking for her, everything changed in a single second. Terry’s car was found in the post office parking lot. The engine was still running. Her keys were still inside.

Whatever had happened to her had happened so fast and so completely that she had not had a moment to stop the car,  to take the keys, to do any of the small, automatic things a person does when they leave a vehicle. Her body was found later that same day wrapped in a white sheet. Bolin had slit her throat.

 He had beaten her head until it was unrecognizable. He had tried to drown her with a garden hose. He had beaten her with a wooden club. His teenage half-brother, Philip, had been there. Philip Bolin had stood and watched his older brother do those things to a woman who had stopped at a post office on her way home from work.

 Three women, three murders, all in 1986, all in the Tampa area, all stabbed, all abducted from the routine moments of ordinary lives. A restaurant parking lot at 1:30 in the morning, a drugstore at the end of a shift, a post office with the engine still running, and no one connected them to Oscar Ray Bolin for 4 years. The investigators working these cases had physical evidence.

 They had crime scenes. They had the bodies of three women and the absence of the person who had put them there. What they did not have was a name. A truck driver and carnival worker who moved between states, who had no single address, and who lived the kind of life that passes through communities without leaving a permanent mark, is not  the kind of person who surfaces easily in an investigation.

Bolin drove his routes, he worked his jobs,  he moved. In 1987, he kept moving. In 1987, Bolin and his cousin Douglas Tedrow drove to Greenville, Texas, where they abducted a 30-year-old woman named Debra Diane Stowe >>  >> outside a convenience store. Tedrow later testified that Bolin raped Stowe in the truck and then  strangled her to death.

Texas prosecutors would later decline to seek an indictment because Bolin was already facing multiple murder charges in Florida. But Debra Stowe was dead in Texas in 1987 and the man who killed her was still on the road. Later that same year, on November 18th, 1987, a Bolin and two accomplices abducted a 20-year-old waitress at gunpoint near Toledo, Ohio.

He drove her across state lines, he raped her, and then, in a decision that would eventually bring everything down on him, he let her go in Pennsylvania. She was alive. She could identify  him. Ohio authorities arrested him, prosecuted him, and sentenced him to 22 to 75 years in prison.  Oscar Ray Bolin went to prison in Ohio for rape >>  >> and three murders in Tampa remained unsolved.

 His marriage to Cheryl had not survived his crimes. In 1989, she divorced him and moved on with her life. She remarried and it was her new husband who made the phone call >>  >> that changed everything. In 1990, a man identifying himself as Cheryl Hefner’s husband contacted an Indiana Crime Stoppers tip line. He told them that Oscar Bolin had confessed to his ex-wife about the murders of three women in the Tampa area.

>>  >> He told them that Bolin’s teenage brother Philip had been present at one of the killings. The tip was anonymous and it was specific and it was the first thread that, when pulled, would eventually unravel the entire thing.  Florida investigators opened the Tampa cases.

 They went looking for witnesses, they found them. Philip Bolin, who had been a teenager when he stood in that place and watched what his brother did to  Terri Matthews, told detectives what he had seen. He described the garden hose, he described the wooden club, he described his brother’s hands and what those hands had done. Cheryl Hefner told investigators that she had been with Bolin on the night Natalie Holley was killed, that she had helped him dispose of evidence afterward, that she had known.

Douglas Tedrow confirmed his role in the Texas murder and what Bolin had done to Debra  Stowe. Florida charged Oscar Ray Bolin with  three counts of first-degree murder. While he sat in county jail awaiting his first murder trial, investigators discovered something that told them everything they needed to know about the man they were dealing with.

Bolin had been caught on tape during a prison visit >>  >> plotting with a female companion who happened to be his cousin. The plot was specific. He intended to kidnap the family members of Hillsborough County Sheriff Walter Heinrich and several top sheriff’s officials. He intended to hold them hostage.

 He intended to use them to secure his own escape. The plot was discovered before it could be executed. It earned him an additional 15-year sentence on top of everything else. The man who claimed he had never hurt anyone was building a hostage plan from inside his jail cell. In July of 1991, the first jury heard the evidence in the murder of Natalie Blanche Holley and returned a verdict of guilty.

Oscar Ray Bolin was sentenced to death. Two more trials followed. Two more guilty verdicts, two more death sentences, three death sentences for three murdered women. And for the families of Natalie Holley, Stephanie Collins, and Terri Lynn Matthews, it appeared that the long wait was finally over. It was not over.

 It was barely beginning. >>  >> In 1995, the Florida Supreme Court overturned all three convictions. The basis for the ruling was this. When Cheryl Hefner testified against her former husband, uh she had still been married to him at the time he confessed. That confession was protected under spousal privilege.

 Her testimony was inadmissible. Without it, the foundation of the prosecution’s case in each trial was legally compromised. All three verdicts were thrown out. Bolin would have to be tried again. He would have to be tried again and this time,  he would not face those retrials alone. Rosalie Martinez was a married woman in 1994.

She was 30-something years old, the wife of a prominent Tampa attorney, the mother of four daughters, a woman living what appeared from the outside to be an enviable life. Wealth, stability, a house in a good neighborhood, a husband with a successful career, four children who needed her. By her own account, something was missing.

 Not in a way she could point to or name  precisely, but in a way that she felt an absence of something she could not identify sitting inside a life that looked complete from every angle except  the one she occupied. She worked as a mitigation specialist at the Hillsborough County Public Defender’s Office. Her job was to find evidence and circumstances that would convince juries to spare the lives of men on death row.

She reviewed their cases, she interviewed them, she built the human picture that prosecutors did not want juries to see. In 1994, she was assigned to the case of Oscar Ray Bolin. She walked into his cell and told him she had been sent to help him. She told him >>  >> she was his guardian angel. Over the next 2 years, working closely on his case, reviewing every  document, every piece of evidence, every claim of innocence he made, Rosalie Martinez became  convinced that Oscar Ray Bolin had not committed the

murders he was  charged with. She also fell in love with him. The prison guard who watched their interactions told her  that Bolin was a convicted serial killer. She decided the guard was wrong. She said she had looked into the eyes of thousands of criminals and there was always something there, a darkness, a toxicity.

She said Oscar did not have that look. During one court hearing, Bolin looked across the room at her and mouthed two words,  “I love you.” A court reporter noticed. The rumor spread.  The marriage of Rosalie Martinez to the prominent Tampa attorney did not survive what came next. She left her husband.

She left her four daughters. She divorced the attorney and the life that went with him. On October 6th, 1996, Rosalie Martinez married Oscar Ray Bolin.  She sat in her apartment wearing a wedding dress. He sat in his death  row cell wearing a prison-issue orange jumpsuit. They exchanged vows over the telephone because Florida >>  >> did not permit contact visits for death row inmates.

12 million people watched it on television. Three days after the wedding, Bolin was sentenced to death again for the murder of Terri Lynn Matthews in his first retrial. Rosalie said, “Oscar came into my life and I thought, this  is bigger than anything I’ve ever done. I want to save his life. If I died in my sleep tonight,  I would know the meaning of true unconditional love.

” She was not shy about what she believed the marriage could do for him. She told people that the notoriety of their union would afford Oscar Bolin a rich man’s justice.  She trained as a private investigator. She spent the next 20 years building the case for his innocence >>  >> and presenting it to anyone who would listen.

The victims’ families watched  all of it. Anita Holley, the sister of Natalie Blanche Holley, who had been stabbed 10 times and left in an orange  grove in January of 1986, said of Rosalie, “She actually went on national television proclaiming  his innocence. She was enjoying the notoriety and that just, oh my goodness.

” Kathleen Reeves, the mother of Terri Lynn Matthews, >>  >> who had been slit across the throat and beaten and drowned with a garden hose in December of 1986, said, “It was taking the attention off what he had done  and putting it on the criminal. Like he was some sort of superstar and she was the superstar’s angel.

” The retrials ground forward through the years. Every original conviction had been overturned at least twice for  legal errors. Each time Bolin was retried, a new jury heard the evidence and delivered a new conviction. He was tried three times in the Matthews case,  three times in the Collins case, and four times in the Holly case.

 10 juries.  10 separate sets of citizens who heard the evidence >>  >> and came back with the same answer every single time. 10 convictions. In the Collins retrial, FBI hair and fiber analyst Michael  Malone testified that black wool fibers from Bolin’s truck were found at all three crime scenes, and that hair evidence matched Bolin to the  Collins murder.

 The fibers, the hair. The science of it laid out for jurors who had no reason to question the credentials  of a senior FBI laboratory analyst. Bolin was convicted again. In 2014, uh the office of the Inspector General of the Justice Department released a report. The report  stated that Michael Malone had repeatedly created scientifically unsupportable laboratory reports, and had provided false, misleading, and inaccurate testimony in criminal trials.

Oscar Ray Bolin’s case was among 52 cases  flagged for review. The hair and fiber evidence that had helped  convict him, the science that jurors had trusted, had been produced by a man the federal government had formally identified as a fabricator. Rosalie said of Malone, “In my mind, Michael Malone is a serial killer with a lab coat.

 There have potentially been people executed based on evidence he handled. That is frightening.” Bolin’s attorneys filed for a new trial. They argued that the discredited  FBI evidence was grounds for reconsideration. They also pointed to an Ohio prison inmate named  Steven Kasler, who had confessed to the murder of Terry Lynn Matthews.

  Prosecutors pushed back. They noted that Kasler had a history of false confessions, that he had  falsely claimed responsibility for other crimes before Matthews. Kasler committed suicide >>  >> in late 2014 before a hearing could be held. The confession died with him. Both the district court  and the Florida Supreme Court denied a stay.

In all of the retrials and the appeals and the decades of legal maneuvering, one verdict changed. A new jury in the Holly case found Bolin guilty, not of first-degree murder, but of second-degree murder. His death sentence for Natalie Holly was converted to life in prison. The death sentences for Matthews and Collins stood.

Governor Rick Scott signed the death warrant  in October of 2015. The warrant was specifically for the murder of Terry Lynn Matthews, the woman whose engine was still running in a post office  parking lot in December of 1986. The execution was scheduled for 6:00 p.m. on January 7th, 2016. That morning, Bolin met with his wife, Rosalie, from 8:00 until 11:00.

3 hours. Whatever was said in those 3 hours between a man who was going to die before midnight and the woman who had given up her previous life to try to prevent it was not made public. From noon until 2:00 in the afternoon, Bolin met with his spiritual adviser, Brother Dale Recinella, who described him as calm and in good spirits.

Then came the last meal. Ribeye steak, medium rare, baked potato with butter and sour cream, a salad of iceberg lettuce, cucumber, and tomato, baked garlic bread, lemon meringue pie, a bottle of Coca-Cola. He ate half the steak and half the potato.  He nibbled at the salad. He drank half his Coke. He finished the slice of pie.

The night before, he had sat in front of a Fox  13 Tampa Bay camera and spoken for the last time on record about the murders he had been convicted of and the execution that was coming for him. He said, >>  >> “I did not murder these women. My conscience is clear. After 28 years of this, being in this box for 28 years, it’s a release.

 They can’t hurt me no more.” He was asked whether the execution would bring peace to the families of the women who died. He said, “Is it going to change anything for them? When they wake up the day after,  is anything going to be different? Now, I’m not going to be there. Where’s the focus of their anger now? They’re still going to be without their child. They’re still going to be numb.

” He did not say he was sorry. And he did not express any regret or acknowledge any loss except his own. At 6:00 p.m., the execution was scheduled to begin. It did not begin.  The US Supreme Court had agreed to review his final appeal for a stay of execution. The families who had driven to Florida State Prison  in Starke to witness the death of the man who had taken their daughters, sat and waited.

The prison sat and waited. The state sat and  waited. Kathleen Reeves was 78 years old. She had outlived her husband. She had outlived three of her children. When Terry would have turned 55 that year, Kathleen had gone to her grave with flowers. Inside the bouquet, rolled up between the stems, was a copy of the newly signed  death warrant.

She had brought it to her daughter’s grave. It was the last thing she could do for her, she said. She had been in those courtrooms across three separate trials for the murder of her daughter. She had watched Bolin’s attorneys argue and appeal  and delay and reverse and retry. She had watched Rosalie Bolin become a television fixture, appearing on national news programs, proclaiming the innocence of the man who had slit  Terry’s throat in a field and tried to drown her with a garden hose.

She had been told to wait. She had waited for 30 years. She said, “I’m always prepared for Rosalie to pull a rabbit out of the hat.” At approximately 10:00 in the evening, the US Supreme Court rejected Bolin’s final appeal without comment. No explanation. No dissent published. >>  >> Just the rejection issued into the night at the last possible hour.

The lethal injection procedure began at 10:05 p.m. There were 36 witnesses. And the families of all three victims were in the room. They sat and watched in silence. Bolin’s chest heaved for several minutes as he took a series of deep, slow breaths. The procedure lasted approximately >>  >> 12 minutes. At 10:16 p.m.

 on January 7th, 2016,  Oscar Ray Bolin Jr. was pronounced dead. He was 53  years old. He was the first person executed in the United States  in 2016. He declined to make a final statement. When the prison official asked him if he had any last words, he said simply, “No, sir.” Outside the prison,  Kathleen Reeves said goodbye to her daughter.

“We miss you, Terry. You were the sunshine in our lives. Rest  in peace, my darling daughter.” Donna Whitmer, the mother of Stephanie Collins,  the 17-year-old who had finished her shift at a drugstore and never made it home. “I stood in the Florida night and said, we all miss Stephanie every day.

 I can’t have her back, but I’ll have sweet memories.” Natalie Holly’s mother had died in 2012, 4 years before the execution. She did not live to see it. Rosalie Bolin did not come to the prison. She released a written statement saying she was heartbroken, and that the execution would create a set of invisible victims.

Tears rolled down the face of Bolin’s attorney, Bjorn Brunvand, as he spoke to reporters outside. “I cannot imagine the pain the families have suffered, but this is not the solution. Executing people is barbaric, and I don’t think it’s healthy for us to find joy in a healthy human being being executed.” Kathleen Reeves had a response to the question of whether justice had been served, even though Bolin was only executed for one of the three murders.

She said, >>  >> “It doesn’t matter. He only dies once.” And here is the question this case refuses to let go of. Not one question, but several that pull in different directions, and that no verdict, no matter how many times it was delivered, ever fully resolved. 10 juries convicted Oscar Ray Bolin. 10.

Not one or two or three, but 10 separate groups of citizens who heard the evidence >>  >> and said guilty every single time across 30 years of retrials and  appeals. The half-brother who witnessed the murder of Terry Matthews, the ex-wife who confirmed the confession, the cousin who admitted his role in the Texas killing, the fiber evidence, yes, later discredited, but not the only evidence.

10 juries. And yet, the FBI analyst who handled the hair and fiber evidence in all three cases  was formally identified by the federal government as a man who fabricated laboratory reports and lied under oath in criminal trials. His evidence helped send Oscar Bolin to death row. That same evidence was found unreliable, the state executed Bolin anyway.

 The Ohio inmate who confessed to the Matthews murder killed himself before a hearing could be held. The confession  died with him and was never tested. Rosalie Boland spent 20 years of her life, left her four daughters, left her marriage, trained as a private investigator, >>  >> and dedicated everything she had to the claim that the state of Florida was about to execute an innocent man.

She was not a naive person. She was not  someone who had read a news story and formed a quick opinion. She was someone who had reviewed every  document, every photograph, every measurement, who knew the case better than almost anyone alive. Was she right? The shoe prints at one scene were a size 10. Bolin wore a size eight.

Was she wrong? 10 juries  said so. Kathleen Reeves visited her daughter’s grave and brought the death warrant inside the flowers. It was the last thing she could do for her. What do you think? When the FBI analyst who handled your evidence is later proven to have lied in  dozens of cases and you’re executed before anyone can fully examine what that means, did Florida get it right? Or did the state,  desperate to close 30 years of legal chaos, execute a man on the strength  of testimony it could no longer

fully trust? Drop your answer in the comments because Kathleen Reeves said it herself. He only dies once. And if she is wrong about who died in that chamber, there is no way to undo it.