Florida Executes Oscar Ray Bolin: Murdered 3 Women in 11 Months, Married His Lawyer on Death Row

Florida Executes Oscar Ray Bolin: Murdered 3 Women in 11 Months, Married His Lawyer on Death Row

Less than an hour, the Bay Area’s most notorious serial killer will be put to death. Oscar Ray Bolin, convicted of killing three women in 1986, will die tonight unless the US Supreme Court grants a last-minute stay. ABC Action News reporter Michael Paluska is live tonight at the Florida State Prison with the latest on all of this for us. Michael?

“Jameson, Bolin ate his last meal at 10:00 this morning. We’re told he had a ribeye steak medium rare with a couple of other sides. We asked about how his spirits were today. We were told that he was calm this morning and that he was in good spirits. Bolin woke up at 6:00 a.m. this morning. The only visitor he had was his wife Rosalie. She was able to see him from 8:00 in the morning until 11:00. Then Bolin met with a Catholic spiritual adviser. Bolin’s attorneys have filed an appeal, but if the state’s highest court doesn’t intervene, Bolin will die by lethal injection at 6:00 p.m.”

On the night of January 25th, 1986, Natalie Blanche Holly did what she did every closing shift. Locked up the Church’s Fried Chicken on the corner, said goodnight to her colleague, and walked out into a Tampa parking lot at 1:30 in the morning. She was 25 years old. The daughter of a man who had once run for governor of Florida. A night manager who took her work seriously, who never cut corners, who finished every shift the same way. Methodically, professionally, without complaint. She walked toward her car. She had done it a hundred times before. She did not make it.

Oscar Ray Bolin Jr. was in that parking lot. He took her, drove her 5 miles north through the dark of Hillsborough County, and stabbed her 10 times in an orange grove off Debuel Road. Eight wounds to the chest, two to the neck. She was dead before most of Tampa finished whatever they were doing at 1:30 in the morning.

Three days later, the space shuttle Challenger exploded above Cape Canaveral, and the world forgot about Blanche Holly. But, Bolin was not finished. 10 months later, he pulled Stephanie Collins, a 17-year-old on her way to choir practice, out of a Carrollwood parking lot and left her body in a ditch 30 days later. That same morning, he took Terri Lynn Matthews from a post office on US 41, drove her to Hollow Road, less than 2 miles from his own home, and beat her head 15 times with a wooden club before cutting her throat.

Three women, 11 months, three open cases that went unsolved for 4 years until a woman told her new husband what her first husband had confessed to her, and her new husband picked up the phone.

The Defense Attorney Who Became a Wife

Then came Rosalie, a married mother of four daughters living in a Tampa socialite’s home with a prominent attorney husband who wore expensive suits to work and kept them pressed and hanging in the closet. She was assigned to Bolin’s case as a mitigation specialist. She walked into his cell and something shifted. She stopped being his investigator. She became his defender. She left her husband. She left her children. And before she walked out of that marriage entirely, she reached into her husband’s closet, pulled out his Glen Plaid Armani suit, and had it tailored to fit a man on death row.

On October 5th, 1996, with 12 million television viewers watching, Rosalie Martinez sat in her apartment in Tampa with a photograph of Oscar Ray Bolin Jr. standing in his place, a speakerphone on the table, and a minister beside her, and she married a convicted serial killer over the phone while he wore her husband’s suit from a cell in Starke. Three days later, she sat in a courtroom and watched a judge sentence her new husband to death.

10 trials, 10 convictions, a half-brother who recanted and unrecanted, a discredited FBI analyst, a confession from a dead man. 28 years on death row. On the last night of his life, January 7th, 2016, Oscar Ray Bolin Jr. ordered a ribeye steak medium rare, a baked potato with butter and sour cream, a salad of iceberg lettuce, cucumber and tomato, baked garlic bread, lemon meringue pie, and a bottle of Coca-Cola. He ate half the steak. He finished his slice of pie. He drank half his Coke. And when a prison official asked him if he had any last words before the needle went in, he said two words, “No, sir.”

But to understand everything that happened between that parking lot in Tampa in 1986 and the execution chamber in Starke in 2016, the women Bolin killed, the family he left behind, the legal saga that consumed three decades, and the woman who gave up everything to fight for him, we have to go back to the beginning.

Early Life and Upbringing

Portland, Indiana, sat 45 miles south of Fort Wayne, close enough to the Ohio state line that a man could be in two places before noon. It was a small town built around modest ambitions, factory work, farming, the kind of life where families stayed put for generations because there was nowhere obvious to go and no particular reason to leave.

In January of 1962, a boy was born there named Oscar Ray Bolin Jr. The first child of Oscar Ray Bolin Sr. and a woman named Mary. Oscar Sr. had roots not in Indiana, but in Morgan County, Kentucky, a stretch of country where the Daniel Boone National Forest gave way to thin strips of bottom land and families worked whatever the ground and the season allowed. The Bolins came from that world, laborers, farm hands, and carnival workers who followed the traveling circuit across multiple states: Indiana, Kentucky, Ohio, Florida. The family moved with the work, and the work was never steady and never quite enough. It was the kind of upbringing that left a child without a fixed address and without a fixed sense of who he was supposed to become.

Oscar Senior ran a traveling carnival amusement show, a business that meant constant movement, town to town, county fair to county fair, setting up and breaking down and loading back onto trucks before dawn. The life produced a particular kind of man, adaptable, unrooted, comfortable in the company of strangers, and accustomed to disappearing when things got complicated. It also produced, in at least one generation, a particular kind of violence.

Oscar Senior beat his son, not in the vague way that phrase was sometimes used to soften what happened inside houses where no one was watching. He beat him physically, repeatedly, in a home the boy shared with a marriage that was described later by those who knew the family as stormy and often violent. The marriage between Oscar Senior and Mary Bolin was not a peaceful one, and the children who grew up inside it absorbed the atmosphere of it the way children always do, through the walls, through the silences, through what they saw and what they learned to expect from the people who were supposed to protect them.

Mary Bolin had her own way of managing the boy. Oscar Junior ran away from home with a frequency that wore her down. He ran and ran, pulled toward something he could not name, or perhaps simply away from something he could not tolerate. He ran so many times that his mother eventually walked him to the school bus stop on a leash, an actual leash, the kind used for dogs, to make sure he boarded and did not simply vanish again into whatever space existed beyond the yard. Neighbors remembered it. The image stayed with people. A boy on a leash getting on a school bus.

His mother was an alcoholic. The household ran on tension and deprivation. Not only material, though there was plenty of that, but the deeper kind that comes from living inside a structure where the adults cannot be trusted and the rules change without warning. Oscar Ray Jr. grew up without the baseline of safety that most children absorb without ever thinking about it. And by the time he was old enough to understand his own circumstances, he had already learned that the world outside the house was no more reliable than the world within it.

He got into trouble. Small things at first, then less small. By the time he was in his mid-teens, he had been arrested for theft in Ohio. He was processed through the juvenile system, served time in a detention center, placed on probation. In 1980, he faced a charge in Portland for dealing in stolen property. That same year in July, he was charged with stealing a car in Union City, Ohio. Because Indiana and Ohio did not yet share criminal information across state lines in any reliable way, each jurisdiction treated him as a first-time offender. No escalated penalties followed.

Moving South to Florida

Oscar Ray Bolin Jr. left home in his mid-teens and aimed himself toward Muncie, Indiana, where he believed there was work. There was some. He took it briefly and moved again. In November of 1978, he drove south. Florida opened up below Georgia like a long exhale. The land flattening, the air warming, the salt smell of Tampa Bay reaching him before the city itself came into view. He was 18 years old. He looked around at the low skyline and the wide roads and the water and for a time he stayed.

Tampa in the late 1970s was a city still figuring out what it wanted to be. The population was growing, construction cranes interrupted the skyline and the roads pushed outward into flat lands that had been swamp and scrub a generation earlier. For a young man arriving from Indiana with no particular plan and no one expecting him, it was a place that absorbed newcomers without asking too many questions. But nothing held him. He looked around, found no reason to stay, and left. He went back north. He traveled between Florida and Portland through the end of the decade, working odd jobs in Muncie, moving between addresses, accumulating nothing that lasted.

It was in Muncie that he met Cheryl Jo Huffner. She was from Portland as he was and the connection between them had the particular gravity of two people from the same small place finding each other far from home. Cheryl Jo was a diabetic, dependent on insulin. They became a couple. They made plans. And at some point in the early 1980s, Oscar Ray Bolin Jr. decided to go back to Florida and he took Cheryl Jo with him.

They settled first in Central Pasco County in a small house on Valencia Drive that belonged to Bolin’s uncle, Jesse Bolin. The arrangement was temporary as most arrangements in Bolin’s life tended to be and before long a neighbor named Claude Kennard allowed the couple to move into the Kennard family’s double-wide mobile home on the same street while the Kennards were away in Ohio. Kennard had known Bolin since he was young. He thought of him as a good boy, an honest worker, a man who presented well and made people like him quickly. He was well-groomed, he was sociable. He had the easy manner of someone who had spent a lifetime learning how to make strangers comfortable.

In 1982, that surface cracked for the first time in a way that left a record. Cheryl Jo told authorities that Bolin had kidnapped her, not in the abstract sense of a domestic dispute that got a dramatic label. She said he had physically taken her, driven her around the Tampa Bay area for hours in his vehicle, and refused to let her go. She was a diabetic who needed her medication at regular intervals. He denied her access to her insulin during those hours, holding her inside the car as he drove. She was eventually released, and she went to the police.

Bolin was arrested and charged with false imprisonment. It was a serious charge, the kind that, if prosecuted fully and taken seriously by the system handling it, might have altered the trajectory of everything that followed. But, the charge was dropped. The case went away. Cheryl Jo did not press it further, or the prosecutors chose not to pursue it, or some combination of the two produced the same result. Oscar Ray Bolin Jr. walked out of the situation without consequence.

A year later, in 1983, Cheryl Jo Hafner married him. They lived in the Gibsonton area, south of Tampa, in a rotation of apartments and mobile homes. Bolin worked a variety of jobs, odd work, physical labor, the kind of employment that came and went without leaving much behind. He drove his own wrecker for a period, hauling disabled vehicles off the roads around Hillsborough and Pasco counties. He knew the roads. He learned which areas were quiet at night, which stretches had no witnesses, which places a vehicle could pull over without drawing attention. The geography of the Tampa Bay area became familiar to him, the way it becomes familiar to anyone who drives it professionally, not as a map of landmarks and destinations, but as a network of routes and hours and empty spaces.

The Work at Cales & Cales

By 1985, Bolin had brought his wife deeper into Tampa’s orbit. He worked for various companies, moved between addresses, and maintained the outward appearance of a man building something, even as the foundation beneath that appearance remained unstable. Then, Cheryl Jo became pregnant. Because of her diabetes, the pregnancy was complicated and dangerous, and she spent months hospitalized. She filled the time the way patients do, accumulating the small domestic materials of extended hospital stays, blankets, sheets, towels marked with the hospital’s name, taken home because they were there, and because no one stopped her.

The pregnancy ended in death. The baby was a boy. Bolin put on a new suit, drove the body back to Indiana, and buried his son in the ground he had grown up near. Neighbors in Pasco County remembered him returning from that trip with the particular flatness of a man who had absorbed something he did not know how to process and had decided not to try.

Cheryl Jo became pregnant again. The second pregnancy also required long hospitalizations. More sheets came home, folded and stacked in the trailer. More time passed in waiting rooms and ward corridors with nurses and orderlies moving around her and Bolin somewhere outside, driving the roads, working the wrecker, learning the county. The second baby survived. They moved back to Pasco County into a mobile home on Hide Road near his uncle Jesse and the Kennards.

Oscar Ray Bolin Jr. was 24 years old, living on a rural road in central Pasco with a wife recovering from her second difficult pregnancy, a newborn son, and hospital bills he had no clear way to pay. He was driving a wrecker. The towing work suited him. It put him behind the wheel of a heavy vehicle at hours when most people were asleep, sent him out alone across Hillsborough and Pasco counties on nothing more than a radio call, and left him entirely to himself between the moment he pulled out of the lot and the moment he returned. No supervisor riding along. No one checking where he went or how long he took to get there. Just the roads and the dark and the radio crackling with the next address.

He knew the roads. He had driven them for years by that point, back and forth across the flat terrain between Gibsonton and Land O’ Lakes and the sprawl of northern Hillsborough. And the familiarity was not the kind that comes from maps, but the kind that comes from hours, from knowing which stretches were dark after midnight, which roads ran without traffic between 2:00 and 4:00 in the morning, which parking lots and orange groves and drainage ditches existed at the edges of things invisible unless you already knew to look.

By the autumn of 1986, he had cycled through several employers and several addresses and several versions of the life he was trying to build in Tampa. None of it had held. He worked for a company until something went wrong or the money ran short or he simply moved on. And then he found another company and started again. The towing industry in the Tampa Bay area in the mid-1980s had enough operators that a man with experience behind the wheel and a willingness to work nights could find employment without difficulty. And Bolin moved through that world with the ease of someone who had spent his entire life presenting himself to strangers and making a passable first impression.

Cales and Cales Inc. was not just another towing operation. Bob and Rosie Cales had driven down from Minnesota in 1981 with $300 between them and a family of seven to feed. They had built the company through the kind of sustained unglamorous effort that produces something real. 21 trucks and wreckers, a body shop on North Florida Avenue, a contract as the largest AAA towing facility in the entire state. They ran it with the precision of people who understood that everything they had could disappear if they stopped paying attention. Bob managed the dispatching and the drivers. Rosie managed the office and the relationships and the thousand small decisions that kept an operation of that size functioning. They had built something from nothing and they knew exactly what it had cost them and they were not casual about protecting it.

Oscar Ray Bolin Jr. arrived at their lot in November of 1986 looking for work. He presented well. He knew how to handle a wrecker. He was hired as a trainee. Rosie Cales noticed something about him almost immediately. Not anything she could name precisely. Not anything that rose to the level of a complaint or a concern she brought to her husband. Just a quality she filed away in the manner of a woman who had spent years reading people across a counter and a dispatch desk. He was always playing with knives, she noticed. Acting tough. The other drivers called him Needles and the name fit him in a way she could not fully articulate but recognized.

The rules at Cales and Cales were straightforward. A new driver completed six weeks of supervised training before going out on a job alone. The roads in Pasco County at night were not the place for a trainee operating without an experienced driver beside him. And Bob Cales enforced the rule because he understood liability and because he ran a professional operation. He was not a man who bent his own standards without a compelling reason.

On December 4th, 1986, a towing call came in from Pasco County. Bolin had been with the company for roughly 3 to 4 weeks. Nowhere near the point at which he should have been dispatched alone. But he asked. He pressed the case with the quiet persistence of someone who had learned that persistence sometimes worked where argument did not. He needed the money, he said. Rosie wanted to give the boy a chance. She persuaded her husband. Bob Cales relented. He sent Bolen out in a 1-ton wrecker with dual rear wheels.

Before Bolin pulled out of the lot, Cales noticed that one of the inner wheels looked slightly under-inflated. He reached into Rosie’s car and handed Bolin a small club she kept there, wooden, 2-ft long with a metal tip at one end, made by one of her sons back in Minnesota for her protection. Bolin could use it to knock on the tire and check the pressure. A practical solution to a minor problem. Bob Cales thought nothing of it beyond that.

Within a few hours, the Caleses could not raise Bolin on the radio. They tried repeatedly. The radio stayed silent. They waited past the point where waiting had a reasonable explanation and began to consider that he had simply stolen the wrecker and driven away with it. That was the first available theory, not the correct one, but the first one the facts supported.

Late that night, a faint transmission broke through on the radio they kept in their home. It was Bolin, his voice crackling in and out across the signal. He said he was lost somewhere in Pasco County. The call dropped before they could get a precise location from him. They heard nothing more until the following morning when Bolin finally returned to the lot at approximately 10:00. Rosie Cales looked at him when he walked through the door.

“He was in bad shape,” she said later.

She could see that he was afraid. She could not identify precisely what he was afraid of because he did not tell her, and she did not yet know enough to ask the right questions. Bob Cales fired him on the spot. The wrecker was returned to the lot. The accounts were settled. The other drivers went back to work. And the small wooden club with the metal tip, the one Bob Cales had handed over to check a tire pressure on a December afternoon, did not come back with the wrecker. Rosie Cales did not notice it was missing. There was no reason, on the morning of December 5th, 1986, for her to inventory what a fired trainee had returned with and what he had not.

The Murder of Natalie Blanche Holly

Somewhere in Hillsborough County that same morning, a jogger moving through an orange grove off Debuel Road came upon something that stopped him cold. A body. A young woman lying in the grass between the trees in the gray light of an early January morning. Her name was Natalie Blanche Holly. She was 25 years old.

Natalie Blanche Holly was 25 years old and known to the people who loved her almost exclusively by her middle name. They called her Blanche. She had grown up in the Tampa Bay area in circumstances that set her apart from most of the people she would later share the city with. Not in a way that she wore on her sleeve, but in a way that made her history more layered than it appeared from the outside. Her father, Charles Holly, was a lawyer from Pinellas County who had served in the Florida House of Representatives and risen to become the Republican minority leader before making a run for governor in 1964. He lost that race to Democrat Hayden Burns, a result that ended his political ambitions, and within a few years the marriage between him and Natalie’s mother fell apart. Charles Holly initiated the divorce in the early 1970s, leaving Natalie’s mother alone with two children, Blanche who was around 12 at the time, and her younger brother Carey.

Charles Holly died in 1981 before his daughter turned 21, and whatever reconciliation or resolution might have existed between them was left unfinished. Natalie’s mother, also named Natalie, rebuilt her life methodically and without self-pity. She had worked for the US State Department in West Germany and spoke multiple languages and held a master’s degree from Duke University. And she found work with the Social Security Administration in Tampa, balancing child-rearing with the kind of professional competence that makes other people’s lives look orderly from the outside, even when they are not. She worked downtown, wore heels to the office, sipped iced tea, and thought about her daughter with a frequency that only mothers understand.

Blanche Holly, by January of 1986, was working as the night manager at a Church’s Fried Chicken restaurant in Tampa. It was not the career her family’s background might have suggested, but she was capable and responsible, and the night shift suited her schedule. She managed the closing procedures, accounted for the registers, walked the floor before the lights went out, and made sure the restaurant was secured before she left. It was unglamorous work done with the quiet professionalism of someone who took seriously whatever task was in front of her, regardless of whether the task warranted it.

On the night of January 25th, 1986, Blanche finished her shift the way she finished every shift, methodically, without cutting corners. She locked up the restaurant with a colleague, said whatever was said between two people parting ways at 1:30 in the morning in a Tampa parking lot, and walked toward her car. The lot was quiet in the way that parking lots are quiet at that hour. Not peaceful, exactly, but empty, with the particular stillness of a place built for daytime activity that has no reason to exist after midnight, except as a geography for other things.

Oscar Ray Bolin Jr. was there. Oscar Ray Bolin moved on her before she could reach her car. He took her from that parking lot at 1:30 in the morning and drove her north through Hillsborough County, away from the restaurant and away from the streetlights, and away from anyone who might have seen what he was doing. He drove her to an orange grove off Debuel Road, east of US 41, more than 5 miles from where her car sat in the parking lot. He pulled her out of the vehicle and he stabbed her eight times in the chest, twice in the neck. He stabbed her through her clothes without pausing, without hesitation, with the directness of someone who had already decided exactly what he was going to do.

Two of the chest wounds were fatal. One reached her heart, one her lung. She had no time to raise her hands. There were no defensive wounds. The attack was so fast and so overwhelming that her body had not yet registered what was happening before the damage was done. The medical examiner established that she lost consciousness within approximately 2 minutes of the first fatal wound reaching her heart. 2 minutes. The length of a short song, the time it takes to boil water.

Oscar Ray Bolin left her there in the orange grove and drove away. She was wearing jewelry when she was found. She was wearing a tampon. She was lying in the grass between the trees in the gray light of an early January morning when a jogger came upon her and stopped. She was 25 years old.

The Impact of the Challenger Disaster

Three days after Oscar Ray Bolin left Blanche Holly’s body in that orange grove on January 28th, 1986, the space shuttle Challenger broke apart 73 seconds after launch above Cape Canaveral. Seven astronauts died. Among them was Christa McAuliffe, a school teacher from New Hampshire whose presence on the mission had made it feel to the vast television audience watching live like something that belonged to all of them.

The explosion happened in clear blue Florida sky in full view of the cameras, and the footage ran on every channel for days without interruption. The nation that had briefly turned its attention toward a young woman’s murder in a Tampa parking lot turned its attention somewhere else entirely. The tip lines went quiet. The reporters who had been covering the Holly case moved to Cape Canaveral. The ambient public pressure that a fresh murder investigation sometimes relies upon, the calls from neighbors, the witnesses who come forward because they saw the story on the news and recognized something, that pressure evaporated almost overnight.

Blanche’s mother noticed it. She said so plainly to anyone who asked her why the case seemed to go quiet in those early weeks. It was the Challenger explosion, she said, that made everybody forget. She did not forget. She kept calling the detectives. She kept asking questions. She kept her daughter’s name in whatever space she could hold open for it. But the investigation had lost the momentum that the first days after a murder sometimes generate, and what replaced it was the long, slow work of a case that the world had stopped watching.

The national grief was enormous and genuine and total. Memorial services were held across the country. President Reagan addressed the nation and quoted a poem about slipping the surly bonds of Earth and touching the face of God. Schools held moments of silence. Children who had watched the launch live in classrooms because a teacher was on board, because NASA had made a point of inviting them to watch, processed what they had seen in the halting way that children process things that adults cannot adequately explain.

In Tampa, the death of Natalie Blanche Holley receded behind it. Not because investigators stopped working the case, but because the public attention that a murder investigation sometimes relies upon to generate tips and witnesses and the kind of ambient pressure that keeps a case alive in a community, all of that attention moved elsewhere. Blanche’s mother noticed it. She said so directly to anyone who asked her why the investigation seemed to go quiet.

“It was the Challenger explosion,” she said, “that made everybody forget.”

She did not forget. She kept calling the detective assigned to the case, preserving whatever information came her way, maintaining the pressure that she alone seemed capable of sustaining. Her friends and former colleagues at the Social Security Administration remembered a woman who smiled but seldom laughed after January of 1986, who wore her grief the way some people wear formal clothing, present at all times, impeccably maintained, never quite removed.

The investigation had what it had. The 10 stab wounds, the shoe impressions, the hair and fiber samples, the location of the body 5 miles from the abandoned car. A white van had been seen in the area. Witnesses described it without being able to provide a license plate or a driver. The description opened more possibilities than it closed. Investigators followed the threads available to them and reached the point that cases reach when they refuse to break, where everything that can be done has been done and what remains is waiting.

Spring became summer, summer became autumn. The orange grove in Lutz sat unremarkable in the same northern Hillsborough County landscape it had always occupied. Her mother went to work each morning and came home each evening and thought about her daughter and waited for the phone to ring with news that did not come. Somewhere in the city, Oscar Ray Bolin Jr. continued his life without anyone connecting him to what had happened in that grove. He worked, he drove, he moved between jobs the way he had always moved between things, present for a time and then gone. Autumn was coming and with it November and somewhere in a shopping center in Carrollwood, a 17-year-old girl was picking up shifts at a drugstore saving money for Christmas and making plans she would not live to keep.

Stephanie Collins

Her name was Stephanie Ann Collins. She was saving money to buy Christmas presents for her family. Chamberlain High School sat in the Carrollwood area of Tampa, a school large enough to absorb the ambitions and anxieties of several hundred students without fully attending to any one of them. Stephanie Collins was a senior there in the autumn of 1986, which meant she was months away from graduation and the particular freedom that seniors carry around with them in the way that only people who have not yet left a place can carry freedom as pure anticipation uncontaminated by what comes after.

She sang in the school chorus. It was not a casual commitment. Chorus required rehearsal schedules and performances and the kind of regular attendance that distinguished the students who treated it as an elective from those who treated it as something that mattered. Stephanie Collins was in the second category. She showed up. She prepared. The director knew her name and her voice and had expectations of her that she worked to meet.

She also worked at the Eckerd drugstore on North Dale Mabry Highway in the Carrollwood Shopping Center not far from the school. It was a part-time job, the kind of employment that high school students took to cover their own costs and ease pressure off families already stretched thin. She worked the counter, managed the routine tasks of a retail pharmacy, and got along well enough with her manager that she felt comfortable coming in on days she was not scheduled to ask for more hours. The money was for Christmas. She was thinking about her family and what she could afford to give them.

On November 5th, 1986, Stephanie was not on the schedule. She drove to the shopping center anyway, walked into the store, talked to her manager about picking up additional shifts, and then walked back out toward her car. The lot was occupied in the way that strip mall parking lots are occupied on an early November afternoon. Cars moving in and out, people running errands, the ordinary traffic of a residential part of Tampa going about its business.