For years, Oscar Ray Bolin got away with the brutal murders of at least four women in Florida and Texas — until his ex-wife’s husband called the police to report that Bolin was responsible for the crimes.
Public DomainOscar Ray Bolin’s mugshot via the Florida Department of Corrections.
Throughout the late-1980s, police were baffled by four brutal murders that had taken place in Florida and Texas between 1986 and 1987. Then, in 1990, the husband of Oscar Ray Bolin’s ex-wife called in with a tip that Bolin was responsible for the horrific crimes.
A former carnival worker, Bolin was already serving time for the 1987 kidnapping and rape of a waitress in Ohio when he was implicated in the murders. He was eventually sentenced to death for these crimes. But even behind bars, Bolin wasn’t done making headlines.
While on death row, the serial killer engaged in a controversial jailhouse romance with Rosalie Martinez, a member of his legal team, whom he married in 1996. And despite the overwhelming evidence that Oscar Ray Bolin had raped and murdered several women, his new wife never stopped believing in his innocence.
The Early Life And Crimes Of Oscar Ray Bolin Before The Murders Began
Born on Jan. 22, 1962 in Portland, Indiana, Oscar Ray Bolin had a turbulent childhood.
Bolin grew up in a family of laborers and carnival workers. His father beat him, and Bolin reportedly ran away from home so many times that his mother once walked him to the school bus on a dog leash to ensure he wouldn’t escape.
His first run-in with the law came in 1977, when he was arrested for theft in Ohio at only 15 years old. In the 1980s, Bolin moved to Florida, where he worked a variety of odd jobs. It was around this time that Bolin exhibited his first signs of deviant behavior.
In 1982, his girlfriend at the time, Cheryl Haffner, reported Bolin to the authorities for kidnapping her. She claimed Bolin drove her around Tampa for hours, refusing to let her take her diabetes medication until he finally let her go. Despite this terrifying ordeal, Haffner agreed to marry Bolin. The two tied the knot in Hillsborough County in 1983.
Only three years later, Oscar Ray Bolin would begin murdering young women in the Tampa area.
Bolin’s Cross-Country Killing Spree
Public DomainBetween 1986 and 1987, Oscar Ray Bolin brutally murdered at least four women in Florida and Texas.
On Jan. 25, 1986, Oscar Ray Bolin abducted 25-year-old Natalie Blanche Holley after she finished her night shift at Church’s Fried Chicken. A jogger discovered her body a few hours later in an overgrown orange grove. Bolin had stabbed her ten times in the chest and the throat.
Then, on Nov. 5, 1986, Bolin kidnapped 17-year-old Stephanie Collins after she finished up her shift at a local drugstore. Her body was discovered a month later, on Dec. 5, 1986, wrapped in towels and sheets off the side of Morris Bridge Road. She had been stabbed, and her skull had been crushed.
That same day, 26-year-old Teri Matthews went missing from a post office parking lot, her car’s engine still running. She had just finished her shift at a bank in Tampa. Hours later, her body was found wrapped in a white sheet. Bolin had slit her throat and brutally bludgeoned her head.
In 1987, Oscar Ray Bolin, aided by his cousin, Douglas Tedrow, abducted 30-year-old Deborah Diane Stowe outside of a convenience store in Greenville, Texas. Bolin brutally raped Stowe in a truck before ultimately strangling her to death.
Finally, on Nov. 18, 1987, Bolin and two accomplices abducted and raped a 20-year-old woman at gunpoint near Toledo, Ohio. Surprisingly, Bolin decided to let her go in Pennsylvania, leaving her free to identify her attacker. This time, the authorities captured Bolin. A court later sentenced him to 22 to 75 years in prison.
Bolin’s marriage fell apart amid his criminal trial, and in 1989, Cheryl Haffner divorced him. She would go on to remarry — and soon, her new husband would help bring Oscar Ray Bolin to justice.
A Police Tip Brings Oscar Ray Bolin’s Crimes To Light
Public DomainBolin’s mugshot in 1991 (left) and his mugshot from 2015 (right).
In 1990, a man identifying himself as Cheryl Haffner’s husband called the police to report that Oscar Ray Bolin was responsible for three murders that had taken place in the Tampa area between 1986 and 1987. The man alleged that Haffner had not only known about her ex-husband’s crimes, but had even gone so far as to help Bolin cover up Natalie Holley’s murder in 1986.
During the investigation, the authorities discovered several more witnesses who claimed to have seen Bolin take part in the murders. Bolin’s half-brother, Phillip Bolin, told the police that he had watched Bolin try to drown Teri Matthews with a garden hose before bludgeoning her to death with a club in 1986. And Bolin’s cousin, Douglas Tedrow, confessed to having helped Bolin kidnap Deborah Stowe.
With eyewitness statements and forensic evidence connecting Oscar Ray Bolin to the crimes, Florida prosecutors finally charged him with the murders of Holley, Collins, and Matthews.
While awaiting his first murder trial, Bolin reportedly concocted an elaborate escape plan. During a visit, he was caught on tape plotting with his then-girlfriend, who happened to be his cousin, to kidnap the family members of Sheriff Walter Heinrich and several other top sheriff’s officials. He also reportedly admitted to being involved in a dangerous drug ring.
“They really think what they got is just a serial killer,” Bolin said in the recording, according to the Tampa Bay Times. “Which is fine with me.”
The plan was foiled, and Oscar Ray Bolin received an additional 15 years for the stunt.
A court ultimately found Bolin guilty of Holley’s murder, and in July 1991, he was sentenced to death. Bolin later received two additional death sentences for the murders of Collins and Matthews. He was also linked to the murder of Deborah Stowe, though Texas authorities declined to officially charge him for the crime.
Finally, Oscar Ray Bolin’s reign of terror was over. But his story didn’t end there.
Rosalie Martinez Woos Bolin While He’s Behind Bars
Rosalie MartinezRosalie Martinez, the woman who fell in love with serial killer Oscar Bolin.
In 1995, Oscar Ray Bolin’s convictions were all overturned. The Florida Supreme Court had determined that Cheryl Haffner’s testimony against her ex-husband violated spousal privilege, making it inadmissible. This meant that Bolin would have to return to court. And this time, he would do so with another woman by his side.
Rosalie Martinez met Bolin while working on his case as a paralegal at a public defender’s office in Hillsborough County, Florida. She quickly became convinced of his innocence.
“I never, never, ever thought for a second that he was guilty of those three murders,” she said in a 2015 20/20 interview.
Though Martinez was married to a prominent Tampa lawyer at the time and had four children, she fell in love with the serial killer. Martinez divorced her husband, who got primary custody of the couple’s children, and began to pursue a relationship with Bolin.
In 1996, the pair married in a ceremony that took place over the phone. For much of their controversial relationship, Martinez and Oscar Ray Bolin were only able to see each other twice a week. They were never granted conjugal visits, and reportedly never consummated their marriage.
Rosalie MartinezRosalie Martinez on the phone with Bolin during their wedding ceremony.
Meanwhile, Oscar Ray Bolin was still on the hook for the Tampa murders.
“This defendant burns a violent flame that must be extinguished,” prosecutor Michael Halkitis said of Bolin at his 1996 retrial for the murder of Teri Matthews.
Once again, Bolin was found guilty of the murders of all three Tampa victims.
For years, he insisted upon his innocence and continued to battle the court system, arguing his case in several additional retrials. But in the end, the outcome was the same: Bolin was sentenced to death.
On Jan. 7, 2016, Oscar Ray Bolin died by lethal injection in Florida State Prison. His last meal consisted of a rib-eye steak, a baked potato, salad, garlic bread, lemon meringue pie, and Coca-Cola.
According to the Daytona Beach News-Journal, shortly before his execution, Bolin declared: “My punishment’s over. They can’t hurt me no more.”
After reading about Oscar Ray Bolin, dive into the story Dennis Rader, the BTK killer who was caught after sending a floppy disk to the police. Then, read about Gary Ridgway, the Green River Killer who was caught with the help of Ted Bundy.
