Florida serial killer Oscar Ray Bolin Jr.'s date with death finally nears

Oscar Ray Bolin Jr. chats with his attorney in 1996 before a sentencing hearing in front of Judge William Webb, who pronounced a death sentence in the 1986 murder of Teri Lynn Matthews of Land O’Lakes.
Oscar Ray Bolin Jr. chats with his attorney in 1996 before a sentencing hearing in front of Judge William Webb, who pronounced a death sentence in the 1986 murder of Teri Lynn Matthews of Land O’Lakes.
Published Dec. 26, 2015

The bride stood in a pink gown beside a priest in a Gainesville apartment. A 5x7 photograph of the groom sat on the kitchen counter. His voice was piped in on a speakerphone, a collect call from the Pasco County jail.

That's how 12 million TV viewers watched serial killer Oscar Ray Bolin Jr. say "I do."

The 1996 wedding of Bolin and Rosalie Martinez, a onetime member of his defense team who left her prominent lawyer-husband to marry a man destined for death row, was a spectacle recounted in countless news stories.

But before the bizarre nuptials, before the murder trials, the retrials and appeals, before the eight death sentences and two life sentences, there was the long-haul truck driver known as "Needles" and the three young women who had the misfortune of crossing his path.

Bolin, 53, is now set to die by lethal injection on Jan. 7.

"This person deliberately took these girls," said Kathleen Reeves, the mother of Teri Lynn Matthews, whose murder may finally mean the end for Bolin. "It's somebody that needs to be dealt with. And this is the way we deal with criminals like this."

• • •

It started with a phone call.

An anonymous tipster phoned an Indiana Crime Stoppers line in 1990 and implicated Bolin in the three murders.

Natalie Blanche Holley, 25, was the first. She was the night manager of a Church's Fried Chicken restaurant on E Fowler Avenue in Tampa.

She vanished after finishing her shift there Jan. 25, 1986. Her body was found the same day in an orange grove off Debuel Road, east of U.S. 41. She was stabbed 10 times.

Stephanie Collins was a 17-year-old Chamberlain High School student who worked part time at a drugstore in Carrollwood. She was last seen there Nov. 5, 1986, walking to her car.

Her body was found a month later off Morris Bridge Road, wrapped in sheets and towels. She was stabbed, her skull crushed. Her Chamberlain class ring helped identify her body.

The same day, Dec. 5, 1986, Teri Lynn Matthews disappeared. The 26-year-old never showed up at her parents' Land O'Lakes home after working the night shift at a Tampa bank.

Her car was found parked at the Land O'Lakes post office, engine running, driver's door left open. Her mail lay scattered.

Her body was found hours later, wrapped in a damp white sheet in the woods off Coon Hide Road, west of U.S. 41. Her throat had been cut, her head bludgeoned.

Bolin's name never surfaced in the investigations. Until that call.

• • •

He came from a sprawling family of carnival workers and laborers spread throughout Indiana, Ohio, Kentucky and Florida.

His father beat him. Once, his mother walked him to a school bus stop on a leash because he ran away so much.

He racked up a smattering of arrests in his youth. His first, for theft, came in 1977 in Ohio. He was 15. He moved to Florida in the early 1980s.

In 1982, his then-girlfriend, Cheryl Haffner, told Tampa police he abducted her, drove her around the bay area for hours and refused to let her take insulin for her diabetes.

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He was arrested on a false imprisonment charge, but it was later dropped. The next year, he and Haffner married in Hillsborough County. They divorced in 1989.

Investigators later learned it was her new husband who called in the 1990 tip that led them to Bolin. The remarried Cheryl Coby said Bolin told her about the three murders in 1986. She was with him before he kidnapped Holley and helped him dispose of the evidence.

By the time investigators started looking at Bolin for the murders of Holley, Collins and Matthews, he was already in an Ohio prison for a 1987 rape.

In that case, he and two other men took turns assaulting a 20-year-old woman as they rolled across the state in a semitrailer truck. Bolin held a gun to her head and pulled the trigger, but it didn't fire. They let her go along a Pennsylvania highway.

By the time he was brought back to Florida, a task force was looking for possible connections to slayings in 26 states. But aside from the three bay area victims, Bolin was officially linked to just one other murder: the strangulation of Deborah Diane Stowe, 30, in 1987 in Greenville, Texas.

His cousin, Douglas Tedrow, told authorities that he and Bolin abducted Stowe outside a convenience store and raped her in a truck before Bolin killed her.

Texas prosecutors declined to seek an indictment in the case. Bolin was all Florida's.

• • •

While awaiting his first murder trial in the Hillsborough County jail, Bolin concocted an elaborate escape plan. It involved kidnapping the relatives of then-Sheriff Walter Heinrich and several high-ranking sheriff's officials and holding them hostage.

The plot was uncovered after Bolin and his girlfriend, who was also his first cousin, were heard discussing it during a visit. Investigators recorded the whole thing. On the tapes, Bolin told wild tales about being connected to a lucrative drug ring.

"They really think what they got is just a serial killer," he said. "Which is fine with me."

The plot netted him a 15-year sentence.

Later on, he swallowed 10 sleeping pills and had to be hospitalized. He left a suicide note for a sheriff's captain. He wrote that if investigators wanted more information, they could get it from Coby, his ex-wife.

Her testimony helped convict him in his first three murder trials. It was backed up by forensic evidence and the words of other witnesses.

One of those was Phillip Bolin, his younger half brother. The younger Bolin, who was 13 in 1986, told a Pasco County jury about the night his brother woke him, brought him outside his home, and showed him a body wrapped in a sheet. He heard a whimpering noise.

He said his older brother claimed it was a woman who had been shot in a drug deal outside the Land O'Lakes post office.

Phillip Bolin said he watched his brother straddle the woman's body, try to drown her with a garden hose and beat her with a wood club.

• • •

Oscar Ray Bolin Jr.'s first death sentence came in July 1991 for Holley's murder.

He got his second three months later for Collins' death.

The third, for Matthews, came a year after that.

But by 1995, all three of his convictions had been overturned. The Florida Supreme Court said jurors shouldn't have heard Coby's testimony because Bolin never waived his "spousal privilege," a legal doctrine that prevents spouses from testifying against each other. Coby died from diabetes complications after the third trial.

Before a 1996 retrial of the Matthews case, Phillip Bolin recanted his story. Later, in court, he recanted his recantation.

He said his brother's new wife, now known as Rosalie Bolin, pressured him to say he made it up. At one point, a judge barred her from the courtroom after she shook her head during Phillip Bolin's testimony.

Oscar Ray Bolin Jr. was convicted three more times. His defense told juries about his troubled childhood. The state questioned psychological experts who dubbed him a "moral imbecile" and a "psychopath."

"This defendant burns a violent flame that must be extinguished," prosecutor Michael Halkitis told the second jury in the Matthews case in 1996.

Three more juries voted for death. One, in the Collins case, took seven minutes to decide.

But again, higher courts overturned the convictions because of legal errors.

A death sentence stuck in 2001. It was Bolin's third conviction for Matthews' murder. Still, he continued to haunt courthouses in Pasco and Hillsborough counties.

The mothers of all three victims sat through trial after trial.

In a 2005 retrial for Holley's murder, a jury decided for the first time not to convict him of first-degree murder. Instead, the jury found him guilty of second-degree murder, which carries a life sentence. That drew the shock and ire of the families of the three women he killed.

"While on the outside the mothers are poised, on the inside, they are filled with tears and anger," Holley's half sister, Anita Holley, said before the 2005 sentencing. "If you, Oscar, were put in an empty room with these three mothers, you would be dead within 30 minutes."

Another death sentence, for Collins' murder, came in 2007.

In 2012, at Bolin's 10th and final trial, he was handed another life sentence.

"He'll be back," said Kathleen Reeves, the mother of Teri Lynn Matthews. "He's like a bad penny."

On Dec. 17, the Florida Supreme Court denied a request to stay Bolin's execution. His attorneys are pursuing an appeal to the U.S. Supreme Court.

Contact Dan Sullivan at or (813) 226-3386. Follow @TimesDan.