Oscar Bolin

Victims
3 murder convictions, from ten jury verdicts. A cousin also tied him to a 1987 Texas killing that was never charged
Years active
January 25, 1986 to December 5, 1986
Location
Florida, USA
Method
Abduction, then stabbing and beating
Status
First sentenced to death in July 1991. Every verdict reversed at least twice; ten juries convicted him. Executed at Florida State Prison, Starke, January 7, 2016

Teri Lynn Matthews was twenty-six, a former high school cheerleader who worked nights at a bank so she could take scuba lessons by day. She had a serious new boyfriend and had just bought a mobile home, which she was fixing up so she could move out of her parents' house in Pasco County, north of Tampa. When she was late home from work on the morning of December 5, 1986, her mother, Kathleen Reeves, assumed she was with the boyfriend, until he called asking for her. Her car was found outside a post office with the engine running. Her body was found later that day in woods, wrapped in a white sheet; her throat had been cut and she had been bludgeoned. The same day, the body of a seventeen-year-old girl missing for a month was found wrapped in sheets and towels.

The man convicted of both killings, and of a third that year, was Oscar Ray Bolin Jr., born on January 22, 1962, in Portland, Indiana, into a family of laborers and carnival workers spread across Florida, Indiana, Kentucky and Ohio. His father beat him, and his mother once walked him to the school bus stop on a leash. He was arrested for theft in Ohio in 1977, at fifteen, and moved to Florida in the early 1980s to work the carnivals. In 1982 his girlfriend, Cheryl Haffner, told police he had kidnapped her and driven her around the Tampa Bay area for hours; he was arrested for false imprisonment and the charge was dropped. They married in Hillsborough County the next year.

On January 25, 1986, Natalie Blanche Holley, twenty-five, night manager of a Church's Fried Chicken in Tampa, locked up with a colleague and walked out to her car at about 1:30 in the morning. A jogger found her body a few hours later. She had been stabbed to death. Stephanie Collins, seventeen, a student at Chamberlain High School, disappeared after her shift at a drugstore, from a shopping center parking lot; one account dates it November 5, 1986, another to October. She had been stabbed and her skull crushed.

In 1987 Bolin and two other men kidnapped and raped a twenty-year-old waitress outside Toledo, Ohio. He tried to shoot her, the gun jammed, and he let her go beside a highway in Pennsylvania. He was caught and sentenced in Ohio to twenty-two to seventy-five years. That same year, according to a cousin who later confessed to helping him, he abducted Deborah Diane Stowe, thirty, outside a convenience store in Greenville, Texas, raped her in a truck and strangled her. Texas prosecutors never sought an indictment, because Florida had already charged him with murder.

Cheryl Haffner divorced him in 1989 and remarried, and she told her new husband that Bolin had told her in 1986 about the killings. In 1990 the new husband called an anonymous tip line. Other witnesses followed. Haffner testified that she had been with Bolin before he took Holley and had helped him get rid of evidence. His younger half-brother testified that he had watched Bolin beat Teri Lynn Matthews and try to drown her with a garden hose.

In July 1991 he was convicted of Holley's murder and sentenced to death, and further death sentences followed for Collins and for Matthews. Then the verdicts began to fall. Every one of them, in all three cases, was reversed by appeals courts at least twice for legal errors, and each time a new jury convicted him again, ten juries in all. Juries returned death sentences again for Matthews and Collins. On April 19, 2012, a jury in Tampa found him guilty of second-degree murder in the Holley case, which turned that death sentence into life. The mothers of the three women went to many of the trials together. Holley's mother died that year.

During one of the trials Bolin and a paralegal at the Hillsborough Public Defender's office, Rosalie Martinez, who was married to a prominent Tampa lawyer, fell in love. She divorced her husband and married Bolin on live television in 1996. As Rosalie Bolin she maintained that he was innocent of the Matthews killing and became one of Florida's most outspoken opponents of the death penalty.

Governor Rick Scott signed a death warrant in October 2015 for the murder of Teri Lynn Matthews. Kathleen Reeves took it, rolled up inside a bouquet of flowers, to her daughter's grave on what would have been her fifty-fifth birthday. In his last motions Bolin argued that an Ohio inmate had confessed to the Matthews murder; the inmate had killed himself in late 2014, and the courts denied a stay. The day before, he told the Tampa television station WTVT that he was innocent and had been framed, and called the execution a release after twenty-eight years locked up. The execution was set for six in the evening on January 7, 2016, and waited until the U.S. Supreme Court turned down his final appeal without comment. Asked whether he wanted to make a statement, he said, "No, sir." He was pronounced dead by lethal injection at 10:16 p.m. at Florida State Prison in Starke, the first person executed in the United States that year. Reeves said it did not matter that he was being executed for only one of the three killings, "because he only dies once." His lawyer, Bjorn Brunvand, wept as he spoke to reporters afterward.