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Background

Oscar Ray Bolin was born in Portland, Indiana, on January 22nd, 1962. Many of his family members were involved with carnival work.

Bolin reportedly had a rough childhood as his father abused him. His mother didn’t treat him much better, and she once walked him to a bus stop on a leash to control him.

By the time he was a teen, he was acting out and committing crimes.

He went to Florida in the early 1980s for a fresh start, and like many of his family members, he became a carnival worker. Despite being in a new state and having a new job, he could not stay out of trouble.

Florida Crimes

In 1982, his girlfriend, Cheryl Haffner, told police he kidnapped her and drove her around the Tampa Bay area while refusing to let her take insulin for her diabetes. Police arrested Bolin and hit him with false imprisonment charges.

The charges were later dropped, and Haffner and Bolin married in 1983.

On January 25th, 1986, three days after his 24th birthday, he abducted  25-year-old Natalie Blanche Holley at around 1:30 am. She had just left her shift as a manager at a Church’s Fried Chicken in Tampa.

Someone found her dead body later that day in an orange grove near US Highway 41. She had been stabbed multiple times.

Bolin struck again on November 5th, 1986. He saw 17-year-old Stephanie Collins leaving her job at a Tampa drugstore. She was never seen alive again.

Her body was found one month later, on December 5th. Just likeHolley, she had been stabbed multiple times. Her skull was also crushed.

The same day authorities found Collins’s body, Bolin went north of Tampa to Pasco County and abducted 26-year-old Teri Lynn Matthews. Her car was found running with the door open just outside a post office.

Matthews was found later that day in a wooded area. She was wrapped in a sheet. Like the others, she suffered a horrible death as she was beaten and had her throat cut.

Bolin was not a suspect in the three murders.

Ohio Crimes

In 1987, he was in Toledo, Ohio, and he decided to kill again, but this time he had two buddies with him. They kidnapped a waitress and violated her. Bolin tried to put a bullet in her head, but the gun jammed.

They let the woman go on a highway in Pennsylvania.

Detectives in Toledo connected Bolin to the crime, and he pleaded guilty. He was given 22 to 75 years in prison. It’s unclear what happened to the other two men.

Breakthrough in the Florida murders

In 1989, Bolin’s wife Cheryl moved on with her life and divorced him. When she met a new man and remarried, she opened up to him and told him that Bolin had killed three women in 1986.

She also revealed that she was with Bolin before his first murder, and she helped him get rid of evidence.

Her husband called Crimestoppers in 1990 and told them that Bolin had killed Holley, Collins, and Matthews.

Authorities took the tip seriously. As the investigation progressed, Bolin was connected to the Greenville, Texas, murder of 30-year-old Deborah Diane Stowe on March 10th, 1987. His cousin told authorities he helped Bolin abduct her, and Bolin violated her. Then he watched Bolin kill her.

Texas never prosecuted Bolin for the murder of Stowe, but he was hit with charges for the three Florida murders.

Legal Proceedings

He was given his first death sentence for the murder of Holley in July 1991. He was convicted of the other murders at later trials, but legal issues led to convictions being tossed. Bolin would face a total of 10 trials for the murders between 1991 and 2012. Each time, he was convicted.

He ended up with death sentences for the murders of Collins and Matthews and a life sentence for the murder of Holley.

On January 6th, 2016, the day before his execution, Bolin spoke with a Florida reporter, and he maintained his innocence.

Execution Day

The following day, on January 7th, 2016, Bolin woke up at 6 am.

People inside the prison reported to ABC that he was “calm and in good spirits.”

Bolin had visiting hours from 8 am to 11 am. The Florida Department of Corrections said he only spent time with his wife, Rosalie. According to policy, physical contact was allowed during the final hour of the visit.

Bolin met with his spiritual advisor, Brother Dale Recinella, from noon until 2 pm.

After that, Bolin was served his last meal.

In Florida, inmates are allowed to pick specific foods and drinks, but they have to be under $40 and cannot include alcohol. That meal is then approved by the food service director, who prepares and serves it.

Bolin had medium-rare rib-eye steak, baked potato, salad, garlic bread, lemon meringue pie, and Coca-Cola.

According to Florida’s execution procedure, at around 4 pm, someone from the execution team speaks to the condemned to explain the lethal injection procedure. They also offer a sedative at that time, although it’s unclear if Bolin took anything.

The execution was supposed to occur at 6 pm, but it was delayed as the US Supreme Court reviewed Bolin’s two last-minute appeals.

While Bolin waited for a response, he was held up in his cell along with the Warden.

At 9:50, word came down that the appeals were denied.

Bolin was taken from his cell to the execution chamber, and he was strapped to the gurney.

Heart monitor pads were placed on his chest, followed by an IV line in each arm.

At the same time, Bolin was being strapped in, witnesses were being transported to the death house by van and escorted to the witness area.

Thirty-six people were on hand to watch Bolin take his last breath. Six reporters, family members from all three Florida victims, and Bolin’s attorney, Bjorn Brunvand, were some of the people there.

Florida law doesn’t allow families of the condemned to witness the execution, so Bolin’s wife and family were not in attendance.

The witnesses were seated by 10 pm, and the curtain opened at 10:04 pm.

Bolin had no interest in making eye contact with the families of his victims, and he stared at the ceiling during the process.

The Warden asked Bolin if he had any last words, and he said, “No, Sir.”

Bolin was injected with midazolam hydrochloride at 10:05 pm. Within moments, his eyes closed, and his mouth fell open.

At 10:09 pm, a prison official shook him, but there was no response.

He was hit with vecuronium bromide, which paralyzed him, and, last of all, potassium chloride, which stopped his heart.

Witnesses reported he stopped breathing at 10:13 pm.

He was pronounced dead three minutes later at 10:16 pm.