Oscar Ray Bolin

Killer

Birthday January 22, 1962

Birth Sign Aquarius

Birthplace Portland, Indiana, U.S.

DEATH DATE 2016, Florida State Prison, Raiford, Florida, U.S. (54 years old)

Nationality United States

#37028 Most Popular

1962

Oscar Ray Bolin Jr. (January 22, 1962 – January 7, 2016) was an American serial killer and convicted rapist who was executed in Florida for murder.

Bolin was born on January 22, 1962, in Portland, Indiana.

His family consisted of laborers and carnival workers who were spread across multiple states including: Florida, Indiana, Kentucky and Ohio.

His father used to beat him when he was a child and his mother once walked him to a school bus stop on a leash.

Bolin frequently got into trouble with the law during his youth.

1977

In 1977, he committed theft in Ohio at the age of 15 and was arrested.

1980

He later moved to Florida in the early 1980s and began working as a carnival worker.

1982

In 1982, his girlfriend, Cheryl Haffner, told authorities Bolin had kidnapped her and driven her around the Tampa Bay area for hours.

He was arrested for false imprisonment, but the charge was dropped.

1983

In 1983, the two were married in Hillsborough County, Florida.

1986

In 1986, Bolin kidnapped and murdered three young women in Tampa, Florida.

On January 25, 1986, 25-year-old Natalie Blanche Holley, a night manager at a Church's Fried Chicken restaurant in Tampa, finished work and locked up the store for the night with a colleague.

She left the store around 1:30 a.m. and headed to her car.

Her body was found hours later by a morning jogger.

She had been stabbed to death.

On November 5, 1986, 17-year-old Stephanie Collins, a Chamberlain High School student, disappeared after finishing her shift at a drug store.

On December 5, 1986, her body was found wrapped in sheets and towels.

She had been stabbed to death and her skull was also crushed.

The same day Collins' body was found, 26-year-old Teri Lynn Matthews went missing.

Her car was found outside a post office with the engine still running.

Her body was located later that day in some woods, wrapped in a white sheet.

Her throat had been cut and she had been bludgeoned.

1987

He was later connected to a fourth murder in Texas in 1987.

The murders went unsolved for nearly four years, until the husband of his ex-wife called a tip line and implicated him.

He maintained his innocence to the end.

In 1987, Bolin and two other men kidnapped and raped a 20-year-old waitress in Toledo, Ohio.

Afterward, Bolin attempted to kill her with a gun, but the gun jammed.

He let the woman go along a highway in Pennsylvania.

Bolin was captured and was sentenced to 22 to 75 years in prison.

Bolin's cousin confessed to aiding Bolin in abducting 30-year-old Deborah Diane Stowe outside a convenience store in Greenville, Texas, in 1987.

He testified that Bolin had raped and strangled the woman.

Texas prosecutors declined to seek an indictment in the case because Bolin was already charged with multiple murders in Florida.

1989

In 1989, Haffner divorced Bolin and later remarried.

She told her new husband that Bolin had told her about committing multiple murders.

Haffner's new husband then called a tip line and implicated Bolin.

More witnesses then came out to testify against him, including his younger half-brother and a cousin.

Haffner testified that she had been with Bolin before he kidnapped Holley and had helped him dispose of some evidence.

Bolin's half-brother testified that he watched Bolin beat Matthews and attempt to drown her with a garden hose.

1991

Bolin was found guilty and was sentenced to death in July 1991 for the murder of Holley.

He was later sentenced to death again for the murder of Collins and received a third death sentence for the murder of Matthews.