Oscar Ray Bolin
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Oscar Ray Bolin Jr. (January 22, 1962 – January 7, 2016) was an American
serial killer A serial killer (also called a serial murderer) is a person who murders three or more people,An offender can be anyone: * * * * * (This source only requires two people) with the killings taking place over a significant period of time in separat ...
and convicted
rapist Rape is a type of sexual assault involving sexual intercourse, or other forms of sexual penetration, carried out against a person without consent. The act may be carried out by physical force, coercion, abuse of authority, or against a person wh ...
who was executed in Florida for murder. In 1986, Bolin kidnapped and murdered three young women in
Tampa, Florida Tampa ( ) is a city on the Gulf Coast of the United States, Gulf Coast of the U.S. state of Florida. Tampa's borders include the north shore of Tampa Bay and the east shore of Old Tampa Bay. Tampa is the largest city in the Tampa Bay area and t ...
. He was later connected to a fourth murder in
Texas Texas ( , ; or ) is the most populous U.S. state, state in the South Central United States, South Central region of the United States. It borders Louisiana to the east, Arkansas to the northeast, Oklahoma to the north, New Mexico to the we ...
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.


Early life

Bolin was born on January 22, 1962, in
Portland, Indiana Portland is a city in and the county seat of Jay County, Indiana, United States. The population was 6,320 at the 2020 census, History Portland was platted in 1837. It was named after Portland, Maine. The Jay County Courthouse, Portland Com ...
. His family consisted of laborers and carnival workers who were spread across multiple states including:
Florida Florida ( ; ) is a U.S. state, state in the Southeastern United States, Southeastern region of the United States. It borders the Gulf of Mexico to the west, Alabama to the northwest, Georgia (U.S. state), Georgia to the north, the Atlantic ...
,
Indiana Indiana ( ) is a U.S. state, state in the Midwestern United States, Midwestern region of the United States. It borders Lake Michigan to the northwest, Michigan to the north and northeast, Ohio to the east, the Ohio River and Kentucky to the s ...
,
Kentucky Kentucky (, ), officially the Commonwealth of Kentucky, is a landlocked U.S. state, state in the Southeastern United States, Southeastern region of the United States. It borders Illinois, Indiana, and Ohio to the north, West Virginia to the ...
and
Ohio Ohio ( ) is a U.S. state, state in the Midwestern United States, Midwestern region of the United States. It borders Lake Erie to the north, Pennsylvania to the east, West Virginia to the southeast, Kentucky to the southwest, Indiana to the ...
. 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. In 1977, he committed theft in Ohio at the age of 15 and was arrested. He later moved to Florida in the early 1980s and began working as a carnival worker. In 1982, his girlfriend, Cheryl Haffner, told authorities Bolin had kidnapped her and driven her around the
Tampa Bay Tampa Bay is a large natural harbor and shallow estuary connected to the Gulf of Mexico on the west-central coast of Florida, comprising Hillsborough Bay, McKay Bay, Old Tampa Bay, Middle Tampa Bay, and Lower Tampa Bay. The largest freshwater i ...
area for hours. He was arrested for false imprisonment, but the charge was dropped. In 1983, the two were married in
Hillsborough County, Florida Hillsborough County is located in the west-central portion of the U.S. state of Florida. In the 2020 census, the population was 1,459,762, making it the fourth-most populous county in Florida and the most populous county outside the Miami metro ...
.


Murders

On January 25, 1986, 25-year-old Natalie Blanche Holley, a night manager at a
Church's Fried Chicken Church's Texas Chicken is an American fast food restaurant chain that specializes in fried chicken and is headquartered in Atlanta, Georgia. The chain was founded as Church's Fried Chicken To-Go by George W. Church Sr. in April 1952, in San Anto ...
restaurant in
Tampa Tampa ( ) is a city on the Gulf Coast of the United States, Gulf Coast of the U.S. state of Florida. Tampa's borders include the north shore of Tampa Bay and the east shore of Old Tampa Bay. Tampa is the largest city in the Tampa Bay area and t ...
, 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 George D. Chamberlain High School is a public high school in Tampa, Florida, United States. It was opened in 1956 on North Boulevard (on the corner of Busch Boulevard). The school is named in honor of George D. Chamberlain, who served for several ...
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.


Investigation

In 1987, Bolin and two other men kidnapped and raped a 20-year-old waitress in
Toledo, Ohio Toledo ( ) is a city in Lucas County, Ohio, United States, and its county seat. It is located at the western end of Lake Erie along the Maumee River. Toledo is the List of cities in Ohio, fourth-most populous city in Ohio and List of United Sta ...
. Afterward, Bolin attempted to kill her with a gun, but the gun jammed. He let the woman go along a highway in
Pennsylvania Pennsylvania, officially the Commonwealth of Pennsylvania, is a U.S. state, state spanning the Mid-Atlantic (United States), Mid-Atlantic, Northeastern United States, Northeastern, Appalachian, and Great Lakes region, Great Lakes regions o ...
. Bolin was captured and was sentenced to 22 to 75 years in prison. 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. Bolin's cousin confessed to aiding Bolin in abducting 30-year-old Deborah Diane Stowe outside a convenience store in
Greenville, Texas Greenville ( ) is the county seat of and the most populous city in Hunt County, Texas, United States, located in Northeast Texas approximately northeast of Dallas, Texas, Dallas and northwest of Canton, Texas, Canton. As of the 2020 United Stat ...
, 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. 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.


Execution

Bolin was interviewed by
WTVT WTVT (channel 13) is a television station licensed to Tampa, Florida, United States, serving as the Fox network outlet for the Tampa Bay area. Owned and operated by the network's Fox Television Stations division, WTVT maintains studios on Ken ...
on the day before his execution. When talking about his upcoming execution, Bolin continued to claim he was innocent and had been framed, and described his execution as a release from his punishment, having been locked up in prison for the past 28 years. Bolin was
executed Capital punishment, also known as the death penalty and formerly called judicial homicide, is the state-sanctioned killing of a person as punishment for actual or supposed misconduct. The sentence (law), sentence ordering that an offender b ...
by
lethal injection Lethal injection is the practice of injecting one or more drugs into a person (typically a barbiturate, paralytic, and potassium) for the express purpose of causing death. The main application for this procedure is capital punishment, but t ...
at 10:16 p.m. EST on January 7, 2016. He was the first person to be executed in the United States in 2016. His
last meal A condemned prisoner's last meal is a customary ritual preceding execution. In many countries, the prisoner may, within reason, select what the last meal will be. Contemporary restrictions in the United States Contrary to the common belief t ...
consisted of a rib-eye steak, a baked potato, salad, garlic bread, lemon meringue pie, and Coca-Cola. He declined to make a final statement. The next execution in Florida did not occur until over nineteen months later when
Mark Asay Mark James Asay (March 12, 1964 – August 24, 2017) was an American spree killer who was executed by the state of Florida for the 1987 racially motivated murders of two men in Jacksonville, Florida. He was convicted, sentenced to death, and su ...
was executed for the murders of two men in
Jacksonville Jacksonville ( ) is the most populous city proper in the U.S. state of Florida, located on the Atlantic coast of North Florida, northeastern Florida. It is the county seat of Duval County, Florida, Duval County, with which the City of Jacksonv ...
.


See also

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Capital punishment in Florida Capital punishment is a legal penalty in the U.S. state of Florida. Since 1976, the state has executed 112 convicted murderers, all at Florida State Prison. As of June 11, 2025, 270 offenders are awaiting execution. History Prior to 1923, ...
*
Capital punishment in the United States In the United States, capital punishment (also known as the death penalty) is a legal penalty in 27 states (of which two, Oregon and Wyoming, do not currently have any inmates sentenced to death), throughout the country at the federal leve ...
*
List of people executed in Florida The following is a list of people executed by the U.S. state of Florida since capital punishment was resumed in the United States in 1976. The total amounts to 112 people. Of the 112 people executed, 44 have been executed by electrocution and 68 ...
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List of people executed in the United States in 2016 Twenty people, all male, were executed in the United States in 2016, all by lethal injection. The state of Georgia executed nine people, setting a record for the most executions conducted there in a calendar year. List of people executed in the U ...
*
List of serial killers in the United States A serial killer is typically a person who kills three or more people, with the murders taking place over more than a month and including a significant period of time between them. The Federal Bureau of Investigation (FBI) defines serial murder a ...


References

! colspan="3" , Executions carried out in Florida , - ! colspan="3" , Executions carried out in the United States {{DEFAULTSORT:Bolin, Oscar Ray 1962 births 2016 deaths 20th-century American murderers 21st-century executions by Florida 21st-century executions of American people American male criminals American people convicted of rape Executed American serial killers Executed people from Indiana People convicted of murder by Florida People executed by Florida by lethal injection People from Portland, Indiana Serial killers from Florida Serial killers from Texas