His crime? Stabbing and cutting the throat of a 29-year-old Lancaster woman, then leaving her for dead.
His punishment? Half of a 20-year sentence.
But this wasn't his first time in prison. In North Carolina, he was arrested in 1984 after robbing a Monroe, N.C., Burger King with a shotgun and kidnapping and raping a restaurant employee.
He served nine years of a 25-year sentence for the North Carolina crimes and was released in 1993. Less than a year later, he was arrested in the Lancaster case.
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Now, four years after his release from a South Carolina prison, Massey is in trouble again. Police say he kidnapped a woman leaving a Lancaster store on July 31, raped her, and tried to run over her with his vehicle. The victim was found running naked on S.C. 9.
Had he been convicted of all charges and served the maximum sentence in either of the first two cases, Massey would still be in prison. Instead, he received two plea deals and served no more than half his sentence in both cases.
Three times, Massey has been accused of kidnapping and raping women. In each case, police say he was armed. Incident reports, court records and newspaper stories offer chilling accounts of the crimes.
Because of the age of the Monroe case, no incident report was available at the Monroe Police Department.
The only court documents filed at the Union County (N.C.) Clerk of Superior Court are four index cards that indicate Massey was convicted of second-degree sexual offense, first-degree kidnapping and robbery with a dangerous weapon. A first-degree rape charged was dismissed as part of a plea deal.
Lancaster County authorities gained additional insight into the Monroe case while searching Massey's home after his recent arrest. There, they found a collection of police and court records from both the previous Monroe and Lancaster cases.
According to Union County arrest warrants found in Massey's house and provided to The Herald, Massey kidnapped and raped a 16-year-old girl. He used a shotgun to hold her against her will, the warrants stated.
During its coverage of the Burger King robbery, The (Monroe) Enquirer-Journal reported that on Feb. 17, 1984, a man wearing a dark blue ski mask and armed with a shotgun came into a Burger King around 5 a.m. and demanded money from three employees.
One employee was quoted as saying the robber pointed the shotgun at his face and pulled the hammer back when he asked how much money was there.
The robber took $65 from one employee's wallet and left with the woman, saying, "I'll leave her at the second light at the gas station," according to the article.
The woman was found more than two hours later at a Pizza Hut a mile away, the story said. She told authorities her kidnapper had dropped her off and left.
Several weeks later, Massey was charged in the Monroe case after Lancaster police arrested him on unrelated charges, the newspaper reported.
The paper quoted then Lancaster Police Chief Frank Harris as saying Massey, then 23, had gone to a Lancaster home a few hours before the Burger King robbery looking for someone. He forced his way inside the home and threatened a woman with a knife but didn't hurt her, the story said.
The paper doesn't say how authorities connected Massey to the Monroe case.
A transcript of a plea agreement found in Massey's house indicates he pleaded guilty to robbery with a dangerous weapon, first-degree kidnapping and second degree sexual assault in exchange for a 25-year sentence.
Thomas Church, who prosecuted the case in North Carolina, said he doesn't remember anything about it. Ronald Cox, Massey's defense attorney for the case, could not be reached for comment.
Massey was released in 1993, but any documents explaining the conditions of his parole have been destroyed, according to the N.C. Department of Corrections.
But Massey's shortened incarceration was not unusual for that time, said department spokesman Keith Acree. Under old sentencing guidelines, inmates were eligible for time credits "that greatly reduced their sentence," Acree said.
Even for violent offenders, sentences could be shaved for things like good behavior or inmate labor.
And during the late 1980s and early 1990s, North Carolina prisons were so crowded that Massey may have been paroled more quickly, Acree said. Most people sentenced to 25 years were actually in prison for only eight to 12, he said.
Because of the weak guidelines, Acree said, the state strengthened its sentencing laws in 1994.
Less than two months after his release in 1993, Massey was arrested in Lancaster County on charges of kidnapping, first-degree criminal sexual conduct and assault and battery with intent to kill.
An incident report states that around 11 p.m., Lancaster County sheriff's deputies respond to a call about a bloody, naked woman yelling "Help me!" at a door step.
When police arrived, the woman was unresponsive, the report stated. A man whose door she went to said she mumbled that she had been raped on a dirt road.
Massey lured the victim into his vehicle, offering to give her a short ride, according to arrest warrants. Then, he pulled out a knife and refused to let her go.
Massey took her to a secluded area, raped her, then stabbed her three times in the chest and stomach area and sliced her throat twice, warrants say. The woman was left for dead and had to spend several days in an intensive care unit.
The victim told investigators from her intensive care room that the man who attacked her was white, had a beard, wore glasses, looked to be in his mid-30s and drove a brown Toyota with a long radio antenna.
Later, a sheriff's office sergeant got a call from a woman who had taken down the license plate number of a dark brown Toyota, the report states.
Authorities learned Massey usually drove the vehicle. He also fit the description. Investigators showed the victim a photo lineup that included Massey's picture.
"(She) examined the line-up and upon seeing Massey's photo immediately turned to Det. Steele with a look of tremendous fright, began to tremble from head to foot and tears began to run down (her) face," the report states. "(She) could not speak."
Authorities tried to find Massey but couldn't locate him or the vehicle. Massey's father told police that his son didn't have a beard and there was no antenna on the back of his Toyota, the report stated.
A day after the conversation with Massey's father, Massey came to the sheriff's office to see why a detective wanted to see him, the report stated. He was immediately arrested. He told investigators he had nothing to say.
Massey's wife told investigators that she and her husband had taken the vehicle to her brother's home in Thomasville, N.C., according to the report. She said the car had been painted silver and the CB antenna had been removed. She also said her husband had shaved his beard.
Massey's mother told investigators that she knew her son didn't rape the victim because he told her he didn't have sex with her and he never lied to his mother, according to the report.
However, Massey's mother did say her son told her, "Mother, I tried to cut her ... head off," according to the report.
Court records show Massey pleaded guilty to assault and battery with intent to kill and was sentenced to 20 years in prison. The other charges were dismissed.
No document indicates why this plea agreement was reached. The late 6th Circuit Solicitor John Justice was the prosecutor. George Speedy, the Camden attorney representing Massey in the case, could not be reached for comment.
Just like North Carolina, South Carolina also had weaker sentencing guidelines at that time, authorities said. In 1996, the law was changed, requiring violent offenders to serve 85 percent of their sentence.
"Twenty years should be a long time," said Lancaster County Sheriff's Office spokesman Tom Holland. "That was the structure at the time. And fortunately, that part has changed somewhat. But still, I don't think he should've gotten out."
Inmate work experience and good behavior helped shorten Massey's stay in South Carolina's prison system, said Josh Gelinas, spokesman for the state Department of Corrections. Massey was released Oct. 31, 2003.
He was not placed on parole because his sentence was officially served through his time in prison, his work while in prison and good behavior, Gelinas said.
'It's like he's in another world'
Shortly before 10 p.m. July 31, a 29-year-old woman left a Meeting Street grocery store in Lancaster and loaded her toddler in a van. As she was walking to the driver's door, someone put a gun to her and forced her into his nearby car, Holland said.
He then drove her to a boat landing under the S.C. 9 bridge that connects Chester and Lancaster counties and raped her inside the car, authorities said.
The man then forced the woman outside the car and tried to rape her again, investigators said. During the scuffle, he set the gun down ,and the woman grabbed it. The attacker retreated to the car and tried to run her over as she escaped, authorities said.
The car never struck the woman, who was able to get back to S.C. 9. A passer-by found her running down the road naked, still holding the .22-caliber handgun.
Massey, a registered sex offender because of the Monroe, N.C., case, was arrested after detectives found his cell phone at the scene, investigators said. They were waiting for him when he came home.
Detectives don't know if Massey has assaulted any other women. Holland said he has been cooperative but added that he couldn't elaborate further because of the investigation.
Massey's criminal record dates back to 1978 and includes charges of marijuana possession, grand larceny, driving under the influence and kidnapping.
But other than a criminal history, court and police records don't offer much insight about Massey.
A North Carolina plea transcript found in Massey's house indicates he had a fourth-grade education at the time of his sentencing in Monroe. Another document says the Union County, N.C., court recommended that he receive treatment for epilepsy.
Court records from his 1993 case in Lancaster County show he was self-employed making $100 per week at the time of that arrest.
South Carolina corrections records indicate that he worked as a gardener, mechanic and custodian while in prison, said Gelinas, the department's spokesman.
Massey's mother, Mary, said she doesn't know what happened to her son.
"He worked every day," she said in an interview with The Herald. "Ain't missed a day's work in over two years."
Mary Massey said her son worked in a factory just across the North Carolina border, but she didn't know the name of it.
She said her lawyer is trying to get Jessie Wayne Massey a psychological evaluation. She wouldn't name her attorney.
"They think he snapped, but they don't know why," she said.
Mary Massey said her son's moods could quickly shift.
"He'll come and just sit on the porch and just talk, talk, talk," she said. "Day or two (later), he won't even speak to me. It's like he's in another world or something."
She ended the conversation quickly, saying she recently lost her husband and talking about her son was difficult.
"It just hurts too bad," she said.
Jessie Wayne Massey is being held without bond at the Lancaster County Detention Center. If convicted of the latest charges, authorities say he could be sentenced to life in prison without parole.