Gary Ray Bowles started his eight-month murderous binge in Daytona Beach by killing John Hardy Roberts on March 14, 1994, inside the victim's beachside home. Now he is set to be the 99th death row inmate executed in Florida in modern times.

DAYONA BEACH, Fla. — The killing spree began in Daytona Beach.

Eventually, in 1994, six men were savagely beaten and choked. One was bludgeoned with a discarded toilet.

Each man fought for his life, but lost.

In every case, the victims had something crammed down their throats — a towel, wads of toilet paper, a fistful of dirt.

On Thursday, their killer, Gary Ray Bowles, is scheduled to be executed by lethal injection.

Executions mark the end of some of society's most heinous killings, but they also elicit objections to the practice of state-sponsored death. Holding the opposing view may become more difficult when it is argued on the behalf of an unrepentant serial murderer like Bowles, but there is still no end to the debate about the death penalty's value.

Bowles, 57, started his eight-month homicidal binge by killing John Hardy Roberts, 59, on March 14, 1994, inside the victim’s beachside home in Daytona Beach. He was arrested a few days after killing his sixth victim, Walter Hinton, 42, in Jacksonville on Nov. 20, 1994.

Bowles committed three murders in Florida — in Daytona Beach, Jacksonville and Hilliard. He killed two other men in Georgia — one in Savannah and the other in Atlanta. He also murdered a man in Wheaton, Maryland.

He would say to the world during a television interview years later how remarkably easy it was to kill someone. Yet every killing he carried out was a bloodbath.

“Each of the murders was brutal,” said Bernie de la Rionda, a long-time Jacksonville-area homicide prosecutor who sought and attained a conviction and death sentence for Bowles.

De la Riona said in every case the victims fought vigorously while suffering from “unexplainable pain” at the hands of their killer.

“It was not an instant death,” he said. “It (wasn’t) like somebody getting shot and dying from that gunshot. … It was a life-and-death struggle.”

De la Rionda, 62, has tried close to 100 homicide cases during his career, with roughly a third of them resulting in death sentences. He attended his first execution in August 2017, when Mark Asay was put to death. Barring any last-minute reprieves, Thursday will be his second.

Few of de la Rionda's successful prosecutions involved anyone who compared to Bowles' notoriety. The elusive serial murderer, dubbed the “I-95 Killer” during a months-long manhunt, was profiled on TV's “America’s Most Wanted” five times and was added to the FBI’s Ten Most Wanted Fugitives list.

Bowles did not answer a News-Journal request last week for an interview.

Learning to hustle

Gary Ray Bowles was born Jan. 25, 1962, in Clifton Forge, Virginia, but he wasn’t raised there. His father died from black lung disease six months before he was born.

While a child, he moved from place to place as his mother married again and again. At least two of Bowles’ stepfathers physically and mentally abused him, according to court testimony.

He told an interviewer in 2013 that he fought back against the last stepfather who beat him, but it didn’t end well. His mother came to the defense of her husband and not her son. Overflowing with resentment, Bowles left home at 14.

With only a middle school education, Bowles discovered a way to earn money. Starting in his teen years, he prostituted himself to gay men.

Tom Youngman, a retired homicide and crime scene investigator with the Daytona Beach Police Department, was one of a battery of investigators who interviewed Bowles following his arrest. He asked Bowles why he chose gay men as his murder victims.

“He said they only perform an act on him and he never did (to) them,” Youngman said last week. “I said, ‘Well, that’s homosexuality,' and he says, ‘No.’

“Then what are you if you’re not a homosexual?” Youngman asked Bowles.

“I’m a hustler,” Bowles replied.

Bowles drifted around the country while a teen. He lived in Illinois, Louisiana, Missouri and Florida. His first arrest, a marijuana charge, came at 17.

In 1982, at age 20, Bowles was sentenced to eight years in prison in Hillsborough County for sexual battery with a weapon. The victim was tortured and her wounds were severe.

John Best, a retired Savannah police homicide detective, said he uncovered a lot of heinous details about Bowles’ criminal life. The 1982 sexual battery in Tampa, he said, was the work of a sadist.

Best provided to The News-Journal a copy of the Florida Department of Corrections Probation Post-Investigation Report related to Bowles' case in which a Tampa police detective stated, "I have never ever seen a case this bad. I have seen better pictures of victims in a morgue."

Bowles served less than three years following his sexual battery conviction and wound up in Volusia County, where he was arrested on robbery and grand theft charges and sentenced to five more years behind bars. He served less than half of his sentence before being paroled again in December 1993.

He gravitated to the bar scene in Daytona Beach. He knew that’s where he could find victims to hustle.

During his time there, he fell for an older woman and lived with her in an apartment on Fairview Avenue. She left him, according to news reports, after she learned how he made money with gay men. Bowles later told police she also had an abortion of his child without telling him.

That, he told authorities, was what led him to hate homosexuals. He blamed them for killing his unborn child.

Before he and the woman broke up, Bowles had met 59-year-old John Hardy Roberts at a beachside bar, the Barn Door on Main Street. Roberts was a single gay man who lived near the Boardwalk.

Shortly after his girlfriend left him, Bowles moved in with Roberts.

Bowles kept pining for his lost girlfriend after he moved in to Roberts’ home. Roberts didn’t like that. He told his new companion he had to make a choice.

The killing starts

Roberts, a native of Tennessee, lived at 504 Vermont Ave.

A friend of his came over to his house on March 15, 1994. No one had seen or heard from Roberts in more than 24 hours.

Every door and window was locked, so the friend broke a rear kitchen door and entered. He found his friend lying on the living room floor. He was bloodied and had a towel stuffed in his mouth.

Daytona Beach police were called to the home. A stream of blood had run from Roberts’ head to a nearby bedroom.

There was a marble-top table overturned. Shards of glass were spread across the room. Food had been flung onto the floor. A broken lamp lay on the couch where it appeared Roberts had been sitting before he was attacked.

“He probably snuck up on him,” Youngman said. “When I talked to (Bowles), that’s what he said. He picked the lamp up, came up behind him and then hit him and then he struggled.”

The struggle was ferocious. One of Roberts’ fingertips was nearly torn off.

The stream of blood that flowed out of Roberts' body indicated he didn’t die quickly. One only bleeds out that much while the heart is still pumping, Youngman said.

Roberts was beaten and choked by his killer. Detectives later said Bowles killed Roberts after the latter gave him an ultimatum — choose me or your ex-girlfriend.

Police spoke to a neighbor who had come home from work around 4 p.m. the day after Roberts was murdered. She reported seeing a man in his 30s “casually standing” in front of Roberts’ house. He was sipping from a mug and behaving as though nothing was wrong. When she walked back outside a few moments later, the man was gone. Police were called hours later and found the body.

A couple days after the news broke about Roberts murder, The News-Journal published Bowles’ name. Police said at the time that Bowles was not a suspect. They needed information from him.

Behind the scenes, investigators had their suspicions.

“We certainly wanted to talk to him,” said Alison Sylvester, a former Daytona Beach police detective who was the lead investigator in the case.

She said a piece of paper was found underneath the flipped table. It was from Probation and Probation Services and it had Bowles’ name and case number on it.

“That nice calling card that he left with his name on it, that was helpful," Sylvester said last week.

A camera from an ATM also captured an image of a smiling Bowles attempting to use Roberts’ bank card. He failed to extract any cash from the machine, but did make use of Roberts’ credit cards and car. He headed north and bought gas and food at various convenience stores before dumping the car near Nashville, Tennessee. That’s where police lost track of him.

He showed up weeks later in Washington D.C.

Killing spree

Bowles’ next murder victim was found in Maryland. David Jarman of Wheaton was found strangled in his home on April 14, 1994.

Witnesses said they saw Jarman with Bowles in a bar in DuPont Circle, a historic district of Washington, D.C. patronized by gay men. The pair left together and Jarman was never seen alive again.

Authorities said a sex toy had been crammed down Jarman’s throat.

The victim's driver’s license, credit cards and vehicle were stolen. Bowles used one of Jarman’s credit cards to book a motel room in Baltimore, according to a story the Washington Post published after the killing.

Again, Bowles remained one step ahead of law enforcement.

In some respects, Bowles was sloppy, Youngman said. There is no other way to explain how he could leave behind such an obvious clue as a parole and probation document at a crime scene and then try to get cash with a stolen ATM card a mile or so away from the victim’s home. On the other hand, he was an experienced drifter. Bowles knew how to remain on the lam.

Bowles headed south again and settled — at least for a few days — in Savannah.

There, he killed 72-year-old Milton Bradley.

A World War II veteran, Bradley suffered a shrapnel wound during the war and later underwent a lobotomy. He was slow, but his pension and his family sustained him financially and locals looked out for him. He was regularly seen around town.

Bowles hung out with Bradley at a tavern on Lincoln Avenue. The two left together and Bowles drove him to an abandoned utility shed on a golf course and killed him.

“It was a violent crime scene,” said retired detective John Best, who had just started investigating homicides for Savannah police. “It was overkill.”

The men in Savannah's gay community were very willing witnesses. Bowles had come on to some of them and they came away “creeped out,” Best said. They had seen him with Bradley.

A palm print was recovered at the scene. An old toilet was used to bludgeon Bradley. The lid and the tank were broken and there were cuts on his body, Best said.

Dirt and leaves had been jammed into Bradley’s mouth. His windpipe was clogged. His pockets had been turned inside out.

Eight days later, Bowles murdered Alverson Carter Jr., 47, of Atlanta. Carter was fatally stabbed.

Six days after that, he murdered Albert Alcie Morris, 37, in Hilliard, a town in Nassau County about 30 minutes northwest of Jacksonville.

Morris’ body was discovered inside his home by his parents.

The scenario was strikingly similar to what had happened two months earlier in Daytona Beach. Morris and Bowles, according to law enforcement, were seen together at a Jacksonville gay bar. Morris invited Bowles to stay at his home for a few days.

Morris, also like Roberts, fought back against his attacker. Bowles used a marble dish to beat Morris and also shot him in the chest. A towel was stuffed into his mouth.

Bowles found something in Morris’ home that helped him prolong his fugitive status. He discovered a driver’s license, Social Security card and birth certificate belonging to a Timothy Whitfield. Morris' relationship to Whitfield is unclear, but Bowles used the Whitfield alias during the next four months.

Bowles was jailed at least twice during that time for minor infractions, but law enforcement unsuspectingly booked him under the fake name. Bowles eventually spent five days in jail for an offense committed by the real Timothy Whitfield, but Bowles didn’t want to blow his cover, so he quietly served the time. Police never figured out Whitfield’s real identity, even though by this time, Bowles had been featured on a prime-time network crime show and had been profiled in Newsweek and USA Today.

On Nov. 19, 1994, Bowles was put on the FBI's Ten Most Wanted list.

One day later, he murdered 42-year-old Walter Hinton, a Jacksonville floral designer who, like Roberts and Morris, invited Bowles to stay with him.

Bowles was arrested at a day labor office the morning of Nov. 22 on suspicion of killing Hinton. When he saw the authorities show up, he tried hiding in the bathroom.

He was brought in for questioning. It took hours, but the suspect known as Timothy Whitfield eventually broke down and admitted everything to Jacksonville Sheriff’s Office detectives.

“Look, I’m tired of this,” he told investigators. “Do you really want to know who I am? I’m Gary Ray Bowles.”

Afterward, he confessed to killing six men and stealing from them. He said he wanted the killings to stop.

“I’m either getting six life sentences or the electric chair,” he reportedly said during his interview.

Death sentence

The Sheriff’s Office called authorities in Maryland, Florida and Atlanta to tell them the news. Best drove down from Savannah and Youngman drove up from Daytona Beach. They were among the out-of-town detectives who showed up to have their face-to-face time with the killer they had been seeking for months.

“He blamed his childhood. He blamed his alcohol abuse,” Best said, recalling Bowles’ answers to his questions.

“He just had a lot of pent-up anger,” he continued. “Sure, his childhood played a role, but he was an opportunist. Once he robbed and killed his first victim, it became easy for him after that.”

In May 1996, Bowles stunned prosecutors when he pleaded guilty to killing Hinton. They still decided to pursue the death penalty, based on the facts of the case. Hinton’s head was bashed with a 40-pound concrete block and he had been suffocated with toilet paper and a wash cloth, according to court testimony.

“(Mr. Hinton) put up a heck of a fight for his life,” de la Rionda told jurors during Bowles’ sentencing hearing, according to a story in The Florida Times-Union. “His skull was fractured, but his brain was still intact. He attempted to live, in a valiant effort.”

Jurors recommended death in a 10-2 vote in July 1996. The judge sentenced him to death later that summer. The following year, Bowles pleaded guilty to murdering Morris and Roberts and received consecutive life sentences for those crimes. Authorities in Georgia and Maryland declined to prosecute him.

In August 1998, the Florida Supreme Court overturned Bowles' death sentence, saying de la Rionda was wrong to introduce Bowles' hatred of homosexuals as evidence.

The following May, jurors heard evidence again on whether to recommend life or death. They were unanimous the second time. Bowles was transported back to death row in September 1999, where he has remained for 20 years living in a 6-by-9-foot cell.

State executions aren't as popular

Public opinion for the death penalty has changed significantly since the mid-1990s, when support for it reached its apex, according to the Death Penalty Information Center in Washington, D.C., a group that doesn't advocate for or against the death penalty, but aims to publicize all of the system's flaws.

Since then, support has fallen about 25 percentage points, said Robert Dunham, the center's executive director.

"There is rising opposition to the death penalty," Dunham said. "People who support it in theory can't support it the way it is being practiced."

Following a U.S. Supreme Court decision in 2016, death sentences were halted for a time in Florida on the basis that the state's death penalty statute violated the Sixth Amendment. The Florida Legislature subsequently made changes to the law. In order for death sentences to be carried out, jurors must now be unanimous in favor of death.

Additionally, circuit judges previously had the power to overturn a jury's life recommendation and sentence a first-degree murder defendant to death. That no longer is the case.

The state required all post-2002 death penalty cases that did not have unanimous juries be reviewed by the state attorneys in their respective judicial circuits. Several of Florida's killers are still awaiting new sentencing hearings for murders they committed more than a decade ago.

But Bowles was sentenced in 1999 and the jury was unanimous, so his case never came under review.

"Virtually everybody (on death row) in Florida was unconstitutionally sentenced to death," Dunham said, referring to those who received death sentences prior to 2002. "The executions that happened were for those who were sentenced under an unconstitutional process."

Gov. Ron DeSantis, who was sworn into office in January, has signed two death warrants. Bowles was the second. It was signed June 11. He will become the 99th inmate executed in Florida since the U.S. Supreme Court restored the death penalty in 1976.

Florida used the electric chair to execute condemned killers until 2000, when the Florida Legislature passed a law that allowed for lethal injection as an alternative method.

When an inmate is executed, the executioner, who is paid $150 and remains anonymous, administers 200 mg of etomidate, an anesthetic agent and 20 ml of a saline solution. Afterward, after it is determined the inmate is unconscious, he or she is given 1,000 mg of rocuronium bromide, a powerful muscle relaxant, and an additional 20 ml of a saline solution. After that, a fatal dose of potassium acetate is injected, which stops the inmate's heart.

Florida's first execution was in 1979. It has averaged more than two executions per year since then — some of whom have been serial killers. Serial killers included Ted Bundy, Aileen Wuornos, David Alan Gore, Danny Rolling, Oscar Ray Bolin and Bobby Joe Long, who was the most recent death row inmate to be executed. He was put to death on May 23.

Florida's long list of notorious killers has likely contributed to its residents' general support of capital punishment.

"I think the majority of Floridians still support the death penalty, although a growing number have serious concerns about it," Dunham said.

Dunham's organization does not take a position on capital punishment, but it does point out that states have shown an "overall inability" to administer the death penalty fairly and non-arbitrarily, he said.

Even still, he admitted that Bowles could never be "the poster child for abolition" of the death penalty.

No one directly involved in the Bowles investigation who spoke to The News-Journal has any second thoughts about executing Bowles.

"I think it's a just sentence," said Best, who pointed out that Bowles' violent streak goes as far back as 1982, when he raped a woman in Tampa. "I don't think he's going to be missed. Even though he's in a prison cell, he can wake up every day. His murder victims can't do that anymore."

Youngman said he thinks a death sentence is the only appropriate punishment for Bowles. To him, the only inappropriate part has been the extended wait.

"He killed six people," he said. "You can prove it, without a doubt. So why not? It's time."

Last Tuesday, the Florida Supreme Court unanimously rejected Bowles' latest appeal, in which Bowles' attorneys claimed he was intellectually disabled and should be spared from execution.

Twenty three years ago, Bowles' trial attorneys pointed to his troubled childhood and the abuse he suffered in an effort to convince jurors not to recommend death. The jurors weren't swayed, and neither was Norma Cole, Hinton's mother, who spoke to The Florida Times-Union after the original jury in the case recommended death.

"I'm sorry the abuse affected him in the way it did," she said. "I'm sorry anyone has difficulty like that in life. But I haven't had such an easy life, either."

Cole was Hinton's last living close relative. She died in January.

Tony Holt is a reporter for The Daytona Beach News-Journal.