STARKE — The long wait for justice for the families of three young women brutally murdered in the bay area in 1986 is finally over. Serial killer Oscar Ray Bolin Jr. was executed Thursday night three decades after his crimes.

Bolin, 53, was pronounced dead at 10:16 p.m.

Minutes before, a prison official asked Bolin if he had any last words.

"No sir," Bolin said.

Family members of Natalie Blanche Holley, 25; Stephanie Collins, 17; and Teri Lynn Matthews, 26; all watched on silently as their killer was executed by lethal injection at Florida State Prison. There were 36 witnesses. Some cried.

Afterward, Matthews' mother Kathleen Reeves thanked a key witness against Bolin: his half-brother Phillip Bolin. He testified that in 1986 he watched Oscar Ray Bolin Jr. brutally beat a woman wrapped in a sheet. It was her daughter.

"God bless you Phillip for your courage," Reeves said, "and for doing the right thing."

The families endured decades of legal wrangling as Bolin was tried and found guilty 10 separate times for the three murders. It was the murder of Matthews, the last of his victims in 1986, that resulted in Gov. Rick Scott signing Bolin's first death warrant in October.

But the families found themselves facing one last delay Thursday. The U.S. Supreme Court spent four hours mulling Bolin's final appeal well past his scheduled 6 p.m. execution time.

The justices denied the appeal just before 10 p.m. Injections of the chemicals midazolam hydrochloride, vecuronium bromide, and potassium chloride started at 10:05 p.m.

Bolin's eyes closed, and not a minute later his mouth fell wide open.

A prison official shook Bolin by the shoulders at 10:09 p.m. No response.

His breathing grew more labored. He appeared to stop breathing by 10:13 p.m.

The doctor entered the execution chamber at 10:15 p.m.

Bolin's execution day preparations started Thursday when he awoke at 6 a.m., according to prison officials. He spent three hours with his wife, Rosalie Bolin, from 8 to 11 a.m. She was a former member of his defense team who left her prominent Tampa husband to marry Bolin a decade ago. A TV audience of 12 million watched their wedding in 1996.

From noon to 2 p.m., Bolin met with his spiritual adviser, Brother Dale Recinella. A prison official said that Bolin was "calm and in good spirits."

Then Bolin ate his last meal: a rib eye steak, medium rare; a baked potato with butter and sour cream; a salad made of iceberg lettuce, cucumber and tomato; baked garlic bread; lemon meringue pie; and a bottle of Coca-Cola.

Bolin ate half the steak and potato, officials said, nibbled on the salad, drank half his coke and finished his slice of pie.

His path to Florida's death row began in 1990, when an anonymous caller to an Indiana Crime Stoppers tip line implicated him in the three unsolved murders of young women in the bay area.

Holley, a night manager at a Church's Fried Chicken in Tampa, vanished after finishing her shift there Jan. 25, 1986.

She was found later that day in an orange grove off Debuel Road, east of U.S. 41. She had been stabbed 10 times.

Collins, a senior who sang in the chorus at Chamberlain High School, was last seen walking to her car outside the Carrollwood drug store where she worked.

Her body was found a month later on Dec. 5, 1986 off Morris Bridge Road, wrapped in sheets and towels. She had been stabbed, her skull crushed.

That was the same day Matthews disappeared. She never arrived at her parents' Pasco County home after she finished the night shift at a Tampa bank.

Her car was found with the engine still running outside the Land O'Lakes post office on U.S. 41. Her body was found the day she disappeared, Dec. 5, 1986, wrapped in a damp white sheet in the woods off Coon Hide Road, west of U.S. 41. Her throat had been cut, her head bludgeoned.

The tip that led local investigators to Bolin came from the new husband of his ex-wife. Bolin, a former carnival worker, was serving time in an Ohio prison for a 1987 rape. In that case, Bolin kidnapped a 20-year-old woman, forced her into the cab of a semitrailer truck with two other men inside, and assaulted her as they rolled across the state. He let her go in Pennsylvania.

When he was brought back to Florida, a task force looked to connect Bolin to slayings in 26 states. But he was only officially linked to just one other. His cousin, Douglas Tedrow, told detectives that he and Bolin kidnapped and raped Deborah Diane Stowe, 30, in 1987 in Greenville, Texas, before Bolin strangled her.

While awaiting his first murder trial, Bolin concocted an elaborate escape plan that involved kidnapping and holding hostage the relatives of then-Hillsborough Sheriff Walter Heinrich and high-ranking sheriff's officials. The plot netted Bolin a 15-year sentence.

The Bolin case captured national attention when the condemned man married in 1996. Rosalie Bolin once bragged that her notoriety would afford him "a rich man's justice."

Still, in retrial after retrial, the state doggedly pursed the death penalty for Bolin.

In the Matthews case, Phillip Bolin, the younger half-brother, repeatedly testified about the night his brother woke him, brought him outside his home, and showed him a body wrapped in a sheet. He heard a whimpering noise.

He said his older brother claimed it was a woman who had been shot in a drug deal outside the Land O'Lakes post office. Phillip Bolin said he watched his brother try to drown her with a garden hose and beat her with a wood club.

Robert Dunham, head of the Death Penalty Information Center, said it's not unusual for the U.S. Supreme Court to delay executions at the last minute.

"They're aware of when the execution is scheduled to start and they're aware that what they do has life or death implication," he said, "but they nonetheless will take a look at it."

Standing outside the prison, Donna Witmer, the mother of Stephanie Collins, talked about her daughter.

"We all miss Stephanie everyday," Witmer said. "I can't have her back but I'll have sweet memories."

Reeves, 78, said goodbye to her daughter, Matthews.

"We miss you Teri," she said. "You were the sunshine in our lives.

"Rest in peace my darling daughter."

Times senior news researcher John Martin contributed to this report. Contact Dan Sullivan at dsullivan@tampabay.com or (813) 226-3386. Follow @TimesDan.