The D.A. charged a man with murder in a notorious Palmdale killing. A decade later, the same office seeks to toss his conviction

From behind bars, Raymond Lee Jennings begged a judge to throw out his murder conviction. He’d been in the dimly lit Palmdale parking that winter night as a security guard, but he swore he had nothing to do with killing 18-year-old Michelle O’Keefe.

Now — more than a decade after his arrest — he has a surprise ally in his request to drop the case: The same district attorney’s office that prosecuted him.

In a letter filed in court this week, Los Angeles County prosecutors said they agree the conviction should be tossed out “based on newly discovered evidence pointing to his factual innocence.”

“It’s finally come to an end,” Jennings said after a court hearing Thursday. “A bit of elation, a bit of sadness.”

Raymond Lee Jennings, right, wipes away tears during a hearing in which Judge William Ryan said he needed more time to decide whether to vacate Jennings’conviction.

(Luis Sinco / Los Angeles Times )

Tears filled his eyes as he spoke of all he’d missed during his 11 years behind bars — mainly watching his five children grow up. At times, he said, he felt like giving up. What’s the point, he wondered? He had been sentenced to 40 years to life in prison.

He could keep calling them and writing letters, but he hated the idea of never making memories with them.

“‘Excruciating’ is the word for it,” he said. Even now he sees the impact of his time away on his relationship with his kids — a certain disconnect, he said.

As Jennings walked slowly into a downtown L.A. courtroom Thursday, he wore a black suit and a broad smile. From a few feet away, the victim’s mother winced.

When Patricia O’Keefe addressed the court, she spoke of her daughter as a little baby with a full head of black hair, who grew into a woman who treated everyone with kindness. As for Jennings — whom she referred to only by his last name — she told Superior Court Judge William Ryan that she hadn’t changed her mind.

“Jennings is still guilty until proven otherwise,” she said.

When the victim’s father spoke, he sometimes sighed and his voice cracked: “Judge Ryan, I don’t have to tell you how big this decision is.”

Michael O’Keefe brought up the original prosecutor’s trial argument: that Jennings seemed to know too many details about the shooting for someone who wasn’t guilty. He urged the judge to speak with the trial prosecutor and review an appellate court decision from years earlier that upheld Jennings’ conviction.

“From what I’ve seen,” the father said, “nothing has changed in my mind.”

He went on to tell the judge of the tremendous loss he’s suffered over the years — after Michelle’s death, his son died of a drug overdose. Ryan nodded sympathetically.

“Think about our daughter. Think about an innocent girl killed 17 years ago,” he said. “I’m relying on you to make the right decision.”

As the parents spoke, Jennings stared ahead, swiveling slightly in his chair and resting his chin on his two index fingers.

Ryan said he plans to issue a written ruling later on whether to throw out the conviction.

The teenage victim was shot to death inside her blue Ford Mustang in February 2000. The case remained unsolved for several years, stoking fear in the Antelope Valley — O’Keefe’s picture adorned a billboard along with the message, “Can you help catch my killer?”

In December 2005 — after initially deciding there wasn’t enough evidence against him — prosecutors charged Jennings.

The prosecutor who took the case to trial characterized the slaying as a sexual advance gone awry, pointing to the $111 found inside O’Keefe’s wallet as proof it wasn’t a botched robbery. In interviews with detectives and lawyers, Jennings knew things that only the killer would know, the prosecutor argued.

There was no forensic evidence directly connecting Jennings to the crime. Two downtown L.A. juries deadlocked before the case was ultimately moved back to the Antelope Valley for a third trial. Jurors there convicted Jennings in 2009.

But he always maintained his innocence, even at his sentencing in 2010.

“This is one sin that I will not be judged for,” he told the judge. “I’m at peace in my life, and I laugh and I smile because I hold no remorse.”

Jennings continued to fight for his freedom until June 2016, when the district attorney’s office sent a letter to the court under seal that said newly discovered evidence raised doubts about his guilt.

At the request of prosecutors, Ryan ordered Jennings released but did not throw out the conviction.

On Thursday, the judge unsealed the letter, which said that other people who had been in the parking lot that night had previously committed similar crimes using handguns. They fled before authorities arrived, wrote Chief Deputy Dist. Atty. John Spillane.

The newly discovered evidence, Spillane wrote, suggests that O’Keefe “may have been killed by gang members during a robbery.”

The letter did not name the possible suspects, citing the ongoing inquiry, but said a 17-year-old woman was in a rented Chevy Malibu in the parking lot that night with at least two others. A documented gang member, she went on to be convicted of possession of a firearm and was later arrested for throwing bleach in her boyfriend’s face, the letter said.

In 2015, she was accused of more violence: stabbing a boyfriend. She was charged with attempted murder but convicted of assault with a deadly weapon, and was sentenced to five years in prison.

An 18-year-old gang member who was with her in the car on the night of O’Keefe’s killing committed a home invasion robbery and carjacking just months later, according to the letter. He was caught after stealing a Mustang. At the time of his arrest, he was wearing an earring with a white stone that was similar to others O’Keefe was wearing the night she was killed.

The man is serving a 31-year prison sentence.

Deputy Dist. Atty. Bobby Grace of the district attorney’s conviction review unit said a prosecutor from the hardcore gang division, along with two sheriff’s detectives, are now conducting a new investigation into O’Keefe’s killing. They’ve uncovered new information since June, Grace said, noting that the O’Keefe family has not been briefed on the findings.

“It is important to note,” Grace said, “that no new information that has been gathered points to Ray Jennings.”

Grace said the district attorney’s office is willing “to tweak things” based on lessons learned from the case.

In a court filing this week, Jennings’ appellate attorney, Jeffrey Ehrlich, asked Ryan to throw out the conviction, saying the original investigators and prosecutors developed “tunnel vision” and “concocted a flimsy case.”

Ehrlich added: “Ray Jennings lost 11 years of his life as a result.”

The original trial prosecutor, Deputy Dist. Atty. Michael Blake, through a spokesperson declined to comment.

In his filing, Ehrlich included a report from Peter Klismet, a retired FBI profiler who reviewed the case for the defense.

Detectives, Klismet said, homed “in on Jennings, developed the theory that he was the killer, and then built a set of facts around Jennings rather than consider other, more viable suspects. It appears Jennings became the only suspect in their minds, and they made the facts fit that theory, while there were other options available.”

marisa.gerber@latimes.com

richard.winton@latimes.com

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UPDATES:

3:55 p.m.: This article was updated with details from Thursday’s hearing and a letter the district attorney’s office previously filed about new evidence in the case.

This article was originally published at 3 a.m.