More than 23 years ago, 15-year-old Damien Riley browsed through the Legends Comics and Sports Cards store on Highland Road, then aimed his gun at the back of the head of 41-year-old store owner Michael Kleban, who was sitting at the counter listening to the radio.

State Judge Richard Anderson of the 19th Judicial District Court on Monday is expected to either revise or reinstate Riley’s life sentence because of a series of decisions by the U.S. Supreme Court finding that adolescents who kill are less culpable because of their still-developing brains and ability to change.

In 2016, justices ruled that the court’s previous rulings about juveniles with life sentences applied retroactively, to prisoners like 71-year-old Henry Montgomery, an inmate at the Louisiana State Penitentiary at Angola.

Prisoners like Montgomery — and Riley — who had committed crimes as juveniles must now be given a “meaningful opportunity” to have their sentences reconsidered, the court ruled. That is no small task in Louisiana, which ranks third in the nation in the number of juveniles serving life.

On that night in December 1994, Riley killed Kleban with one shot and ran down Highland Road with a wad of the store’s money. He was soon caught by police, confessed to what he’d done and led detectives to the Stallard Arms Maverick pistol he’d thrown into Bayou Fountain, telling them he’d paid $20 for the gun and one bullet.

There was no question about guilt: Riley had slain a beloved community merchant.

The details of that case are still vivid to former Judge Curtis Calloway more than two decades later. “I don’t know why this kid stands out in my mind,” said Calloway, now 78. “He just seemed different. He was mild-mannered. He looked like a little baby.”

The judge, who has long worked with youth in his spare time, saw an adolescent who “probably had no idea what he was doing.” After all, he said: “Who goes in to rob someone with a gun with one bullet?”

After listening to the evidence in Riley’s trial and hearing his taped confession, the jury, which voted 11 to 1 to convict him, was reluctant to put him away for life.

The jurors sent a note to Calloway asking for a lesser sentence. He couldn’t comply: Anyone convicted of second-degree murder received a mandatory life sentence.

Kleban family members left Calloway’s court more than 20 years ago thinking that they’d put a painful process behind them. For them, raising the issue again is difficult.

Kleban’s nephew, Douglas Saltz, who was with his uncle at the store 20 minutes before the shooting, said he understands the Supreme Court’s decision about adolescent brain function. But he doesn’t believe it should apply to Riley.

“I think three life sentences isn’t enough for him,” Saltz said.

'Worst of the worst'

Like other states, Louisiana now allows juveniles with life sentences a chance at a parole hearing after they’ve served a certain amount of time — in Louisiana’s case, 25 years. But Louisiana also created a safety valve that allows prosecutors to pursue life-without-parole sentences for certain defendants they considered incorrigible.

The U.S. Supreme Court mandated that juvenile life sentences should be “rare” and “uncommon,” Sen. Dan Claitor (R-Baton Rouge), a former district attorney, emphasized in a legislative hearing last year. “It will be up to the DAs … to follow the law,” he said. “You can’t declare everything the ‘worst of the worst.’”

Statewide, prosecutors sought life sentences for 84 of the state’s remaining 255 juveniles with life sentences, roughly one-third of the cases. In East Baton Rouge Parish, District Attorney Hillar Moore III has decided to fight parole hearings for 12 defendants out of 31 — or 38 percent. This includes Riley.

Last fall, Moore said the cases they want back before a judge are those that deserve extra scrutiny, which he can ensure happens in a court hearing.

“That’s like sending an embossed invitation to the Supreme Court to tell us that we’ve done it wrong yet again,” said Katherine Mattes, director of the Tulane University Law School’s Criminal Litigation Clinic.

Providing one defendant with a court-mandated “individualized” hearing runs about $58,000, said James Dixon, head of the Louisiana Public Defender Board, who calls the hearings “an unfunded mandate.”

A few judges have awarded mitigation money so that defense attorneys can hire specialists to look deeper into a client’s life.

Not in Riley’s case. Mummi Ibrahim, who is representing Riley pro bono, requested money for a mitigation expert during the hearing but was turned down, she said. So she handled the case solo.

That’s a near-impossible task, Dixon said. “Let’s say I did this investigation. I can’t call myself to the stand,” he said. “You’re probably also going to have to have expert testimony beyond the mitigation specialist, including psychologists and psychiatrists, people to testify about that child. All of this is necessary but expensive.”

'Not all peaches and cream'

Moore is pursuing life without parole in Riley’s case partly because of the heinous nature of the crime. The DA's office pointed out in a recent filing that Riley had not expressed remorse in public for the killing and didn't take the stand in his October hearing, where he would have been questioned under oath.

First Assistant District Attorney Tracey Barbera asserted his infractions in prison, including possession of a contraband cellphone last year, further merit the judge's consideration.

Also, Riley’s upbringing shouldn’t have created a murderer.

“It is without question that Damien Riley’s family members love and support him, just as they have his entire life," Barbera wrote. “This factor alone distinguishes him from the vast majority of individuals involved in the criminal-justice system.”

It’s inaccurate to summarize Riley’s life in such an idyllic way, said his mother, Melvina Jones. “It was not all peaches and cream,” she said. “I’m not a psychiatrist, but there was lots going on.”

Just last week, Jones got a call from her sister about an old Christmas card letter describing how she’d put Riley in a boys’ home.

Only then did Jones remember how she and her husband, Danny Jones, brought Riley to a place for wayward teens after he was disrespectful. It was in 1994, not long before the shooting, she said, wishing that she had remembered it so that Ibrahim could have gotten records for the hearing.

She mentioned the boys’ home to Riley when he made his daily call on a recent afternoon. They agreed that he stayed there about a month. “I remember wondering, ‘Why did they send me here?’ he told her. “I really felt like I was being pushed away.”

Sitting in court in October, he’d seen Kleban’s sister and felt overwhelmed with shame. “I wanted to tell her how sorry I was. I wanted to ask for her forgiveness,” he said.

He recalled how they’d moved from a quiet part of St. Gabriel to an apartment in the Gardere area, which was rough. He’d seen a young man killed. A man in a car had pointed a gun at him and his younger sister when they were walking to the corner store. “It was scary,” he recalled. “I wanted to be able to protect her. To protect myself.”

He didn’t tell his parents about the man. But he bought the pistol.

At that time, he really didn’t feel safe at home, he said. In response, his mother slumped in her chair. She and his stepfather had gotten in a bad cycle, where they were drinking too much and fighting, in a way that sometimes turned violent, she said.

That fateful night, Riley told his mother he had taken the bus to a friend’s house, hoping to escape the drinking and fussing. He’d called his friend from a pay phone. No answer. So he walked to Kleban’s store. He looked at football cards of John Elway and Steve Atwater. Then, as he leaned over, the gun in his pocket tapped against the store’s glass case. He’d forgotten he had it. But knowing he had the gun, he acted, in a way that he will never quite understand.

At home, things changed rapidly, Jones said. “After the shooting, we figured out that it was everything — the bad neighborhood we were living in, how we were living, all of it. So we moved and we changed to save the other two kids.”

“If only we’d done it earlier,” Jones said. “Maybe we could have saved all three.”