Kelly Burke took a few labored steps to the witness stand and looked toward a large video screen in a rural Georgia courtroom. There, he saw the face of a man, beamed in from a nearby prison, whom he had sent away 25 years earlier for life without parole.

Mr. Burke, a former district attorney, hadn’t seen the man, Jessie Askew Jr., since the sentencing in 1998. He had insisted at the time that Mr. Askew, then 24 years old, deserved to die in prison. On this spring morning in 2023, Mr. Burke planned to tell the court it was the biggest mistake of his career.

Both men had changed since then, though Mr. Burke’s transformation was more dramatic. Once an imposing 6-foot-7, he was now a hunched cancer patient who relied on a motorized wheelchair. Complications from the disease had left him thin and unable to swallow. And he was deeply troubled by a self-inflicted wound to his conscience.

“Good morning, Mr. Burke,” Mr. Askew said, representing himself because he couldn’t afford a lawyer. “Would it be fair to say you remember my case?”

“Very much,” said Mr. Burke, whose trouble swallowing caused saliva to build up, making him at times hard to understand.

Mr. Askew was hoping to persuade a judge to overturn his sentence for an armed robbery in 1997. Mr. Burke was his only witness.

Mr. Burke had already outlived his doctors’ expectations. After almost 20 years of trying to get Mr. Askew’s sentence reduced, he knew this was likely his last chance to help.

An Angry Prosecutor

In September 1997, Mr. Askew and his cousin, wearing masks and carrying unloaded shotguns, burst into Morrison’s Fresh Cooking, a restaurant where Mr. Askew once worked. They herded Mr. Askew’s former co-workers into a cooler and fled with nearly $5,000 from cash registers, but they were quickly arrested.

Mr. Burke, then 38, was the new district attorney for Georgia’s Houston County, a community dominated by agriculture and the Robins Air Force Base. During his campaign, residents and police had told him the justice system was too easy on people charged with crimes. That sentiment was widespread, prompting lawmakers across the United States to enact sometimes draconian new sentencing laws. Mr. Burke agreed that tougher punishment was needed, though he had never prosecuted a case before he was elected district attorney.

The holdup at Morrison’s angered Mr. Burke. No one had been injured, but the crime had terrified workers who could not have known the shotguns weren’t loaded. And Mr. Burke was certain of Mr. Askew’s guilt. Despite the mask Mr. Askew wore, his co-workers easily identified him. His cousin was wearing the same worn-out striped shirt Mr. Askew often had on at work because he couldn’t afford other clothes.

During the trial, Mr. Burke said, he offered a 15-year sentence if Mr. Askew pleaded guilty. If he didn’t take the deal, Mr. Burke recalled telling Mr. Askew’s lawyer, he would file what he called a recidivist motion. He was referring to a new law saying that people could be sentenced to life without parole for their fourth felony if the crime was a serious offense, such as armed robbery. Mr. Askew was eligible because the robbery was his fourth felony; the first three were nonviolent crimes.

According to Mr. Burke, Mr. Askew’s lawyer, Rodney Davis, turned down the deal. Mr. Davis, who declined to comment, testified a decade after the trial that prosecutors never made an offer.

Whatever the truth, the trial proceeded and Mr. Askew was found guilty. (His cousin, who had fewer prior convictions, pleaded guilty in exchange for a 10-year sentence.)

Mr. Burke ultimately blamed his own inexperience for his failure to explain his plans to Mr. Askew’s lawyer clearly. The law Mr. Burke had planned to enforce was just one in a batch of new statutes meant to lengthen sentences. Mr. Askew’s lawyer appeared confused in court, arguing against a different statute from the one Mr. Burke cited.

Because of the misunderstanding, Mr. Askew and his supporters didn’t realize when they arrived at his sentencing in March 1998 that he might never go home again.

Before revealing the sentence he sought, Mr. Burke listened to Mr. Askew’s relatives and pastor testify for mercy. They described the 24-year-old as the son of working-class parents who toiled long hours for their children and raised him and his four siblings in church and sports. After dropping out of high school, he struggled to keep even the low-paying jobs he could find. Like many young men who can’t see past the weekend, Mr. Askew dreamed of fast money. He tried harder when the birth of his daughter brought a jolt of reality. But it meant he needed more money now and grew desperate.

Witnesses said he was a good person who had the drive to overcome his past mistakes. Even some of the former co-workers he had robbed spoke on his behalf, testifying that he doted over his baby, whom he often brought to work because he had no child care.

Dora Clarington, Mr. Askew’s aunt, said her husband, a barber, had a job waiting for him; Mr. Askew dreamed of opening a barbershop with his brothers, Nortrell and James.

Nortrell Askew spoke of his immense gratitude to Jessie for saving him from drowning when they were boys. Nortrell said they wanted to use the barbershop to find ways to empower local young people to build better lives.

“I got a lot of dreams,” Jessie said crying on the stand, “mainly raising my little girl.”

When Mr. Burke told the judge he was seeking life without parole, a gasp rose from Mr. Askew’s supporters. Mr. Burke turned, surprised by their surprise, and saw shocked faces.

“His family appears to be fine folks, but Jessie isn’t,” Mr. Burke said, his voice still sturdy and clear. “And so the law has a remedy for Jessie Askew.”

Under the law, the court had no choice but to impose life without parole. After watching the judge pronounce the sentence, Mr. Burke told a reporter, “Mr. Askew will never breathe another breath of free air.”

‘I Take Full Responsibility’

In early 2000, The Atlanta Journal-Constitution began reporting on the rise in sentences of life without parole in Georgia. A reporter called Mr. Burke to ask about the Askew case, noting that his sentence stood out as harsh considering that he had not physically harmed anyone.

Mr. Burke told the reporter that Mr. Askew should have pleaded guilty. “He didn’t want to admit to his family that he did it,” he said.

Time in the job began to change Mr. Burke’s perspective. A year later, he prosecuted a man for stabbing a person to death, but couldn’t seek life without parole because the crime didn’t meet state guidelines. In 2002, Mr. Burke won a murder conviction against another man who ended up with a chance at parole.

In his second term, Mr. Burke came to believe that life without parole ought to be reserved for people who commit horrific violent crimes — not someone who robbed a restaurant with an unloaded gun and was caught when people recognized his shirt.

He began to feel he had gone too far and hadn’t considered how poverty and desperation affected Mr. Askew’s life. Mr. Burke believed his own immaturity played a role in the case, too. He realized he had pushed for life without parole because he was angry that Mr. Askew demanded a trial.

Mr. Burke decided that pushing to reduce Mr. Askew’s sentence was his responsibility. But Georgia, which doesn’t give its governor pardoning powers, has no second-look law to allow for disproportionate sentences to be reviewed. Experts consider such laws critical in addressing disproportionate sentences imposed in the tough-on-crime 1990s.

So, in 2005, Mr. Burke tried a simple plan: He checked the trial records for errors to overturn Mr. Askew’s conviction. Seeing none, he contacted the parole board, which told him they couldn’t help Mr. Askew because of the “without parole” part of his sentence. Mr. Askew remained in Telfair State Prison.

A thought pursued Mr. Burke: I was too damn hard on him.

In 2009, Mr. Burke sent a message to Mr. Askew through his uncle. Mr. Burke wanted to tell Mr. Askew he had been too harsh and wanted to help him be resentenced.

For more than a decade, Mr. Askew woke up every morning in a dorm surrounded by other men condemned for life, but he never gave up. He stayed out of trouble, worked as a medical orderly and earned certifications in trades like forklift operation and industrial painting. Through a prison program, he worked with young people at risk, trying to prevent future incarcerations with his “testimony.” He was overwhelmed to learn that Mr. Burke, who knew nothing about his transformation, also saw his worth.

With Mr. Burke on his side, Mr. Askew finally saw a path toward his own freedom. He asked his lawyer, L. Elizabeth Lane, to arrange for Mr. Burke to testify on his behalf in a habeas corpus hearing, a proceeding that challenged the legality of his incarceration. But she told him in a letter that Mr. Burke declined to “go on the record.” Mr. Askew was confused and hurt, and his habeas corpus petition was denied in 2011.

Years later, Mr. Burke would testify that Ms. Lane never contacted him. And Ms. Lane would turn in her law license as she faced disbarment over her handling of a different case. She didn’t respond to calls and emails requesting comment.

After Mr. Askew hired a new lawyer, Mr. Burke swore out multiple affidavits in hopes that they could sway the current district attorney or bolster a legal filing. Mr. Burke said in the affidavits that he took “full responsibility” for the sentence Mr. Askew had received. But the way forward wasn’t clear because Mr. Askew had exhausted his appeals, and while Mr. Burke had changed, the law had not.

Mr. Burke asked his two succeeding district attorneysto support resentencing Mr. Askew, but they declined.

In 2017, Mr. Burke was diagnosed with skin cancer that soon migrated to his spine. By 2021, it had ravaged his body and nearly taken his voice. He saw the disadvantages young Black men like Mr. Askew faced and hated that he pushed for the system to destroy his life. He feared he would die before he could find a way to help.

Jessie Askew’s Only Witness

In March 2021, a friend of Mr. Askew emailed Mr. Burke. Was he still willing to help Mr. Askew?

“I continue to believe his sentence is, in hindsight, too harsh,” Mr. Burke responded two hours later. “I’m sorry I had a part in it but I will do whatever I can to change it. Please tell Jessie that I am praying for him and his release.”

Mr. Askew, who later started to represent himself, was overcome and wrote an email to Mr. Burke. For many years, he had been angry with Mr. Burke, but he came to see him as an honorable man. Mr. Askew realized they were both trying to overcome mistakes they had made when they were less mature.

“God bless you forever,” Mr. Askew wrote, apologizing for his “stupid” crime — the worst mistake of his life. “From the bottom of my heart, I want to say thank you for all you have done and your mercy.”

It was two more years before Mr. Askew could ask Mr. Burke about his regret under oath.

The hearing on Mr. Askew’s habeas corpus petition was held on April 4, 2023, before Judge Howard C. Kaufold Jr. Mr. Askew, in a small room at the prison, noticed that Mr. Burke was the only witness who had shown up. Mr. Davis and Ms. Lane, his previous lawyers whose testimony he said he had requested through letters, weren’t there.

An assistant state attorney general, Ronald Daniels, began by asking Judge Kaufold to dismiss Mr. Askew’s petition, saying he didn’t have any appeals left and had already failed with a habeas petition that raised some of the same issues as the latest filing.

The judge said he would allow the proceeding to go ahead and decide on the state’s motion to dismiss later, clearing the way for Mr. Askew and Mr. Burke to start.

“Mr. Burke,” Mr. Askew, 49, said into the web camera, “what sentence did you believe was fair?”

“Fifteen years.” Mr. Askew had been in prison for 26 years.

“Did you have frustrations that my attorney appeared to be wasting your time?” Mr. Askew said.

“You and your attorney, as far as I was concerned, were wasting my time,” Mr. Burke said, citing the hard evidence against Mr. Askew. “In hindsight that was the wrong position for me to take, and I regret it because I think I violated your rights.”

Mr. Burke testified that during a break in the sentencing, the judge had privately tried to convince him to withdraw his motion for life without parole because it wasn’t fair.

“But I stood stubborn,” Mr. Burke testified, still frustrated that he hadn’t listened.

To Mr. Askew, the moment felt unreal. Here he was, condemned for life, compelling his former prosecutor to say he had violated Mr. Askew’s right to due process by purposefully enacting a disproportionate sentence.

Mr. Burke’s testimony was crucial to his case for freedom. But it wasn’t the only evidence that Mr. Askew needed the judge to hear.

The Cost of a Broken Car Window

Mr. Askew was eligible for life without parole after the Morrison’s robbery because he had pleaded guilty to three other felony cases in 1994, the year he turned 20: forgery, burglary and criminal damage to property. Nobody had been hurt in any of the crimes.

Mr. Askew’s uncle and close friend, Bernard Askew, was the victim of the forgery. In 1993, when Jessie needed money, he signed Bernard’s name on a check. The uncle was away in the Army and Jessie didn’t know how to reach him, but he was sure he would have been told yes. Bernard learned that someone had passed his check from his bank, which called the police before he knew who was responsible.

Bernard said in an interview that he considered it a misunderstanding between loved ones and not a crime. He hated that it had played a role in his nephew’s sentence. “I’ve got a burden on me,” he said.

The burglary conviction came after Mr. Askew broke into an unstaffed concessions stand at a city park in the summer of 1994, hoping to get snacks or money.

The criminal damage to property charge stemmed from an incident at S&E Auto, a used car lot. Trying to steal a radio, Mr. Askew broke the passenger’s window of a 1986 Honda Accord.

While Mr. Askew was preparing his petition, a fellow prisoner, a self-taught legal adviser pointed out that he had pleaded guilty to criminal damage worth more than $500. But the adviser said there was no way a car window cost $500 back then. That meant the crime was actually a misdemeanor, which meant Mr. Askew had two prior felonies, not three. He wasn’t eligible for life without parole. Crushed, he realized that he should’ve been home long ago.

“Did you know,” Mr. Askew said in court, “the actual damage was $100 as opposed to in excess of $500?”

“I didn’t know that, but it wouldn’t surprise me,” Mr. Burke said, impressed by how well Mr. Askew was doing during the hearing. They hadn’t gone over the questions.

Both Mr. Burke and Mr. Askew knew that if one of the three prior felonies was in fact a misdemeanor, then the sentence was never legal.

As Mr. Askew prepared to wrap up, he thought he saw a familiar fire in Mr. Burke’s blue eyes. They were all he recognized through the years and toll of disease. The last time Mr. Askew saw that fire was in the hearing in 1998, when Mr. Askew thought Mr. Burke made him look like a monster.

“Is there anything that you would like to add?” Mr. Askew said.

“Yes, sir,” said Mr. Burke, turning to look at the judge. “I’ve been in hospice twice. And I’m convinced that the reason I’m back is to make sure this court is aware of my feelings about the sentence of Mr. Askew.” He paused to accommodate the excess saliva.

“My biggest regret in my 40 years being an attorney is that Mr. Askew got treated the way he did because of my actions.”

The Decision

More than a year passed while Mr. Askew awaited the judge’s decision.

Most victims of Mr. Askew’s crimes knew little about his situation. Reached by phone, the founder of S&E Auto, Stephen Wiley, said he didn’t remember the broken window. He said he could replace a window for less than $500 — even today. “They need to let him go,” Mr. Wiley, 82, said.

Deitra Robinson was one of the Morrison’s victims who testified for mercy in 1998.On the phone, she said she was surprised to hear Mr. Askew was still serving life without parole. “That’s terrible,” she said. Ms. Robinson added that she didn’t think any of the victims had wanted Mr. Askew to die in prison.

Two days before Thanksgiving, Judge Kaufold announced his decision. He granted the state’s motion to throw out Mr. Askew’s petition.

The judge ruled that Mr. Askew never had a right to the hearing at which Mr. Burke testified. Because Mr. Askew had been aware of Mr. Burke’s regrets before his last petition was turned down in 2011, the judge wrote, he should have been able to get him to testify back then. Judge Kaufold wasn’t swayed by the evidence that Mr. Askew’s lawyer had never contacted Mr. Burke.

So the testimony Mr. Burke gave at the hearing in 2023 didn’t matter. He had failed to help Mr. Askew, again.

The ruling was crushing for Mr. Askew. He called his mother, broken to have to tell her. He could hardly talk through the tears. “Mama, the judge denied me,” he said. “It’s not fair.”

He hated that he still couldn’t be with his family, including the daughter he had doted over at Morrison’s. He had envisioned her life much differently. He tried to speak hope into existence through her name: Justyce. Today, Justyce’s kids want to know if their grandfather will ever be free.

Mr. Burke, 66, was disappointed, but not deterred. Though his cancer was in remission, his condition hadn’t changed and he was worried once again that he would die before he could successfully help. But he had an idea: “I think Jessie needs a constitutional appeals lawyer.”

Mr. Burke wanted Mr. Askew to sue him, in his capacity as the former district attorney, for violating his rights. Such suits are notoriously difficult to win, but then, prisoners almost never go to court with the prosecutors on their side. Mr. Burke said he is willing to do whatever he can to help, with whatever time he has left.